Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
COc1cc2cc3c(Nc4ccc(Sc5nccn5C)c(Cl)c4)c(C#N)cnc3cc2cc1OCCN1CCN(C)CC1
InChiKey
IEHZWINDMIVDML-UHFFFAOYSA-N
Route Signature
20a952be397941fb29f54a1fe5842188e38a0d9b5ad86a16203a23290af47bae
Synthesis route with 5 steps
Route tree structure (JSON format)
{
"route": {
"id": "sa_a88310d7de5fb149bbc04c36",
"signature": "20a952be397941fb29f54a1fe5842188e38a0d9b5ad86a16203a23290af47bae",
"contentHash": "8b964c7bd7e820c8b3cacd70bfcf5b0af4c9681766787db776802cd75437da39",
"length": 5,
"isConvergent": false
},
"target": {
"id": "sa_8efece90f0e6236e13d0f50e",
"benchmarkSetId": "61e696668b63e77d7c2a29c0821768e1c383de8313852d6e995224859494442e",
"targetId": "n5-00842",
"moleculeId": "sa_c3bcf70606a16b25791c4869",
"smiles": "COc1cc2cc3c(Nc4ccc(Sc5nccn5C)c(Cl)c4)c(C#N)cnc3cc2cc1OCCN1CCN(C)CC1",
"routeLength": 5,
"isConvergent": false,
"metadata": null,
"molecule": {
"id": "sa_c3bcf70606a16b25791c4869",
"inchikey": "IEHZWINDMIVDML-UHFFFAOYSA-N",
"smiles": "COc1cc2cc3c(Nc4ccc(Sc5nccn5C)c(Cl)c4)c(C#N)cnc3cc2cc1OCCN1CCN(C)CC1"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "13834",
"routeId": "sa_a88310d7de5fb149bbc04c36",
"moleculeId": "sa_c3bcf70606a16b25791c4869",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_c3bcf70606a16b25791c4869",
"inchikey": "IEHZWINDMIVDML-UHFFFAOYSA-N",
"smiles": "COc1cc2cc3c(Nc4ccc(Sc5nccn5C)c(Cl)c4)c(C#N)cnc3cc2cc1OCCN1CCN(C)CC1"
},
"smiles": "COc1cc2cc3c(Nc4ccc(Sc5nccn5C)c(Cl)c4)c(C#N)cnc3cc2cc1OCCN1CCN(C)CC1",
"reactionStepId": "sa_48c3ee1e3d24b21c176531a2",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20080171874A1;0222;592693\",\"rsmi\":\"Cl[CH2:36][CH2:35][O:34][c:33]1[c:3]([O:2][CH3:1])[cH:4][c:5]2[c:6]([cH:7][c:8]3[n:9][cH:10][c:11]([C:12]#[N:13])[c:14]([NH:15][c:16]4[cH:17][c:18]([Cl:19])[c:20]([S:21][c:22]5[n:23][cH:24][cH:25][n:26]5[CH3:27])[cH:28][cH:29]4)[c:30]3[cH:31]2)[cH:32]1.[NH:37]1[CH2:38][CH2:39][N:40]([CH3:41])[CH2:42][CH2:43]1>I.[Na+]>[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([cH:7][c:8]3[n:9][cH:10][c:11]([C:12]#[N:13])[c:14]([NH:15][c:16]4[cH:17][c:18]([Cl:19])[c:20]([S:21][c:22]5[n:23][cH:24][cH:25][n:26]5[CH3:27])[cH:28][cH:29]4)[c:30]3[cH:31]2)[cH:32][c:33]1[O:34][CH2:35][CH2:36][N:37]1[CH2:38][CH2:39][N:40]([CH3:41])[CH2:42][CH2:43]1\"},\"mapped_reaction_smiles\":\"Cl[CH2:36][CH2:35][O:34][c:33]1[c:3]([O:2][CH3:1])[cH:4][c:5]2[c:6]([cH:7][c:8]3[n:9][cH:10][c:11]([C:12]#[N:13])[c:14]([NH:15][c:16]4[cH:17][c:18]([Cl:19])[c:20]([S:21][c:22]5[n:23][cH:24][cH:25][n:26]5[CH3:27])[cH:28][cH:29]4)[c:30]3[cH:31]2)[cH:32]1.[NH:37]1[CH2:38][CH2:39][N:40]([CH3:41])[CH2:42][CH2:43]1>I.[Na+]>[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([cH:7][c:8]3[n:9][cH:10][c:11]([C:12]#[N:13])[c:14]([NH:15][c:16]4[cH:17][c:18]([Cl:19])[c:20]([S:21][c:22]5[n:23][cH:24][cH:25][n:26]5[CH3:27])[cH:28][cH:29]4)[c:30]3[cH:31]2)[cH:32][c:33]1[O:34][CH2:35][CH2:36][N:37]1[CH2:38][CH2:39][N:40]([CH3:41])[CH2:42][CH2:43]1\"}",
