From 9314f69556763c1f895596191ee4f7bbb7cf7a93 Mon Sep 17 00:00:00 2001 From: Philippe Schwaller Date: Wed, 8 Mar 2023 23:49:22 +0100 Subject: [PATCH 1/4] adding Buchwald-Hartwig dataset --- .../Dreher_and_Doyle_input_data.csv | 3956 +++++++++++++++++ data/buchwald_hartwig/data_clean.csv | 3956 +++++++++++++++++ .../example_processing_and_templates.ipynb | 1452 ++++++ data/buchwald_hartwig/meta.yaml | 40 + data/buchwald_hartwig/transform.py | 162 + 5 files changed, 9566 insertions(+) create mode 100644 data/buchwald_hartwig/Dreher_and_Doyle_input_data.csv create mode 100644 data/buchwald_hartwig/data_clean.csv create mode 100644 data/buchwald_hartwig/example_processing_and_templates.ipynb create mode 100644 data/buchwald_hartwig/meta.yaml create mode 100644 data/buchwald_hartwig/transform.py diff --git a/data/buchwald_hartwig/Dreher_and_Doyle_input_data.csv b/data/buchwald_hartwig/Dreher_and_Doyle_input_data.csv new file mode 100644 index 000000000..13e5f6bf4 --- /dev/null +++ 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"markdown", + "id": "6ef172b9-aad2-47da-bf4c-844a2a07ee8c", + "metadata": {}, + "source": [ + "Original data repository: https://github.com/doylelab/rxnpredict\n", + "\n", + "Data from: https://github.com/reymond-group/drfp/tree/main/data" + ] + }, + { + "cell_type": "markdown", + "id": "7d18c95d-2ec6-45e1-addc-54a890097b8e", + "metadata": {}, + "source": [ + "# Imports" + ] + }, + { + "cell_type": "code", + "execution_count": 21, + "id": "cf59e3e9-8061-4022-9eae-e978311b4155", + "metadata": { + "tags": [] + }, + "outputs": [], + "source": [ + "import pandas as pd\n", + "import yaml\n", + "from rdkit import Chem # 2022.9.5\n", + "from rdkit.Chem import rdChemReactions" + ] + }, + { + "cell_type": "markdown", + "id": "a6751ff9-2e3e-4d01-8395-7a5ae0c200d7", + "metadata": {}, + "source": [ + "# Data processing" + ] + }, + { + "cell_type": "markdown", + "id": "a1169ad2-e4bb-41c6-9625-6d1644c44a5b", + "metadata": {}, + "source": [ + "## Download data" + ] + }, + { + "cell_type": "code", + "execution_count": 7, + "id": "7bb8eb5e-f513-40d2-a68c-7cda1a51ad31", + "metadata": { + "tags": [] + }, + "outputs": [], + "source": [ + "fn_data_original = \"Dreher_and_Doyle_input_data.csv\"" + ] + }, + { + "cell_type": "code", + "execution_count": 8, + "id": "b39a142e-ccbc-49d2-98b0-a5f9bde9fd27", + "metadata": { + "tags": [] + }, + "outputs": [], + "source": [ + "data = pd.read_excel('https://github.com/reymond-group/drfp/raw/main/data/Dreher_and_Doyle_input_data.xlsx')" + ] + }, + { + "cell_type": "code", + "execution_count": 9, + "id": "26d9f62a-07f5-4113-8161-d5dfcf0bfb71", + "metadata": { + "tags": [] + }, + "outputs": [], + "source": [ + "data.to_csv(fn_data_original, index=False)" + ] + }, + { + "cell_type": "code", + "execution_count": 10, + "id": "43873fc3-20a8-487d-a7c5-33bd58414159", + "metadata": { + "tags": [] + }, + "outputs": [ + { + "name": "stdout", + "output_type": "stream", + "text": [ + "total 1344\n", + "-rw-r--r-- 1 pschwllr staff 618K Mar 8 22:34 Dreher_and_Doyle_input_data.csv\n", + "-rw-r--r-- 1 pschwllr staff 38K Mar 8 22:13 example_processing_and_templates.ipynb\n", + "-rw-r--r-- 1 pschwllr staff 1.6K Mar 8 22:13 meta.yaml\n", + "-rw-r--r-- 1 pschwllr staff 4.5K Mar 8 22:13 transform.py\n" + ] + } + ], + "source": [ + "!ls -lh" + ] + }, + { + "cell_type": "markdown", + "id": "d9cda29a-a133-4f0e-992b-e77c9070ee93", + "metadata": {}, + "source": [ + "## Load original data" + ] + }, + { + "cell_type": "code", + "execution_count": 11, + "id": "77f614e7-b133-40bc-8759-2d930e4c120e", + "metadata": { + "tags": [] + }, + "outputs": [ + { + "name": "stdout", + "output_type": "stream", + "text": [ + "Ligand,Additive,Base,Aryl halide,Output\n", + "CC(C)C(C=C(C(C)C)C=C1C(C)C)=C1C2=C(P([C@@]3(C[C@@H]4C5)C[C@H](C4)C[C@H]5C3)[C@]6(C7)C[C@@H](C[C@@H]7C8)C[C@@H]8C6)C(OC)=CC=C2OC,CC1=CC(C)=NO1,CN(C)P(N(C)C)(N(C)C)=NP(N(C)C)(N(C)C)=NCC,ClC1=NC=CC=C1,70.41045785\n", + "CC(C)C(C=C(C(C)C)C=C1C(C)C)=C1C2=C(P([C@@]3(C[C@@H]4C5)C[C@H](C4)C[C@H]5C3)[C@]6(C7)C[C@@H](C[C@@H]7C8)C[C@@H]8C6)C(OC)=CC=C2OC,O=C(OC)C1=CC=NO1,CN(C)P(N(C)C)(N(C)C)=NP(N(C)C)(N(C)C)=NCC,BrC1=NC=CC=C1,11.06445724\n", + "CC(C)C(C=C(C(C)C)C=C1C(C)C)=C1C2=C(P(C3CCCCC3)C4CCCCC4)C=CC=C2,O=C(OC)C1=CC=NO1,CN(C)P(N(C)C)(N(C)C)=NP(N(C)C)(N(C)C)=NCC,IC1=CC=C(CC)C=C1,10.22354965\n", + "CC(C)C(C=C(C(C)C)C=C1C(C)C)=C1C2=C(P(C(C)(C)C)C(C)(C)C)C(OC)=CC=C2OC,CCOC(C1=CON=C1)=O,CN1CCCN2C1=NCCC2,ClC1=CC=C(C(F)(F)F)C=C1,20.0833829\n" + ] + } + ], + "source": [ + "!head -n 5 {fn_data_original}" + ] + }, + { + "cell_type": "code", + "execution_count": 50, + "id": "8f5a0387-f9e3-4e1a-8d14-5df618195f70", + "metadata": { + "tags": [] + }, + "outputs": [], + "source": [ + "df = pd.read_csv(fn_data_original, delimiter=\",\")" + ] + }, + { + "cell_type": "code", + "execution_count": 51, + "id": "55b0bd63-62a0-469e-9d8a-e9ada3fe01c4", + "metadata": { + "scrolled": true, + "tags": [] + }, + "outputs": [ + { + 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4CC(C)C(C=C(C(C)C)C=C1C(C)C)=C1C2=C(P([C@@]3(C[...CC1=CC(C)=NO1CN1CCCN2C1=NCCC2ClC1=CC=C(OC)C=C10.492663
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" + ], + "text/plain": [ + " Ligand Additive \\\n", + "0 CC(C)C(C=C(C(C)C)C=C1C(C)C)=C1C2=C(P([C@@]3(C[... CC1=CC(C)=NO1 \n", + "1 CC(C)C(C=C(C(C)C)C=C1C(C)C)=C1C2=C(P([C@@]3(C[... O=C(OC)C1=CC=NO1 \n", + "2 CC(C)C(C=C(C(C)C)C=C1C(C)C)=C1C2=C(P(C3CCCCC3)... O=C(OC)C1=CC=NO1 \n", + "3 CC(C)C(C=C(C(C)C)C=C1C(C)C)=C1C2=C(P(C(C)(C)C)... CCOC(C1=CON=C1)=O \n", + "4 CC(C)C(C=C(C(C)C)C=C1C(C)C)=C1C2=C(P([C@@]3(C[... CC1=CC(C)=NO1 \n", + "\n", + " Base Aryl halide \\\n", + "0 CN(C)P(N(C)C)(N(C)C)=NP(N(C)C)(N(C)C)=NCC ClC1=NC=CC=C1 \n", + "1 CN(C)P(N(C)C)(N(C)C)=NP(N(C)C)(N(C)C)=NCC BrC1=NC=CC=C1 \n", + "2 CN(C)P(N(C)C)(N(C)C)=NP(N(C)C)(N(C)C)=NCC IC1=CC=C(CC)C=C1 \n", + "3 CN1CCCN2C1=NCCC2 ClC1=CC=C(C(F)(F)F)C=C1 \n", + "4 CN1CCCN2C1=NCCC2 ClC1=CC=C(OC)C=C1 \n", + "\n", + " Output \n", + "0 70.410458 \n", + "1 11.064457 \n", + "2 10.223550 \n", + "3 20.083383 \n", + "4 0.492663 " + ] + }, + "execution_count": 51, + "metadata": {}, + "output_type": "execute_result" + } + ], + "source": [ + "df.head()" + ] + }, + { + "cell_type": "markdown", + "id": "95158ac1-05d7-4a21-b8e4-7f720306d331", + "metadata": {}, + "source": [ + "## Add column = field names\n", + "Clean column names (`fields_clean`) and keep original names (`fields_orig`)" + ] + }, + { + "cell_type": "code", + "execution_count": 52, + "id": "ec2458e5-455f-4f03-8ce9-c0d12e9ed371", + "metadata": { + "tags": [] + }, + "outputs": [ + { + "data": { + "text/plain": [ + "['Ligand', 'Additive', 'Base', 'Aryl halide', 'Output']" + ] + }, + "execution_count": 52, + "metadata": {}, + "output_type": "execute_result" + } + ], + "source": [ + "fields_orig = df.columns.tolist()\n", + "fields_orig" + ] + }, + { + "cell_type": "code", + "execution_count": 53, + "id": "28c9b695", + "metadata": {}, + "outputs": [], + "source": [ + "assert fields_orig == ['Ligand', 'Additive', 'Base', 'Aryl halide', 'Output']" + ] + }, + { + "cell_type": "code", + "execution_count": 54, + "id": "a46dd8ff-37b3-4894-8226-3bf98226dd09", + "metadata": { + "tags": [] + }, + "outputs": [], + "source": [ + "fields_clean = [\n", + " \"ligand\",\n", + " \"additive\",\n", + " \"base\",\n", + " \"aryl_halide\",\n", + " 'yield'\n", + "]" + ] + }, + { + "cell_type": "code", + "execution_count": 55, + "id": "785d37cb-1fb4-4a91-a923-d5a78a37f36a", + "metadata": { + "tags": [] + }, + "outputs": [], + "source": [ + "df.columns = fields_clean" + ] + }, + { + "cell_type": "code", + "execution_count": 56, + "id": "aaad8f07", + "metadata": {}, + "outputs": [], + "source": [ + "assert fields_orig != fields_clean" + ] + }, + { + "cell_type": "code", + "execution_count": 57, + "id": "1bf212cb-1653-457b-9f5d-416d4dd14b53", + "metadata": { + "tags": [] + }, + "outputs": [ + { + "data": { + "text/html": [ + "
\n", + "\n", + "\n", + " \n", + " \n", + " \n", + " \n", + " \n", + " \n", + " \n", + " \n", + " \n", + " \n", + " \n", + " \n", + " \n", + " \n", + " \n", + " \n", + " \n", + " \n", + " \n", + " \n", + " \n", + " \n", + " \n", + " \n", + " \n", + " \n", + " \n", + " \n", + " \n", + " \n", + " \n", + " \n", + " \n", + " \n", + " \n", + " \n", + " \n", + " \n", + " \n", + " \n", + " \n", + " \n", + " \n", + " \n", + " \n", + " \n", + " \n", + " \n", + " \n", + " \n", + " \n", + " \n", + "
ligandadditivebasearyl_halideyield
0CC(C)C(C=C(C(C)C)C=C1C(C)C)=C1C2=C(P([C@@]3(C[...CC1=CC(C)=NO1CN(C)P(N(C)C)(N(C)C)=NP(N(C)C)(N(C)C)=NCCClC1=NC=CC=C170.410458
1CC(C)C(C=C(C(C)C)C=C1C(C)C)=C1C2=C(P([C@@]3(C[...O=C(OC)C1=CC=NO1CN(C)P(N(C)C)(N(C)C)=NP(N(C)C)(N(C)C)=NCCBrC1=NC=CC=C111.064457
2CC(C)C(C=C(C(C)C)C=C1C(C)C)=C1C2=C(P(C3CCCCC3)...O=C(OC)C1=CC=NO1CN(C)P(N(C)C)(N(C)C)=NP(N(C)C)(N(C)C)=NCCIC1=CC=C(CC)C=C110.223550
3CC(C)C(C=C(C(C)C)C=C1C(C)C)=C1C2=C(P(C(C)(C)C)...CCOC(C1=CON=C1)=OCN1CCCN2C1=NCCC2ClC1=CC=C(C(F)(F)F)C=C120.083383
4CC(C)C(C=C(C(C)C)C=C1C(C)C)=C1C2=C(P([C@@]3(C[...CC1=CC(C)=NO1CN1CCCN2C1=NCCC2ClC1=CC=C(OC)C=C10.492663
\n", + "
" + ], + "text/plain": [ + " ligand additive \\\n", + "0 CC(C)C(C=C(C(C)C)C=C1C(C)C)=C1C2=C(P([C@@]3(C[... CC1=CC(C)=NO1 \n", + "1 CC(C)C(C=C(C(C)C)C=C1C(C)C)=C1C2=C(P([C@@]3(C[... O=C(OC)C1=CC=NO1 \n", + "2 CC(C)C(C=C(C(C)C)C=C1C(C)C)=C1C2=C(P(C3CCCCC3)... O=C(OC)C1=CC=NO1 \n", + "3 CC(C)C(C=C(C(C)C)C=C1C(C)C)=C1C2=C(P(C(C)(C)C)... CCOC(C1=CON=C1)=O \n", + "4 CC(C)C(C=C(C(C)C)C=C1C(C)C)=C1C2=C(P([C@@]3(C[... CC1=CC(C)=NO1 \n", + "\n", + " base aryl_halide \\\n", + "0 CN(C)P(N(C)C)(N(C)C)=NP(N(C)C)(N(C)C)=NCC ClC1=NC=CC=C1 \n", + "1 CN(C)P(N(C)C)(N(C)C)=NP(N(C)C)(N(C)C)=NCC BrC1=NC=CC=C1 \n", + "2 CN(C)P(N(C)C)(N(C)C)=NP(N(C)C)(N(C)C)=NCC IC1=CC=C(CC)C=C1 \n", + "3 CN1CCCN2C1=NCCC2 ClC1=CC=C(C(F)(F)F)C=C1 \n", + "4 CN1CCCN2C1=NCCC2 ClC1=CC=C(OC)C=C1 \n", + "\n", + " yield \n", + "0 70.410458 \n", + "1 11.064457 \n", + "2 10.223550 \n", + "3 20.083383 \n", + "4 0.492663 " + ] + }, + "execution_count": 57, + "metadata": {}, + "output_type": "execute_result" + } + ], + "source": [ + "df.head()" + ] + }, + { + "cell_type": "markdown", + "id": "1bfaeb22-26fb-4964-a71f-cae8335e5372", + "metadata": {}, + "source": [ + "## Data cleaning" + ] + }, + { + "cell_type": "code", + "execution_count": 60, + "id": "7e746003-cb1f-434f-bba6-00f0c439c4ac", + "metadata": { + "tags": [] + }, + "outputs": [], + "source": [ + "def generate_buchwald_hartwig_rxns(df):\n", + " \"\"\"\n", + " Converts the entries in the excel files to reaction SMILES.\n", + " From: https://github.com/reymond-group/drfp/blob/main/scripts/encoding/encode_buchwald_hartwig_reactions.py\n", + " and https://github.com/rxn4chemistry/rxn_yields/blob/master/rxn_yields/data.py\n", + " \"\"\"\n", + " df = df.copy()\n", + " fwd_template = \"[F,Cl,Br,I]-[c;H0;D3;+0:1](:[c,n:2]):[c,n:3].[NH2;D1;+0:4]-[c:5]>>[c,n:2]:[c;H0;D3;+0:1](:[c,n:3])-[NH;D2;+0:4]-[c:5]\"\n", + " methylaniline = \"Cc1ccc(N)cc1\"\n", + " pd_catalyst = \"O=S(=O)(O[Pd]1~[NH2]C2C=CC=CC=2C2C=CC=CC1=2)C(F)(F)F\"\n", + " methylaniline_mol = Chem.MolFromSmiles(methylaniline)\n", + " rxn = rdChemReactions.ReactionFromSmarts(fwd_template)\n", + " products = []\n", + "\n", + " for i, row in df.iterrows():\n", + " reacts = (Chem.MolFromSmiles(row[\"aryl_halide\"]), methylaniline_mol)\n", + " rxn_products = rxn.RunReactants(reacts)\n", + "\n", + " rxn_products_smiles = set([Chem.MolToSmiles(mol[0]) for mol in rxn_products])\n", + " assert len(rxn_products_smiles) == 1\n", + " products.append(list(rxn_products_smiles)[0])\n", + "\n", + " df[\"product\"] = products\n", + " rxns = []\n", + "\n", + " for i, row in df.iterrows():\n", + " reactants = Chem.MolToSmiles(\n", + " Chem.MolFromSmiles(\n", + " f\"{row['aryl_halide']}.{methylaniline}.{pd_catalyst}.{row['ligand']}.{row['base']}.{row['additive']}\"\n", + " )\n", + " )\n", + " rxns.append(f\"{reactants.replace('N~', '[NH2]')}>>{row['product']}\")\n", + "\n", + " return rxns\n", + "\n", + "reaction_SMILES = generate_buchwald_hartwig_rxns(df)\n", + "df.insert(4, 'reaction_SMILES', reaction_SMILES)" + ] + }, + { + "cell_type": "code", + "execution_count": 62, + "id": "d544fa60-343e-40e1-bd0c-4750f07a7145", + "metadata": { + "tags": [] + }, + "outputs": [], + "source": [ + "assert not df.duplicated().sum()" + ] + }, + { + "cell_type": "markdown", + "id": "bc6f52c1-e0f6-48b3-95f4-e36d9a5ecde8", + "metadata": {}, + "source": [ + "## Save to csv" + ] + }, + { + "cell_type": "code", + "execution_count": 63, + "id": "d6d5efa5-b4b4-4a25-8626-e10f3d691e83", + "metadata": { + "tags": [] + }, + "outputs": [], + "source": [ + "fn_data_csv = \"data_clean.csv\"" + ] + }, + { + "cell_type": "code", + "execution_count": 65, + "id": "727f8d7b-cbb6-43c7-9eab-9d4d65be6b3f", + "metadata": { + "tags": [] + }, + "outputs": [], + "source": [ + "df.to_csv(fn_data_csv, index=False)" + ] + }, + { + "cell_type": "code", + "execution_count": 66, + "id": "63c8d4a4-906e-418d-be39-879365b4dfa0", + "metadata": { + "tags": [] + }, + "outputs": [ + { + "name": "stdout", + "output_type": "stream", + "text": [ + "-rw-r--r-- 1 pschwllr staff 1.4M Mar 8 23:00 data_clean.csv\n" + ] + } + ], + "source": [ + "!ls -lh {fn_data_csv}" + ] + }, + { + "cell_type": "code", + "execution_count": 67, + "id": "a51b9001-25d7-4e0e-a607-477cfc4a9f1c", + "metadata": { + "tags": [] + }, + "outputs": [ + { + "name": "stdout", + "output_type": "stream", + "text": [ + "ligand,additive,base,aryl_halide,reaction_SMILES,yield\n", + "CC(C)C(C=C(C(C)C)C=C1C(C)C)=C1C2=C(P([C@@]3(C[C@@H]4C5)C[C@H](C4)C[C@H]5C3)[C@]6(C7)C[C@@H](C[C@@H]7C8)C[C@@H]8C6)C(OC)=CC=C2OC,CC1=CC(C)=NO1,CN(C)P(N(C)C)(N(C)C)=NP(N(C)C)(N(C)C)=NCC,ClC1=NC=CC=C1,CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C.COc1ccc(OC)c(P([C@]23C[C@H]4C[C@H](C[C@H](C4)C2)C3)[C@]23C[C@H]4C[C@H](C[C@H](C4)C2)C3)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C.Cc1cc(C)on1.Cc1ccc(N)cc1.Clc1ccccn1.O=S(=O)(O[Pd]1c2ccccc2-c2ccccc2[NH2]1)C(F)(F)F>>Cc1ccc(Nc2ccccn2)cc1,70.41045785\n", + "CC(C)C(C=C(C(C)C)C=C1C(C)C)=C1C2=C(P([C@@]3(C[C@@H]4C5)C[C@H](C4)C[C@H]5C3)[C@]6(C7)C[C@@H](C[C@@H]7C8)C[C@@H]8C6)C(OC)=CC=C2OC,O=C(OC)C1=CC=NO1,CN(C)P(N(C)C)(N(C)C)=NP(N(C)C)(N(C)C)=NCC,BrC1=NC=CC=C1,Brc1ccccn1.CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C.COC(=O)c1ccno1.COc1ccc(OC)c(P([C@]23C[C@H]4C[C@H](C[C@H](C4)C2)C3)[C@]23C[C@H]4C[C@H](C[C@H](C4)C2)C3)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C.Cc1ccc(N)cc1.O=S(=O)(O[Pd]1c2ccccc2-c2ccccc2[NH2]1)C(F)(F)F>>Cc1ccc(Nc2ccccn2)cc1,11.06445724\n", + "CC(C)C(C=C(C(C)C)C=C1C(C)C)=C1C2=C(P(C3CCCCC3)C4CCCCC4)C=CC=C2,O=C(OC)C1=CC=NO1,CN(C)P(N(C)C)(N(C)C)=NP(N(C)C)(N(C)C)=NCC,IC1=CC=C(CC)C=C1,CC(C)c1cc(C(C)C)c(-c2ccccc2P(C2CCCCC2)C2CCCCC2)c(C(C)C)c1.CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C.CCc1ccc(I)cc1.COC(=O)c1ccno1.Cc1ccc(N)cc1.O=S(=O)(O[Pd]1c2ccccc2-c2ccccc2[NH2]1)C(F)(F)F>>CCc1ccc(Nc2ccc(C)cc2)cc1,10.22354965\n", + "CC(C)C(C=C(C(C)C)C=C1C(C)C)=C1C2=C(P(C(C)(C)C)C(C)(C)C)C(OC)=CC=C2OC,CCOC(C1=CON=C1)=O,CN1CCCN2C1=NCCC2,ClC1=CC=C(C(F)(F)F)C=C1,CCOC(=O)c1cnoc1.CN1CCCN2CCCN=C12.COc1ccc(OC)c(P(C(C)(C)C)C(C)(C)C)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C.Cc1ccc(N)cc1.FC(F)(F)c1ccc(Cl)cc1.O=S(=O)(O[Pd]1c2ccccc2-c2ccccc2[NH2]1)C(F)(F)F>>Cc1ccc(Nc2ccc(C(F)(F)F)cc2)cc1,20.0833829\n" + ] + } + ], + "source": [ + "!head -n 5 {fn_data_csv}" + ] + }, + { + "cell_type": "code", + "execution_count": 68, + "id": "1a512943-4909-4d56-867d-50c151d8d607", + "metadata": { + "tags": [] + }, + "outputs": [ + { + "data": { + "text/html": [ + "
