Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
Cc1cc(Nc2cc(C3CCCC3)[nH]n2)nc(Nc2ccc(C(=O)Nc3cccc(C(F)(F)F)c3)cc2)n1
InChiKey
BCFYOLGCMFQGPA-UHFFFAOYSA-N
Route Signature
0fad86130e5a8f83f8841d54c720b02d8bacda87a9edbdba8fa80ac3ecd94e94
Synthesis route with 4 steps (convergent)
Route tree structure (JSON format)
{
"route": {
"id": "sa_f4ec989b915e98223f2c4acc",
"signature": "0fad86130e5a8f83f8841d54c720b02d8bacda87a9edbdba8fa80ac3ecd94e94",
"contentHash": "75f0efd97d413a06519dd30330fc45f8c68fb5c9db02b8302e8ce3a85c2e518e",
"length": 4,
"isConvergent": true
},
"target": {
"id": "sa_b77d9caf739414d95bbb2e00",
"benchmarkSetId": "3895c2909c53593560c5ba610abc7e6df80513dfd8624165c560451735097d36",
"targetId": "n5-01256",
"moleculeId": "sa_8f179cd5cd01d77e731c6b89",
"smiles": "Cc1cc(Nc2cc(C3CCCC3)[nH]n2)nc(Nc2ccc(C(=O)Nc3cccc(C(F)(F)F)c3)cc2)n1",
"routeLength": 4,
"isConvergent": true,
"metadata": null,
"molecule": {
"id": "sa_8f179cd5cd01d77e731c6b89",
"inchikey": "BCFYOLGCMFQGPA-UHFFFAOYSA-N",
"smiles": "Cc1cc(Nc2cc(C3CCCC3)[nH]n2)nc(Nc2ccc(C(=O)Nc3cccc(C(F)(F)F)c3)cc2)n1"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "10032",
"routeId": "sa_f4ec989b915e98223f2c4acc",
"moleculeId": "sa_8f179cd5cd01d77e731c6b89",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_8f179cd5cd01d77e731c6b89",
"inchikey": "BCFYOLGCMFQGPA-UHFFFAOYSA-N",
"smiles": "Cc1cc(Nc2cc(C3CCCC3)[nH]n2)nc(Nc2ccc(C(=O)Nc3cccc(C(F)(F)F)c3)cc2)n1"
},
"smiles": "Cc1cc(Nc2cc(C3CCCC3)[nH]n2)nc(Nc2ccc(C(=O)Nc3cccc(C(F)(F)F)c3)cc2)n1",
"reactionStepId": "sa_45d8c07f5d468beb66aabd4c",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20160250211A1;0287;1926500\",\"rsmi\":\"Cl[c:17]1[n:16][c:4]([NH:5][c:6]2[n:7][nH:8][c:9]([CH:10]3[CH2:11][CH2:12][CH2:13][CH2:14]3)[cH:15]2)[cH:3][c:2]([CH3:1])[n:38]1.[NH2:18][c:19]1[cH:20][cH:21][c:22]([C:23](=[O:24])[NH:25][c:26]2[cH:27][c:28]([C:29]([F:30])([F:31])[F:32])[cH:33][cH:34][cH:35]2)[cH:36][cH:37]1>CCCCO.Cl>[CH3:1][c:2]1[cH:3][c:4]([NH:5][c:6]2[n:7][nH:8][c:9]([CH:10]3[CH2:11][CH2:12][CH2:13][CH2:14]3)[cH:15]2)[n:16][c:17]([NH:18][c:19]2[cH:20][cH:21][c:22]([C:23](=[O:24])[NH:25][c:26]3[cH:27][c:28]([C:29]([F:30])([F:31])[F:32])[cH:33][cH:34][cH:35]3)[cH:36][cH:37]2)[n:38]1\"},\"mapped_reaction_smiles\":\"Cl[c:17]1[n:16][c:4]([NH:5][c:6]2[n:7][nH:8][c:9]([CH:10]3[CH2:11][CH2:12][CH2:13][CH2:14]3)[cH:15]2)[cH:3][c:2]([CH3:1])[n:38]1.[NH2:18][c:19]1[cH:20][cH:21][c:22]([C:23](=[O:24])[NH:25][c:26]2[cH:27][c:28]([C:29]([F:30])([F:31])[F:32])[cH:33][cH:34][cH:35]2)[cH:36][cH:37]1>CCCCO.Cl>[CH3:1][c:2]1[cH:3][c:4]([NH:5][c:6]2[n:7][nH:8][c:9]([CH:10]3[CH2:11][CH2:12][CH2:13][CH2:14]3)[cH:15]2)[n:16][c:17]([NH:18][c:19]2[cH:20][cH:21][c:22]([C:23](=[O:24])[NH:25][c:26]3[cH:27][c:28]([C:29]([F:30])([F:31])[F:32])[cH:33][cH:34][cH:35]3)[cH:36][cH:37]2)[n:38]1\"}",