"reactionStep": {
"id": "sa_48c3ee1e3d24b21c176531a2",
"reactionHash": "347aead7e423465c84dfe61f022aaab4632ed4d3a657a53bc8de0a18a0daa34f"
},
"children": [
{
"id": "13835",
"routeId": "sa_a88310d7de5fb149bbc04c36",
"moleculeId": "sa_56beac43e963b864d3b34186",
"parentId": "13834",
"isLeaf": false,
"molecule": {
"id": "sa_56beac43e963b864d3b34186",
"inchikey": "DJKIDWDDWUSYTA-UHFFFAOYSA-N",
"smiles": "COc1cc2cc3c(Nc4ccc(Sc5nccn5C)c(Cl)c4)c(C#N)cnc3cc2cc1OCCCl"
},
"smiles": "COc1cc2cc3c(Nc4ccc(Sc5nccn5C)c(Cl)c4)c(C#N)cnc3cc2cc1OCCCl",
"reactionStepId": "sa_3b4c20f4d41a20755a5e4571",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20080171874A1;0195;592689\",\"rsmi\":\"Cc1ccc(S(=O)(=O)O[CH2:35][CH2:36][Cl:37])cc1.[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([cH:7][c:8]3[n:9][cH:10][c:11]([C:12]#[N:13])[c:14]([NH:15][c:16]4[cH:17][c:18]([Cl:19])[c:20]([S:21][c:22]5[n:23][cH:24][cH:25][n:26]5[CH3:27])[cH:28][cH:29]4)[c:30]3[cH:31]2)[cH:32][c:33]1[OH:34]>CN(C)C=O.O=C(O)O.[Cs+].[Cs+]>[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([cH:7][c:8]3[n:9][cH:10][c:11]([C:12]#[N:13])[c:14]([NH:15][c:16]4[cH:17][c:18]([Cl:19])[c:20]([S:21][c:22]5[n:23][cH:24][cH:25][n:26]5[CH3:27])[cH:28][cH:29]4)[c:30]3[cH:31]2)[cH:32][c:33]1[O:34][CH2:35][CH2:36][Cl:37]\"},\"mapped_reaction_smiles\":\"Cc1ccc(S(=O)(=O)O[CH2:35][CH2:36][Cl:37])cc1.[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([cH:7][c:8]3[n:9][cH:10][c:11]([C:12]#[N:13])[c:14]([NH:15][c:16]4[cH:17][c:18]([Cl:19])[c:20]([S:21][c:22]5[n:23][cH:24][cH:25][n:26]5[CH3:27])[cH:28][cH:29]4)[c:30]3[cH:31]2)[cH:32][c:33]1[OH:34]>CN(C)C=O.O=C(O)O.[Cs+].[Cs+]>[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([cH:7][c:8]3[n:9][cH:10][c:11]([C:12]#[N:13])[c:14]([NH:15][c:16]4[cH:17][c:18]([Cl:19])[c:20]([S:21][c:22]5[n:23][cH:24][cH:25][n:26]5[CH3:27])[cH:28][cH:29]4)[c:30]3[cH:31]2)[cH:32][c:33]1[O:34][CH2:35][CH2:36][Cl:37]\"}",
"reactionStep": {
"id": "sa_3b4c20f4d41a20755a5e4571",
"reactionHash": "856f348a44b5ac0d472e067b725949dd95aeffaedfc87184d13aff67078e45bd"
},
"children": [
{
"id": "13836",
"routeId": "sa_a88310d7de5fb149bbc04c36",
"moleculeId": "sa_e62cb08c61682b951c9a322e",
"parentId": "13835",
"isLeaf": false,
"molecule": {
"id": "sa_e62cb08c61682b951c9a322e",
"inchikey": "LFVSDXRDHOZQLZ-UHFFFAOYSA-N",
"smiles": "COc1cc2cc3c(Nc4ccc(Sc5nccn5C)c(Cl)c4)c(C#N)cnc3cc2cc1O"
},
"smiles": "COc1cc2cc3c(Nc4ccc(Sc5nccn5C)c(Cl)c4)c(C#N)cnc3cc2cc1O",
