Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
CC(C)Nc1nc2c(nc1N1CCN(Cc3ccc(F)cc3F)CC1)CCN(S(C)(=O)=O)C2
InChiKey
LLDFGRFJUUBZCG-UHFFFAOYSA-N
Route Signature
caa7ebb3eaa3593e2193b27796e399c5a1fcbdcb158ebef495bb3a7b03828244
Synthesis route with 6 steps
Route tree structure (JSON format)
{
"route": {
"id": "sa_031b608886c549a5bddddf0b",
"signature": "caa7ebb3eaa3593e2193b27796e399c5a1fcbdcb158ebef495bb3a7b03828244",
"contentHash": "251b55ef1f538e6a87ea4708e4cc68b5d9e64c7ddf78aac58309a71ba431cddd",
"length": 6,
"isConvergent": false
},
"target": {
"id": "sa_f002bd63bb072c9d09198469",
"benchmarkSetId": "f925e688d731a0ad4e3aa6a505df094f6d3ca64ce3facc312bc5f64731921b33",
"targetId": "n5-00288",
"moleculeId": "sa_fd51156de5d3dccb039c6f98",
"smiles": "CC(C)Nc1nc2c(nc1N1CCN(Cc3ccc(F)cc3F)CC1)CCN(S(C)(=O)=O)C2",
"routeLength": 6,
"isConvergent": false,
"metadata": null,
"molecule": {
"id": "sa_fd51156de5d3dccb039c6f98",
"inchikey": "LLDFGRFJUUBZCG-UHFFFAOYSA-N",
"smiles": "CC(C)Nc1nc2c(nc1N1CCN(Cc3ccc(F)cc3F)CC1)CCN(S(C)(=O)=O)C2"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 2
},
"rootNode": {
"id": "3856",
"routeId": "sa_031b608886c549a5bddddf0b",
"moleculeId": "sa_fd51156de5d3dccb039c6f98",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_fd51156de5d3dccb039c6f98",
"inchikey": "LLDFGRFJUUBZCG-UHFFFAOYSA-N",
"smiles": "CC(C)Nc1nc2c(nc1N1CCN(Cc3ccc(F)cc3F)CC1)CCN(S(C)(=O)=O)C2"
},
"smiles": "CC(C)Nc1nc2c(nc1N1CCN(Cc3ccc(F)cc3F)CC1)CCN(S(C)(=O)=O)C2",
"reactionStepId": "sa_4b83ecc73345bf97712667ca",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20160031881A1;0588;1832836\",\"rsmi\":\"Cl[S:27]([CH3:28])(=[O:29])=[O:30].[CH3:1][CH:2]([CH3:3])[NH:4][c:5]1[c:6]([N:7]2[CH2:8][CH2:9][N:10]([CH2:11][c:12]3[c:13]([F:14])[cH:15][c:16]([F:17])[cH:18][cH:19]3)[CH2:20][CH2:21]2)[n:22][c:23]2[c:32]([n:33]1)[CH2:31][NH:26][CH2:25][CH2:24]2>CCN(C(C)C)C(C)C.ClCCl>[CH3:1][CH:2]([CH3:3])[NH:4][c:5]1[c:6]([N:7]2[CH2:8][CH2:9][N:10]([CH2:11][c:12]3[c:13]([F:14])[cH:15][c:16]([F:17])[cH:18][cH:19]3)[CH2:20][CH2:21]2)[n:22][c:23]2[c:32]([n:33]1)[CH2:31][N:26]([S:27]([CH3:28])(=[O:29])=[O:30])[CH2:25][CH2:24]2\"},\"mapped_reaction_smiles\":\"Cl[S:27]([CH3:28])(=[O:29])=[O:30].