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ligandadditivebasearyl_halidereaction_SMILESyield
0CC(C)C(C=C(C(C)C)C=C1C(C)C)=C1C2=C(P([C@@]3(C[...CC1=CC(C)=NO1CN(C)P(N(C)C)(N(C)C)=NP(N(C)C)(N(C)C)=NCCClC1=NC=CC=C1CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C.COc1...70.410458
1CC(C)C(C=C(C(C)C)C=C1C(C)C)=C1C2=C(P([C@@]3(C[...O=C(OC)C1=CC=NO1CN(C)P(N(C)C)(N(C)C)=NP(N(C)C)(N(C)C)=NCCBrC1=NC=CC=C1Brc1ccccn1.CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C...11.064457
2CC(C)C(C=C(C(C)C)C=C1C(C)C)=C1C2=C(P(C3CCCCC3)...O=C(OC)C1=CC=NO1CN(C)P(N(C)C)(N(C)C)=NP(N(C)C)(N(C)C)=NCCIC1=CC=C(CC)C=C1CC(C)c1cc(C(C)C)c(-c2ccccc2P(C2CCCCC2)C2CCCCC2...10.223550
3CC(C)C(C=C(C(C)C)C=C1C(C)C)=C1C2=C(P(C(C)(C)C)...CCOC(C1=CON=C1)=OCN1CCCN2C1=NCCC2ClC1=CC=C(C(F)(F)F)C=C1CCOC(=O)c1cnoc1.CN1CCCN2CCCN=C12.COc1ccc(OC)c(...20.083383
4CC(C)C(C=C(C(C)C)C=C1C(C)C)=C1C2=C(P([C@@]3(C[...CC1=CC(C)=NO1CN1CCCN2C1=NCCC2ClC1=CC=C(OC)C=C1CN1CCCN2CCCN=C12.COc1ccc(Cl)cc1.COc1ccc(OC)c(P...0.492663
\n", + "
" + ], + "text/plain": [ + " ligand additive \\\n", + "0 CC(C)C(C=C(C(C)C)C=C1C(C)C)=C1C2=C(P([C@@]3(C[... CC1=CC(C)=NO1 \n", + "1 CC(C)C(C=C(C(C)C)C=C1C(C)C)=C1C2=C(P([C@@]3(C[... O=C(OC)C1=CC=NO1 \n", + "2 CC(C)C(C=C(C(C)C)C=C1C(C)C)=C1C2=C(P(C3CCCCC3)... O=C(OC)C1=CC=NO1 \n", + "3 CC(C)C(C=C(C(C)C)C=C1C(C)C)=C1C2=C(P(C(C)(C)C)... CCOC(C1=CON=C1)=O \n", + "4 CC(C)C(C=C(C(C)C)C=C1C(C)C)=C1C2=C(P([C@@]3(C[... CC1=CC(C)=NO1 \n", + "\n", + " base aryl_halide \\\n", + "0 CN(C)P(N(C)C)(N(C)C)=NP(N(C)C)(N(C)C)=NCC ClC1=NC=CC=C1 \n", + "1 CN(C)P(N(C)C)(N(C)C)=NP(N(C)C)(N(C)C)=NCC BrC1=NC=CC=C1 \n", + "2 CN(C)P(N(C)C)(N(C)C)=NP(N(C)C)(N(C)C)=NCC IC1=CC=C(CC)C=C1 \n", + "3 CN1CCCN2C1=NCCC2 ClC1=CC=C(C(F)(F)F)C=C1 \n", + "4 CN1CCCN2C1=NCCC2 ClC1=CC=C(OC)C=C1 \n", + "\n", + " reaction_SMILES yield \n", + "0 CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C.COc1... 70.410458 \n", + "1 Brc1ccccn1.CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C... 11.064457 \n", + "2 CC(C)c1cc(C(C)C)c(-c2ccccc2P(C2CCCCC2)C2CCCCC2... 10.223550 \n", + "3 CCOC(=O)c1cnoc1.CN1CCCN2CCCN=C12.COc1ccc(OC)c(... 20.083383 \n", + "4 CN1CCCN2CCCN=C12.COc1ccc(Cl)cc1.COc1ccc(OC)c(P... 0.492663 " + ] + }, + "execution_count": 68, + "metadata": {}, + "output_type": "execute_result" + } + ], + "source": [ + "df.head()" + ] + }, + { + "cell_type": "markdown", + "id": "f3d730ce-fce0-49df-9eb8-b917e945fa9a", + "metadata": {}, + "source": [ + "## Load from csv" + ] + }, + { + "cell_type": "code", + "execution_count": 69, + "id": "077b0c5f-8772-4879-9317-3fa28799689b", + "metadata": { + "tags": [] + }, + "outputs": [], + "source": [ + "fn_data_csv = \"data_clean.csv\"" + ] + }, + { + "cell_type": "code", + "execution_count": 70, + "id": "6eaef0e6-2115-4793-ac43-a196b25d47a0", + "metadata": { + "tags": [] + }, + "outputs": [], + "source": [ + "df = pd.read_csv(fn_data_csv)" + ] + }, + { + "cell_type": "code", + "execution_count": 71, + "id": "43619e7c-9c82-4ff0-ae25-403861304635", + "metadata": { + "tags": [] + }, + "outputs": [ + { + "data": { + "text/html": [ + "
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ligandadditivebasearyl_halidereaction_SMILESyield
0CC(C)C(C=C(C(C)C)C=C1C(C)C)=C1C2=C(P([C@@]3(C[...CC1=CC(C)=NO1CN(C)P(N(C)C)(N(C)C)=NP(N(C)C)(N(C)C)=NCCClC1=NC=CC=C1CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C.COc1...70.410458
1CC(C)C(C=C(C(C)C)C=C1C(C)C)=C1C2=C(P([C@@]3(C[...O=C(OC)C1=CC=NO1CN(C)P(N(C)C)(N(C)C)=NP(N(C)C)(N(C)C)=NCCBrC1=NC=CC=C1Brc1ccccn1.CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C...11.064457
2CC(C)C(C=C(C(C)C)C=C1C(C)C)=C1C2=C(P(C3CCCCC3)...O=C(OC)C1=CC=NO1CN(C)P(N(C)C)(N(C)C)=NP(N(C)C)(N(C)C)=NCCIC1=CC=C(CC)C=C1CC(C)c1cc(C(C)C)c(-c2ccccc2P(C2CCCCC2)C2CCCCC2...10.223550
3CC(C)C(C=C(C(C)C)C=C1C(C)C)=C1C2=C(P(C(C)(C)C)...CCOC(C1=CON=C1)=OCN1CCCN2C1=NCCC2ClC1=CC=C(C(F)(F)F)C=C1CCOC(=O)c1cnoc1.CN1CCCN2CCCN=C12.COc1ccc(OC)c(...20.083383
4CC(C)C(C=C(C(C)C)C=C1C(C)C)=C1C2=C(P([C@@]3(C[...CC1=CC(C)=NO1CN1CCCN2C1=NCCC2ClC1=CC=C(OC)C=C1CN1CCCN2CCCN=C12.COc1ccc(Cl)cc1.COc1ccc(OC)c(P...0.492663
\n", + "
" + ], + "text/plain": [ + " ligand additive \\\n", + "0 CC(C)C(C=C(C(C)C)C=C1C(C)C)=C1C2=C(P([C@@]3(C[... CC1=CC(C)=NO1 \n", + "1 CC(C)C(C=C(C(C)C)C=C1C(C)C)=C1C2=C(P([C@@]3(C[... O=C(OC)C1=CC=NO1 \n", + "2 CC(C)C(C=C(C(C)C)C=C1C(C)C)=C1C2=C(P(C3CCCCC3)... O=C(OC)C1=CC=NO1 \n", + "3 CC(C)C(C=C(C(C)C)C=C1C(C)C)=C1C2=C(P(C(C)(C)C)... CCOC(C1=CON=C1)=O \n", + "4 CC(C)C(C=C(C(C)C)C=C1C(C)C)=C1C2=C(P([C@@]3(C[... CC1=CC(C)=NO1 \n", + "\n", + " base aryl_halide \\\n", + "0 CN(C)P(N(C)C)(N(C)C)=NP(N(C)C)(N(C)C)=NCC ClC1=NC=CC=C1 \n", + "1 CN(C)P(N(C)C)(N(C)C)=NP(N(C)C)(N(C)C)=NCC BrC1=NC=CC=C1 \n", + "2 CN(C)P(N(C)C)(N(C)C)=NP(N(C)C)(N(C)C)=NCC IC1=CC=C(CC)C=C1 \n", + "3 CN1CCCN2C1=NCCC2 ClC1=CC=C(C(F)(F)F)C=C1 \n", + "4 CN1CCCN2C1=NCCC2 ClC1=CC=C(OC)C=C1 \n", + "\n", + " reaction_SMILES yield \n", + "0 CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C.COc1... 70.410458 \n", + "1 Brc1ccccn1.CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C... 11.064457 \n", + "2 CC(C)c1cc(C(C)C)c(-c2ccccc2P(C2CCCCC2)C2CCCCC2... 10.223550 \n", + "3 CCOC(=O)c1cnoc1.CN1CCCN2CCCN=C12.COc1ccc(OC)c(... 20.083383 \n", + "4 CN1CCCN2CCCN=C12.COc1ccc(Cl)cc1.COc1ccc(OC)c(P... 0.492663 " + ] + }, + "execution_count": 71, + "metadata": {}, + "output_type": "execute_result" + } + ], + "source": [ + "df.head()" + ] + }, + { + "cell_type": "markdown", + "id": "2f06e57c-02c5-493b-af65-c8bb9ac59421", + "metadata": {}, + "source": [ + "# meta YAML" + ] + }, + { + "cell_type": "code", + "execution_count": 72, + "id": "49771077-471d-4d71-a9a7-d6b094bbc4f3", + "metadata": { + "tags": [] + }, + "outputs": [ + { + "data": { + "text/html": [ + "
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ligandadditivebasearyl_halidereaction_SMILESyield
0CC(C)C(C=C(C(C)C)C=C1C(C)C)=C1C2=C(P([C@@]3(C[...CC1=CC(C)=NO1CN(C)P(N(C)C)(N(C)C)=NP(N(C)C)(N(C)C)=NCCClC1=NC=CC=C1CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C.COc1...70.410458
1CC(C)C(C=C(C(C)C)C=C1C(C)C)=C1C2=C(P([C@@]3(C[...O=C(OC)C1=CC=NO1CN(C)P(N(C)C)(N(C)C)=NP(N(C)C)(N(C)C)=NCCBrC1=NC=CC=C1Brc1ccccn1.CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C...11.064457
2CC(C)C(C=C(C(C)C)C=C1C(C)C)=C1C2=C(P(C3CCCCC3)...O=C(OC)C1=CC=NO1CN(C)P(N(C)C)(N(C)C)=NP(N(C)C)(N(C)C)=NCCIC1=CC=C(CC)C=C1CC(C)c1cc(C(C)C)c(-c2ccccc2P(C2CCCCC2)C2CCCCC2...10.223550
3CC(C)C(C=C(C(C)C)C=C1C(C)C)=C1C2=C(P(C(C)(C)C)...CCOC(C1=CON=C1)=OCN1CCCN2C1=NCCC2ClC1=CC=C(C(F)(F)F)C=C1CCOC(=O)c1cnoc1.CN1CCCN2CCCN=C12.COc1ccc(OC)c(...20.083383
4CC(C)C(C=C(C(C)C)C=C1C(C)C)=C1C2=C(P([C@@]3(C[...CC1=CC(C)=NO1CN1CCCN2C1=NCCC2ClC1=CC=C(OC)C=C1CN1CCCN2CCCN=C12.COc1ccc(Cl)cc1.COc1ccc(OC)c(P...0.492663
\n", + "
" + ], + "text/plain": [ + " ligand additive \\\n", + "0 CC(C)C(C=C(C(C)C)C=C1C(C)C)=C1C2=C(P([C@@]3(C[... CC1=CC(C)=NO1 \n", + "1 CC(C)C(C=C(C(C)C)C=C1C(C)C)=C1C2=C(P([C@@]3(C[... O=C(OC)C1=CC=NO1 \n", + "2 CC(C)C(C=C(C(C)C)C=C1C(C)C)=C1C2=C(P(C3CCCCC3)... O=C(OC)C1=CC=NO1 \n", + "3 CC(C)C(C=C(C(C)C)C=C1C(C)C)=C1C2=C(P(C(C)(C)C)... CCOC(C1=CON=C1)=O \n", + "4 CC(C)C(C=C(C(C)C)C=C1C(C)C)=C1C2=C(P([C@@]3(C[... CC1=CC(C)=NO1 \n", + "\n", + " base aryl_halide \\\n", + "0 CN(C)P(N(C)C)(N(C)C)=NP(N(C)C)(N(C)C)=NCC ClC1=NC=CC=C1 \n", + "1 CN(C)P(N(C)C)(N(C)C)=NP(N(C)C)(N(C)C)=NCC BrC1=NC=CC=C1 \n", + "2 CN(C)P(N(C)C)(N(C)C)=NP(N(C)C)(N(C)C)=NCC IC1=CC=C(CC)C=C1 \n", + "3 CN1CCCN2C1=NCCC2 ClC1=CC=C(C(F)(F)F)C=C1 \n", + "4 CN1CCCN2C1=NCCC2 ClC1=CC=C(OC)C=C1 \n", + "\n", + " reaction_SMILES yield \n", + "0 CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C.COc1... 70.410458 \n", + "1 Brc1ccccn1.CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C... 11.064457 \n", + "2 CC(C)c1cc(C(C)C)c(-c2ccccc2P(C2CCCCC2)C2CCCCC2... 10.223550 \n", + "3 CCOC(=O)c1cnoc1.CN1CCCN2CCCN=C12.COc1ccc(OC)c(... 20.083383 \n", + "4 CN1CCCN2CCCN=C12.COc1ccc(Cl)cc1.COc1ccc(OC)c(P... 0.492663 " + ] + }, + "execution_count": 72, + "metadata": {}, + "output_type": "execute_result" + } + ], + "source": [ + "df.head()" + ] + }, + { + "cell_type": "code", + "execution_count": 73, + "id": "d3890961-444e-4a26-b8fc-ed8c4e959af9", + "metadata": { + "tags": [] + }, + "outputs": [], + "source": [ + "meta = {\n", + " \"name\": \"buchwald_hartwig_doyle\", # unique identifier, we will also use this for directory names\n", + " \"description\": \"\"\"High-throughput experimentation palladium-catalyzed Buchwald Hardwig data set with yields.\"\"\",\n", + " \"targets\": [\n", + " {\n", + " \"id\": \"yield\", # name of the column in a tabular dataset\n", + " \"description\": \"Reaction yields analyzed by UPLC\", # description of what this column means\n", + " \"units\": \"%\", # units of the values in this column (leave empty if unitless)\n", + " \"type\": \"continuous\", # can be \"categorical\", \"ordinal\", \"continuous\"\n", + " \"names\": [ # names for the property (to sample from for building the prompts)\n", + " \"Reaction yield\",\n", + " \"yield\",\n", + " ],\n", + " },\n", + " ],\n", + " \"identifiers\": [\n", + " {\n", + " \"id\": \"reaction_SMILES\", # column name\n", + " \"type\": \"SMILES\", # can be \"SMILES\", \"SELFIES\", \"IUPAC\", \"Other\"\n", + " \"description\": \"SMILES\", # description (optional, except for \"Other\")\n", + " },\n", + " ],\n", + " \"license\": \"MIT license\", # license under which the original dataset was published\n", + " \"links\": [ # list of relevant links (original dataset, other uses, etc.)\n", + " {\n", + " \"url\": \"https://doi.org/10.1126/science.aar5169\",\n", + " \"description\": \"corresponding publication\",\n", + " },\n", + " {\n", + " \"url\": \"https://www.sciencedirect.com/science/article/pii/S2451929420300851\",\n", + " \"description\": \"publication with data processing\",\n", + " },\n", + " {\n", + " \"url\": \"https://github.com/rxn4chemistry/rxn_yields/blob/master/rxn_yields/data.py\",\n", + " \"description\": \"preprocessing\",\n", + " },\n", + " {\n", + " \"url\": \"https://github.com/reymond-group/drfp/tree/main/data\",\n", + " \"description\": \"dataset\",\n", + " }\n", + " ],\n", + " \"num_points\": len(df), # number of datapoints in this dataset\n", + " \"url\": \"https://tdcommons.ai/single_pred_tasks/tox/#acute-toxicity-ld50\",\n", + " \"bibtex\": [\n", + " \"\"\"@article{ahneman2018predicting,\n", + " title={Predicting reaction performance in C--N cross-coupling using machine learning},\n", + " author={Ahneman, Derek T and Estrada, Jes{\\'u}s G and Lin, Shishi and Dreher, Spencer D and Doyle, Abigail G},\n", + " journal={Science},\n", + " volume={360},\n", + " number={6385},\n", + " pages={186--190},\n", + " year={2018},\n", + " publisher={American Association for the Advancement of Science}\n", + "}\n", + "}\"\"\",\n", + " ],\n", + "}" + ] + }, + { + "cell_type": "code", + "execution_count": 74, + "id": "ec455cf0-962a-4c0d-bb3e-066e415ffd9b", + "metadata": { + "tags": [] + }, + "outputs": [], + "source": [ + "def str_presenter(dumper, data):\n", + " \"\"\"configures yaml for dumping multiline strings\n", + " Ref: https://stackoverflow.com/questions/8640959/how-can-i-control-what-scalar-form-pyyaml-uses-for-my-data\n", + " \"\"\"\n", + " if data.count(\"\\n\") > 0: # check for multiline string\n", + " return dumper.represent_scalar(\"tag:yaml.org,2002:str\", data, style=\"|\")\n", + " return dumper.represent_scalar(\"tag:yaml.org,2002:str\", data)\n", + "\n", + "\n", + "yaml.add_representer(str, str_presenter)\n", + "yaml.representer.SafeRepresenter.add_representer(\n", + " str, str_presenter\n", + ") # to use with safe_dum" + ] + }, + { + "cell_type": "code", + "execution_count": 75, + "id": "580bbd79-4845-4515-be94-3e4a9815d048", + "metadata": { + "tags": [] + }, + "outputs": [], + "source": [ + "fn_meta = \"meta.yaml\"" + ] + }, + { + "cell_type": "code", + "execution_count": 76, + "id": "873fa5dd-9b60-40f5-b537-4d7a206414ea", + "metadata": { + "tags": [] + }, + "outputs": [], + "source": [ + "with open(fn_meta, \"w\") as f:\n", + " yaml.dump(meta, f, sort_keys=False)" + ] + }, + { + "cell_type": "code", + "execution_count": 77, + "id": "d01686c0-6746-4fc4-b019-350270dfc26f", + "metadata": { + "tags": [] + }, + "outputs": [ + { + "name": "stdout", + "output_type": "stream", + "text": [ + "-rw-r--r-- 1 pschwllr staff 975B Mar 8 23:36 meta.yaml\n" + ] + } + ], + "source": [ + "!ls -lh {fn_meta}" + ] + }, + { + "cell_type": "code", + "execution_count": 78, + "id": "ef6063c5-7a8b-4344-bccf-a073443feebf", + "metadata": { + "tags": [] + }, + "outputs": [ + { + "name": "stdout", + "output_type": "stream", + "text": [ + "name: buchwald_hartwig_doyle\n", + "description: High-throughput experimentation palladium-catalyzed Buchwald Hardwig\n", + " data set with yields.