"reactionStepId": "sa_0f47e39d20a03e538695a306",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20080171874A1;0189;592688\",\"rsmi\":\"Cl[c:17]1[c:14]([C:15]#[N:16])[cH:13][n:12][c:11]2[cH:10][c:6]3[c:5]([cH:4][c:3]([O:2][CH3:1])[c:8]([OH:9])[cH:7]3)[cH:34][c:33]21.[NH2:18][c:19]1[cH:20][c:21]([Cl:22])[c:23]([S:24][c:25]2[n:26][cH:27][cH:28][n:29]2[CH3:30])[cH:31][cH:32]1>CCOCCO.Cl.O=C(O)O.[Na+].[Na+].c1ccncc1>[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([cH:7][c:8]1[OH:9])[cH:10][c:11]1[n:12][cH:13][c:14]([C:15]#[N:16])[c:17]([NH:18][c:19]3[cH:20][c:21]([Cl:22])[c:23]([S:24][c:25]4[n:26][cH:27][cH:28][n:29]4[CH3:30])[cH:31][cH:32]3)[c:33]1[cH:34]2\"},\"mapped_reaction_smiles\":\"Cl[c:17]1[c:14]([C:15]#[N:16])[cH:13][n:12][c:11]2[cH:10][c:6]3[c:5]([cH:4][c:3]([O:2][CH3:1])[c:8]([OH:9])[cH:7]3)[cH:34][c:33]21.[NH2:18][c:19]1[cH:20][c:21]([Cl:22])[c:23]([S:24][c:25]2[n:26][cH:27][cH:28][n:29]2[CH3:30])[cH:31][cH:32]1>CCOCCO.Cl.O=C(O)O.[Na+].[Na+].c1ccncc1>[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([cH:7][c:8]1[OH:9])[cH:10][c:11]1[n:12][cH:13][c:14]([C:15]#[N:16])[c:17]([NH:18][c:19]3[cH:20][c:21]([Cl:22])[c:23]([S:24][c:25]4[n:26][cH:27][cH:28][n:29]4[CH3:30])[cH:31][cH:32]3)[c:33]1[cH:34]2\"}",
"reactionStep": {
"id": "sa_0f47e39d20a03e538695a306",
"reactionHash": "057a834e8ee930c3efdd482a69079a80a69c35244a8d94f6abd8d690cf2778c4"
},
"children": [
{
"id": "13837",
"routeId": "sa_a88310d7de5fb149bbc04c36",
"moleculeId": "sa_9b37d193e59ea0e25d82b8bb",
"parentId": "13836",
"isLeaf": false,
"molecule": {
"id": "sa_9b37d193e59ea0e25d82b8bb",
"inchikey": "IOYHLUXVJXTLSH-UHFFFAOYSA-N",
"smiles": "COc1cc2cc3c(Cl)c(C#N)cnc3cc2cc1O"
},
"smiles": "COc1cc2cc3c(Cl)c(C#N)cnc3cc2cc1O",
"reactionStepId": "sa_f59abec33db358dee7ceb0b2",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20080171874A1;0183;592687\",\"rsmi\":\"O=P(Cl)(Cl)[Cl:18].O=[c:17]1[c:14]([C:15]#[N:16])[cH:13][nH:12][c:11]2[cH:10][c:6]3[c:5]([cH:4][c:3]([O:2][CH3:1])[c:8]([OH:9])[cH:7]3)[cH:20][c:19]21>Cc1ccccc1>[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([cH:7][c:8]1[OH:9])[cH:10][c:11]1[n:12][cH:13][c:14]([C:15]#[N:16])[c:17]([Cl:18])[c:19]1[cH:20]2\"},\"mapped_reaction_smiles\":\"O=P(Cl)(Cl)[Cl:18].O=[c:17]1[c:14]([C:15]#[N:16])[cH:13][nH:12][c:11]2[cH:10][c:6]3[c:5]([cH:4][c:3]([O:2][CH3:1])[c:8]([OH:9])[cH:7]3)[cH:20][c:19]21>Cc1ccccc1>[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([cH:7][c:8]1[OH:9])[cH:10][c:11]1[n:12][cH:13][c:14]([C:15]#[N:16])[c:17]([Cl:18])[c:19]1[cH:20]2\"}",
"reactionStep": {
"id": "sa_f59abec33db358dee7ceb0b2",
"reactionHash": "da09a968136948d937f28c29bc3c332626b883c656f50b96b043bcfd2742e7ea"
},
"children": [
{
"id": "13838",
"routeId": "sa_a88310d7de5fb149bbc04c36",
"moleculeId": "sa_3f8613028148f9b660a14320",
"parentId": "13837",
"isLeaf": false,
"molecule": {
"id": "sa_3f8613028148f9b660a14320",
"inchikey": "HAIDIZXQSBGAJI-UHFFFAOYSA-N",
"smiles": "COc1cc2cc3c(=O)c(C#N)c[nH]c3cc2cc1O"
},
"smiles": "COc1cc2cc3c(=O)c(C#N)c[nH]c3cc2cc1O",