[CH3:1][CH:2]([CH3:3])[NH:4][c:5]1[c:6]([N:7]2[CH2:8][CH2:9][N:10]([CH2:11][c:12]3[c:13]([F:14])[cH:15][c:16]([F:17])[cH:18][cH:19]3)[CH2:20][CH2:21]2)[n:22][c:23]2[c:32]([n:33]1)[CH2:31][NH:26][CH2:25][CH2:24]2>CCN(C(C)C)C(C)C.ClCCl>[CH3:1][CH:2]([CH3:3])[NH:4][c:5]1[c:6]([N:7]2[CH2:8][CH2:9][N:10]([CH2:11][c:12]3[c:13]([F:14])[cH:15][c:16]([F:17])[cH:18][cH:19]3)[CH2:20][CH2:21]2)[n:22][c:23]2[c:32]([n:33]1)[CH2:31][N:26]([S:27]([CH3:28])(=[O:29])=[O:30])[CH2:25][CH2:24]2\"}",
"reactionStep": {
"id": "sa_4b83ecc73345bf97712667ca",
"reactionHash": "d644d41685cb76f1ad6f7cd1e2b3ded0da7a97497c1b323e2e27f33523040723"
},
"children": [
{
"id": "3857",
"routeId": "sa_031b608886c549a5bddddf0b",
"moleculeId": "sa_d2a31ea58046b00856f61ca5",
"parentId": "3856",
"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": []
},
{
"id": "3858",
"routeId": "sa_031b608886c549a5bddddf0b",
"moleculeId": "sa_556e5d41d376a824339cbabd",
"parentId": "3856",
"isLeaf": false,
"molecule": {
"id": "sa_556e5d41d376a824339cbabd",
"inchikey": "RMILUJXQCUFCNA-UHFFFAOYSA-N",
"smiles": "CC(C)Nc1nc2c(nc1N1CCN(Cc3ccc(F)cc3F)CC1)CCNC2"
},
"smiles": "CC(C)Nc1nc2c(nc1N1CCN(Cc3ccc(F)cc3F)CC1)CCNC2",
"reactionStepId": "sa_8d7d1c65977f350ae1013c5f",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20160031881A1;0288;1832705\",\"rsmi\":\"CC(=O)[N:26]1[CH2:25][CH2:24][c:23]2[n:22][c:6]([N:7]3[CH2:8][CH2:9][N:10]([CH2:11][c:12]4[c:13]([F:14])[cH:15][c:16]([F:17])[cH:18][cH:19]4)[CH2:20][CH2:21]3)[c:5]([NH:4][CH:2]([CH3:1])[CH3:3])[n:29][c:28]2[CH2:27]1>CO.Cl.[Na+].O>[CH3:1][CH:2]([CH3:3])[NH:4][c:5]1[c:6]([N:7]2[CH2:8][CH2:9][N:10]([CH2:11][c:12]3[c:13]([F:14])[cH:15][c:16]([F:17])[cH:18][cH:19]3)[CH2:20][CH2:21]2)[n:22][c:23]2[c:28]([n:29]1)[CH2:27][NH:26][CH2:25][CH2:24]2\"},\"mapped_reaction_smiles\":\"CC(=O)[N:26]1[CH2:25][CH2:24][c:23]2[n:22][c:6]([N:7]3[CH2:8][CH2:9][N:10]([CH2:11][c:12]4[c:13]([F:14])[cH:15][c:16]([F:17])[cH:18][cH:19]4)[CH2:20][CH2:21]3)[c:5]([NH:4][CH:2]([CH3:1])[CH3:3])[n:29][c:28]2[CH2:27]1>CO.Cl.[Na+].O>[CH3:1][CH:2]([CH3:3])[NH:4][c:5]1[c:6]([N:7]2[CH2:8][CH2:9][N:10]([CH2:11][c:12]3[c:13]([F:14])[cH:15][c:16]([F:17])[cH:18][cH:19]3)[CH2:20][CH2:21]2)[n:22][c:23]2[c:28]([n:29]1)[CH2:27][NH:26][CH2:25][CH2:24]2\"}",
"reactionStep": {
"id": "sa_8d7d1c65977f350ae1013c5f",
"reactionHash": "08b8c07f013e18bbe211674e20c057c2f3ea106f5f33b1a7eb8f560222f5c138"
},
"children": [
