Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
COc1cc(NCCN2C3C=C(c4ccc5ccccc5c4)CC2CC3)c2ncccc2c1
InChiKey
WOQOCASFWYMVKW-UHFFFAOYSA-N
Route Signature
dcc611a15bb99973e24245fa738353fcbaf526acfc481c8841868958838d0d95
Synthesis route with 3 steps (convergent)
Route tree structure (JSON format)
{
"route": {
"id": "sa_f458e10860be9e6c2ca849ab",
"signature": "dcc611a15bb99973e24245fa738353fcbaf526acfc481c8841868958838d0d95",
"contentHash": "1a94644afe77148590484bf752a73e2899cbe6f3540e20aa4bf5de7676a038c1",
"length": 3,
"isConvergent": true
},
"target": {
"id": "sa_cdd588a832981e6cb2de87ba",
"benchmarkSetId": "3895c2909c53593560c5ba610abc7e6df80513dfd8624165c560451735097d36",
"targetId": "n5-07772",
"moleculeId": "sa_92f4d85b71fc405544674adc",
"smiles": "COc1cc(NCCN2C3C=C(c4ccc5ccccc5c4)CC2CC3)c2ncccc2c1",
"routeLength": 3,
"isConvergent": true,
"metadata": null,
"molecule": {
"id": "sa_92f4d85b71fc405544674adc",
"inchikey": "WOQOCASFWYMVKW-UHFFFAOYSA-N",
"smiles": "COc1cc(NCCN2C3C=C(c4ccc5ccccc5c4)CC2CC3)c2ncccc2c1"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "11805",
"routeId": "sa_f458e10860be9e6c2ca849ab",
"moleculeId": "sa_92f4d85b71fc405544674adc",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_92f4d85b71fc405544674adc",
"inchikey": "WOQOCASFWYMVKW-UHFFFAOYSA-N",
"smiles": "COc1cc(NCCN2C3C=C(c4ccc5ccccc5c4)CC2CC3)c2ncccc2c1"
},
"smiles": "COc1cc(NCCN2C3C=C(c4ccc5ccccc5c4)CC2CC3)c2ncccc2c1",
"reactionStepId": "sa_478a2ce6464a8b3ad455c7ee",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US06632824B2;;623385\",\"rsmi\":\"Br[c:5]1[cH:4][c:3]([O:2][CH3:1])[cH:33][c:32]2[c:27]1[n:28][cH:29][cH:30][cH:31]2.[NH2:6][CH2:7][CH2:8][N:9]1[CH:10]2[CH:11]=[C:12]([c:13]3[cH:14][c:15]4[cH:16][cH:17][cH:18][cH:19][c:20]4[cH:21][cH:22]3)[CH2:23][CH:24]1[CH2:25][CH2:26]2>CC(C)(C)P(c1ccccc1-c1ccccc1)C(C)(C)C.Cc1ccccc1.O.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.[Pd].[Pd]>[CH3:1][O:2][c:3]1[cH:4][c:5]([NH:6][CH2:7][CH2:8][N:9]2[CH:10]3[CH:11]=[C:12]([c:13]4[cH:14][c:15]5[cH:16][cH:17][cH:18][cH:19][c:20]5[cH:21][cH:22]4)[CH2:23][CH:24]2[CH2:25][CH2:26]3)[c:27]2[n:28][cH:29][cH:30][cH:31][c:32]2[cH:33]1\"},\"mapped_reaction_smiles\":\"Br[c:5]1[cH:4][c:3]([O:2][CH3:1])[cH:33][c:32]2[c:27]1[n:28][cH:29][cH:30][cH:31]2.[NH2:6][CH2:7][CH2:8][N:9]1[CH:10]2[CH:11]=[C:12]([c:13]3[cH:14][c:15]4[cH:16][cH:17][cH:18][cH:19][c:20]4[cH:21][cH:22]3)[CH2:23][CH:24]1[CH2:25][CH2:26]2>CC(C)(C)P(c1ccccc1-c1ccccc1)C(C)(C)C.Cc1ccccc1.O.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.[Pd].[Pd]>[CH3:1][O:2][c:3]1[cH:4][c:5]([NH:6][CH2:7][CH2:8][N:9]2[CH:10]3[CH:11]=[C:12]([c:13]4[cH:14][c:15]5[cH:16][cH:17][cH:18][cH:19][c:20]5[cH:21][cH:22]4)[CH2:23][CH:24]2[CH2:25][CH2:26]3)[c:27]2[n:28][cH:29][cH:30][cH:31][c:32]2[cH:33]1\"}",
