Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
COc1ccccc1C(=O)Nc1cccc(-c2nn3ccccc3c2-c2ccnc(Nc3cccc(F)c3)n2)c1
InChiKey
DVAMYPPVGUECJY-UHFFFAOYSA-N
Route Signature
6d64a9d56d2627e2f387e636258076e85c20bb034ff08f3d187056d3087ffc0b
Synthesis route with 6 steps
Route tree structure (JSON format)
{
"route": {
"id": "sa_a059a178eec596303bd914d1",
"signature": "6d64a9d56d2627e2f387e636258076e85c20bb034ff08f3d187056d3087ffc0b",
"contentHash": "0ea3aaf203c25b4094ebc282c7e23aad1c7e36fd136cf73f291dcc6de9a92d86",
"length": 6,
"isConvergent": false
},
"target": {
"id": "sa_81f7612ded57ea18bf7cf647",
"benchmarkSetId": "61e696668b63e77d7c2a29c0821768e1c383de8313852d6e995224859494442e",
"targetId": "n5-00497",
"moleculeId": "sa_eccdb4ecae6a31850d8ee453",
"smiles": "COc1ccccc1C(=O)Nc1cccc(-c2nn3ccccc3c2-c2ccnc(Nc3cccc(F)c3)n2)c1",
"routeLength": 6,
"isConvergent": false,
"metadata": null,
"molecule": {
"id": "sa_eccdb4ecae6a31850d8ee453",
"inchikey": "DVAMYPPVGUECJY-UHFFFAOYSA-N",
"smiles": "COc1ccccc1C(=O)Nc1cccc(-c2nn3ccccc3c2-c2ccnc(Nc3cccc(F)c3)n2)c1"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "4346",
"routeId": "sa_a059a178eec596303bd914d1",
"moleculeId": "sa_eccdb4ecae6a31850d8ee453",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_eccdb4ecae6a31850d8ee453",
"inchikey": "DVAMYPPVGUECJY-UHFFFAOYSA-N",
"smiles": "COc1ccccc1C(=O)Nc1cccc(-c2nn3ccccc3c2-c2ccnc(Nc3cccc(F)c3)n2)c1"
},
"smiles": "COc1ccccc1C(=O)Nc1cccc(-c2nn3ccccc3c2-c2ccnc(Nc3cccc(F)c3)n2)c1",
"reactionStepId": "sa_e8aa4de6173b85e811cc2508",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20080051395A1;0582;551382\",\"rsmi\":\"Cl[C:5]([c:4]1[c:3]([O:2][CH3:1])[cH:40][cH:39][cH:38][cH:37]1)=[O:6].[NH2:7][c:8]1[cH:9][c:10](-[c:11]2[n:12][n:13]3[cH:14][cH:15][cH:16][cH:17][c:18]3[c:19]2-[c:20]2[n:21][c:22]([NH:23][c:24]3[cH:25][c:26]([F:27])[cH:28][cH:29][cH:30]3)[n:31][cH:32][cH:33]2)[cH:34][cH:35][cH:36]1>O=C(Nc1cccc(-c2nn3ccccc3c2-c2ccnc(Nc3ccc4c(c3)CNCC4)n2)c1)c1ccccc1>[CH3:1][O:2][c:3]1[c:4]([C:5](=[O:6])[NH:7][c:8]2[cH:9][c:10](-[c:11]3[n:12][n:13]4[cH:14][cH:15][cH:16][cH:17][c:18]4[c:19]3-[c:20]3[n:21][c:22]([NH:23][c:24]4[cH:25][c:26]([F:27])[cH:28][cH:29][cH:30]4)[n:31][cH:32][cH:33]3)[cH:34][cH:35][cH:36]2)[cH:37][cH:38][cH:39][cH:40]1\"},\"mapped_reaction_smiles\":\"Cl[C:5]([c:4]1[c:3]([O:2][CH3:1])[cH:40][cH:39][cH:38][cH:37]1)=[O:6].[NH2:7][c:8]1[cH:9][c:10](-[c:11]2[n:12][n:13]3[cH:14][cH:15][cH:16][cH:17][c:18]3[c:19]2-[c:20]2[n:21][c:22]([NH:23][c:24]3[cH:25][c:26]([F:27])[cH:28][cH:29][cH:30]3)[n:31][cH:32][cH:33]2)[cH:34][cH:35][cH:36]1>O=C(Nc1cccc(-c2nn3ccccc3c2-c2ccnc(Nc3ccc4c(c3)CNCC4)n2)c1)c1ccccc1>[CH3:1][O:2][c:3]1[c:4]([C:5](=[O:6])[NH:7][c:8]2[cH:9][c:10](-[c:11]3[n:12][n:13]4[cH:14][cH:15][cH:16][cH:17][c:18]4[c:19]3-[c:20]3[n:21][c:22]([NH:23][c:24]4[cH:25][c:26]([F:27])[cH:28][cH:29][cH:30]4)[n:31][cH:32][cH:33]3)[cH:34][cH:35][cH:36]2)[cH:37][cH:38][cH:39][cH:40]1\"}",