{
"id": "3859",
"routeId": "sa_031b608886c549a5bddddf0b",
"moleculeId": "sa_6bcc95ebf52fde351ad412ad",
"parentId": "3858",
"isLeaf": false,
"molecule": {
"id": "sa_6bcc95ebf52fde351ad412ad",
"inchikey": "OZCTVPBBFJSIPB-UHFFFAOYSA-N",
"smiles": "CC(=O)N1CCc2nc(N3CCN(Cc4ccc(F)cc4F)CC3)c(NC(C)C)nc2C1"
},
"smiles": "CC(=O)N1CCc2nc(N3CCN(Cc4ccc(F)cc4F)CC3)c(NC(C)C)nc2C1",
"reactionStepId": "sa_ed3e40576b8d5bbe51b59e1e",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20160031881A1;0584;1832834\",\"rsmi\":\"CC(=O)O[C:2]([CH3:1])=[O:3].[n:4]1[cH:5][cH:6][c:7]2[n:8][c:9]([N:10]3[CH2:11][CH2:12][N:13]([CH2:14][c:15]4[c:16]([F:17])[cH:18][c:19]([F:20])[cH:21][cH:22]4)[CH2:23][CH2:24]3)[c:25]([NH:26][CH:27]([CH3:28])[CH3:29])[n:30][c:31]2[cH:32]1>C1COCCO1.CC(C)=O.[Pd]>[CH3:1][C:2](=[O:3])[N:4]1[CH2:5][CH2:6][c:7]2[n:8][c:9]([N:10]3[CH2:11][CH2:12][N:13]([CH2:14][c:15]4[c:16]([F:17])[cH:18][c:19]([F:20])[cH:21][cH:22]4)[CH2:23][CH2:24]3)[c:25]([NH:26][CH:27]([CH3:28])[CH3:29])[n:30][c:31]2[CH2:32]1\"},\"mapped_reaction_smiles\":\"CC(=O)O[C:2]([CH3:1])=[O:3].[n:4]1[cH:5][cH:6][c:7]2[n:8][c:9]([N:10]3[CH2:11][CH2:12][N:13]([CH2:14][c:15]4[c:16]([F:17])[cH:18][c:19]([F:20])[cH:21][cH:22]4)[CH2:23][CH2:24]3)[c:25]([NH:26][CH:27]([CH3:28])[CH3:29])[n:30][c:31]2[cH:32]1>C1COCCO1.CC(C)=O.[Pd]>[CH3:1][C:2](=[O:3])[N:4]1[CH2:5][CH2:6][c:7]2[n:8][c:9]([N:10]3[CH2:11][CH2:12][N:13]([CH2:14][c:15]4[c:16]([F:17])[cH:18][c:19]([F:20])[cH:21][cH:22]4)[CH2:23][CH2:24]3)[c:25]([NH:26][CH:27]([CH3:28])[CH3:29])[n:30][c:31]2[CH2:32]1\"}",
"reactionStep": {
"id": "sa_ed3e40576b8d5bbe51b59e1e",
"reactionHash": "5f0ecf403450bdfc501ea16c33917025a467c42f204deb14137406364182c097"
},
"children": [
{
"id": "3860",
"routeId": "sa_031b608886c549a5bddddf0b",
"moleculeId": "sa_a7893fcf81826693d9b4bed4",
"parentId": "3859",
"isLeaf": true,
"molecule": {
"id": "sa_a7893fcf81826693d9b4bed4",
"inchikey": "WFDIJRYMOXRFFG-UHFFFAOYSA-N",
"smiles": "CC(=O)OC(C)=O"
},
"smiles": "CC(=O)OC(C)=O",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "3861",
"routeId": "sa_031b608886c549a5bddddf0b",
"moleculeId": "sa_34770b1db8de703db6c35fc7",
"parentId": "3859",
"isLeaf": false,
"molecule": {
"id": "sa_34770b1db8de703db6c35fc7",
"inchikey": "XLVBRHCJIMUAEC-UHFFFAOYSA-N",
"smiles": "CC(C)Nc1nc2cnccc2nc1N1CCN(Cc2ccc(F)cc2F)CC1"