"reactionStep": {
"id": "sa_478a2ce6464a8b3ad455c7ee",
"reactionHash": "cae45a7a30f742aa2cd732aabe07b24ed58be2e8eb144e340f6d1a25884f9e31"
},
"children": [
{
"id": "11806",
"routeId": "sa_f458e10860be9e6c2ca849ab",
"moleculeId": "sa_324cb58fb9f9ae79ceba5fcd",
"parentId": "11805",
"isLeaf": false,
"molecule": {
"id": "sa_324cb58fb9f9ae79ceba5fcd",
"inchikey": "LNUAJWGHXLNCMU-UHFFFAOYSA-N",
"smiles": "NCCN1C2C=C(c3ccc4ccccc4c3)CC1CC2"
},
"smiles": "NCCN1C2C=C(c3ccc4ccccc4c3)CC1CC2",
"reactionStepId": "sa_ca2749f4c3b2847c4bd6145d",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US06632824B2;;623381\",\"rsmi\":\"CC(C)(C)OC(=O)[NH:1][CH2:2][CH2:3][N:4]1[CH:5]2[CH:6]=[C:7]([c:8]3[cH:9][c:10]4[cH:11][cH:12][cH:13][cH:14][c:15]4[cH:16][cH:17]3)[CH2:18][CH:19]1[CH2:20][CH2:21]2>ClCCl.O=C(O)C(F)(F)F>[NH2:1][CH2:2][CH2:3][N:4]1[CH:5]2[CH:6]=[C:7]([c:8]3[cH:9][c:10]4[cH:11][cH:12][cH:13][cH:14][c:15]4[cH:16][cH:17]3)[CH2:18][CH:19]1[CH2:20][CH2:21]2\"},\"mapped_reaction_smiles\":\"CC(C)(C)OC(=O)[NH:1][CH2:2][CH2:3][N:4]1[CH:5]2[CH:6]=[C:7]([c:8]3[cH:9][c:10]4[cH:11][cH:12][cH:13][cH:14][c:15]4[cH:16][cH:17]3)[CH2:18][CH:19]1[CH2:20][CH2:21]2>ClCCl.O=C(O)C(F)(F)F>[NH2:1][CH2:2][CH2:3][N:4]1[CH:5]2[CH:6]=[C:7]([c:8]3[cH:9][c:10]4[cH:11][cH:12][cH:13][cH:14][c:15]4[cH:16][cH:17]3)[CH2:18][CH:19]1[CH2:20][CH2:21]2\"}",
"reactionStep": {
"id": "sa_ca2749f4c3b2847c4bd6145d",
"reactionHash": "bf45d0965dbc343aac23df0c346ab92ef784c39cf36a5d2d70c67b34a32e8102"
},
"children": [
{
"id": "11807",
"routeId": "sa_f458e10860be9e6c2ca849ab",
"moleculeId": "sa_cbb4afd99b8409a5700661cc",
"parentId": "11806",
"isLeaf": true,
"molecule": {
"id": "sa_cbb4afd99b8409a5700661cc",
"inchikey": "SNCOLMCZWLCTSO-UHFFFAOYSA-N",
"smiles": "CC(C)(C)OC(=O)NCCN1C2C=C(c3ccc4ccccc4c3)CC1CC2"
},
"smiles": "CC(C)(C)OC(=O)NCCN1C2C=C(c3ccc4ccccc4c3)CC1CC2",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
},
{
"id": "11808",
"routeId": "sa_f458e10860be9e6c2ca849ab",
"moleculeId": "sa_9d35c899008ea850ee18fbd8",
"parentId": "11805",
"isLeaf": false,
"molecule": {
"id": "sa_9d35c899008ea850ee18fbd8",
"inchikey": "MXMVLWCWCLMAHP-UHFFFAOYSA-N",