"reactionStep": {
"id": "sa_45d8c07f5d468beb66aabd4c",
"reactionHash": "d3f312d93a665ff4ee3ade1eff77322c9a3e5f7163a3fe528768d7d8e5d56bef"
},
"children": [
{
"id": "10033",
"routeId": "sa_f4ec989b915e98223f2c4acc",
"moleculeId": "sa_411adfb59ee2030aa2d21ada",
"parentId": "10032",
"isLeaf": false,
"molecule": {
"id": "sa_411adfb59ee2030aa2d21ada",
"inchikey": "BIVQEHDNRFPDON-UHFFFAOYSA-N",
"smiles": "Nc1ccc(C(=O)Nc2cccc(C(F)(F)F)c2)cc1"
},
"smiles": "Nc1ccc(C(=O)Nc2cccc(C(F)(F)F)c2)cc1",
"reactionStepId": "sa_7089262a4ae0a51d5af7b31d",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20160250211A1;0282;1926497\",\"rsmi\":\"O=[N+:1]([O-])[c:2]1[cH:3][cH:4][c:5]([C:6](=[O:7])[NH:8][c:9]2[cH:10][c:11]([C:12]([F:13])([F:14])[F:15])[cH:16][cH:17][cH:18]2)[cH:19][cH:20]1>C1CCOC1.CC(=O)O.[Zn]>[NH2:1][c:2]1[cH:3][cH:4][c:5]([C:6](=[O:7])[NH:8][c:9]2[cH:10][c:11]([C:12]([F:13])([F:14])[F:15])[cH:16][cH:17][cH:18]2)[cH:19][cH:20]1\"},\"mapped_reaction_smiles\":\"O=[N+:1]([O-])[c:2]1[cH:3][cH:4][c:5]([C:6](=[O:7])[NH:8][c:9]2[cH:10][c:11]([C:12]([F:13])([F:14])[F:15])[cH:16][cH:17][cH:18]2)[cH:19][cH:20]1>C1CCOC1.CC(=O)O.[Zn]>[NH2:1][c:2]1[cH:3][cH:4][c:5]([C:6](=[O:7])[NH:8][c:9]2[cH:10][c:11]([C:12]([F:13])([F:14])[F:15])[cH:16][cH:17][cH:18]2)[cH:19][cH:20]1\"}",
"reactionStep": {
"id": "sa_7089262a4ae0a51d5af7b31d",
"reactionHash": "aac56a581adba43a9a9870e9d319235435b2c283fdcce541e8d0aa2cb9b8f4be"
},
"children": [
{
"id": "10034",
"routeId": "sa_f4ec989b915e98223f2c4acc",
"moleculeId": "sa_aeacfbbb5ed993bc1064450d",
"parentId": "10033",
"isLeaf": false,
"molecule": {
"id": "sa_aeacfbbb5ed993bc1064450d",
"inchikey": "JJJCKJORTNOIAC-UHFFFAOYSA-N",
"smiles": "O=C(Nc1cccc(C(F)(F)F)c1)c1ccc([N+](=O)[O-])cc1"
},
"smiles": "O=C(Nc1cccc(C(F)(F)F)c1)c1ccc([N+](=O)[O-])cc1",
"reactionStepId": "sa_eb57b0ade96b5260dde5f4d9",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20160250211A1;0281;1926496\",\"rsmi\":\"Cl[C:2](=[O:1])[c:14]1[cH:15][cH:16][c:17]([N+:18](=[O:19])[O-:20])[cH:21][cH:22]1.[NH2:3][c:4]1[cH:5][c:6]([C:7]([F:8])([F:9])[F:10])[cH:11][cH:12][cH:13]1>c1ccncc1>[O:1]=[C:2]([NH:3][c:4]1[cH:5][c:6]([C:7]([F:8])([F:9])[F:10])[cH:11][cH:12][cH:13]1)[c:14]1[cH:15][cH:16][c:17]([N+:18](=[O:19])[O-:20])[cH:21][cH:22]1\"},\"mapped_reaction_smiles\":\"Cl[C:2](=[O:1])[c:14]1[cH:15][cH:16][c:17]([N+:18](=[O:19])[O-:20])[cH:21][cH:22]1.[NH2:3][c:4]1[cH:5][c:6]([C:7]([F:8])([F:9])[F:10])[cH:11][cH:12][cH:13]1>c1ccncc1>[O:1]=[C:2]([NH:3][c:4]1[cH:5][c:6]([C:7]([F:8])([F:9])[F:10])[cH:11][cH:12][cH:13]1)[c:14]1[cH:15][cH:16][c:17]([N+:18](=[O:19])[O-:20])[cH:21][cH:22]1\"}",
"reactionStep": {
"id": "sa_eb57b0ade96b5260dde5f4d9",
"reactionHash": "45da68c3c0fbcdcf1b1ff8ef7a1296557a78120a3c02c6d9649ecaa9c59f23b1"
