Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
[N-]=[N+]=NCC1(C2CCCCC2)CCNCC1
InChiKey
WUZAFJKEBCQJMO-UHFFFAOYSA-N
Route Signature
0e041a60aaa5f36d757b97776b0cd34e5f0914cec49b460c1aec097adff1f515
Synthesis route with 5 steps
Route tree structure (JSON format)
{
"route": {
"id": "sa_765924969d4e2e6251b07018",
"signature": "0e041a60aaa5f36d757b97776b0cd34e5f0914cec49b460c1aec097adff1f515",
"contentHash": "cb0f28d678a4310fe7ba4429fb7ac73d608a6e4e83df396dda1f3fe3f867c71e",
"length": 5,
"isConvergent": false
},
"target": {
"id": "sa_b36b2e0d2d14cdeb139d3940",
"benchmarkSetId": "61e696668b63e77d7c2a29c0821768e1c383de8313852d6e995224859494442e",
"targetId": "n5-00618",
"moleculeId": "sa_cba97635ea90ab31a44a0988",
"smiles": "[N-]=[N+]=NCC1(C2CCCCC2)CCNCC1",
"routeLength": 5,
"isConvergent": false,
"metadata": null,
"molecule": {
"id": "sa_cba97635ea90ab31a44a0988",
"inchikey": "WUZAFJKEBCQJMO-UHFFFAOYSA-N",
"smiles": "[N-]=[N+]=NCC1(C2CCCCC2)CCNCC1"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "13606",
"routeId": "sa_765924969d4e2e6251b07018",
"moleculeId": "sa_cba97635ea90ab31a44a0988",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_cba97635ea90ab31a44a0988",
"inchikey": "WUZAFJKEBCQJMO-UHFFFAOYSA-N",
"smiles": "[N-]=[N+]=NCC1(C2CCCCC2)CCNCC1"
},
"smiles": "[N-]=[N+]=NCC1(C2CCCCC2)CCNCC1",
"reactionStepId": "sa_38dbb8c5d984d941219bb017",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20050239835A1;0210;294322\",\"rsmi\":\"CC(C)(C)OC(=O)[N:14]1[CH2:13][CH2:12][C:5]([CH2:4][N:3]=[N+:2]=[N-:1])([CH:6]2[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11]2)[CH2:16][CH2:15]1>ClCCl.O.O=C(O)C(F)(F)F.O=C(O)C(F)(F)F>[N-:1]=[N+:2]=[N:3][CH2:4][C:5]1([CH:6]2[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11]2)[CH2:12][CH2:13][NH:14][CH2:15][CH2:16]1\"},\"mapped_reaction_smiles\":\"CC(C)(C)OC(=O)[N:14]1[CH2:13][CH2:12][C:5]([CH2:4][N:3]=[N+:2]=[N-:1])([CH:6]2[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11]2)[CH2:16][CH2:15]1>ClCCl.O.O=C(O)C(F)(F)F.O=C(O)C(F)(F)F>[N-:1]=[N+:2]=[N:3][CH2:4][C:5]1([CH:6]2[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11]2)[CH2:12][CH2:13][NH:14][CH2:15][CH2:16]1\"}",
"reactionStep": {
"id": "sa_38dbb8c5d984d941219bb017",
"reactionHash": "397f90b826639d9a32e1e391dce8d303e3ba1c3770e72749487ea8444d6a4938"
},
"children": [
{
"id": "13607",
"routeId": "sa_765924969d4e2e6251b07018",
"moleculeId": "sa_570c99aa331d40f52090a2eb",
"parentId": "13606",
"isLeaf": false,
"molecule": {
"id": "sa_570c99aa331d40f52090a2eb",
"inchikey": "ZLXFHQVRNVOZNZ-UHFFFAOYSA-N",
"smiles": "CC(C)(C)OC(=O)N1CCC(CN=[N+]=[N-])(C2CCCCC2)CC1"
},
"smiles": "CC(C)(C)OC(=O)N1CCC(CN=[N+]=[N-])(C2CCCCC2)CC1",