\n", + "targets:\n", + "- id: yield\n", + " description: Reaction yields analyzed by UPLC\n", + " units: '%'\n", + " type: continuous\n", + " names:\n", + " - Reaction yield\n", + " - yield\n", + "identifiers:\n", + "- id: reaction_SMILES\n", + " type: SMILES\n", + " description: SMILES\n", + "license: MIT license\n", + "links:\n", + "- url: https://doi.org/10.1126/science.aar5169\n", + " description: corresponding publication\n", + "num_points: 3955\n", + "url: https://tdcommons.ai/single_pred_tasks/tox/#acute-toxicity-ld50\n", + "bibtex:\n", + "- |-\n", + " @article{ahneman2018predicting,\n", + " title={Predicting reaction performance in C--N cross-coupling using machine learning},\n", + " author={Ahneman, Derek T and Estrada, Jes{'u}s G and Lin, Shishi and Dreher, Spencer D and Doyle, Abigail G},\n", + " journal={Science},\n", + " volume={360},\n", + " number={6385},\n", + " pages={186--190},\n", + " year={2018},\n", + " publisher={American Association for the Advancement of Science}\n", + " }\n", + " }\n" + ] + } + ], + "source": [ + "!cat {fn_meta}" + ] + }, + { + "cell_type": "markdown", + "id": "bd3f930a-638b-4bb7-a1d2-80688f2f6891", + "metadata": {}, + "source": [ + "# create transform.py" + ] + }, + { + "cell_type": "code", + "execution_count": 32, + "id": "9aab00fd-58a8-40b0-be30-1e269e0d323b", + "metadata": { + "tags": [] + }, + "outputs": [], + "source": [ + "path_file = \"transform.py\"" + ] + }, + { + "cell_type": "code", + "execution_count": 33, + "id": "8368bb20-8e1c-4b7d-b0e2-b39da36b5972", + "metadata": { + "tags": [] + }, + "outputs": [ + { + "name": "stdout", + "output_type": "stream", + "text": [ + "Overwriting transform.py\n" + ] + } + ], + "source": [ + "%%writefile $path_file\n", + "import pandas as pd\n", + "import yaml\n", + "from tdc.single_pred import Tox\n", + "\n", + "\n", + "def get_and_transform_data():\n", + " # get raw data\n", + " data = Tox(name = 'LD50_Zhu')\n", + " fn_data_original = \"data_original.csv\"\n", + " data.get_data().to_csv(fn_data_original, index=False)\n", + "\n", + " # create dataframe\n", + " df = pd.read_csv(\n", + " fn_data_original,\n", + " delimiter=\",\",\n", + " ) # not necessary but ensure we can load the saved data\n", + "\n", + " # check if fields are the same\n", + " fields_orig = df.columns.tolist()\n", + " assert fields_orig == [\n", + " \"Drug_ID\",\n", + " \"Drug\",\n", + " \"Y\",\n", + " ]\n", + "\n", + " # overwrite column names = fields\n", + " fields_clean = [\n", + " \"compound_name\",\n", + " \"SMILES\",\n", + " \"acute_toxicity\",\n", + " ]\n", + " df.columns = fields_clean\n", + "\n", + " # data cleaning\n", + " df.compound_name = (\n", + " df.compound_name.str.strip()\n", + " ) # remove leading and trailing white space characters\n", + "\n", + " assert not df.duplicated().sum()\n", + "\n", + " # save to csv\n", + " fn_data_csv = \"data_clean.csv\"\n", + " df.to_csv(fn_data_csv, index=False)\n", + "\n", + " # create meta yaml\n", + " meta = {\n", + " \"name\": \"ld50_zhu\", # unique identifier, we will also use this for directory names\n", + " \"description\": \"\"\"Acute toxicity LD50 measures the most conservative dose that can lead to lethal adverse effects. The higher the dose, the more lethal of a drug.\"\"\",\n", + " \"targets\": [\n", + " {\n", + " \"id\": \"acute_toxicity\", # name of the column in a tabular dataset\n", + " \"description\": \"Acute Toxicity LD50.\", # description of what this column means\n", + " \"units\": \"ld50\", # units of the values in this column (leave empty if unitless)\n", + " \"type\": \"continuous\", # can be \"categorical\", \"ordinal\", \"continuous\"\n", + " \"names\": [ # names for the property (to sample from for building the prompts)\n", + " \"Acute Toxicity LD50\",\n", + " \"ld50\",\n", + " \"conservative dose that can lead to lethal adverse effects.\",\n", + " \"Rat Acute Toxicity by Oral Exposure\",\n", + " \"Toxicity\",\n", + " ],\n", + " },\n", + " ],\n", + " \"identifiers\": [\n", + " {\n", + " \"id\": \"SMILES\", # column name\n", + " \"type\": \"SMILES\", # can be \"SMILES\", \"SELFIES\", \"IUPAC\", \"Other\"\n", + " \"description\": \"SMILES\", # description (optional, except for \"Other\")\n", + " },\n", + " {\n", + " \"id\": \"compound_name\",\n", + " \"type\": \"Synonyms\",\n", + " \"description\": \"compound name\",\n", + " \"names\": [\n", + " \"compound\",\n", + " \"compound name\",\n", + " \"drug\",\n", + " ],\n", + " },\n", + " ],\n", + " \"license\": \"CC BY 4.0\", # license under which the original dataset was published\n", + " \"links\": [ # list of relevant links (original dataset, other uses, etc.)\n", + " {\n", + " \"url\": \"https://doi.org/10.1021/tx900189p\",\n", + " \"description\": \"corresponding publication\",\n", + " },\n", + " ],\n", + " \"num_points\": len(df), # number of datapoints in this dataset\n", + " \"url\": \"https://tdcommons.ai/single_pred_tasks/tox/#acute-toxicity-ld50\",\n", + " \"bibtex\": [\n", + " \"\"\"@article{Zhu2009,\n", + " doi = {10.1021/tx900189p},\n", + " url = {https://doi.org/10.1021/tx900189p},\n", + " year = {2009},\n", + " month = oct,\n", + " publisher = {American Chemical Society ({ACS})},\n", + " volume = {22},\n", + " number = {12},\n", + " pages = {1913--1921},\n", + " author = {Hao Zhu and Todd M. Martin and Lin Ye and Alexander Sedykh and Douglas M. Young and Alexander Tropsha},\n", + " title = {Quantitative Structure-Activity Relationship Modeling of Rat Acute Toxicity by Oral Exposure},\n", + " journal = {Chemical Research in Toxicology}}\"\"\",\n", + " ],\n", + " }\n", + "\n", + " def str_presenter(dumper, data):\n", + " \"\"\"configures yaml for dumping multiline strings\n", + " Ref: https://stackoverflow.com/questions/8640959/how-can-i-control-what-scalar-form-pyyaml-uses-for-my-data\n", + " \"\"\"\n", + " if data.count(\"\\n\") > 0: # check for multiline string\n", + " return dumper.represent_scalar(\"tag:yaml.org,2002:str\", data, style=\"|\")\n", + " return dumper.represent_scalar(\"tag:yaml.org,2002:str\", data)\n", + "\n", + " yaml.add_representer(str, str_presenter)\n", + " yaml.representer.SafeRepresenter.add_representer(\n", + " str, str_presenter\n", + " ) # to use with safe_dum\n", + " fn_meta = \"meta.yaml\"\n", + " with open(fn_meta, \"w\") as f:\n", + " yaml.dump(meta, f, sort_keys=False)\n", + "\n", + " print(f\"Finished processing {meta['name']} dataset!\")\n", + "\n", + "\n", + "if __name__ == \"__main__\":\n", + " get_and_transform_data()" + ] + }, + { + "cell_type": "code", + "execution_count": 34, + "id": "d0474f26-70f3-4655-b81a-df4ada90e7a6", + "metadata": { + "tags": [] + }, + "outputs": [ + { + "name": "stdout", + "output_type": "stream", + "text": [ + "Found local copy...\n", + "Loading...\n", + "Done!\n", + "Finished processing ld50_zhu dataset!\n" + ] + } + ], + "source": [ + "!python3 transform.py" + ] + }, + { + "cell_type": "code", + "execution_count": 35, + "id": "953e7bee-bd5e-41d0-a2be-506e0bc97727", + "metadata": { + "tags": [] + }, + "outputs": [ + { + "name": "stdout", + "output_type": "stream", + "text": [ + "total 1.4M\r\n", + "drwxrwxr-x 2 melo melo 4.0K مار 2 16:58 \u001b[0m\u001b[01;34mdata\u001b[0m/\r\n", + "-rw-rw-r-- 1 melo melo 661K مار 2 16:58 data_clean.csv\r\n", + "-rw-rw-r-- 1 melo melo 661K مار 2 16:58 data_original.csv\r\n", + "-rw-rw-r-- 1 melo melo 39K مار 1 22:23 example_processing_and_templates.ipynb\r\n", + "-rw-rw-r-- 1 melo melo 1.5K مار 2 16:58 meta.yaml\r\n", + "-rw-rw-r-- 1 melo melo 4.8K مار 2 16:58 transform.py\r\n" + ] + } + ], + "source": [ + "ls -lh # fmt: skip" + ] + }, + { + "cell_type": "markdown", + "id": "0b08ed06-ba66-4f76-bde1-368ea77d1739", + "metadata": {}, + "source": [ + "# End" + ] + } + ], + "metadata": { + "kernelspec": { + "display_name": "Python 3 (ipykernel)", + "language": "python", + "name": "python3" + }, + "language_info": { + "codemirror_mode": { + "name": "ipython", + "version": 3 + }, + "file_extension": ".py", + "mimetype": "text/x-python", + "name": "python", + "nbconvert_exporter": "python", + "pygments_lexer": "ipython3", + "version": "3.8.16" + } + }, + "nbformat": 4, + "nbformat_minor": 5 +} diff --git a/data/buchwald_hartwig/meta.yaml b/data/buchwald_hartwig/meta.yaml new file mode 100644 index 000000000..fc22ac55d --- /dev/null +++ b/data/buchwald_hartwig/meta.yaml @@ -0,0 +1,40 @@ +name: buchwald_hartwig_doyle +description: High-throughput experimentation palladium-catalyzed Buchwald Hardwig + data set with yields. +targets: +- id: yield + description: Reaction yields analyzed by UPLC + units: '%' + type: continuous + names: + - Reaction yield + - yield +identifiers: +- id: reaction_SMILES + type: SMILES + description: SMILES +license: MIT license +links: +- url: https://doi.org/10.1126/science.aar5169 + description: corresponding publication +- url: https://www.sciencedirect.com/science/article/pii/S2451929420300851 + description: publication with data in compressed format +- url: https://github.com/rxn4chemistry/rxn_yields/blob/master/rxn_yields/data.py + description: preprocessing +- url: https://github.com/reymond-group/drfp/tree/main/data + description: dataset +num_points: 3955 +url: https://tdcommons.ai/single_pred_tasks/tox/#acute-toxicity-ld50 +bibtex: +- |- + @article{ahneman2018predicting, + title={Predicting reaction performance in C--N cross-coupling using machine learning}, + author={Ahneman, Derek T and Estrada, Jes{'u}s G and Lin, Shishi and Dreher, Spencer D and Doyle, Abigail G}, + journal={Science}, + volume={360}, + number={6385}, + pages={186--190}, + year={2018}, + publisher={American Association for the Advancement of Science} + } + } diff --git a/data/buchwald_hartwig/transform.py b/data/buchwald_hartwig/transform.py new file mode 100644 index 000000000..ff51ef84a --- /dev/null +++ b/data/buchwald_hartwig/transform.py @@ -0,0 +1,162 @@ +import pandas as pd +import yaml +from rdkit import Chem # 2022.9.5 +from rdkit.Chem import rdChemReactions + +def generate_buchwald_hartwig_rxns(df): + """ + Converts the entries in the excel files to reaction SMILES. + From: https://github.com/reymond-group/drfp/blob/main/scripts/encoding/encode_buchwald_hartwig_reactions.py + and https://github.com/rxn4chemistry/rxn_yields/blob/master/rxn_yields/data.py + """ + df = df.copy() + fwd_template = "[F,Cl,Br,I]-[c;H0;D3;+0:1](:[c,n:2]):[c,n:3].[NH2;D1;+0:4]-[c:5]>>[c,n:2]:[c;H0;D3;+0:1](:[c,n:3])-[NH;D2;+0:4]-[c:5]" + methylaniline = "Cc1ccc(N)cc1" + pd_catalyst = "O=S(=O)(O[Pd]1~[NH2]C2C=CC=CC=2C2C=CC=CC1=2)C(F)(F)F" + methylaniline_mol = Chem.MolFromSmiles(methylaniline) + rxn = rdChemReactions.ReactionFromSmarts(fwd_template) + products = [] + + for i, row in df.iterrows(): + reacts = (Chem.MolFromSmiles(row["aryl_halide"]), methylaniline_mol) + rxn_products = rxn.RunReactants(reacts) + + rxn_products_smiles = set([Chem.MolToSmiles(mol[0]) for mol in rxn_products]) + assert len(rxn_products_smiles) == 1 + products.append(list(rxn_products_smiles)[0]) + + df["product"] = products + rxns = [] + + for i, row in df.iterrows(): + reactants = Chem.MolToSmiles( + Chem.MolFromSmiles( + f"{row['aryl_halide']}.{methylaniline}.{pd_catalyst}.{row['ligand']}.{row['base']}.{row['additive']}" + ) + ) + rxns.append(f"{reactants.replace('N~', '[NH2]')}>>{row['product']}") + + return rxns + +def get_and_transform_data(): + # get raw data + fn_data_original = "Dreher_and_Doyle_input_data.csv" + data = pd.read_excel('https://github.com/reymond-group/drfp/raw/main/data/Dreher_and_Doyle_input_data.xlsx') + data.to_csv(fn_data_original, index=False) + + # create dataframe + df = pd.read_csv( + fn_data_original, + delimiter=",", + ) # not necessary but ensure we can load the saved data + + # check if fields are the same + fields_orig = df.columns.tolist() + assert fields_orig == [ + 'Ligand', + 'Additive', + 'Base', + 'Aryl halide', + 'Output' + ] + + # overwrite column names = fields + fields_clean = [ + "ligand", + "additive", + "base", + "aryl_halide", + 'yield' + ] + df.columns = fields_clean + + # data cleaning + reaction_SMILES = generate_buchwald_hartwig_rxns(df) # compile reactions + df.insert(4, 'reaction_SMILES', reaction_SMILES) # add reaction SMILES column + + assert not df.duplicated().sum() + + # save to csv + fn_data_csv = "data_clean.csv" + df.to_csv(fn_data_csv, index=False) + + # create meta yaml + meta = { + "name": "buchwald_hartwig_doyle", # unique identifier, we will also use this for directory names + "description": """High-throughput experimentation palladium-catalyzed Buchwald Hardwig data set with yields.""", + "targets": [ + { + "id": "yield", # name of the column in a tabular dataset + "description": "Reaction yields analyzed by UPLC", # description of what this column means + "units": "%", # units of the values in this column (leave empty if unitless) + "type": "continuous", # can be "categorical", "ordinal", "continuous" + "names": [ # names for the property (to sample from for building the prompts) + "Reaction yield", + "yield", + ], + }, + ], + "identifiers": [ + { + "id": "reaction_SMILES", # column name + "type": "SMILES", # can be "SMILES", "SELFIES", "IUPAC", "Other" + "description": "SMILES", # description (optional, except for "Other") + }, + ], + "license": "MIT license", # license under which the original dataset was published + "links": [ # list of relevant links (original dataset, other uses, etc.) + { + "url": "https://doi.org/10.1126/science.aar5169", + "description": "corresponding publication", + }, + { + "url": "https://www.sciencedirect.com/science/article/pii/S2451929420300851", + "description": "publication with data in compressed format", + }, + { + "url": "https://github.com/rxn4chemistry/rxn_yields/blob/master/rxn_yields/data.py", + "description": "preprocessing", + }, + { + "url": "https://github.com/reymond-group/drfp/tree/main/data", + "description": "dataset", + } + ], + "num_points": len(df), # number of datapoints in this dataset + "url": "https://tdcommons.ai/single_pred_tasks/tox/#acute-toxicity-ld50", + "bibtex": [ + """@article{ahneman2018predicting, + title={Predicting reaction performance in C--N cross-coupling using machine learning}, + author={Ahneman, Derek T and Estrada, Jes{\'u}s G and Lin, Shishi and Dreher, Spencer D and Doyle, Abigail G}, + journal={Science}, + volume={360}, + number={6385}, + pages={186--190}, + year={2018}, + publisher={American Association for the Advancement of Science} + } + }""", + ], + } + + def str_presenter(dumper, data): + """configures yaml for dumping multiline strings + Ref: https://stackoverflow.com/questions/8640959/how-can-i-control-what-scalar-form-pyyaml-uses-for-my-data + """ + if data.count("\n") > 0: # check for multiline string + return dumper.represent_scalar("tag:yaml.org,2002:str", data, style="|") + return dumper.represent_scalar("tag:yaml.org,2002:str", data) + + yaml.add_representer(str, str_presenter) + yaml.representer.SafeRepresenter.add_representer( + str, str_presenter + ) # to use with safe_dum + fn_meta = "meta.yaml" + with open(fn_meta, "w") as f: + yaml.dump(meta, f, sort_keys=False) + + print(f"Finished processing {meta['name']} dataset!") + + +if __name__ == "__main__": + get_and_transform_data() From 1574d116981194cad8ae7be7d671dac9df375f2e Mon Sep 17 00:00:00 2001 From: Philippe Schwaller Date: Wed, 8 Mar 2023 23:50:33 +0100 Subject: [PATCH 2/4] removing data files --- .../Dreher_and_Doyle_input_data.csv | 3956 ----------------- data/buchwald_hartwig/data_clean.csv | 3956 ----------------- 2 files changed, 7912 deletions(-) delete mode 100644 data/buchwald_hartwig/Dreher_and_Doyle_input_data.csv delete mode 100644 data/buchwald_hartwig/data_clean.csv diff --git