"reactionStepId": "sa_267aaca4b21e10d05f1b4566",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20080171874A1;0177;592686\",\"rsmi\":\"c1ccc(C[O:9][c:8]2[c:3]([O:2][CH3:1])[cH:4][c:5]3[c:6]([cH:7]2)[cH:10][c:11]2[nH:12][cH:13][c:14]([C:15]#[N:16])[c:17](=[O:18])[c:19]2[cH:20]3)cc1>CCOCC.CN(C)C=O.[Pd]>[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([cH:7][c:8]1[OH:9])[cH:10][c:11]1[nH:12][cH:13][c:14]([C:15]#[N:16])[c:17](=[O:18])[c:19]1[cH:20]2\"},\"mapped_reaction_smiles\":\"c1ccc(C[O:9][c:8]2[c:3]([O:2][CH3:1])[cH:4][c:5]3[c:6]([cH:7]2)[cH:10][c:11]2[nH:12][cH:13][c:14]([C:15]#[N:16])[c:17](=[O:18])[c:19]2[cH:20]3)cc1>CCOCC.CN(C)C=O.[Pd]>[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([cH:7][c:8]1[OH:9])[cH:10][c:11]1[nH:12][cH:13][c:14]([C:15]#[N:16])[c:17](=[O:18])[c:19]1[cH:20]2\"}",
"reactionStep": {
"id": "sa_267aaca4b21e10d05f1b4566",
"reactionHash": "ae7ebc47b9ecbfb90f39630ac21ba52dc2297ddd8e89f7b190daa7d1712540eb"
},
"children": [
{
"id": "13839",
"routeId": "sa_a88310d7de5fb149bbc04c36",
"moleculeId": "sa_09ab55a048c893f53ed89622",
"parentId": "13838",
"isLeaf": true,
"molecule": {
"id": "sa_09ab55a048c893f53ed89622",
"inchikey": "MVRYYBDBEYYHRV-UHFFFAOYSA-N",
"smiles": "COc1cc2cc3c(=O)c(C#N)c[nH]c3cc2cc1OCc1ccccc1"
},
"smiles": "COc1cc2cc3c(=O)c(C#N)c[nH]c3cc2cc1OCc1ccccc1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
},
{
"id": "13840",
"routeId": "sa_a88310d7de5fb149bbc04c36",
"moleculeId": "sa_312a7cd3d48a055e9bc98180",
"parentId": "13837",
"isLeaf": true,
"molecule": {
"id": "sa_312a7cd3d48a055e9bc98180",
"inchikey": "XHXFXVLFKHQFAL-UHFFFAOYSA-N",
"smiles": "O=P(Cl)(Cl)Cl"
},
"smiles": "O=P(Cl)(Cl)Cl",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
},
{
"id": "13841",
"routeId": "sa_a88310d7de5fb149bbc04c36",
"moleculeId": "sa_08772e8b5271aca3e0209b89",
"parentId": "13836",
"isLeaf": true,
"molecule": {
"id": "sa_08772e8b5271aca3e0209b89",
"inchikey": "VEKOZCQMIHXUDA-UHFFFAOYSA-N",
"smiles": "Cn1ccnc1Sc1ccc(N)cc1Cl"
},
"smiles": "Cn1ccnc1Sc1ccc(N)cc1Cl",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
},
{
"id": "13842",
"routeId": "sa_a88310d7de5fb149bbc04c36",
"moleculeId": "sa_bf8953522263b3720f2f873b",
"parentId": "13835",
"isLeaf": true,
"molecule": {
"id": "sa_bf8953522263b3720f2f873b",
"inchikey": "ZXNMIUJDTOMBPV-UHFFFAOYSA-N",
"smiles": "Cc1ccc(S(=O)(=O)OCCCl)cc1"
},
"smiles": "Cc1ccc(S(=O)(=O)OCCCl)cc1",
"reactionStepId": null,
"template": null,
"metadata": null,
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"children": []
}
]
},
{
"id": "13843",
"routeId": "sa_a88310d7de5fb149bbc04c36",
"moleculeId": "sa_513cbf1b8d13aff0b62eb838",
"parentId": "13834",
"isLeaf": true,
"molecule": {
"id": "sa_513cbf1b8d13aff0b62eb838",
"inchikey": "PVOAHINGSUIXLS-UHFFFAOYSA-N",
"smiles": "CN1CCNCC1"
},
"smiles": "CN1CCNCC1",
"reactionStepId": null,
"template": null,
"metadata": null,
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"children": []
}
]
}
}