"reactionStepId": "sa_fcc7b1e1b8c8af6faa6a72f5",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20050239835A1;0189;294315\",\"rsmi\":\"CS(=O)(=O)O[CH2:12][C:11]1([CH:16]2[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21]2)[CH2:10][CH2:9][N:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:23][CH2:22]1.[N-:13]=[N+:14]=[N-:15]>CN(C)C=O.[Na+]>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][C:11]([CH2:12][N:13]=[N+:14]=[N-:15])([CH:16]2[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21]2)[CH2:22][CH2:23]1\"},\"mapped_reaction_smiles\":\"CS(=O)(=O)O[CH2:12][C:11]1([CH:16]2[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21]2)[CH2:10][CH2:9][N:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:23][CH2:22]1.[N-:13]=[N+:14]=[N-:15]>CN(C)C=O.[Na+]>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][C:11]([CH2:12][N:13]=[N+:14]=[N-:15])([CH:16]2[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21]2)[CH2:22][CH2:23]1\"}",
"reactionStep": {
"id": "sa_fcc7b1e1b8c8af6faa6a72f5",
"reactionHash": "fd2b174c1094282f14b3d64b4a41613f5743766358abf115e30f2f8e18e40178"
},
"children": [
{
"id": "13608",
"routeId": "sa_765924969d4e2e6251b07018",
"moleculeId": "sa_50a8f83dd89c267fbada1205",
"parentId": "13607",
"isLeaf": true,
"molecule": {
"id": "sa_50a8f83dd89c267fbada1205",
"inchikey": "IVRMZWNICZWHMI-UHFFFAOYSA-N",
"smiles": "[N]N=[N-]"
},
"smiles": "[N-]=[N+]=[N-]",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "13609",
"routeId": "sa_765924969d4e2e6251b07018",
"moleculeId": "sa_88fc5879e4d9fe6c1eff961c",
"parentId": "13607",
"isLeaf": false,
"molecule": {
"id": "sa_88fc5879e4d9fe6c1eff961c",
"inchikey": "JKKXRUOPAPMBQK-UHFFFAOYSA-N",
"smiles": "CC(C)(C)OC(=O)N1CCC(COS(C)(=O)=O)(C2CCCCC2)CC1"
},
"smiles": "CC(C)(C)OC(=O)N1CCC(COS(C)(=O)=O)(C2CCCCC2)CC1",
"reactionStepId": "sa_ecbbc4ea5d3d7a663ef4e8e5",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20050239835A1;0187;294313\",\"rsmi\":\"Cl[S:14]([CH3:15])(=[O:16])=[O:17].[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][C:11]([CH2:12][OH:13])([CH:18]2[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23]2)[CH2:24][CH2:25]1>CCN(CC)CC.ClCCl>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][C:11]([CH2:12][O:13][S:14]([CH3:15])(=[O:16])=[O:17])([CH:18]2[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23]2)[CH2:24][CH2:25]1\"},\"mapped_reaction_smiles\":\"Cl[S:14]([CH3:15])(=[O:16])=[O:17].[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][C:11]([CH2:12][OH:13])([CH:18]2[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23]2)[CH2:24][CH2:25]1>CCN(CC)CC.ClCCl>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][C:11]([CH2:12][O:13][S:14]([CH3:15])(=[O:16])=[O:17])([CH:18]2[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23]2)[CH2:24][CH2:25]1\"}",
"reactionStep": {
"id": "sa_ecbbc4ea5d3d7a663ef4e8e5",
"reactionHash": "6e997031ed85dbf9fad6405843a367449251971473c6072219b48f237ae02058"
},
"children": [
{
"id": "13610",
"routeId": "sa_765924969d4e2e6251b07018",
"moleculeId": "sa_eec4038933fb4c226757d912",
"parentId": "13609",
"isLeaf": false,
"molecule": {
"id": "sa_eec4038933fb4c226757d912",
"inchikey": "MCWICGADBUTRHW-UHFFFAOYSA-N",
"smiles": "CC(C)(C)OC(=O)N1CCC(CO)(C2CCCCC2)CC1"
},
"smiles": "CC(C)(C)OC(=O)N1CCC(CO)(C2CCCCC2)CC1",