"reactionStep": {
"id": "sa_e8aa4de6173b85e811cc2508",
"reactionHash": "bc2142d3051867c29753148b3bc5fecbbd0813fd8fef5e0eeb0310ae82816ca4"
},
"children": [
{
"id": "4347",
"routeId": "sa_a059a178eec596303bd914d1",
"moleculeId": "sa_4439a5ed62096790cd898596",
"parentId": "4346",
"isLeaf": false,
"molecule": {
"id": "sa_4439a5ed62096790cd898596",
"inchikey": "GMXBLJMKACTXLV-UHFFFAOYSA-N",
"smiles": "Nc1cccc(-c2nn3ccccc3c2-c2ccnc(Nc3cccc(F)c3)n2)c1"
},
"smiles": "Nc1cccc(-c2nn3ccccc3c2-c2ccnc(Nc3cccc(F)c3)n2)c1",
"reactionStepId": "sa_a1c30972d55c13fb9fdbffb4",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20080051395A1;0433;551364\",\"rsmi\":\"O=C(C(F)(F)F)[NH:1][c:2]1[cH:3][cH:4][cH:5][c:6](-[c:7]2[n:8][n:9]3[cH:10][cH:11][cH:12][cH:13][c:14]3[c:15]2-[c:16]2[n:17][c:18]([NH:19][c:20]3[cH:21][c:22]([F:23])[cH:24][cH:25][cH:26]3)[n:27][cH:28][cH:29]2)[cH:30]1>C1CCOC1.O.[Li+].O>[NH2:1][c:2]1[cH:3][cH:4][cH:5][c:6](-[c:7]2[n:8][n:9]3[cH:10][cH:11][cH:12][cH:13][c:14]3[c:15]2-[c:16]2[n:17][c:18]([NH:19][c:20]3[cH:21][c:22]([F:23])[cH:24][cH:25][cH:26]3)[n:27][cH:28][cH:29]2)[cH:30]1\"},\"mapped_reaction_smiles\":\"O=C(C(F)(F)F)[NH:1][c:2]1[cH:3][cH:4][cH:5][c:6](-[c:7]2[n:8][n:9]3[cH:10][cH:11][cH:12][cH:13][c:14]3[c:15]2-[c:16]2[n:17][c:18]([NH:19][c:20]3[cH:21][c:22]([F:23])[cH:24][cH:25][cH:26]3)[n:27][cH:28][cH:29]2)[cH:30]1>C1CCOC1.O.[Li+].O>[NH2:1][c:2]1[cH:3][cH:4][cH:5][c:6](-[c:7]2[n:8][n:9]3[cH:10][cH:11][cH:12][cH:13][c:14]3[c:15]2-[c:16]2[n:17][c:18]([NH:19][c:20]3[cH:21][c:22]([F:23])[cH:24][cH:25][cH:26]3)[n:27][cH:28][cH:29]2)[cH:30]1\"}",
"reactionStep": {
"id": "sa_a1c30972d55c13fb9fdbffb4",
"reactionHash": "6d4c9472427e5ad6220560e90a3b09e77819af6446fdbd2ae0d94b72cca9123f"
},
"children": [
{
"id": "4348",
"routeId": "sa_a059a178eec596303bd914d1",
"moleculeId": "sa_af953ed6dbe0153f83080a44",
"parentId": "4347",
"isLeaf": false,
"molecule": {
"id": "sa_af953ed6dbe0153f83080a44",
"inchikey": "CXBVOBHLHAKKER-UHFFFAOYSA-N",
"smiles": "O=C(Nc1cccc(-c2nn3ccccc3c2-c2ccnc(Nc3cccc(F)c3)n2)c1)C(F)(F)F"
},
"smiles": "O=C(Nc1cccc(-c2nn3ccccc3c2-c2ccnc(Nc3cccc(F)c3)n2)c1)C(F)(F)F",