a/data/buchwald_hartwig/Dreher_and_Doyle_input_data.csv b/data/buchwald_hartwig/Dreher_and_Doyle_input_data.csv deleted file mode 100644 index 13e5f6bf4..000000000 --- a/data/buchwald_hartwig/Dreher_and_Doyle_input_data.csv +++ /dev/null @@ -1,3956 +0,0 @@ -Ligand,Additive,Base,Aryl halide,Output -CC(C)C(C=C(C(C)C)C=C1C(C)C)=C1C2=C(P([C@@]3(C[C@@H]4C5)C[C@H](C4)C[C@H]5C3)[C@]6(C7)C[C@@H](C[C@@H]7C8)C[C@@H]8C6)C(OC)=CC=C2OC,CC1=CC(C)=NO1,CN(C)P(N(C)C)(N(C)C)=NP(N(C)C)(N(C)C)=NCC,ClC1=NC=CC=C1,70.41045785 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-CC(C)C(C=C(C(C)C)C=C1C(C)C)=C1C2=C(P(C(C)(C)C)C(C)(C)C)C=CC=C2,CC1=NOC=C1,CN(C)P(N(C)C)(N(C)C)=NP(N(C)C)(N(C)C)=NCC,IC1=CN=CC=C1,CC(C)c1cc(C(C)C)c(-c2ccccc2P(C(C)(C)C)C(C)(C)C)c(C(C)C)c1.CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C.Cc1ccc(N)cc1.Cc1ccon1.Ic1cccnc1.O=S(=O)(O[Pd]1c2ccccc2-c2ccccc2[NH2]1)C(F)(F)F>>Cc1ccc(Nc2cccnc2)cc1,0.0 -CC(C)C(C=C(C(C)C)C=C1C(C)C)=C1C2=C(P(C(C)(C)C)C(C)(C)C)C=CC=C2,O=C(OC)C1=NOC(C2=CC=CS2)=C1,CN(C)P(N(C)C)(N(C)C)=NP(N(C)C)(N(C)C)=NCC,ClC1=CC=C(C(F)(F)F)C=C1,CC(C)c1cc(C(C)C)c(-c2ccccc2P(C(C)(C)C)C(C)(C)C)c(C(C)C)c1.CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C.COC(=O)c1cc(-c2cccs2)on1.Cc1ccc(N)cc1.FC(F)(F)c1ccc(Cl)cc1.O=S(=O)(O[Pd]1c2ccccc2-c2ccccc2[NH2]1)C(F)(F)F>>Cc1ccc(Nc2ccc(C(F)(F)F)cc2)cc1,15.75654156 -CC(C)C(C=C(C(C)C)C=C1C(C)C)=C1C2=C(P(C(C)(C)C)C(C)(C)C)C=CC=C2,CCOC(C1=NOC=C1)=O,CN1CCCN2C1=NCCC2,BrC1=CN=CC=C1,Brc1cccnc1.CC(C)c1cc(C(C)C)c(-c2ccccc2P(C(C)(C)C)C(C)(C)C)c(C(C)C)c1.CCOC(=O)c1ccon1.CN1CCCN2CCCN=C12.Cc1ccc(N)cc1.O=S(=O)(O[Pd]1c2ccccc2-c2ccccc2[NH2]1)C(F)(F)F>>Cc1ccc(Nc2cccnc2)cc1,85.8122803 -CC(C)C(C=C(C(C)C)C=C1C(C)C)=C1C2=C(P(C(C)(C)C)C(C)(C)C)C(OC)=CC=C2OC,CC1=CC(C(OCC)=O)=NO1,CN1CCCN2C1=NCCC2,ClC1=CN=CC=C1,CCOC(=O)c1cc(C)on1.CN1CCCN2CCCN=C12.COc1ccc(OC)c(P(C(C)(C)C)C(C)(C)C)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C.Cc1ccc(N)cc1.Clc1cccnc1.O=S(=O)(O[Pd]1c2ccccc2-c2ccccc2[NH2]1)C(F)(F)F>>Cc1ccc(Nc2cccnc2)cc1,23.84150703 -CC(C)C(C=C(C(C)C)C=C1C(C)C)=C1C2=C(P(C3CCCCC3)C4CCCCC4)C=CC=C2,C1(C2=CC=CC=C2)=CON=C1,CN(C)P(N(C)C)(N(C)C)=NP(N(C)C)(N(C)C)=NCC,BrC1=CC=C(OC)C=C1,CC(C)c1cc(C(C)C)c(-c2ccccc2P(C2CCCCC2)C2CCCCC2)c(C(C)C)c1.CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C.COc1ccc(Br)cc1.Cc1ccc(N)cc1.O=S(=O)(O[Pd]1c2ccccc2-c2ccccc2[NH2]1)C(F)(F)F.c1ccc(-c2cnoc2)cc1>>COc1ccc(Nc2ccc(C)cc2)cc1,4.344676685 -CC(C)C(C=C(C(C)C)C=C1C(C)C)=C1C2=C(P(C(C)(C)C)C(C)(C)C)C(OC)=CC=C2OC,CC1=CC(N2C=CC=C2)=NO1,CN1CCCN2C1=NCCC2,BrC1=CC=C(OC)C=C1,CN1CCCN2CCCN=C12.COc1ccc(Br)cc1.COc1ccc(OC)c(P(C(C)(C)C)C(C)(C)C)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C.Cc1cc(-n2cccc2)no1.Cc1ccc(N)cc1.O=S(=O)(O[Pd]1c2ccccc2-c2ccccc2[NH2]1)C(F)(F)F>>COc1ccc(Nc2ccc(C)cc2)cc1,47.15627467 -CC(C)C(C=C(C(C)C)C=C1C(C)C)=C1C2=C(P(C(C)(C)C)C(C)(C)C)C(OC)=CC=C2OC,CCOC(C1=CON=C1)=O,CC(C)(C)/N=C(N(C)C)/N(C)C,ClC1=CC=C(C(F)(F)F)C=C1,CCOC(=O)c1cnoc1.CN(C)C(=NC(C)(C)C)N(C)C.COc1ccc(OC)c(P(C(C)(C)C)C(C)(C)C)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C.Cc1ccc(N)cc1.FC(F)(F)c1ccc(Cl)cc1.O=S(=O)(O[Pd]1c2ccccc2-c2ccccc2[NH2]1)C(F)(F)F>>Cc1ccc(Nc2ccc(C(F)(F)F)cc2)cc1,0.701552228 -CC(C)C(C=C(C(C)C)C=C1C(C)C)=C1C2=C(P([C@@]3(C[C@@H]4C5)C[C@H](C4)C[C@H]5C3)[C@]6(C7)C[C@@H](C[C@@H]7C8)C[C@@H]8C6)C(OC)=CC=C2OC,C1(N(CC2=CC=CC=C2)CC3=CC=CC=C3)=CC=NO1,CN(C)P(N(C)C)(N(C)C)=NP(N(C)C)(N(C)C)=NCC,ClC1=CC=C(C(F)(F)F)C=C1,CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C.COc1ccc(OC)c(P([C@]23C[C@H]4C[C@H](C[C@H](C4)C2)C3)[C@]23C[C@H]4C[C@H](C[C@H](C4)C2)C3)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C.Cc1ccc(N)cc1.FC(F)(F)c1ccc(Cl)cc1.O=S(=O)(O[Pd]1c2ccccc2-c2ccccc2[NH2]1)C(F)(F)F.c1ccc(CN(Cc2ccccc2)c2ccno2)cc1>>Cc1ccc(Nc2ccc(C(F)(F)F)cc2)cc1,15.5615648 -CC(C)C(C=C(C(C)C)C=C1C(C)C)=C1C2=C(P([C@@]3(C[C@@H]4C5)C[C@H](C4)C[C@H]5C3)[C@]6(C7)C[C@@H](C[C@@H]7C8)C[C@@H]8C6)C(OC)=CC=C2OC,C1(C2=CC=CC=C2)=CC=NO1,CC(C)(C)/N=C(N(C)C)/N(C)C,IC1=CC=C(CC)C=C1,CCc1ccc(I)cc1.CN(C)C(=NC(C)(C)C)N(C)C.COc1ccc(OC)c(P([C@]23C[C@H]4C[C@H](C[C@H](C4)C2)C3)[C@]23C[C@H]4C[C@H](C[C@H](C4)C2)C3)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C.Cc1ccc(N)cc1.O=S(=O)(O[Pd]1c2ccccc2-c2ccccc2[NH2]1)C(F)(F)F.c1ccc(-c2ccno2)cc1>>CCc1ccc(Nc2ccc(C)cc2)cc1,73.73993868 From 78e716780b601be7577ee1d710aff75e4b2dc460 Mon Sep 17 00:00:00 2001 From: Philippe Schwaller Date: Sun, 7 May 2023 00:23:01 +0200 Subject: [PATCH 3/4] License specification and reaction/reagents identifiers --- .../example_processing_and_templates.ipynb | 981 ++++-------------- data/buchwald_hartwig/meta.yaml | 41 +- data/buchwald_hartwig/transform.py | 123 ++- 3 files changed, 295 insertions(+), 850 deletions(-) diff --git a/data/buchwald_hartwig/example_processing_and_templates.ipynb b/data/buchwald_hartwig/example_processing_and_templates.ipynb index 6c446ef65..fd7cf27fc 100644 --- a/data/buchwald_hartwig/example_processing_and_templates.ipynb +++ b/data/buchwald_hartwig/example_processing_and_templates.ipynb @@ -30,7 +30,7 @@ }, { "cell_type": "code", - "execution_count": 21, + "execution_count": null, "id": "cf59e3e9-8061-4022-9eae-e978311b4155", "metadata": { "tags": [] @@ -61,7 +61,7 @@ }, { "cell_type": "code", - "execution_count": 7, + "execution_count": null, "id": "7bb8eb5e-f513-40d2-a68c-7cda1a51ad31", "metadata": { "tags": [] @@ -73,7 +73,7 @@ }, { "cell_type": "code", - "execution_count": 8, + "execution_count": null, "id": "b39a142e-ccbc-49d2-98b0-a5f9bde9fd27", "metadata": { "tags": [] @@ -85,7 +85,7 @@ }, { "cell_type": "code", - "execution_count": 9, + "execution_count": null, "id": "26d9f62a-07f5-4113-8161-d5dfcf0bfb71", "metadata": { "tags": [] @@ -97,24 +97,12 @@ }, { "cell_type": "code", - "execution_count": 10, + "execution_count": null, "id": "43873fc3-20a8-487d-a7c5-33bd58414159", "metadata": { "tags": [] }, - "outputs": [ - { - "name": "stdout", - "output_type": "stream", - "text": [ - "total 1344\n", - "-rw-r--r-- 1 pschwllr staff 618K Mar 8 22:34 Dreher_and_Doyle_input_data.csv\n", - "-rw-r--r-- 1 pschwllr staff 38K Mar 8 22:13 example_processing_and_templates.ipynb\n", - "-rw-r--r-- 1 pschwllr staff 1.6K Mar 8 22:13 meta.yaml\n", - "-rw-r--r-- 1 pschwllr staff 4.5K Mar 8 22:13 transform.py\n" - ] - } - ], + "outputs": [], "source": [ "!ls -lh" ] @@ -129,31 +117,19 @@ }, { "cell_type": "code", - "execution_count": 11, + "execution_count": null, "id": "77f614e7-b133-40bc-8759-2d930e4c120e", "metadata": { "tags": [] }, - "outputs": [ - { - "name": "stdout", - "output_type": "stream", - "text": [ - "Ligand,Additive,Base,Aryl halide,Output\n", - "CC(C)C(C=C(C(C)C)C=C1C(C)C)=C1C2=C(P([C@@]3(C[C@@H]4C5)C[C@H](C4)C[C@H]5C3)[C@]6(C7)C[C@@H](C[C@@H]7C8)C[C@@H]8C6)C(OC)=CC=C2OC,CC1=CC(C)=NO1,CN(C)P(N(C)C)(N(C)C)=NP(N(C)C)(N(C)C)=NCC,ClC1=NC=CC=C1,70.41045785\n", - "CC(C)C(C=C(C(C)C)C=C1C(C)C)=C1C2=C(P([C@@]3(C[C@@H]4C5)C[C@H](C4)C[C@H]5C3)[C@]6(C7)C[C@@H](C[C@@H]7C8)C[C@@H]8C6)C(OC)=CC=C2OC,O=C(OC)C1=CC=NO1,CN(C)P(N(C)C)(N(C)C)=NP(N(C)C)(N(C)C)=NCC,BrC1=NC=CC=C1,11.06445724\n", - "CC(C)C(C=C(C(C)C)C=C1C(C)C)=C1C2=C(P(C3CCCCC3)C4CCCCC4)C=CC=C2,O=C(OC)C1=CC=NO1,CN(C)P(N(C)C)(N(C)C)=NP(N(C)C)(N(C)C)=NCC,IC1=CC=C(CC)C=C1,10.22354965\n", - "CC(C)C(C=C(C(C)C)C=C1C(C)C)=C1C2=C(P(C(C)(C)C)C(C)(C)C)C(OC)=CC=C2OC,CCOC(C1=CON=C1)=O,CN1CCCN2C1=NCCC2,ClC1=CC=C(C(F)(F)F)C=C1,20.0833829\n" - ] - } - ], + "outputs": [], "source": [ "!head -n 5 {fn_data_original}" ] }, { "cell_type": "code", - "execution_count": 50, + "execution_count": null, "id": "8f5a0387-f9e3-4e1a-8d14-5df618195f70", "metadata": { "tags": [] @@ -165,114 +141,13 @@ }, { "cell_type": "code", - "execution_count": 51, + "execution_count": null, "id": "55b0bd63-62a0-469e-9d8a-e9ada3fe01c4", "metadata": { "scrolled": true, "tags": [] }, - "outputs": [ - { - "data": { - "text/html": [ - "
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LigandAdditiveBaseAryl halideOutput
0CC(C)C(C=C(C(C)C)C=C1C(C)C)=C1C2=C(P([C@@]3(C[...CC1=CC(C)=NO1CN(C)P(N(C)C)(N(C)C)=NP(N(C)C)(N(C)C)=NCCClC1=NC=CC=C170.410458
1CC(C)C(C=C(C(C)C)C=C1C(C)C)=C1C2=C(P([C@@]3(C[...O=C(OC)C1=CC=NO1CN(C)P(N(C)C)(N(C)C)=NP(N(C)C)(N(C)C)=NCCBrC1=NC=CC=C111.064457
2CC(C)C(C=C(C(C)C)C=C1C(C)C)=C1C2=C(P(C3CCCCC3)...O=C(OC)C1=CC=NO1CN(C)P(N(C)C)(N(C)C)=NP(N(C)C)(N(C)C)=NCCIC1=CC=C(CC)C=C110.223550
3CC(C)C(C=C(C(C)C)C=C1C(C)C)=C1C2=C(P(C(C)(C)C)...CCOC(C1=CON=C1)=OCN1CCCN2C1=NCCC2ClC1=CC=C(C(F)(F)F)C=C120.083383
4CC(C)C(C=C(C(C)C)C=C1C(C)C)=C1C2=C(P([C@@]3(C[...CC1=CC(C)=NO1CN1CCCN2C1=NCCC2ClC1=CC=C(OC)C=C10.492663
\n", - "
" - ], - "text/plain": [ - " Ligand Additive \\\n", - "0 CC(C)C(C=C(C(C)C)C=C1C(C)C)=C1C2=C(P([C@@]3(C[... CC1=CC(C)=NO1 \n", - "1 CC(C)C(C=C(C(C)C)C=C1C(C)C)=C1C2=C(P([C@@]3(C[... O=C(OC)C1=CC=NO1 \n", - "2 CC(C)C(C=C(C(C)C)C=C1C(C)C)=C1C2=C(P(C3CCCCC3)... O=C(OC)C1=CC=NO1 \n", - "3 CC(C)C(C=C(C(C)C)C=C1C(C)C)=C1C2=C(P(C(C)(C)C)... CCOC(C1=CON=C1)=O \n", - "4 CC(C)C(C=C(C(C)C)C=C1C(C)C)=C1C2=C(P([C@@]3(C[... CC1=CC(C)=NO1 \n", - "\n", - " Base Aryl halide \\\n", - "0 CN(C)P(N(C)C)(N(C)C)=NP(N(C)C)(N(C)C)=NCC ClC1=NC=CC=C1 \n", - "1 CN(C)P(N(C)C)(N(C)C)=NP(N(C)C)(N(C)C)=NCC BrC1=NC=CC=C1 \n", - "2 CN(C)P(N(C)C)(N(C)C)=NP(N(C)C)(N(C)C)=NCC IC1=CC=C(CC)C=C1 \n", - "3 CN1CCCN2C1=NCCC2 ClC1=CC=C(C(F)(F)F)C=C1 \n", - "4 CN1CCCN2C1=NCCC2 ClC1=CC=C(OC)C=C1 \n", - "\n", - " Output \n", - "0 70.410458 \n", - "1 11.064457 \n", - "2 10.223550 \n", - "3 20.083383 \n", - "4 0.492663 " - ] - }, - "execution_count": 51, - "metadata": {}, - "output_type": "execute_result" - } - ], + "outputs": [], "source": [ "df.head()" ] @@ -288,23 +163,12 @@ }, { "cell_type": "code", - "execution_count": 52, + "execution_count": null, "id": "ec2458e5-455f-4f03-8ce9-c0d12e9ed371", "metadata": { "tags": [] }, - "outputs": [ - { - "data": { - "text/plain": [ - "['Ligand', 'Additive', 'Base', 'Aryl halide', 'Output']" - ] - }, - "execution_count": 52, - "metadata": {}, - "output_type": "execute_result" - } - ], + "outputs": [], "source": [ "fields_orig = df.columns.tolist()\n", "fields_orig" @@ -312,7 +176,7 @@ }, { "cell_type": "code", - "execution_count": 53, + "execution_count": null, "id": "28c9b695", "metadata": {}, "outputs": [], @@ -322,7 +186,7 @@ }, { "cell_type": "code", - "execution_count": 54, + "execution_count": null, "id": "a46dd8ff-37b3-4894-8226-3bf98226dd09", "metadata": { "tags": [] @@ -340,7 +204,7 @@ }, { "cell_type": "code", - "execution_count": 55, + "execution_count": null, "id": "785d37cb-1fb4-4a91-a923-d5a78a37f36a", "metadata": { "tags": [] @@ -352,7 +216,7 @@ }, { "cell_type": "code", - "execution_count": 56, + "execution_count": null, "id": "aaad8f07", "metadata": {}, "outputs": [], @@ -362,113 +226,12 @@ }, { "cell_type": "code", - "execution_count": 57, + "execution_count": null, "id": "1bf212cb-1653-457b-9f5d-416d4dd14b53", "metadata": { "tags": [] }, - "outputs": [ - { - "data": { - "text/html": [ - "
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ligandadditivebasearyl_halideyield
0CC(C)C(C=C(C(C)C)C=C1C(C)C)=C1C2=C(P([C@@]3(C[...CC1=CC(C)=NO1CN(C)P(N(C)C)(N(C)C)=NP(N(C)C)(N(C)C)=NCCClC1=NC=CC=C170.410458
1CC(C)C(C=C(C(C)C)C=C1C(C)C)=C1C2=C(P([C@@]3(C[...O=C(OC)C1=CC=NO1CN(C)P(N(C)C)(N(C)C)=NP(N(C)C)(N(C)C)=NCCBrC1=NC=CC=C111.064457
2CC(C)C(C=C(C(C)C)C=C1C(C)C)=C1C2=C(P(C3CCCCC3)...O=C(OC)C1=CC=NO1CN(C)P(N(C)C)(N(C)C)=NP(N(C)C)(N(C)C)=NCCIC1=CC=C(CC)C=C110.223550
3CC(C)C(C=C(C(C)C)C=C1C(C)C)=C1C2=C(P(C(C)(C)C)...CCOC(C1=CON=C1)=OCN1CCCN2C1=NCCC2ClC1=CC=C(C(F)(F)F)C=C120.083383
4CC(C)C(C=C(C(C)C)C=C1C(C)C)=C1C2=C(P([C@@]3(C[...CC1=CC(C)=NO1CN1CCCN2C1=NCCC2ClC1=CC=C(OC)C=C10.492663
\n", - "
" - ], - "text/plain": [ - " ligand additive \\\n", - "0 CC(C)C(C=C(C(C)C)C=C1C(C)C)=C1C2=C(P([C@@]3(C[... CC1=CC(C)=NO1 \n", - "1 CC(C)C(C=C(C(C)C)C=C1C(C)C)=C1C2=C(P([C@@]3(C[... O=C(OC)C1=CC=NO1 \n", - "2 CC(C)C(C=C(C(C)C)C=C1C(C)C)=C1C2=C(P(C3CCCCC3)... O=C(OC)C1=CC=NO1 \n", - "3 CC(C)C(C=C(C(C)C)C=C1C(C)C)=C1C2=C(P(C(C)(C)C)... CCOC(C1=CON=C1)=O \n", - "4 CC(C)C(C=C(C(C)C)C=C1C(C)C)=C1C2=C(P([C@@]3(C[... CC1=CC(C)=NO1 \n", - "\n", - " base aryl_halide \\\n", - "0 CN(C)P(N(C)C)(N(C)C)=NP(N(C)C)(N(C)C)=NCC ClC1=NC=CC=C1 \n", - "1 CN(C)P(N(C)C)(N(C)C)=NP(N(C)C)(N(C)C)=NCC BrC1=NC=CC=C1 \n", - "2 CN(C)P(N(C)C)(N(C)C)=NP(N(C)C)(N(C)C)=NCC IC1=CC=C(CC)C=C1 \n", - "3 CN1CCCN2C1=NCCC2 ClC1=CC=C(C(F)(F)F)C=C1 \n", - "4 CN1CCCN2C1=NCCC2 ClC1=CC=C(OC)C=C1 \n", - "\n", - " yield \n", - "0 70.410458 \n", - "1 11.064457 \n", - "2 10.223550 \n", - "3 20.083383 \n", - "4 0.492663 " - ] - }, - "execution_count": 57, - "metadata": {}, - "output_type": "execute_result" - } - ], + "outputs": [], "source": [ "df.head()" ] @@ -483,7 +246,7 @@ }, { "cell_type": "code", - "execution_count": 60, + "execution_count": null, "id": "7e746003-cb1f-434f-bba6-00f0c439c4ac", "metadata": { "tags": [] @@ -531,7 +294,7 @@ }, { "cell_type": "code", - "execution_count": 62, + "execution_count": null, "id": "d544fa60-343e-40e1-bd0c-4750f07a7145", "metadata": { "tags": [] @@ -551,7 +314,7 @@ }, { "cell_type": "code", - "execution_count": 63, + "execution_count": null, "id": "d6d5efa5-b4b4-4a25-8626-e10f3d691e83", "metadata": { "tags": [] @@ -563,7 +326,7 @@ }, { "cell_type": "code", - "execution_count": 65, + "execution_count": null, "id": "727f8d7b-cbb6-43c7-9eab-9d4d65be6b3f", "metadata": { "tags": [] @@ -575,163 +338,36 @@ }, { "cell_type": "code", - "execution_count": 66, + "execution_count": null, "id": "63c8d4a4-906e-418d-be39-879365b4dfa0", "metadata": { "tags": [] }, - "outputs": [ - { - "name": "stdout", - "output_type": "stream", - "text": [ - "-rw-r--r-- 1 pschwllr staff 1.4M Mar 8 23:00 data_clean.csv\n" - ] - } - ], + "outputs": [], "source": [ "!ls -lh {fn_data_csv}" ] }, { "cell_type": "code", - "execution_count": 67, + "execution_count": null, "id": "a51b9001-25d7-4e0e-a607-477cfc4a9f1c", "metadata": { "tags": [] }, - "outputs": [ - { - "name": "stdout", - "output_type": "stream", - "text": [ - "ligand,additive,base,aryl_halide,reaction_SMILES,yield\n", - "CC(C)C(C=C(C(C)C)C=C1C(C)C)=C1C2=C(P([C@@]3(C[C@@H]4C5)C[C@H](C4)C[C@H]5C3)[C@]6(C7)C[C@@H](C[C@@H]7C8)C[C@@H]8C6)C(OC)=CC=C2OC,CC1=CC(C)=NO1,CN(C)P(N(C)C)(N(C)C)=NP(N(C)C)(N(C)C)=NCC,ClC1=NC=CC=C1,CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C.COc1ccc(OC)c(P([C@]23C[C@H]4C[C@H](C[C@H](C4)C2)C3)[C@]23C[C@H]4C[C@H](C[C@H](C4)C2)C3)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C.Cc1cc(C)on1.Cc1ccc(N)cc1.Clc1ccccn1.O=S(=O)(O[Pd]1c2ccccc2-c2ccccc2[NH2]1)C(F)(F)F>>Cc1ccc(Nc2ccccn2)cc1,70.41045785\n", - "CC(C)C(C=C(C(C)C)C=C1C(C)C)=C1C2=C(P([C@@]3(C[C@@H]4C5)C[C@H](C4)C[C@H]5C3)[C@]6(C7)C[C@@H](C[C@@H]7C8)C[C@@H]8C6)C(OC)=CC=C2OC,O=C(OC)C1=CC=NO1,CN(C)P(N(C)C)(N(C)C)=NP(N(C)C)(N(C)C)=NCC,BrC1=NC=CC=C1,Brc1ccccn1.CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C.COC(=O)c1ccno1.COc1ccc(OC)c(P([C@]23C[C@H]4C[C@H](C[C@H](C4)C2)C3)[C@]23C[C@H]4C[C@H](C[C@H](C4)C2)C3)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C.Cc1ccc(N)cc1.O=S(=O)(O[Pd]1c2ccccc2-c2ccccc2[NH2]1)C(F)(F)F>>Cc1ccc(Nc2ccccn2)cc1,11.06445724\n", - "CC(C)C(C=C(C(C)C)C=C1C(C)C)=C1C2=C(P(C3CCCCC3)C4CCCCC4)C=CC=C2,O=C(OC)C1=CC=NO1,CN(C)P(N(C)C)(N(C)C)=NP(N(C)C)(N(C)C)=NCC,IC1=CC=C(CC)C=C1,CC(C)c1cc(C(C)C)c(-c2ccccc2P(C2CCCCC2)C2CCCCC2)c(C(C)C)c1.CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C.CCc1ccc(I)cc1.COC(=O)c1ccno1.Cc1ccc(N)cc1.O=S(=O)(O[Pd]1c2ccccc2-c2ccccc2[NH2]1)C(F)(F)F>>CCc1ccc(Nc2ccc(C)cc2)cc1,10.22354965\n", - "CC(C)C(C=C(C(C)C)C=C1C(C)C)=C1C2=C(P(C(C)(C)C)C(C)(C)C)C(OC)=CC=C2OC,CCOC(C1=CON=C1)=O,CN1CCCN2C1=NCCC2,ClC1=CC=C(C(F)(F)F)C=C1,CCOC(=O)c1cnoc1.CN1CCCN2CCCN=C12.COc1ccc(OC)c(P(C(C)(C)C)C(C)(C)C)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C.Cc1ccc(N)cc1.FC(F)(F)c1ccc(Cl)cc1.O=S(=O)(O[Pd]1c2ccccc2-c2ccccc2[NH2]1)C(F)(F)F>>Cc1ccc(Nc2ccc(C(F)(F)F)cc2)cc1,20.0833829\n" - ] - } - ], + "outputs": [], "source": [ "!head -n 5 {fn_data_csv}" ] }, { "cell_type": "code", - "execution_count": 68, + "execution_count": null, "id": "1a512943-4909-4d56-867d-50c151d8d607", "metadata": { "tags": [] }, - "outputs": [ - { - "data": { - "text/html": [ - "