"reactionStepId": "sa_7d12a74e690cc5052ee57477",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20050239835A1;0184;294312\",\"rsmi\":\"CC(C)(C)OC(=O)O[C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7].[NH:8]1[CH2:9][CH2:10][C:11]([CH2:12][OH:13])([CH:14]2[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19]2)[CH2:20][CH2:21]1>CCN(CC)CC.CO>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][C:11]([CH2:12][OH:13])([CH:14]2[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19]2)[CH2:20][CH2:21]1\"},\"mapped_reaction_smiles\":\"CC(C)(C)OC(=O)O[C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7].[NH:8]1[CH2:9][CH2:10][C:11]([CH2:12][OH:13])([CH:14]2[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19]2)[CH2:20][CH2:21]1>CCN(CC)CC.CO>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][C:11]([CH2:12][OH:13])([CH:14]2[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19]2)[CH2:20][CH2:21]1\"}",
"reactionStep": {
"id": "sa_7d12a74e690cc5052ee57477",
"reactionHash": "0db3d084c245c45abd106c56731f30e61efd745d443799e99aade701ce87647e"
},
"children": [
{
"id": "13611",
"routeId": "sa_765924969d4e2e6251b07018",
"moleculeId": "sa_c8b01995022c931fe19bab43",
"parentId": "13610",
"isLeaf": false,
"molecule": {
"id": "sa_c8b01995022c931fe19bab43",
"inchikey": "BLYNJUPGKWMAJS-UHFFFAOYSA-N",
"smiles": "OCC1(C2CCCCC2)CCNCC1"
},
"smiles": "OCC1(C2CCCCC2)CCNCC1",
"reactionStepId": "sa_fb2b1b6c2f669e9792f3e566",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20050239835A1;0183;294311\",\"rsmi\":\"CCO[C:2](=[O:1])[C:3]1([CH:4]2[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9]2)[CH2:10][CH2:11][NH:12][CH2:13][CH2:14]1>C1CCOC1.[Al+3].[HH].[HH].[HH].[HH].[Li+]>[OH:1][CH2:2][C:3]1([CH:4]2[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9]2)[CH2:10][CH2:11][NH:12][CH2:13][CH2:14]1\"},\"mapped_reaction_smiles\":\"CCO[C:2](=[O:1])[C:3]1([CH:4]2[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9]2)[CH2:10][CH2:11][NH:12][CH2:13][CH2:14]1>C1CCOC1.[Al+3].[HH].[HH].[HH].[HH].[Li+]>[OH:1][CH2:2][C:3]1([CH:4]2[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9]2)[CH2:10][CH2:11][NH:12][CH2:13][CH2:14]1\"}",
"reactionStep": {
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"reactionHash": "b85a9ac478d0b3c9280d47360c178096f0aa317ff7dff7c0e00059af75b0fa2d"
},
"children": [
{
"id": "13612",
"routeId": "sa_765924969d4e2e6251b07018",
"moleculeId": "sa_b0ef2974465d69ba3a26756c",
"parentId": "13611",
"isLeaf": true,
"molecule": {
"id": "sa_b0ef2974465d69ba3a26756c",
"inchikey": "JSMBTKFFHHEAHY-UHFFFAOYSA-N",
"smiles": "CCOC(=O)C1(C2CCCCC2)CCNCC1"
},
"smiles": "CCOC(=O)C1(C2CCCCC2)CCNCC1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
},
{
"id": "13613",
"routeId": "sa_765924969d4e2e6251b07018",
"moleculeId": "sa_b273d4d4546165bca2b249b5",
"parentId": "13610",
"isLeaf": true,
"molecule": {
"id": "sa_b273d4d4546165bca2b249b5",
"inchikey": "DYHSDKLCOJIUFX-UHFFFAOYSA-N",
"smiles": "CC(C)(C)OC(=O)OC(=O)OC(C)(C)C"
},
"smiles": "CC(C)(C)OC(=O)OC(=O)OC(C)(C)C",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
},
{
"id": "13614",
"routeId": "sa_765924969d4e2e6251b07018",
"moleculeId": "sa_d2a31ea58046b00856f61ca5",
"parentId": "13609",
"isLeaf": true,
"molecule": {
"id": "sa_d2a31ea58046b00856f61ca5",
"inchikey": "QARBMVPHQWIHKH-UHFFFAOYSA-N",
"smiles": "CS(=O)(=O)Cl"
},
"smiles": "CS(=O)(=O)Cl",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
}
]
}
]
}
}