"reactionStepId": "sa_d4ca0759cfb71e4d329b45d3",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20080051395A1;0431;551363\",\"rsmi\":\"Cl[c:18]1[n:17][c:16](-[c:15]2[c:7](-[c:6]3[cH:5][c:4]([NH:3][C:2](=[O:1])[C:33]([F:34])([F:35])[F:36])[cH:32][cH:31][cH:30]3)[n:8][n:9]3[cH:10][cH:11][cH:12][cH:13][c:14]32)[cH:29][cH:28][n:27]1.[NH2:19][c:20]1[cH:21][c:22]([F:23])[cH:24][cH:25][cH:26]1>CCO.Cl>[O:1]=[C:2]([NH:3][c:4]1[cH:5][c:6](-[c:7]2[n:8][n:9]3[cH:10][cH:11][cH:12][cH:13][c:14]3[c:15]2-[c:16]2[n:17][c:18]([NH:19][c:20]3[cH:21][c:22]([F:23])[cH:24][cH:25][cH:26]3)[n:27][cH:28][cH:29]2)[cH:30][cH:31][cH:32]1)[C:33]([F:34])([F:35])[F:36]\"},\"mapped_reaction_smiles\":\"Cl[c:18]1[n:17][c:16](-[c:15]2[c:7](-[c:6]3[cH:5][c:4]([NH:3][C:2](=[O:1])[C:33]([F:34])([F:35])[F:36])[cH:32][cH:31][cH:30]3)[n:8][n:9]3[cH:10][cH:11][cH:12][cH:13][c:14]32)[cH:29][cH:28][n:27]1.[NH2:19][c:20]1[cH:21][c:22]([F:23])[cH:24][cH:25][cH:26]1>CCO.Cl>[O:1]=[C:2]([NH:3][c:4]1[cH:5][c:6](-[c:7]2[n:8][n:9]3[cH:10][cH:11][cH:12][cH:13][c:14]3[c:15]2-[c:16]2[n:17][c:18]([NH:19][c:20]3[cH:21][c:22]([F:23])[cH:24][cH:25][cH:26]3)[n:27][cH:28][cH:29]2)[cH:30][cH:31][cH:32]1)[C:33]([F:34])([F:35])[F:36]\"}",
"reactionStep": {
"id": "sa_d4ca0759cfb71e4d329b45d3",
"reactionHash": "361ace9b06710cdfdf02a7c1f4f5dd79e9320224d0701973263d2004ce4b2fd3"
},
"children": [
{
"id": "4349",
"routeId": "sa_a059a178eec596303bd914d1",
"moleculeId": "sa_7cef75cd2e714b119ac11e9b",
"parentId": "4348",
"isLeaf": false,
"molecule": {
"id": "sa_7cef75cd2e714b119ac11e9b",
"inchikey": "KCOPUHFXXXTSSJ-UHFFFAOYSA-N",
"smiles": "O=C(Nc1cccc(-c2nn3ccccc3c2-c2ccnc(Cl)n2)c1)C(F)(F)F"
},
"smiles": "O=C(Nc1cccc(-c2nn3ccccc3c2-c2ccnc(Cl)n2)c1)C(F)(F)F",
"reactionStepId": "sa_c9a897cd17cfe04e94365adf",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20080051395A1;0429;551362\",\"rsmi\":\"[NH2:8][n+:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1.[O:1]=[C:2]([NH:3][c:4]1[cH:5][c:6]([C:7]#[C:15][c:16]2[n:17][c:18]([Cl:19])[n:20][cH:21][cH:22]2)[cH:23][cH:24][cH:25]1)[C:26]([F:27])([F:28])[F:29]>CCOC(C)=O.CS(C)=O.O=C(O)O.I.[K+].[K+].[K+].O>[O:1]=[C:2]([NH:3][c:4]1[cH:5][c:6](-[c:7]2[n:8][n:9]3[cH:10][cH:11][cH:12][cH:13][c:14]3[c:15]2-[c:16]2[n:17][c:18]([Cl:19])[n:20][cH:21][cH:22]2)[cH:23][cH:24][cH:25]1)[C:26]([F:27])([F:28])[F:29]\"},\"mapped_reaction_smiles\":\"[NH2:8][n+:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1.[O:1]=[C:2]([NH:3][c:4]1[cH:5][c:6]([C:7]#[C:15][c:16]2[n:17][c:18]([Cl:19])[n:20][cH:21][cH:22]2)[cH:23][cH:24][cH:25]1)[C:26]([F:27])([F:28])[F:29]>CCOC(C)=O.CS(C)=O.O=C(O)O.I.[K+].[K+].[K+].O>[O:1]=[C:2]([NH:3][c:4]1[cH:5][c:6](-[c:7]2[n:8][n:9]3[cH:10][cH:11][cH:12][cH:13][c:14]3[c:15]2-[c:16]2[n:17][c:18]([Cl:19])[n:20][cH:21][cH:22]2)[cH:23][cH:24][cH:25]1)[C:26]([F:27])([F:28])[F:29]\"}",