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ligandadditivebasearyl_halidereaction_SMILESyield
0CC(C)C(C=C(C(C)C)C=C1C(C)C)=C1C2=C(P([C@@]3(C[...CC1=CC(C)=NO1CN(C)P(N(C)C)(N(C)C)=NP(N(C)C)(N(C)C)=NCCClC1=NC=CC=C1CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C.COc1...70.410458
1CC(C)C(C=C(C(C)C)C=C1C(C)C)=C1C2=C(P([C@@]3(C[...O=C(OC)C1=CC=NO1CN(C)P(N(C)C)(N(C)C)=NP(N(C)C)(N(C)C)=NCCBrC1=NC=CC=C1Brc1ccccn1.CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C...11.064457
2CC(C)C(C=C(C(C)C)C=C1C(C)C)=C1C2=C(P(C3CCCCC3)...O=C(OC)C1=CC=NO1CN(C)P(N(C)C)(N(C)C)=NP(N(C)C)(N(C)C)=NCCIC1=CC=C(CC)C=C1CC(C)c1cc(C(C)C)c(-c2ccccc2P(C2CCCCC2)C2CCCCC2...10.223550
3CC(C)C(C=C(C(C)C)C=C1C(C)C)=C1C2=C(P(C(C)(C)C)...CCOC(C1=CON=C1)=OCN1CCCN2C1=NCCC2ClC1=CC=C(C(F)(F)F)C=C1CCOC(=O)c1cnoc1.CN1CCCN2CCCN=C12.COc1ccc(OC)c(...20.083383
4CC(C)C(C=C(C(C)C)C=C1C(C)C)=C1C2=C(P([C@@]3(C[...CC1=CC(C)=NO1CN1CCCN2C1=NCCC2ClC1=CC=C(OC)C=C1CN1CCCN2CCCN=C12.COc1ccc(Cl)cc1.COc1ccc(OC)c(P...0.492663
\n", - "
" - ], - "text/plain": [ - " ligand additive \\\n", - "0 CC(C)C(C=C(C(C)C)C=C1C(C)C)=C1C2=C(P([C@@]3(C[... CC1=CC(C)=NO1 \n", - "1 CC(C)C(C=C(C(C)C)C=C1C(C)C)=C1C2=C(P([C@@]3(C[... O=C(OC)C1=CC=NO1 \n", - "2 CC(C)C(C=C(C(C)C)C=C1C(C)C)=C1C2=C(P(C3CCCCC3)... O=C(OC)C1=CC=NO1 \n", - "3 CC(C)C(C=C(C(C)C)C=C1C(C)C)=C1C2=C(P(C(C)(C)C)... CCOC(C1=CON=C1)=O \n", - "4 CC(C)C(C=C(C(C)C)C=C1C(C)C)=C1C2=C(P([C@@]3(C[... CC1=CC(C)=NO1 \n", - "\n", - " base aryl_halide \\\n", - "0 CN(C)P(N(C)C)(N(C)C)=NP(N(C)C)(N(C)C)=NCC ClC1=NC=CC=C1 \n", - "1 CN(C)P(N(C)C)(N(C)C)=NP(N(C)C)(N(C)C)=NCC BrC1=NC=CC=C1 \n", - "2 CN(C)P(N(C)C)(N(C)C)=NP(N(C)C)(N(C)C)=NCC IC1=CC=C(CC)C=C1 \n", - "3 CN1CCCN2C1=NCCC2 ClC1=CC=C(C(F)(F)F)C=C1 \n", - "4 CN1CCCN2C1=NCCC2 ClC1=CC=C(OC)C=C1 \n", - "\n", - " reaction_SMILES yield \n", - "0 CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C.COc1... 70.410458 \n", - "1 Brc1ccccn1.CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C... 11.064457 \n", - "2 CC(C)c1cc(C(C)C)c(-c2ccccc2P(C2CCCCC2)C2CCCCC2... 10.223550 \n", - "3 CCOC(=O)c1cnoc1.CN1CCCN2CCCN=C12.COc1ccc(OC)c(... 20.083383 \n", - "4 CN1CCCN2CCCN=C12.COc1ccc(Cl)cc1.COc1ccc(OC)c(P... 0.492663 " - ] - }, - "execution_count": 68, - "metadata": {}, - "output_type": "execute_result" - } - ], + "outputs": [], "source": [ "df.head()" ] @@ -746,7 +382,7 @@ }, { "cell_type": "code", - "execution_count": 69, + "execution_count": null, "id": "077b0c5f-8772-4879-9317-3fa28799689b", "metadata": { "tags": [] @@ -758,7 +394,7 @@ }, { "cell_type": "code", - "execution_count": 70, + "execution_count": null, "id": "6eaef0e6-2115-4793-ac43-a196b25d47a0", "metadata": { "tags": [] @@ -770,119 +406,12 @@ }, { "cell_type": "code", - "execution_count": 71, + "execution_count": null, "id": "43619e7c-9c82-4ff0-ae25-403861304635", "metadata": { "tags": [] }, - "outputs": [ - { - "data": { - "text/html": [ - "
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ligandadditivebasearyl_halidereaction_SMILESyield
0CC(C)C(C=C(C(C)C)C=C1C(C)C)=C1C2=C(P([C@@]3(C[...CC1=CC(C)=NO1CN(C)P(N(C)C)(N(C)C)=NP(N(C)C)(N(C)C)=NCCClC1=NC=CC=C1CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C.COc1...70.410458
1CC(C)C(C=C(C(C)C)C=C1C(C)C)=C1C2=C(P([C@@]3(C[...O=C(OC)C1=CC=NO1CN(C)P(N(C)C)(N(C)C)=NP(N(C)C)(N(C)C)=NCCBrC1=NC=CC=C1Brc1ccccn1.CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C...11.064457
2CC(C)C(C=C(C(C)C)C=C1C(C)C)=C1C2=C(P(C3CCCCC3)...O=C(OC)C1=CC=NO1CN(C)P(N(C)C)(N(C)C)=NP(N(C)C)(N(C)C)=NCCIC1=CC=C(CC)C=C1CC(C)c1cc(C(C)C)c(-c2ccccc2P(C2CCCCC2)C2CCCCC2...10.223550
3CC(C)C(C=C(C(C)C)C=C1C(C)C)=C1C2=C(P(C(C)(C)C)...CCOC(C1=CON=C1)=OCN1CCCN2C1=NCCC2ClC1=CC=C(C(F)(F)F)C=C1CCOC(=O)c1cnoc1.CN1CCCN2CCCN=C12.COc1ccc(OC)c(...20.083383
4CC(C)C(C=C(C(C)C)C=C1C(C)C)=C1C2=C(P([C@@]3(C[...CC1=CC(C)=NO1CN1CCCN2C1=NCCC2ClC1=CC=C(OC)C=C1CN1CCCN2CCCN=C12.COc1ccc(Cl)cc1.COc1ccc(OC)c(P...0.492663
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" - ], - "text/plain": [ - " ligand additive \\\n", - "0 CC(C)C(C=C(C(C)C)C=C1C(C)C)=C1C2=C(P([C@@]3(C[... CC1=CC(C)=NO1 \n", - "1 CC(C)C(C=C(C(C)C)C=C1C(C)C)=C1C2=C(P([C@@]3(C[... O=C(OC)C1=CC=NO1 \n", - "2 CC(C)C(C=C(C(C)C)C=C1C(C)C)=C1C2=C(P(C3CCCCC3)... O=C(OC)C1=CC=NO1 \n", - "3 CC(C)C(C=C(C(C)C)C=C1C(C)C)=C1C2=C(P(C(C)(C)C)... CCOC(C1=CON=C1)=O \n", - "4 CC(C)C(C=C(C(C)C)C=C1C(C)C)=C1C2=C(P([C@@]3(C[... CC1=CC(C)=NO1 \n", - "\n", - " base aryl_halide \\\n", - "0 CN(C)P(N(C)C)(N(C)C)=NP(N(C)C)(N(C)C)=NCC ClC1=NC=CC=C1 \n", - "1 CN(C)P(N(C)C)(N(C)C)=NP(N(C)C)(N(C)C)=NCC BrC1=NC=CC=C1 \n", - "2 CN(C)P(N(C)C)(N(C)C)=NP(N(C)C)(N(C)C)=NCC IC1=CC=C(CC)C=C1 \n", - "3 CN1CCCN2C1=NCCC2 ClC1=CC=C(C(F)(F)F)C=C1 \n", - "4 CN1CCCN2C1=NCCC2 ClC1=CC=C(OC)C=C1 \n", - "\n", - " reaction_SMILES yield \n", - "0 CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C.COc1... 70.410458 \n", - "1 Brc1ccccn1.CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C... 11.064457 \n", - "2 CC(C)c1cc(C(C)C)c(-c2ccccc2P(C2CCCCC2)C2CCCCC2... 10.223550 \n", - "3 CCOC(=O)c1cnoc1.CN1CCCN2CCCN=C12.COc1ccc(OC)c(... 20.083383 \n", - "4 CN1CCCN2CCCN=C12.COc1ccc(Cl)cc1.COc1ccc(OC)c(P... 0.492663 " - ] - }, - "execution_count": 71, - "metadata": {}, - "output_type": "execute_result" - } - ], + "outputs": [], "source": [ "df.head()" ] @@ -897,126 +426,19 @@ }, { "cell_type": "code", - "execution_count": 72, + "execution_count": null, "id": "49771077-471d-4d71-a9a7-d6b094bbc4f3", "metadata": { "tags": [] }, - "outputs": [ - { - "data": { - "text/html": [ - "
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ligandadditivebasearyl_halidereaction_SMILESyield
0CC(C)C(C=C(C(C)C)C=C1C(C)C)=C1C2=C(P([C@@]3(C[...CC1=CC(C)=NO1CN(C)P(N(C)C)(N(C)C)=NP(N(C)C)(N(C)C)=NCCClC1=NC=CC=C1CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C.COc1...70.410458
1CC(C)C(C=C(C(C)C)C=C1C(C)C)=C1C2=C(P([C@@]3(C[...O=C(OC)C1=CC=NO1CN(C)P(N(C)C)(N(C)C)=NP(N(C)C)(N(C)C)=NCCBrC1=NC=CC=C1Brc1ccccn1.CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C...11.064457
2CC(C)C(C=C(C(C)C)C=C1C(C)C)=C1C2=C(P(C3CCCCC3)...O=C(OC)C1=CC=NO1CN(C)P(N(C)C)(N(C)C)=NP(N(C)C)(N(C)C)=NCCIC1=CC=C(CC)C=C1CC(C)c1cc(C(C)C)c(-c2ccccc2P(C2CCCCC2)C2CCCCC2...10.223550
3CC(C)C(C=C(C(C)C)C=C1C(C)C)=C1C2=C(P(C(C)(C)C)...CCOC(C1=CON=C1)=OCN1CCCN2C1=NCCC2ClC1=CC=C(C(F)(F)F)C=C1CCOC(=O)c1cnoc1.CN1CCCN2CCCN=C12.COc1ccc(OC)c(...20.083383
4CC(C)C(C=C(C(C)C)C=C1C(C)C)=C1C2=C(P([C@@]3(C[...CC1=CC(C)=NO1CN1CCCN2C1=NCCC2ClC1=CC=C(OC)C=C1CN1CCCN2CCCN=C12.COc1ccc(Cl)cc1.COc1ccc(OC)c(P...0.492663
\n", - "
" - ], - "text/plain": [ - " ligand additive \\\n", - "0 CC(C)C(C=C(C(C)C)C=C1C(C)C)=C1C2=C(P([C@@]3(C[... CC1=CC(C)=NO1 \n", - "1 CC(C)C(C=C(C(C)C)C=C1C(C)C)=C1C2=C(P([C@@]3(C[... O=C(OC)C1=CC=NO1 \n", - "2 CC(C)C(C=C(C(C)C)C=C1C(C)C)=C1C2=C(P(C3CCCCC3)... O=C(OC)C1=CC=NO1 \n", - "3 CC(C)C(C=C(C(C)C)C=C1C(C)C)=C1C2=C(P(C(C)(C)C)... CCOC(C1=CON=C1)=O \n", - "4 CC(C)C(C=C(C(C)C)C=C1C(C)C)=C1C2=C(P([C@@]3(C[... CC1=CC(C)=NO1 \n", - "\n", - " base aryl_halide \\\n", - "0 CN(C)P(N(C)C)(N(C)C)=NP(N(C)C)(N(C)C)=NCC ClC1=NC=CC=C1 \n", - "1 CN(C)P(N(C)C)(N(C)C)=NP(N(C)C)(N(C)C)=NCC BrC1=NC=CC=C1 \n", - "2 CN(C)P(N(C)C)(N(C)C)=NP(N(C)C)(N(C)C)=NCC IC1=CC=C(CC)C=C1 \n", - "3 CN1CCCN2C1=NCCC2 ClC1=CC=C(C(F)(F)F)C=C1 \n", - "4 CN1CCCN2C1=NCCC2 ClC1=CC=C(OC)C=C1 \n", - "\n", - " reaction_SMILES yield \n", - "0 CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C.COc1... 70.410458 \n", - "1 Brc1ccccn1.CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C... 11.064457 \n", - "2 CC(C)c1cc(C(C)C)c(-c2ccccc2P(C2CCCCC2)C2CCCCC2... 10.223550 \n", - "3 CCOC(=O)c1cnoc1.CN1CCCN2CCCN=C12.COc1ccc(OC)c(... 20.083383 \n", - "4 CN1CCCN2CCCN=C12.COc1ccc(Cl)cc1.COc1ccc(OC)c(P... 0.492663 " - ] - }, - "execution_count": 72, - "metadata": {}, - "output_type": "execute_result" - } - ], + "outputs": [], "source": [ "df.head()" ] }, { "cell_type": "code", - "execution_count": 73, + "execution_count": null, "id": "d3890961-444e-4a26-b8fc-ed8c4e959af9", "metadata": { "tags": [] @@ -1025,7 +447,7 @@ "source": [ "meta = {\n", " \"name\": \"buchwald_hartwig_doyle\", # unique identifier, we will also use this for directory names\n", - " \"description\": \"\"\"High-throughput experimentation palladium-catalyzed Buchwald Hardwig data set with yields.\"\"\",\n", + " \"description\": \"\"\"High-throughput experimentation palladium-catalyzed Buchwald Hardwig C-N cross-coupling data set with yields.\"\"\",\n", " \"targets\": [\n", " {\n", " \"id\": \"yield\", # name of the column in a tabular dataset\n", @@ -1041,11 +463,31 @@ " \"identifiers\": [\n", " {\n", " \"id\": \"reaction_SMILES\", # column name\n", + " \"type\": \"RXN-SMILES\", # can be \"SMILES\", \"SELFIES\", \"IUPAC\", \"Other\"\n", + " \"description\": \"RXN-SMILES\", # description (optional, except for \"Other\")\n", + " },\n", + " {\n", + " \"id\": \"ligand\", # column name\n", + " \"type\": \"SMILES\", # can be \"SMILES\", \"SELFIES\", \"IUPAC\", \"Other\"\n", + " \"description\": \"ligand SMILES\", # description (optional, except for \"Other\")\n", + " },\n", + " {\n", + " \"id\": \"additive\", # column name\n", " \"type\": \"SMILES\", # can be \"SMILES\", \"SELFIES\", \"IUPAC\", \"Other\"\n", - " \"description\": \"SMILES\", # description (optional, except for \"Other\")\n", + " \"description\": \"additive SMILES\", # description (optional, except for \"Other\")\n", + " },\n", + " {\n", + " \"id\": \"base\", # column name\n", + " \"type\": \"SMILES\", # can be \"SMILES\", \"SELFIES\", \"IUPAC\", \"Other\"\n", + " \"description\": \"base SMILES\", # description (optional, except for \"Other\")\n", + " },\n", + " {\n", + " \"id\": \"aryl_halide\", # column name\n", + " \"type\": \"SMILES\", # can be \"SMILES\", \"SELFIES\", \"IUPAC\", \"Other\"\n", + " \"description\": \"aryl halide SMILES\", # description (optional, except for \"Other\")\n", " },\n", " ],\n", - " \"license\": \"MIT license\", # license under which the original dataset was published\n", + " \"license\": \"MIT\", # license under which the original dataset was published\n", " \"links\": [ # list of relevant links (original dataset, other uses, etc.)\n", " {\n", " \"url\": \"https://doi.org/10.1126/science.aar5169\",\n", @@ -1084,7 +526,7 @@ }, { "cell_type": "code", - "execution_count": 74, + "execution_count": null, "id": "ec455cf0-962a-4c0d-bb3e-066e415ffd9b", "metadata": { "tags": [] @@ -1108,7 +550,7 @@ }, { "cell_type": "code", - "execution_count": 75, + "execution_count": null, "id": "580bbd79-4845-4515-be94-3e4a9815d048", "metadata": { "tags": [] @@ -1120,7 +562,7 @@ }, { "cell_type": "code", - "execution_count": 76, + "execution_count": null, "id": "873fa5dd-9b60-40f5-b537-4d7a206414ea", "metadata": { "tags": [] @@ -1133,73 +575,24 @@ }, { "cell_type": "code", - "execution_count": 77, + "execution_count": null, "id": "d01686c0-6746-4fc4-b019-350270dfc26f", "metadata": { "tags": [] }, - "outputs": [ - { - "name": "stdout", - "output_type": "stream", - "text": [ - "-rw-r--r-- 1 pschwllr staff 975B Mar 8 23:36 meta.yaml\n" - ] - } - ], + "outputs": [], "source": [ "!ls -lh {fn_meta}" ] }, { "cell_type": "code", - "execution_count": 78, + "execution_count": null, "id": "ef6063c5-7a8b-4344-bccf-a073443feebf", "metadata": { "tags": [] }, - "outputs": [ - { - "name": "stdout", - "output_type": "stream", - "text": [ - "name: buchwald_hartwig_doyle\n", - "description: High-throughput experimentation palladium-catalyzed Buchwald Hardwig\n", - " data set with yields.\n", - "targets:\n", - "- id: yield\n", - " description: Reaction yields analyzed by UPLC\n", - " units: '%'\n", - " type: continuous\n", - " names:\n", - " - Reaction yield\n", - " - yield\n", - "identifiers:\n", - "- id: reaction_SMILES\n", - " type: SMILES\n", - " description: SMILES\n", - "license: MIT license\n", - "links:\n", - "- url: https://doi.org/10.1126/science.aar5169\n", - " description: corresponding publication\n", - "num_points: 3955\n", - "url: https://tdcommons.ai/single_pred_tasks/tox/#acute-toxicity-ld50\n", - "bibtex:\n", - "- |-\n", - " @article{ahneman2018predicting,\n", - " title={Predicting reaction performance in C--N cross-coupling using machine learning},\n", - " author={Ahneman, Derek T and Estrada, Jes{'u}s G and Lin, Shishi and Dreher, Spencer D and Doyle, Abigail G},\n", - " journal={Science},\n", - " volume={360},\n", - " number={6385},\n", - " pages={186--190},\n", - " year={2018},\n", - " publisher={American Association for the Advancement of Science}\n", - " }\n", - " }\n" - ] - } - ], + "outputs": [], "source": [ "!cat {fn_meta}" ] @@ -1214,7 +607,7 @@ }, { "cell_type": "code", - "execution_count": 32, + "execution_count": null, "id": "9aab00fd-58a8-40b0-be30-1e269e0d323b", "metadata": { "tags": [] @@ -1226,33 +619,60 @@ }, { "cell_type": "code", - "execution_count": 33, + "execution_count": null, "id": "8368bb20-8e1c-4b7d-b0e2-b39da36b5972", "metadata": { "tags": [] }, - "outputs": [ - { - "name": "stdout", - "output_type": "stream", - "text": [ - "Overwriting transform.py\n" - ] - } - ], + "outputs": [], "source": [ "%%writefile $path_file\n", "import pandas as pd\n", "import yaml\n", - "from tdc.single_pred import Tox\n", + "from rdkit import Chem # 2022.9.5\n", + "from rdkit.Chem import rdChemReactions\n", "\n", + "def generate_buchwald_hartwig_rxns(df):\n", + " \"\"\"\n", + " Converts the entries in the excel files to reaction SMILES.