},
"children": [
{
"id": "10035",
"routeId": "sa_f4ec989b915e98223f2c4acc",
"moleculeId": "sa_a9c9831d94f67e76c2c09138",
"parentId": "10034",
"isLeaf": true,
"molecule": {
"id": "sa_a9c9831d94f67e76c2c09138",
"inchikey": "SKDHHIUENRGTHK-UHFFFAOYSA-N",
"smiles": "O=C(Cl)c1ccc([N+](=O)[O-])cc1"
},
"smiles": "O=C(Cl)c1ccc([N+](=O)[O-])cc1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "10036",
"routeId": "sa_f4ec989b915e98223f2c4acc",
"moleculeId": "sa_78d3054322042c794bc218f6",
"parentId": "10034",
"isLeaf": true,
"molecule": {
"id": "sa_78d3054322042c794bc218f6",
"inchikey": "VIUDTWATMPPKEL-UHFFFAOYSA-N",
"smiles": "Nc1cccc(C(F)(F)F)c1"
},
"smiles": "Nc1cccc(C(F)(F)F)c1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
}
]
},
{
"id": "10037",
"routeId": "sa_f4ec989b915e98223f2c4acc",
"moleculeId": "sa_745d76107fc1c07c4b6bb54b",
"parentId": "10032",
"isLeaf": false,
"molecule": {
"id": "sa_745d76107fc1c07c4b6bb54b",
"inchikey": "QNGNWIQVLCPJHH-UHFFFAOYSA-N",
"smiles": "Cc1cc(Nc2cc(C3CCCC3)[nH]n2)nc(Cl)n1"
},
"smiles": "Cc1cc(Nc2cc(C3CCCC3)[nH]n2)nc(Cl)n1",
"reactionStepId": "sa_b83e754e942fbe6f83629e79",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20160250211A1;0269;1926490\",\"rsmi\":\"Cl[c:4]1[cH:3][c:2]([CH3:1])[n:19][c:17]([Cl:18])[n:16]1.[NH2:5][c:6]1[n:7][nH:8][c:9]([CH:10]2[CH2:11][CH2:12][CH2:13][CH2:14]2)[cH:15]1>C1CCOC1.CC(=O)O.O.[K+]>[CH3:1][c:2]1[cH:3][c:4]([NH:5][c:6]2[n:7][nH:8][c:9]([CH:10]3[CH2:11][CH2:12][CH2:13][CH2:14]3)[cH:15]2)[n:16][c:17]([Cl:18])[n:19]1\"},\"mapped_reaction_smiles\":\"Cl[c:4]1[cH:3][c:2]([CH3:1])[n:19][c:17]([Cl:18])[n:16]1.[NH2:5][c:6]1[n:7][nH:8][c:9]([CH:10]2[CH2:11][CH2:12][CH2:13][CH2:14]2)[cH:15]1>C1CCOC1.CC(=O)O.O.[K+]>[CH3:1][c:2]1[cH:3][c:4]([NH:5][c:6]2[n:7][nH:8][c:9]([CH:10]3[CH2:11][CH2:12][CH2:13][CH2:14]3)[cH:15]2)[n:16][c:17]([Cl:18])[n:19]1\"}",
"reactionStep": {
"id": "sa_b83e754e942fbe6f83629e79",
"reactionHash": "ce6e0d271cd500f61ee46a87671917b65fa22a943ef79eb78cf30178a9c0af64"
},
"children": [
{
"id": "10038",
"routeId": "sa_f4ec989b915e98223f2c4acc",
"moleculeId": "sa_a33a02690ecb3abc53024eeb",
"parentId": "10037",
"isLeaf": true,
"molecule": {
"id": "sa_a33a02690ecb3abc53024eeb",
"inchikey": "BTLKROSJMNFSQZ-UHFFFAOYSA-N",
"smiles": "Cc1cc(Cl)nc(Cl)n1"
},
"smiles": "Cc1cc(Cl)nc(Cl)n1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "10039",
"routeId": "sa_f4ec989b915e98223f2c4acc",
"moleculeId": "sa_c47ddc909b91cbd2a46e9cc2",
"parentId": "10037",
"isLeaf": false,
"molecule": {
"id": "sa_c47ddc909b91cbd2a46e9cc2",
"inchikey": "PXEDPQCHOFQXCW-UHFFFAOYSA-N",
"smiles": "Nc1cc(C2CCCC2)n[nH]1"
},
"smiles": "Nc1cc(C2CCCC2)[nH]n1",