"reactionStep": {
"id": "sa_c9a897cd17cfe04e94365adf",
"reactionHash": "f84cee5574ab59a7b4838a518927cd94a09dd18a6797066c55d4f7473cf5bead"
},
"children": [
{
"id": "4350",
"routeId": "sa_a059a178eec596303bd914d1",
"moleculeId": "sa_e3628d1ef585524d88c5837c",
"parentId": "4349",
"isLeaf": true,
"molecule": {
"id": "sa_e3628d1ef585524d88c5837c",
"inchikey": "PFZCOWLKXHIVII-UHFFFAOYSA-N",
"smiles": "N[n+]1ccccc1"
},
"smiles": "N[n+]1ccccc1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "4351",
"routeId": "sa_a059a178eec596303bd914d1",
"moleculeId": "sa_7c182719a8aeab12252141b7",
"parentId": "4349",
"isLeaf": false,
"molecule": {
"id": "sa_7c182719a8aeab12252141b7",
"inchikey": "XERBXSYUCWBBDL-UHFFFAOYSA-N",
"smiles": "O=C(Nc1cccc(C#Cc2ccnc(Cl)n2)c1)C(F)(F)F"
},
"smiles": "O=C(Nc1cccc(C#Cc2ccnc(Cl)n2)c1)C(F)(F)F",
"reactionStepId": "sa_047fe07ff2909369520e2a58",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20080051395A1;0427;551361\",\"rsmi\":\"Cl[c:9]1[n:10][c:11]([Cl:12])[n:13][cH:14][cH:15]1.[O:1]=[C:2]([NH:3][c:4]1[cH:5][c:6]([C:7]#[CH:8])[cH:16][cH:17][cH:18]1)[C:19]([F:20])([F:21])[F:22]>C1CCOC1.CCN(CC)CC.ClCCl.Cl[Pd](Cl)([PH](c1ccccc1)(c1ccccc1)c1ccccc1)[PH](c1ccccc1)(c1ccccc1)c1ccccc1.[Cu]I>[O:1]=[C:2]([NH:3][c:4]1[cH:5][c:6]([C:7]#[C:8][c:9]2[n:10][c:11]([Cl:12])[n:13][cH:14][cH:15]2)[cH:16][cH:17][cH:18]1)[C:19]([F:20])([F:21])[F:22]\"},\"mapped_reaction_smiles\":\"Cl[c:9]1[n:10][c:11]([Cl:12])[n:13][cH:14][cH:15]1.[O:1]=[C:2]([NH:3][c:4]1[cH:5][c:6]([C:7]#[CH:8])[cH:16][cH:17][cH:18]1)[C:19]([F:20])([F:21])[F:22]>C1CCOC1.CCN(CC)CC.ClCCl.Cl[Pd](Cl)([PH](c1ccccc1)(c1ccccc1)c1ccccc1)[PH](c1ccccc1)(c1ccccc1)c1ccccc1.[Cu]I>[O:1]=[C:2]([NH:3][c:4]1[cH:5][c:6]([C:7]#[C:8][c:9]2[n:10][c:11]([Cl:12])[n:13][cH:14][cH:15]2)[cH:16][cH:17][cH:18]1)[C:19]([F:20])([F:21])[F:22]\"}",
"reactionStep": {
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"reactionHash": "be9a8cfe4269947fa64af48c312ae6b2daa68e784ec909189da92b71f9161da8"
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"children": [
{
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"parentId": "4351",
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"molecule": {
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"inchikey": "BTTNYQZNBZNDOR-UHFFFAOYSA-N",
"smiles": "Clc1ccnc(Cl)n1"
},
"smiles": "Clc1ccnc(Cl)n1",
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},
{
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"molecule": {