\n", + " From: https://github.com/reymond-group/drfp/blob/main/scripts/encoding/encode_buchwald_hartwig_reactions.py\n", + " and https://github.com/rxn4chemistry/rxn_yields/blob/master/rxn_yields/data.py\n", + " \"\"\"\n", + " df = df.copy()\n", + " fwd_template = \"[F,Cl,Br,I]-[c;H0;D3;+0:1](:[c,n:2]):[c,n:3].[NH2;D1;+0:4]-[c:5]>>[c,n:2]:[c;H0;D3;+0:1](:[c,n:3])-[NH;D2;+0:4]-[c:5]\"\n", + " methylaniline = \"Cc1ccc(N)cc1\"\n", + " pd_catalyst = \"O=S(=O)(O[Pd]1~[NH2]C2C=CC=CC=2C2C=CC=CC1=2)C(F)(F)F\"\n", + " methylaniline_mol = Chem.MolFromSmiles(methylaniline)\n", + " rxn = rdChemReactions.ReactionFromSmarts(fwd_template)\n", + " products = []\n", + "\n", + " for i, row in df.iterrows():\n", + " reacts = (Chem.MolFromSmiles(row[\"aryl_halide\"]), methylaniline_mol)\n", + " rxn_products = rxn.RunReactants(reacts)\n", + "\n", + " rxn_products_smiles = set([Chem.MolToSmiles(mol[0]) for mol in rxn_products])\n", + " assert len(rxn_products_smiles) == 1\n", + " products.append(list(rxn_products_smiles)[0])\n", + "\n", + " df[\"product\"] = products\n", + " rxns = []\n", + "\n", + " for i, row in df.iterrows():\n", + " reactants = Chem.MolToSmiles(\n", + " Chem.MolFromSmiles(\n", + " f\"{row['aryl_halide']}.{methylaniline}.{pd_catalyst}.{row['ligand']}.{row['base']}.{row['additive']}\"\n", + " )\n", + " )\n", + " rxns.append(f\"{reactants.replace('N~', '[NH2]')}>>{row['product']}\")\n", + "\n", + " return rxns\n", "\n", "def get_and_transform_data():\n", " # get raw data\n", - " data = Tox(name = 'LD50_Zhu')\n", - " fn_data_original = \"data_original.csv\"\n", - " data.get_data().to_csv(fn_data_original, index=False)\n", - "\n", + " fn_data_original = \"Dreher_and_Doyle_input_data.csv\"\n", + " data = pd.read_excel('https://github.com/reymond-group/drfp/raw/main/data/Dreher_and_Doyle_input_data.xlsx')\n", + " data.to_csv(fn_data_original, index=False)\n", + " \n", " # create dataframe\n", " df = pd.read_csv(\n", " fn_data_original,\n", @@ -1262,23 +682,26 @@ " # check if fields are the same\n", " fields_orig = df.columns.tolist()\n", " assert fields_orig == [\n", - " \"Drug_ID\",\n", - " \"Drug\",\n", - " \"Y\",\n", + " 'Ligand',\n", + " 'Additive', \n", + " 'Base', \n", + " 'Aryl halide', \n", + " 'Output'\n", " ]\n", "\n", " # overwrite column names = fields\n", " fields_clean = [\n", - " \"compound_name\",\n", - " \"SMILES\",\n", - " \"acute_toxicity\",\n", + " \"ligand\",\n", + " \"additive\",\n", + " \"base\",\n", + " \"aryl_halide\",\n", + " 'yield'\n", " ]\n", " df.columns = fields_clean\n", "\n", " # data cleaning\n", - " df.compound_name = (\n", - " df.compound_name.str.strip()\n", - " ) # remove leading and trailing white space characters\n", + " reaction_SMILES = generate_buchwald_hartwig_rxns(df) # compile reactions\n", + " df.insert(4, 'reaction_SMILES', reaction_SMILES) # add reaction SMILES column\n", "\n", " assert not df.duplicated().sum()\n", "\n", @@ -1288,64 +711,81 @@ "\n", " # create meta yaml\n", " meta = {\n", - " \"name\": \"ld50_zhu\", # unique identifier, we will also use this for directory names\n", - " \"description\": \"\"\"Acute toxicity LD50 measures the most conservative dose that can lead to lethal adverse effects. The higher the dose, the more lethal of a drug.\"\"\",\n", - " \"targets\": [\n", - " {\n", - " \"id\": \"acute_toxicity\", # name of the column in a tabular dataset\n", - " \"description\": \"Acute Toxicity LD50.\", # description of what this column means\n", - " \"units\": \"ld50\", # units of the values in this column (leave empty if unitless)\n", - " \"type\": \"continuous\", # can be \"categorical\", \"ordinal\", \"continuous\"\n", - " \"names\": [ # names for the property (to sample from for building the prompts)\n", - " \"Acute Toxicity LD50\",\n", - " \"ld50\",\n", - " \"conservative dose that can lead to lethal adverse effects.\",\n", - " \"Rat Acute Toxicity by Oral Exposure\",\n", - " \"Toxicity\",\n", - " ],\n", - " },\n", - " ],\n", - " \"identifiers\": [\n", - " {\n", - " \"id\": \"SMILES\", # column name\n", - " \"type\": \"SMILES\", # can be \"SMILES\", \"SELFIES\", \"IUPAC\", \"Other\"\n", - " \"description\": \"SMILES\", # description (optional, except for \"Other\")\n", - " },\n", - " {\n", - " \"id\": \"compound_name\",\n", - " \"type\": \"Synonyms\",\n", - " \"description\": \"compound name\",\n", - " \"names\": [\n", - " \"compound\",\n", - " \"compound name\",\n", - " \"drug\",\n", - " ],\n", - " },\n", - " ],\n", - " \"license\": \"CC BY 4.0\", # license under which the original dataset was published\n", - " \"links\": [ # list of relevant links (original dataset, other uses, etc.)\n", - " {\n", - " \"url\": \"https://doi.org/10.1021/tx900189p\",\n", - " \"description\": \"corresponding publication\",\n", - " },\n", - " ],\n", - " \"num_points\": len(df), # number of datapoints in this dataset\n", - " \"url\": \"https://tdcommons.ai/single_pred_tasks/tox/#acute-toxicity-ld50\",\n", - " \"bibtex\": [\n", - " \"\"\"@article{Zhu2009,\n", - " doi = {10.1021/tx900189p},\n", - " url = {https://doi.org/10.1021/tx900189p},\n", - " year = {2009},\n", - " month = oct,\n", - " publisher = {American Chemical Society ({ACS})},\n", - " volume = {22},\n", - " number = {12},\n", - " pages = {1913--1921},\n", - " author = {Hao Zhu and Todd M. Martin and Lin Ye and Alexander Sedykh and Douglas M. Young and Alexander Tropsha},\n", - " title = {Quantitative Structure-Activity Relationship Modeling of Rat Acute Toxicity by Oral Exposure},\n", - " journal = {Chemical Research in Toxicology}}\"\"\",\n", + " \"name\": \"buchwald_hartwig_doyle\", # unique identifier, we will also use this for directory names\n", + " \"description\": \"\"\"High-throughput experimentation palladium-catalyzed Buchwald Hardwig C-N cross-coupling data set with yields.\"\"\",\n", + " \"targets\": [\n", + " {\n", + " \"id\": \"yield\", # name of the column in a tabular dataset\n", + " \"description\": \"Reaction yields analyzed by UPLC\", # description of what this column means\n", + " \"units\": \"%\", # units of the values in this column (leave empty if unitless)\n", + " \"type\": \"continuous\", # can be \"categorical\", \"ordinal\", \"continuous\"\n", + " \"names\": [ # names for the property (to sample from for building the prompts)\n", + " \"Reaction yield\",\n", + " \"yield\",\n", " ],\n", + " },\n", + " ],\n", + " \"identifiers\": [\n", + " {\n", + " \"id\": \"reaction_SMILES\", # column name\n", + " \"type\": \"RXN-SMILES\", # can be \"SMILES\", \"SELFIES\", \"IUPAC\", \"Other\"\n", + " \"description\": \"RXN-SMILES\", # description (optional, except for \"Other\")\n", + " },\n", + " {\n", + " \"id\": \"ligand\", # column name\n", + " \"type\": \"SMILES\", # can be \"SMILES\", \"SELFIES\", \"IUPAC\", \"Other\"\n", + " \"description\": \"ligand SMILES\", # description (optional, except for \"Other\")\n", + " },\n", + " {\n", + " \"id\": \"additive\", # column name\n", + " \"type\": \"SMILES\", # can be \"SMILES\", \"SELFIES\", \"IUPAC\", \"Other\"\n", + " \"description\": \"additive SMILES\", # description (optional, except for \"Other\")\n", + " },\n", + " {\n", + " \"id\": \"base\", # column name\n", + " \"type\": \"SMILES\", # can be \"SMILES\", \"SELFIES\", \"IUPAC\", \"Other\"\n", + " \"description\": \"base SMILES\", # description (optional, except for \"Other\")\n", + " },\n", + " {\n", + " \"id\": \"aryl_halide\", # column name\n", + " \"type\": \"SMILES\", # can be \"SMILES\", \"SELFIES\", \"IUPAC\", \"Other\"\n", + " \"description\": \"aryl halide SMILES\", # description (optional, except for \"Other\")\n", + " },\n", + " ],\n", + " \"license\": \"MIT\", # license under which the original dataset was published\n", + " \"links\": [ # list of relevant links (original dataset, other uses, etc.)\n", + " {\n", + " \"url\": \"https://doi.org/10.1126/science.aar5169\",\n", + " \"description\": \"corresponding publication\",\n", + " },\n", + " {\n", + " \"url\": \"https://www.sciencedirect.com/science/article/pii/S2451929420300851\",\n", + " \"description\": \"publication with data processing\",\n", + " },\n", + " {\n", + " \"url\": \"https://github.com/rxn4chemistry/rxn_yields/blob/master/rxn_yields/data.py\",\n", + " \"description\": \"preprocessing\",\n", + " },\n", + " {\n", + " \"url\": \"https://github.com/reymond-group/drfp/tree/main/data\",\n", + " \"description\": \"dataset\",\n", " }\n", + " ],\n", + " \"num_points\": len(df), # number of datapoints in this dataset\n", + " \"url\": \"https://doi.org/10.1126/science.aar5169\",\n", + " \"bibtex\": [\n", + " \"\"\"@article{ahneman2018predicting,\n", + "title={Predicting reaction performance in C--N cross-coupling using machine learning},\n", + "author={Ahneman, Derek T and Estrada, Jes{\\'u}s G and Lin, Shishi and Dreher, Spencer D and Doyle, Abigail G},\n", + "journal={Science},\n", + "volume={360},\n", + "number={6385},\n", + "pages={186--190},\n", + "year={2018},\n", + "publisher={American Association for the Advancement of Science},\n", + "}\"\"\",\n", + " ],\n", + " }\n", "\n", " def str_presenter(dumper, data):\n", " \"\"\"configures yaml for dumping multiline strings\n", @@ -1372,49 +812,24 @@ }, { "cell_type": "code", - "execution_count": 34, + "execution_count": null, "id": "d0474f26-70f3-4655-b81a-df4ada90e7a6", "metadata": { "tags": [] }, - "outputs": [ - { - "name": "stdout", - "output_type": "stream", - "text": [ - "Found local copy...\n", - "Loading...\n", - "Done!\n", - "Finished processing ld50_zhu dataset!\n" - ] - } - ], + "outputs": [], "source": [ "!python3 transform.py" ] }, { "cell_type": "code", - "execution_count": 35, + "execution_count": null, "id": "953e7bee-bd5e-41d0-a2be-506e0bc97727", "metadata": { "tags": [] }, - "outputs": [ - { - "name": "stdout", - "output_type": "stream", - "text": [ - "total 1.4M\r\n", - "drwxrwxr-x 2 melo melo 4.0K مار 2 16:58 \u001b[0m\u001b[01;34mdata\u001b[0m/\r\n", - "-rw-rw-r-- 1 melo melo 661K مار 2 16:58 data_clean.csv\r\n", - "-rw-rw-r-- 1 melo melo 661K مار 2 16:58 data_original.csv\r\n", - "-rw-rw-r-- 1 melo melo 39K مار 1 22:23 example_processing_and_templates.ipynb\r\n", - "-rw-rw-r-- 1 melo melo 1.5K مار 2 16:58 meta.yaml\r\n", - "-rw-rw-r-- 1 melo melo 4.8K مار 2 16:58 transform.py\r\n" - ] - } - ], + "outputs": [], "source": [ "ls -lh # fmt: skip" ] diff --git a/data/buchwald_hartwig/meta.yaml b/data/buchwald_hartwig/meta.yaml index fc22ac55d..367821f63 100644 --- a/data/buchwald_hartwig/meta.yaml +++ b/data/buchwald_hartwig/meta.yaml @@ -1,6 +1,6 @@ name: buchwald_hartwig_doyle description: High-throughput experimentation palladium-catalyzed Buchwald Hardwig - data set with yields. + C-N cross-coupling data set with yields. targets: - id: yield description: Reaction yields analyzed by UPLC @@ -11,30 +11,41 @@ targets: - yield identifiers: - id: reaction_SMILES + type: RXN-SMILES + description: RXN-SMILES +- id: ligand type: SMILES - description: SMILES -license: MIT license + description: ligand SMILES +- id: additive + type: SMILES + description: additive SMILES +- id: base + type: SMILES + description: base SMILES +- id: aryl_halide + type: SMILES + description: aryl halide SMILES +license: MIT links: - url: https://doi.org/10.1126/science.aar5169 description: corresponding publication - url: https://www.sciencedirect.com/science/article/pii/S2451929420300851 - description: publication with data in compressed format + description: publication with data processing - url: https://github.com/rxn4chemistry/rxn_yields/blob/master/rxn_yields/data.py description: preprocessing - url: https://github.com/reymond-group/drfp/tree/main/data description: dataset num_points: 3955 -url: https://tdcommons.ai/single_pred_tasks/tox/#acute-toxicity-ld50 +url: https://doi.org/10.1126/science.aar5169 bibtex: - |- @article{ahneman2018predicting, - title={Predicting reaction performance in C--N cross-coupling using machine learning}, - author={Ahneman, Derek T and Estrada, Jes{'u}s G and Lin, Shishi and Dreher, Spencer D and Doyle, Abigail G}, - journal={Science}, - volume={360}, - number={6385}, - pages={186--190}, - year={2018}, - publisher={American Association for the Advancement of Science} - } - } + title={Predicting reaction performance in C--N cross-coupling using machine learning}, + author={Ahneman, Derek T and Estrada, Jes{'u}s G and Lin, Shishi and Dreher, Spencer D and Doyle, Abigail G}, + journal={Science}, + volume={360}, + number={6385}, + pages={186--190}, + year={2018}, + publisher={American Association for the Advancement of Science}, + } diff --git a/data/buchwald_hartwig/transform.py b/data/buchwald_hartwig/transform.py index ff51ef84a..4192fdf01 100644 --- a/data/buchwald_hartwig/transform.py +++ b/data/buchwald_hartwig/transform.py @@ -82,61 +82,80 @@ def get_and_transform_data(): # create meta yaml meta = { - "name": "buchwald_hartwig_doyle", # unique identifier, we will also use this for directory names - "description": """High-throughput experimentation palladium-catalyzed Buchwald Hardwig data set with yields.""", - "targets": [ - { - "id": "yield", # name of the column in a tabular dataset - "description": "Reaction yields analyzed by UPLC", # description of what this column means - "units": "%", # units of the values in this column (leave empty if unitless) - "type": "continuous", # can be "categorical", "ordinal", "continuous" - "names": [ # names for the property (to sample from for building the prompts) - "Reaction yield", - "yield", - ], - }, - ], - "identifiers": [ - { - "id": "reaction_SMILES", # column name - "type": "SMILES", # can be "SMILES", "SELFIES", "IUPAC", "Other" - "description": "SMILES", # description (optional, except for "Other") - }, - ], - "license": "MIT license", # license under which the original dataset was published - "links": [ # list of relevant links (original dataset, other uses, etc.) - { - "url": "https://doi.org/10.1126/science.aar5169", - "description": "corresponding publication", - }, - { - "url": "https://www.sciencedirect.com/science/article/pii/S2451929420300851", - "description": "publication with data in compressed format", - }, - { - "url": "https://github.com/rxn4chemistry/rxn_yields/blob/master/rxn_yields/data.py", - "description": "preprocessing", - }, - { - "url": "https://github.com/reymond-group/drfp/tree/main/data", - "description": "dataset", - } - ], + "name": "buchwald_hartwig_doyle", # unique identifier, we will also use this for directory names + "description": """High-throughput experimentation palladium-catalyzed Buchwald Hardwig C-N cross-coupling data set with yields.""", + "targets": [ + { + "id": "yield", # name of the column in a tabular dataset + "description": "Reaction yields analyzed by UPLC", # description of what this column means + "units": "%", # units of the values in this column (leave empty if unitless) + "type": "continuous", # can be "categorical", "ordinal", "continuous" + "names": [ # names for the property (to sample from for building the prompts) + "Reaction yield", + "yield", + ], + }, + ], + "identifiers": [ + { + "id": "reaction_SMILES", # column name + "type": "RXN-SMILES", # can be "SMILES", "SELFIES", "IUPAC", "Other" + "description": "RXN-SMILES", # description (optional, except for "Other") + }, + { + "id": "ligand", # column name + "type": "SMILES", # can be "SMILES", "SELFIES", "IUPAC", "Other" + "description": "ligand SMILES", # description (optional, except for "Other") + }, + { + "id": "additive", # column name + "type": "SMILES", # can be "SMILES", "SELFIES", "IUPAC", "Other" + "description": "additive SMILES", # description (optional, except for "Other") + }, + { + "id": "base", # column name + "type": "SMILES", # can be "SMILES", "SELFIES", "IUPAC", "Other" + "description": "base SMILES", # description (optional, except for "Other") + }, + { + "id": "aryl_halide", # column name + "type": "SMILES", # can be "SMILES", "SELFIES", "IUPAC", "Other" + "description": "aryl halide SMILES", # description (optional, except for "Other") + }, + ], + "license": "MIT", # license under which the original dataset was published + "links": [ # list of relevant links (original dataset, other uses, etc.) + { + "url": "https://doi.org/10.1126/science.aar5169", + "description": "corresponding publication", + }, + { + "url": "https://www.sciencedirect.com/science/article/pii/S2451929420300851", + "description": "publication with data processing", + }, + { + "url": "https://github.com/rxn4chemistry/rxn_yields/blob/master/rxn_yields/data.py", + "description": "preprocessing", + }, + { + "url": "https://github.com/reymond-group/drfp/tree/main/data", + "description": "dataset", + } + ], "num_points": len(df), # number of datapoints in this dataset - "url": "https://tdcommons.ai/single_pred_tasks/tox/#acute-toxicity-ld50", + "url": "https://doi.org/10.1126/science.aar5169", "bibtex": [ """@article{ahneman2018predicting, - title={Predicting reaction performance in C--N cross-coupling using machine learning}, - author={Ahneman, Derek T and Estrada, Jes{\'u}s G and Lin, Shishi and Dreher, Spencer D and Doyle, Abigail G}, - journal={Science}, - volume={360}, - number={6385}, - pages={186--190}, - year={2018}, - publisher={American Association for the Advancement of Science} - } - }""", - ], +title={Predicting reaction performance in C--N cross-coupling using machine learning}, +author={Ahneman, Derek T and Estrada, Jes{\'u}s G and Lin, Shishi and Dreher, Spencer D and Doyle, Abigail G}, +journal={Science}, +volume={360}, +number={6385}, +pages={186--190}, +year={2018}, +publisher={American Association for the Advancement of Science}, +}""", + ], } def str_presenter(dumper, data): From 4c15f0b178a427c0d3c7d9bbb00270a8ae1eb978 Mon Sep 17 00:00:00 2001 From: Philippe Schwaller Date: Sun, 7 May 2023 11:23:02 +0200 Subject: [PATCH 4/4] Removed example ipynb and SMILES identifiers, changed RXN-SMILES to RXNSMILES --- .../example_processing_and_templates.ipynb | 867 ------------------ data/buchwald_hartwig/meta.yaml | 16 +- data/buchwald_hartwig/transform.py | 24 +- 3 files changed, 4 insertions(+), 903 deletions(-) delete mode 100644 data/buchwald_hartwig/example_processing_and_templates.ipynb diff --git a/data/buchwald_hartwig/example_processing_and_templates.ipynb b/data/buchwald_hartwig/example_processing_and_templates.ipynb deleted file mode 100644 index fd7cf27fc..000000000 --- a/data/buchwald_hartwig/example_processing_and_templates.ipynb +++ /dev/null @@ -1,867 +0,0 @@ -{ - "cells": [ - { - "attachments": {}, - "cell_type": "markdown", - "id": "27c08f91-3fa0-4800-8f6a-96a96f665cad", - "metadata": {}, - "source": [ - "# Buchwald-Hartwig Reaction Yield Dataset" - ] - }, - { - "attachments": {}, - "cell_type": "markdown", - "id": "6ef172b9-aad2-47da-bf4c-844a2a07ee8c", - "metadata": {}, - "source": [ - "Original data repository: https://github.com/doylelab/rxnpredict\n", - "\n", - "Data from: https://github.com/reymond-group/drfp/tree/main/data" - ] - }, - { - "cell_type": "markdown", - "id": "7d18c95d-2ec6-45e1-addc-54a890097b8e", - "metadata": {}, - "source": [ - "# Imports" - ] - }, - { - "cell_type": "code", - "execution_count": null, - "id": "cf59e3e9-8061-4022-9eae-e978311b4155", - "metadata": { - "tags": [] - }, - "outputs": [], - "source": [ - "import pandas as pd\n", - "import yaml\n", - "from rdkit import Chem # 2022.9.5\n", - "from rdkit.Chem import rdChemReactions" - ] - }, - { - "cell_type": "markdown", - "id": "a6751ff9-2e3e-4d01-8395-7a5ae0c200d7", - "metadata": {}, - "source": [ - "# Data processing" - ] - }, - { - "cell_type": "markdown", - "id": "a1169ad2-e4bb-41c6-9625-6d1644c44a5b", - "metadata": {}, - "source": [ - "## Download data" - ] - }, - { - "cell_type": "code", - "execution_count": null, - "id": "7bb8eb5e-f513-40d2-a68c-7cda1a51ad31", - "metadata": { - "tags": [] - }, - "outputs": [], - "source": [ - "fn_data_original = \"Dreher_and_Doyle_input_data.csv\"" - ] - }, - { - "cell_type": "code", - "execution_count": null, - "id": "b39a142e-ccbc-49d2-98b0-a5f9bde9fd27", - "metadata": { - "tags": [] - }, - "outputs": [], - "source": [ - "data = pd.read_excel('https://github.com/reymond-group/drfp/raw/main/data/Dreher_and_Doyle_input_data.xlsx')" - ] - }, - { - "cell_type": "code", - "execution_count": null, - "id": "26d9f62a-07f5-4113-8161-d5dfcf0bfb71", - "metadata": { - "tags": [] - }, - "outputs": [], - "source": [ - "data.to_csv(fn_data_original, index=False)" - ] - }, - { - "cell_type": "code", - "execution_count": null, - "id": "43873fc3-20a8-487d-a7c5-33bd58414159", - "metadata": { - "tags": [] - }, - "outputs": [], - "source": [ - "!ls -lh" - ] - }, - { - "cell_type": "markdown", - "id": "d9cda29a-a133-4f0e-992b-e77c9070ee93", - "metadata": {}, - "source": [ - "## Load original data" - ] - }, - { - "cell_type": "code", - "execution_count": null, - "id": "77f614e7-b133-40bc-8759-2d930e4c120e", - "metadata": { - "tags": [] - }, - "outputs": [], - "source": [ - "!head -n 5 {fn_data_original}" - ] - }, - { - "cell_type": "code", - "execution_count": null, - "id": "8f5a0387-f9e3-4e1a-8d14-5df618195f70", - "metadata": { - "tags": [] - }, - "outputs": [], - "source": [ - "df = pd.read_csv(fn_data_original, delimiter=\",\")" - ] - }, - { - "cell_type": "code", - "execution_count": null, - "id": "55b0bd63-62a0-469e-9d8a-e9ada3fe01c4", - "metadata": { - "scrolled": true, - "tags": [] - }, - "outputs": [], - "source": [ - "df.head()" - ] - }, - { - "cell_type": "markdown", - "id": "95158ac1-05d7-4a21-b8e4-7f720306d331", - "metadata": {}, - "source": [ - "## Add column = field names\n", - "Clean column names (`fields_clean`) and keep original names (`fields_orig`)" - ] - }, - { - "cell_type": "code", - "execution_count": null, - "id": "ec2458e5-455f-4f03-8ce9-c0d12e9ed371", - "metadata": { - "tags": [] - }, - "outputs": [], - "source": [ - "fields_orig = df.columns.tolist()\n", - "fields_orig" - ] - }, - { - "cell_type": "code", - "execution_count": null, - "id": "28c9b695", - "metadata": {}, - "outputs": [], - "source": [ - "assert fields_orig == ['Ligand', 'Additive', 'Base', 'Aryl halide', 'Output']" - ] - }, - { - "cell_type": "code", - "execution_count": null, - "id": "a46dd8ff-37b3-4894-8226-3bf98226dd09", - "metadata": { - "tags": [] - }, - "outputs": [], - "source": [ - "fields_clean = [\n", - " \"ligand\",\n", - " \"additive\",\n", - " \"base\",\n", - " \"aryl_halide\",\n", - " 'yield'\n", - "]" - ] - }, - { - "cell_type": "code", - "execution_count": null, - "id": "785d37cb-1fb4-4a91-a923-d5a78a37f36a", - "metadata": { - "tags": [] - }, - "outputs": [], - "source": [ - "df.columns = fields_clean" - ] - }, - { - "cell_type": "code", - "execution_count": null, - "id": "aaad8f07", - "metadata": {}, - "outputs": [], - "source": [ - "assert fields_orig != fields_clean" - ] - }, - { - "cell_type": "code", - "execution_count": null, - "id": "1bf212cb-1653-457b-9f5d-416d4dd14b53", - "metadata": { - "tags": [] - }, - "outputs": [], - "source": [ - "df.head()" - ] - }, - { - "cell_type": "markdown", - "id": "1bfaeb22-26fb-4964-a71f-cae8335e5372", - "metadata": {}, - "source": [ - "## Data cleaning" - ] - }, - { - "cell_type": "code", - "execution_count": null, - "id": "7e746003-cb1f-434f-bba6-00f0c439c4ac", - "metadata": { - "tags": [] - }, - "outputs": [], - "source": [ - "def generate_buchwald_hartwig_rxns(df):\n", - " \"\"\"\n", - " Converts the entries in the excel files to reaction SMILES.\n", - " From: https://github.com/reymond-group/drfp/blob/main/scripts/encoding/encode_buchwald_hartwig_reactions.py\n", - " and https://github.com/rxn4chemistry/rxn_yields/blob/master/rxn_yields/data.py\n", - " \"\"\"\n", - " df = df.copy()\n", - " fwd_template = \"[F,Cl,Br,I]-[c;H0;D3;+0:1](:[c,n:2]):[c,n:3].[NH2;D1;+0:4]-[c:5]>>[c,n:2]:[c;H0;D3;+0:1](:[c,n:3])-[NH;D2;+0:4]-[c:5]\"\n", - " methylaniline = \"Cc1ccc(N)cc1\"\n", - " pd_catalyst = \"O=S(=O)(O[Pd]1~[NH2]C2C=CC=CC=2C2C=CC=CC1=2)C(F)(F)F\"\n", - " methylaniline_mol = Chem.MolFromSmiles(methylaniline)\n", - " rxn = rdChemReactions.ReactionFromSmarts(fwd_template)\n", - " products = []\n", - "\n", - " for i, row in df.iterrows():\n", - " reacts = (Chem.MolFromSmiles(row[\"aryl_halide\"]), methylaniline_mol)\n", - " rxn_products = rxn.RunReactants(reacts)\n", - "\n", - " rxn_products_smiles = set([Chem.MolToSmiles(mol[0]) for mol in rxn_products])\n", - " assert len(rxn_products_smiles) == 1\n", - " products.append(list(rxn_products_smiles)[0])\n", - "\n", - " df[\"product\"] = products\n", - " rxns = []\n", - "\n", - " for i, row in df.iterrows():\n", - " reactants = Chem.MolToSmiles(\n", - " Chem.MolFromSmiles(\n", - " f\"{row['aryl_halide']}.{methylaniline}.{pd_catalyst}.{row['ligand']}.{row['base']}.{row['additive']}\"\n", - " )\n", - " )\n", - " rxns.append(f\"{reactants.replace('N~', '[NH2]')}>>{row['product']}\")\n", - "\n", - " return rxns\n", - "\n", - "reaction_SMILES = generate_buchwald_hartwig_rxns(df)\n", - "df.insert(4, 'reaction_SMILES', reaction_SMILES)" - ] - }, - { - "cell_type": "code", - "execution_count": null, - "id": "d544fa60-343e-40e1-bd0c-4750f07a7145", - "metadata": { - "tags": [] - }, - "outputs": [], - "source": [ - "assert not df.duplicated().sum()" - ] - }, - { - "cell_type": "markdown", - "id": "bc6f52c1-e0f6-48b3-95f4-e36d9a5ecde8", - "metadata": {}, - "source": [ - "## Save to csv" - ] - }, - { - "cell_type": "code", - "execution_count": null, - "id": "d6d5efa5-b4b4-4a25-8626-e10f3d691e83", - "metadata": { - "tags": [] - }, - "outputs": [], - "source": [ - "fn_data_csv = \"data_clean.csv\"" - ] - }, - { - "cell_type": "code", - "execution_count": null, - "id": "727f8d7b-cbb6-43c7-9eab-9d4d65be6b3f", - "metadata": { - "tags": [] - }, - "outputs": [], - "source": [ - "df.to_csv(fn_data_csv, index=False)" - ] - }, - { - "cell_type": "code", - "execution_count": null, - "id": "63c8d4a4-906e-418d-be39-879365b4dfa0", - "metadata": { - "tags": [] - }, - "outputs": [], - "source": [ - "!ls -lh {fn_data_csv}" - ] - }, - { - "cell_type": "code", - "execution_count": null, - "id": "a51b9001-25d7-4e0e-a607-477cfc4a9f1c", - "metadata": { - "tags": [] - }, - "outputs": [], - "source": [ - "!head -n 5 {fn_data_csv}" - ] - }, - { - "cell_type": "code", - "execution_count": null, - "id": "1a512943-4909-4d56-867d-50c151d8d607", - "metadata": { - "tags": [] - }, - "outputs": [], - "source": [ - "df.head()" - ] - }, - { - "cell_type": "markdown", - "id": "f3d730ce-fce0-49df-9eb8-b917e945fa9a", - "metadata": {}, - "source": [ - "## Load from csv" - ] - }, - { - "cell_type": "code", - "execution_count": null, - "id": "077b0c5f-8772-4879-9317-3fa28799689b", - "metadata": { - "tags": [] - }, - "outputs": [], - "source": [ - "fn_data_csv = \"data_clean.csv\"" - ] - }, - { - "cell_type": "code", - "execution_count": null, - "id": "6eaef0e6-2115-4793-ac43-a196b25d47a0", - "metadata": { - "tags": [] - }, - "outputs": [], - "source": [ - "df = pd.read_csv(fn_data_csv)" - ] - }, - { - "cell_type": "code", - "execution_count": null, - "id": "43619e7c-9c82-4ff0-ae25-403861304635", - "metadata": { - "tags": [] - }, - "outputs": [], - "source": [ - "df.head()" - ] - }, - { - "cell_type": "markdown", - "id": "2f06e57c-02c5-493b-af65-c8bb9ac59421", - "metadata": {}, - "source": [ - "# meta YAML" - ] - }, - { - "cell_type": "code", - "execution_count": null, - "id": "49771077-471d-4d71-a9a7-d6b094bbc4f3", - "metadata": { - "tags": [] - }, - "outputs": [], - "source": [ - "df.head()" - ] - }, - { - "cell_type": "code", - "execution_count": null, - "id": "d3890961-444e-4a26-b8fc-ed8c4e959af9", - "metadata": { - "tags": [] - }, - "outputs": [], - "source": [ - "meta = {\n", - " \"name\": \"buchwald_hartwig_doyle\", # unique identifier, we will also use this for directory names\n", - " \"description\": \"\"\"High-throughput experimentation palladium-catalyzed Buchwald Hardwig C-N cross-coupling data set with yields.\"\"\",\n", - " \"targets\": [\n", - " {\n", - " \"id\": \"yield\", # name of the column in a tabular dataset\n", - " \"description\": \"Reaction yields analyzed by UPLC\", # description of what this column means\n", - " \"units\": \"%\", # units of the values in this column (leave empty if unitless)\n", - " \"type\": \"continuous\", # can be \"categorical\", \"ordinal\", \"continuous\"\n", - " \"names\": [ # names for the property (to sample from for building the prompts)\n", - " \"Reaction yield\",\n", - " \"yield\",\n", - " ],\n", - " },\n", - " ],\n", - " \"identifiers\": [\n", - " {\n", - " \"id\": \"reaction_SMILES\", # column name\n", - " \"type\": \"RXN-SMILES\", # can be \"SMILES\", \"SELFIES\", \"IUPAC\", \"Other\"\n", - " \"description\": \"RXN-SMILES\", # description (optional, except for \"Other\")\n", - " },\n", - " {\n", - " \"id\": \"ligand\", # column name\n", - " \"type\": \"SMILES\", # can be \"SMILES\", \"SELFIES\", \"IUPAC\", \"Other\"\n", - " \"description\": \"ligand SMILES\", # description (optional, except for \"Other\")\n", - " },\n", - " {\n", - " \"id\": \"additive\", # column name\n", - " \"type\": \"SMILES\", # can be \"SMILES\", \"SELFIES\", \"IUPAC\", \"Other\"\n", - " \"description\": \"additive SMILES\", # description (optional, except for \"Other\")\n", - " },\n", - " {\n", - " \"id\": \"base\", # column name\n", - " \"type\": \"SMILES\", # can be \"SMILES\", \"SELFIES\", \"IUPAC\", \"Other\"\n", - " \"description\": \"base SMILES\", # description (optional, except for \"Other\")\n", - " },\n", - " {\n", - " \"id\": \"aryl_halide\", # column name\n", - " \"type\": \"SMILES\", # can be \"SMILES\", \"SELFIES\", \"IUPAC\", \"Other\"\n", - " \"description\": \"aryl halide SMILES\", # description (optional, except for \"Other\")\n", - " },\n", - " ],\n", - " \"license\": \"MIT\", # license under which the original dataset was published\n", - " \"links\": [ # list of relevant links (original dataset, other uses, etc.)