"smiles": "COc1cc(Br)c2ncccc2c1"
},
"smiles": "COc1cc(Br)c2ncccc2c1",
"reactionStepId": "sa_265671cc9b9334182d86c340",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US06632824B2;;623384\",\"rsmi\":\"N[c:5]1[cH:4][c:3]([O:2][CH3:1])[cH:13][c:12]2[c:7]1[n:8][cH:9][cH:10][cH:11]2.[BrH:6]>CCOC(C)=O.O>[CH3:1][O:2][c:3]1[cH:4][c:5]([Br:6])[c:7]2[n:8][cH:9][cH:10][cH:11][c:12]2[cH:13]1\"},\"mapped_reaction_smiles\":\"N[c:5]1[cH:4][c:3]([O:2][CH3:1])[cH:13][c:12]2[c:7]1[n:8][cH:9][cH:10][cH:11]2.[BrH:6]>CCOC(C)=O.O>[CH3:1][O:2][c:3]1[cH:4][c:5]([Br:6])[c:7]2[n:8][cH:9][cH:10][cH:11][c:12]2[cH:13]1\"}",
"reactionStep": {
"id": "sa_265671cc9b9334182d86c340",
"reactionHash": "d814989871e9956f23ca65dc16d0a7515b13133f5edf9ffc78d255178b2a2242"
},
"children": [
{
"id": "11809",
"routeId": "sa_f458e10860be9e6c2ca849ab",
"moleculeId": "sa_70f4de2e51ba34b93e025a04",
"parentId": "11808",
"isLeaf": true,
"molecule": {
"id": "sa_70f4de2e51ba34b93e025a04",
"inchikey": "CPELXLSAUQHCOX-UHFFFAOYSA-N",
"smiles": "Br"
},
"smiles": "Br",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "11810",
"routeId": "sa_f458e10860be9e6c2ca849ab",
"moleculeId": "sa_69b2f9e9ed33a1b43b0b5932",
"parentId": "11808",
"isLeaf": false,
"molecule": {
"id": "sa_69b2f9e9ed33a1b43b0b5932",
"inchikey": "YGGTVPCTAKYCSQ-UHFFFAOYSA-N",
"smiles": "COc1cc(N)c2ncccc2c1"
},
"smiles": "COc1cc(N)c2ncccc2c1",
"reactionStepId": "sa_1af06576b1f9ad45202f7856",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US06632824B2;;623383\",\"rsmi\":\"O=[N+:6]([O-])[c:5]1[cH:4][c:3]([O:2][CH3:1])[cH:13][c:12]2[c:7]1[n:8][cH:9][cH:10][cH:11]2>C1CCOC1.[Pd]>[CH3:1][O:2][c:3]1[cH:4][c:5]([NH2:6])[c:7]2[n:8][cH:9][cH:10][cH:11][c:12]2[cH:13]1\"},\"mapped_reaction_smiles\":\"O=[N+:6]([O-])[c:5]1[cH:4][c:3]([O:2][CH3:1])[cH:13][c:12]2[c:7]1[n:8][cH:9][cH:10][cH:11]2>C1CCOC1.[Pd]>[CH3:1][O:2][c:3]1[cH:4][c:5]([NH2:6])[c:7]2[n:8][cH:9][cH:10][cH:11][c:12]2[cH:13]1\"}",
"reactionStep": {
"id": "sa_1af06576b1f9ad45202f7856",
"reactionHash": "89b7c7419cc00e10b2a5d5b2fa18b1322facab360e21497bdec4366b96613dec"
},
"children": [
{
"id": "11811",
"routeId": "sa_f458e10860be9e6c2ca849ab",
"moleculeId": "sa_84a3e19dba2f587b0428ca3d",
"parentId": "11810",
"isLeaf": true,
"molecule": {
"id": "sa_84a3e19dba2f587b0428ca3d",
"inchikey": "MIMUSZHMZBJBPO-UHFFFAOYSA-N",
"smiles": "COc1cc([N+](=O)[O-])c2ncccc2c1"
},
"smiles": "COc1cc([N+](=O)[O-])c2ncccc2c1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
}
]
}
]
}
}