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"inchikey": "COKSSWIDWMHFIJ-UHFFFAOYSA-N",
"smiles": "C#Cc1cccc(NC(=O)C(F)(F)F)c1"
},
"smiles": "C#Cc1cccc(NC(=O)C(F)(F)F)c1",
"reactionStepId": "sa_a1581cfdc3034f23456d7a7e",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20080051395A1;0425;551360\",\"rsmi\":\"O=C(O[C:9](=[O:10])[C:11]([F:12])([F:13])[F:14])C(F)(F)F.[CH:1]#[C:2][c:3]1[cH:4][cH:5][cH:6][c:7]([NH2:8])[cH:15]1>CCN(CC)CC.ClCCl.O>[CH:1]#[C:2][c:3]1[cH:4][cH:5][cH:6][c:7]([NH:8][C:9](=[O:10])[C:11]([F:12])([F:13])[F:14])[cH:15]1\"},\"mapped_reaction_smiles\":\"O=C(O[C:9](=[O:10])[C:11]([F:12])([F:13])[F:14])C(F)(F)F.[CH:1]#[C:2][c:3]1[cH:4][cH:5][cH:6][c:7]([NH2:8])[cH:15]1>CCN(CC)CC.ClCCl.O>[CH:1]#[C:2][c:3]1[cH:4][cH:5][cH:6][c:7]([NH:8][C:9](=[O:10])[C:11]([F:12])([F:13])[F:14])[cH:15]1\"}",
"reactionStep": {
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"reactionHash": "057d4069d1263fccedd0fd8bb82bdfe9820086fb7409bf257d1c1ed4cd4bc3f0"
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"children": [
{
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"moleculeId": "sa_8c445d9cf27dba67d86b6886",
"parentId": "4353",
"isLeaf": true,
"molecule": {
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"inchikey": "NNKQLUVBPJEUOR-UHFFFAOYSA-N",
"smiles": "C#Cc1cccc(N)c1"
},
"smiles": "C#Cc1cccc(N)c1",
"reactionStepId": null,
"template": null,
"metadata": null,
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},
{
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"molecule": {
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"inchikey": "QAEDZJGFFMLHHQ-UHFFFAOYSA-N",
"smiles": "O=C(OC(=O)C(F)(F)F)C(F)(F)F"
},
"smiles": "O=C(OC(=O)C(F)(F)F)C(F)(F)F",
"reactionStepId": null,
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}
]
}
]
}
]
},
{
"id": "4356",
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"moleculeId": "sa_83571f2399894ffd67beb08b",
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"molecule": {
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"inchikey": "QZVQQUVWFIZUBQ-UHFFFAOYSA-N",
"smiles": "Nc1cccc(F)c1"
},
"smiles": "Nc1cccc(F)c1",
"reactionStepId": null,
"template": null,
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"children": []
}
]
}
]
},
{
"id": "4357",
"routeId": "sa_a059a178eec596303bd914d1",
"moleculeId": "sa_eea0e162407e4f21e051c9b9",
"parentId": "4346",
"isLeaf": true,
"molecule": {
"id": "sa_eea0e162407e4f21e051c9b9",
"inchikey": "RZNHSEZOLFEFGB-UHFFFAOYSA-N",
"smiles": "COc1ccccc1C(=O)Cl"
},
"smiles": "COc1ccccc1C(=O)Cl",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
}
}