\n", - " {\n", - " \"url\": \"https://doi.org/10.1126/science.aar5169\",\n", - " \"description\": \"corresponding publication\",\n", - " },\n", - " {\n", - " \"url\": \"https://www.sciencedirect.com/science/article/pii/S2451929420300851\",\n", - " \"description\": \"publication with data processing\",\n", - " },\n", - " {\n", - " \"url\": \"https://github.com/rxn4chemistry/rxn_yields/blob/master/rxn_yields/data.py\",\n", - " \"description\": \"preprocessing\",\n", - " },\n", - " {\n", - " \"url\": \"https://github.com/reymond-group/drfp/tree/main/data\",\n", - " \"description\": \"dataset\",\n", - " }\n", - " ],\n", - " \"num_points\": len(df), # number of datapoints in this dataset\n", - " \"url\": \"https://tdcommons.ai/single_pred_tasks/tox/#acute-toxicity-ld50\",\n", - " \"bibtex\": [\n", - " \"\"\"@article{ahneman2018predicting,\n", - " title={Predicting reaction performance in C--N cross-coupling using machine learning},\n", - " author={Ahneman, Derek T and Estrada, Jes{\\'u}s G and Lin, Shishi and Dreher, Spencer D and Doyle, Abigail G},\n", - " journal={Science},\n", - " volume={360},\n", - " number={6385},\n", - " pages={186--190},\n", - " year={2018},\n", - " publisher={American Association for the Advancement of Science}\n", - "}\n", - "}\"\"\",\n", - " ],\n", - "}" - ] - }, - { - "cell_type": "code", - "execution_count": null, - "id": "ec455cf0-962a-4c0d-bb3e-066e415ffd9b", - "metadata": { - "tags": [] - }, - "outputs": [], - "source": [ - "def str_presenter(dumper, data):\n", - " \"\"\"configures yaml for dumping multiline strings\n", - " Ref: https://stackoverflow.com/questions/8640959/how-can-i-control-what-scalar-form-pyyaml-uses-for-my-data\n", - " \"\"\"\n", - " if data.count(\"\\n\") > 0: # check for multiline string\n", - " return dumper.represent_scalar(\"tag:yaml.org,2002:str\", data, style=\"|\")\n", - " return dumper.represent_scalar(\"tag:yaml.org,2002:str\", data)\n", - "\n", - "\n", - "yaml.add_representer(str, str_presenter)\n", - "yaml.representer.SafeRepresenter.add_representer(\n", - " str, str_presenter\n", - ") # to use with safe_dum" - ] - }, - { - "cell_type": "code", - "execution_count": null, - "id": "580bbd79-4845-4515-be94-3e4a9815d048", - "metadata": { - "tags": [] - }, - "outputs": [], - "source": [ - "fn_meta = \"meta.yaml\"" - ] - }, - { - "cell_type": "code", - "execution_count": null, - "id": "873fa5dd-9b60-40f5-b537-4d7a206414ea", - "metadata": { - "tags": [] - }, - "outputs": [], - "source": [ - "with open(fn_meta, \"w\") as f:\n", - " yaml.dump(meta, f, sort_keys=False)" - ] - }, - { - "cell_type": "code", - "execution_count": null, - "id": "d01686c0-6746-4fc4-b019-350270dfc26f", - "metadata": { - "tags": [] - }, - "outputs": [], - "source": [ - "!ls -lh {fn_meta}" - ] - }, - { - "cell_type": "code", - "execution_count": null, - "id": "ef6063c5-7a8b-4344-bccf-a073443feebf", - "metadata": { - "tags": [] - }, - "outputs": [], - "source": [ - "!cat {fn_meta}" - ] - }, - { - "cell_type": "markdown", - "id": "bd3f930a-638b-4bb7-a1d2-80688f2f6891", - "metadata": {}, - "source": [ - "# create transform.py" - ] - }, - { - "cell_type": "code", - "execution_count": null, - "id": "9aab00fd-58a8-40b0-be30-1e269e0d323b", - "metadata": { - "tags": [] - }, - "outputs": [], - "source": [ - "path_file = \"transform.py\"" - ] - }, - { - "cell_type": "code", - "execution_count": null, - "id": "8368bb20-8e1c-4b7d-b0e2-b39da36b5972", - "metadata": { - "tags": [] - }, - "outputs": [], - "source": [ - "%%writefile $path_file\n", - "import pandas as pd\n", - "import yaml\n", - "from rdkit import Chem # 2022.9.5\n", - "from rdkit.Chem import rdChemReactions\n", - "\n", - "def generate_buchwald_hartwig_rxns(df):\n", - " \"\"\"\n", - " Converts the entries in the excel files to reaction SMILES.\n", - " From: https://github.com/reymond-group/drfp/blob/main/scripts/encoding/encode_buchwald_hartwig_reactions.py\n", - " and https://github.com/rxn4chemistry/rxn_yields/blob/master/rxn_yields/data.py\n", - " \"\"\"\n", - " df = df.copy()\n", - " fwd_template = \"[F,Cl,Br,I]-[c;H0;D3;+0:1](:[c,n:2]):[c,n:3].[NH2;D1;+0:4]-[c:5]>>[c,n:2]:[c;H0;D3;+0:1](:[c,n:3])-[NH;D2;+0:4]-[c:5]\"\n", - " methylaniline = \"Cc1ccc(N)cc1\"\n", - " pd_catalyst = \"O=S(=O)(O[Pd]1~[NH2]C2C=CC=CC=2C2C=CC=CC1=2)C(F)(F)F\"\n", - " methylaniline_mol = Chem.MolFromSmiles(methylaniline)\n", - " rxn = rdChemReactions.ReactionFromSmarts(fwd_template)\n", - " products = []\n", - "\n", - " for i, row in df.iterrows():\n", - " reacts = (Chem.MolFromSmiles(row[\"aryl_halide\"]), methylaniline_mol)\n", - " rxn_products = rxn.RunReactants(reacts)\n", - "\n", - " rxn_products_smiles = set([Chem.MolToSmiles(mol[0]) for mol in rxn_products])\n", - " assert len(rxn_products_smiles) == 1\n", - " products.append(list(rxn_products_smiles)[0])\n", - "\n", - " df[\"product\"] = products\n", - " rxns = []\n", - "\n", - " for i, row in df.iterrows():\n", - " reactants = Chem.MolToSmiles(\n", - " Chem.MolFromSmiles(\n", - " f\"{row['aryl_halide']}.{methylaniline}.{pd_catalyst}.{row['ligand']}.{row['base']}.{row['additive']}\"\n", - " )\n", - " )\n", - " rxns.append(f\"{reactants.replace('N~', '[NH2]')}>>{row['product']}\")\n", - "\n", - " return rxns\n", - "\n", - "def get_and_transform_data():\n", - " # get raw data\n", - " fn_data_original = \"Dreher_and_Doyle_input_data.csv\"\n", - " data = pd.read_excel('https://github.com/reymond-group/drfp/raw/main/data/Dreher_and_Doyle_input_data.xlsx')\n", - " data.to_csv(fn_data_original, index=False)\n", - " \n", - " # create dataframe\n", - " df = pd.read_csv(\n", - " fn_data_original,\n", - " delimiter=\",\",\n", - " ) # not necessary but ensure we can load the saved data\n", - "\n", - " # check if fields are the same\n", - " fields_orig = df.columns.tolist()\n", - " assert fields_orig == [\n", - " 'Ligand',\n", - " 'Additive', \n", - " 'Base', \n", - " 'Aryl halide', \n", - " 'Output'\n", - " ]\n", - "\n", - " # overwrite column names = fields\n", - " fields_clean = [\n", - " \"ligand\",\n", - " \"additive\",\n", - " \"base\",\n", - " \"aryl_halide\",\n", - " 'yield'\n", - " ]\n", - " df.columns = fields_clean\n", - "\n", - " # data cleaning\n", - " reaction_SMILES = generate_buchwald_hartwig_rxns(df) # compile reactions\n", - " df.insert(4, 'reaction_SMILES', reaction_SMILES) # add reaction SMILES column\n", - "\n", - " assert not df.duplicated().sum()\n", - "\n", - " # save to csv\n", - " fn_data_csv = \"data_clean.csv\"\n", - " df.to_csv(fn_data_csv, index=False)\n", - "\n", - " # create meta yaml\n", - " meta = {\n", - " \"name\": \"buchwald_hartwig_doyle\", # unique identifier, we will also use this for directory names\n", - " \"description\": \"\"\"High-throughput experimentation palladium-catalyzed Buchwald Hardwig C-N cross-coupling data set with yields.\"\"\",\n", - " \"targets\": [\n", - " {\n", - " \"id\": \"yield\", # name of the column in a tabular dataset\n", - " \"description\": \"Reaction yields analyzed by UPLC\", # description of what this column means\n", - " \"units\": \"%\", # units of the values in this column (leave empty if unitless)\n", - " \"type\": \"continuous\", # can be \"categorical\", \"ordinal\", \"continuous\"\n", - " \"names\": [ # names for the property (to sample from for building the prompts)\n", - " \"Reaction yield\",\n", - " \"yield\",\n", - " ],\n", - " },\n", - " ],\n", - " \"identifiers\": [\n", - " {\n", - " \"id\": \"reaction_SMILES\", # column name\n", - " \"type\": \"RXN-SMILES\", # can be \"SMILES\", \"SELFIES\", \"IUPAC\", \"Other\"\n", - " \"description\": \"RXN-SMILES\", # description (optional, except for \"Other\")\n", - " },\n", - " {\n", - " \"id\": \"ligand\", # column name\n", - " \"type\": \"SMILES\", # can be \"SMILES\", \"SELFIES\", \"IUPAC\", \"Other\"\n", - " \"description\": \"ligand SMILES\", # description (optional, except for \"Other\")\n", - " },\n", - " {\n", - " \"id\": \"additive\", # column name\n", - " \"type\": \"SMILES\", # can be \"SMILES\", \"SELFIES\", \"IUPAC\", \"Other\"\n", - " \"description\": \"additive SMILES\", # description (optional, except for \"Other\")\n", - " },\n", - " {\n", - " \"id\": \"base\", # column name\n", - " \"type\": \"SMILES\", # can be \"SMILES\", \"SELFIES\", \"IUPAC\", \"Other\"\n", - " \"description\": \"base SMILES\", # description (optional, except for \"Other\")\n", - " },\n", - " {\n", - " \"id\": \"aryl_halide\", # column name\n", - " \"type\": \"SMILES\", # can be \"SMILES\", \"SELFIES\", \"IUPAC\", \"Other\"\n", - " \"description\": \"aryl halide SMILES\", # description (optional, except for \"Other\")\n", - " },\n", - " ],\n", - " \"license\": \"MIT\", # license under which the original dataset was published\n", - " \"links\": [ # list of relevant links (original dataset, other uses, etc.)\n", - " {\n", - " \"url\": \"https://doi.org/10.1126/science.aar5169\",\n", - " \"description\": \"corresponding publication\",\n", - " },\n", - " {\n", - " \"url\": \"https://www.sciencedirect.com/science/article/pii/S2451929420300851\",\n", - " \"description\": \"publication with data processing\",\n", - " },\n", - " {\n", - " \"url\": \"https://github.com/rxn4chemistry/rxn_yields/blob/master/rxn_yields/data.py\",\n", - " \"description\": \"preprocessing\",\n", - " },\n", - " {\n", - " \"url\": \"https://github.com/reymond-group/drfp/tree/main/data\",\n", - " \"description\": \"dataset\",\n", - " }\n", - " ],\n", - " \"num_points\": len(df), # number of datapoints in this dataset\n", - " \"url\": \"https://doi.org/10.1126/science.aar5169\",\n", - " \"bibtex\": [\n", - " \"\"\"@article{ahneman2018predicting,\n", - "title={Predicting reaction performance in C--N cross-coupling using machine learning},\n", - "author={Ahneman, Derek T and Estrada, Jes{\\'u}s G and Lin, Shishi and Dreher, Spencer D and Doyle, Abigail G},\n", - "journal={Science},\n", - "volume={360},\n", - "number={6385},\n", - "pages={186--190},\n", - "year={2018},\n", - "publisher={American Association for the Advancement of Science},\n", - "}\"\"\",\n", - " ],\n", - " }\n", - "\n", - " def str_presenter(dumper, data):\n", - " \"\"\"configures yaml for dumping multiline strings\n", - " Ref: https://stackoverflow.com/questions/8640959/how-can-i-control-what-scalar-form-pyyaml-uses-for-my-data\n", - " \"\"\"\n", - " if data.count(\"\\n\") > 0: # check for multiline string\n", - " return dumper.represent_scalar(\"tag:yaml.org,2002:str\", data, style=\"|\")\n", - " return dumper.represent_scalar(\"tag:yaml.org,2002:str\", data)\n", - "\n", - " yaml.add_representer(str, str_presenter)\n", - " yaml.representer.SafeRepresenter.add_representer(\n", - " str, str_presenter\n", - " ) # to use with safe_dum\n", - " fn_meta = \"meta.yaml\"\n", - " with open(fn_meta, \"w\") as f:\n", - " yaml.dump(meta, f, sort_keys=False)\n", - "\n", - " print(f\"Finished processing {meta['name']} dataset!\")\n", - "\n", - "\n", - "if __name__ == \"__main__\":\n", - " get_and_transform_data()" - ] - }, - { - "cell_type": "code", - "execution_count": null, - "id": "d0474f26-70f3-4655-b81a-df4ada90e7a6", - "metadata": { - "tags": [] - }, - "outputs": [], - "source": [ - "!python3 transform.py" - ] - }, - { - "cell_type": "code", - "execution_count": null, - "id": "953e7bee-bd5e-41d0-a2be-506e0bc97727", - "metadata": { - "tags": [] - }, - "outputs": [], - "source": [ - "ls -lh # fmt: skip" - ] - }, - { - "cell_type": "markdown", - "id": "0b08ed06-ba66-4f76-bde1-368ea77d1739", - "metadata": {}, - "source": [ - "# End" - ] - } - ], - "metadata": { - "kernelspec": { - "display_name": "Python 3 (ipykernel)", - "language": "python", - "name": "python3" - }, - "language_info": { - "codemirror_mode": { - "name": "ipython", - "version": 3 - }, - "file_extension": ".py", - "mimetype": "text/x-python", - "name": "python", - "nbconvert_exporter": "python", - "pygments_lexer": "ipython3", - "version": "3.8.16" - } - }, - "nbformat": 4, - "nbformat_minor": 5 -} diff --git a/data/buchwald_hartwig/meta.yaml b/data/buchwald_hartwig/meta.yaml index 367821f63..988a03dc9 100644 --- a/data/buchwald_hartwig/meta.yaml +++ b/data/buchwald_hartwig/meta.yaml @@ -11,20 +11,8 @@ targets: - yield identifiers: - id: reaction_SMILES - type: RXN-SMILES - description: RXN-SMILES -- id: ligand - type: SMILES - description: ligand SMILES -- id: additive - type: SMILES - description: additive SMILES -- id: base - type: SMILES - description: base SMILES -- id: aryl_halide - type: SMILES - description: aryl halide SMILES + type: RXNSMILES + description: RXNSMILES license: MIT links: - url: https://doi.org/10.1126/science.aar5169 diff --git a/data/buchwald_hartwig/transform.py b/data/buchwald_hartwig/transform.py index 4192fdf01..88da56838 100644 --- a/data/buchwald_hartwig/transform.py +++ b/data/buchwald_hartwig/transform.py @@ -99,28 +99,8 @@ def get_and_transform_data(): "identifiers": [ { "id": "reaction_SMILES", # column name - "type": "RXN-SMILES", # can be "SMILES", "SELFIES", "IUPAC", "Other" - "description": "RXN-SMILES", # description (optional, except for "Other") - }, - { - "id": "ligand", # column name - "type": "SMILES", # can be "SMILES", "SELFIES", "IUPAC", "Other" - "description": "ligand SMILES", # description (optional, except for "Other") - }, - { - "id": "additive", # column name - "type": "SMILES", # can be "SMILES", "SELFIES", "IUPAC", "Other" - "description": "additive SMILES", # description (optional, except for "Other") - }, - { - "id": "base", # column name - "type": "SMILES", # can be "SMILES", "SELFIES", "IUPAC", "Other" - "description": "base SMILES", # description (optional, except for "Other") - }, - { - "id": "aryl_halide", # column name - "type": "SMILES", # can be "SMILES", "SELFIES", "IUPAC", "Other" - "description": "aryl halide SMILES", # description (optional, except for "Other") + "type": "RXNSMILES", # can be "SMILES", "SELFIES", "IUPAC", "Other" + "description": "RXNSMILES", # description (optional, except for "Other") }, ], "license": "MIT", # license under which the original dataset was published