"reactionStepId": "sa_3078623019f84e8b8b6e3775",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20160250211A1;0263;1926489\",\"rsmi\":\"O=[C:5]([CH:6]1[CH2:7][CH2:8][CH2:9][CH2:10]1)[CH2:11][C:2]#[N:1].[NH2:3][NH2:4]>CCO.O>[NH2:1][c:2]1[n:3][nH:4][c:5]([CH:6]2[CH2:7][CH2:8][CH2:9][CH2:10]2)[cH:11]1\"},\"mapped_reaction_smiles\":\"O=[C:5]([CH:6]1[CH2:7][CH2:8][CH2:9][CH2:10]1)[CH2:11][C:2]#[N:1].[NH2:3][NH2:4]>CCO.O>[NH2:1][c:2]1[n:3][nH:4][c:5]([CH:6]2[CH2:7][CH2:8][CH2:9][CH2:10]2)[cH:11]1\"}",
"reactionStep": {
"id": "sa_3078623019f84e8b8b6e3775",
"reactionHash": "e14d5d26fbfbcaf51f5e19e341011dac8d0c0d56707719ae3bccdb13b7db9b43"
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"children": [
{
"id": "10040",
"routeId": "sa_f4ec989b915e98223f2c4acc",
"moleculeId": "sa_e6ad988acc020f4cc36788d1",
"parentId": "10039",
"isLeaf": false,
"molecule": {
"id": "sa_e6ad988acc020f4cc36788d1",
"inchikey": "FOCJXECLIBAZSA-UHFFFAOYSA-N",
"smiles": "N#CCC(=O)C1CCCC1"
},
"smiles": "N#CCC(=O)C1CCCC1",
"reactionStepId": "sa_a2fa390a9a0d224ec56a9649",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20160250211A1;0262;1926488\",\"rsmi\":\"CO[C:4](=[O:5])[CH:6]1[CH2:7][CH2:8][CH2:9][CH2:10]1.[N:1]#[C:2][CH3:3]>C1CCOC1.[Li]CCCC>[N:1]#[C:2][CH2:3][C:4](=[O:5])[CH:6]1[CH2:7][CH2:8][CH2:9][CH2:10]1\"},\"mapped_reaction_smiles\":\"CO[C:4](=[O:5])[CH:6]1[CH2:7][CH2:8][CH2:9][CH2:10]1.[N:1]#[C:2][CH3:3]>C1CCOC1.[Li]CCCC>[N:1]#[C:2][CH2:3][C:4](=[O:5])[CH:6]1[CH2:7][CH2:8][CH2:9][CH2:10]1\"}",
"reactionStep": {
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"reactionHash": "20756685453463319a65a52819fc41680d8eb5c381a23edadfd5e6ff6c01a5d6"
},
"children": [
{
"id": "10041",
"routeId": "sa_f4ec989b915e98223f2c4acc",
"moleculeId": "sa_d2ba209e3e57887198b40d68",
"parentId": "10040",
"isLeaf": true,
"molecule": {
"id": "sa_d2ba209e3e57887198b40d68",
"inchikey": "IIHIJFJSXPDTNO-UHFFFAOYSA-N",
"smiles": "COC(=O)C1CCCC1"
},
"smiles": "COC(=O)C1CCCC1",
"reactionStepId": null,
"template": null,
"metadata": null,
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},
{
"id": "10042",
"routeId": "sa_f4ec989b915e98223f2c4acc",
"moleculeId": "sa_94d2c90dcb818823484fce3a",
"parentId": "10040",
"isLeaf": true,
"molecule": {
"id": "sa_94d2c90dcb818823484fce3a",
"inchikey": "WEVYAHXRMPXWCK-UHFFFAOYSA-N",
"smiles": "CC#N"
},
"smiles": "CC#N",
"reactionStepId": null,
"template": null,
"metadata": null,
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"children": []
}
]
},
{
"id": "10043",
"routeId": "sa_f4ec989b915e98223f2c4acc",
"moleculeId": "sa_681b90bfe3789a310096845b",
"parentId": "10039",
"isLeaf": true,
"molecule": {
"id": "sa_681b90bfe3789a310096845b",
"inchikey": "OAKJQQAXSVQMHS-UHFFFAOYSA-N",
"smiles": "NN"
},
"smiles": "NN",
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"children": []
}
]
}
]
}
]
}
}