},
"smiles": "CC(C)Nc1nc2cnccc2nc1N1CCN(Cc2ccc(F)cc2F)CC1",
"reactionStepId": "sa_48d0b85e8aaf869d16532385",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20160031881A1;0223;1832666\",\"rsmi\":\"Cl[c:5]1[c:6]([N:7]2[CH2:8][CH2:9][N:10]([CH2:11][c:12]3[c:13]([F:14])[cH:15][c:16]([F:17])[cH:18][cH:19]3)[CH2:20][CH2:21]2)[n:22][c:23]2[cH:24][cH:25][n:26][cH:27][c:28]2[n:29]1.[CH3:1][CH:2]([CH3:3])[NH2:4]>CCN(C(C)C)C(C)C.CS(C)=O.O.F.[K+]>[CH3:1][CH:2]([CH3:3])[NH:4][c:5]1[c:6]([N:7]2[CH2:8][CH2:9][N:10]([CH2:11][c:12]3[c:13]([F:14])[cH:15][c:16]([F:17])[cH:18][cH:19]3)[CH2:20][CH2:21]2)[n:22][c:23]2[cH:24][cH:25][n:26][cH:27][c:28]2[n:29]1\"},\"mapped_reaction_smiles\":\"Cl[c:5]1[c:6]([N:7]2[CH2:8][CH2:9][N:10]([CH2:11][c:12]3[c:13]([F:14])[cH:15][c:16]([F:17])[cH:18][cH:19]3)[CH2:20][CH2:21]2)[n:22][c:23]2[cH:24][cH:25][n:26][cH:27][c:28]2[n:29]1.[CH3:1][CH:2]([CH3:3])[NH2:4]>CCN(C(C)C)C(C)C.CS(C)=O.O.F.[K+]>[CH3:1][CH:2]([CH3:3])[NH:4][c:5]1[c:6]([N:7]2[CH2:8][CH2:9][N:10]([CH2:11][c:12]3[c:13]([F:14])[cH:15][c:16]([F:17])[cH:18][cH:19]3)[CH2:20][CH2:21]2)[n:22][c:23]2[cH:24][cH:25][n:26][cH:27][c:28]2[n:29]1\"}",
"reactionStep": {
"id": "sa_48d0b85e8aaf869d16532385",
"reactionHash": "6105977cc900d1839375133e75d1e9c626445a1d29d39d7bfc35cde45c70c701"
},
"children": [
{
"id": "3862",
"routeId": "sa_031b608886c549a5bddddf0b",
"moleculeId": "sa_2e72c1c53065e4af6ee24789",
"parentId": "3861",
"isLeaf": true,
"molecule": {
"id": "sa_2e72c1c53065e4af6ee24789",
"inchikey": "JJWLVOIRVHMVIS-UHFFFAOYSA-N",
"smiles": "CC(C)N"
},
"smiles": "CC(C)N",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "3863",
"routeId": "sa_031b608886c549a5bddddf0b",
"moleculeId": "sa_9b9d4b57f92c7a2842cdbcff",
"parentId": "3861",
"isLeaf": false,
"molecule": {
"id": "sa_9b9d4b57f92c7a2842cdbcff",
"inchikey": "ZGHYSLWULTUYLU-UHFFFAOYSA-N",
"smiles": "Fc1ccc(CN2CCN(c3nc4ccncc4nc3Cl)CC2)c(F)c1"
},
"smiles": "Fc1ccc(CN2CCN(c3nc4ccncc4nc3Cl)CC2)c(F)c1",
"reactionStepId": "sa_3a6387f92af8f67c0cab429f",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20160031881A1;0209;1832657\",\"rsmi\":\"Cl[c:12]1[c:13]([Cl:14])[n:15][c:16]2[cH:17][n:18][cH:19][cH:20][c:21]2[n:22]1.[F:1][c:2]1[cH:3][c:4]([F:5])[c:6]([CH2:7][N:8]2[CH2:9][CH2:10][NH:11][CH2:23][CH2:24]2)[cH:25][cH:26]1>CCN(CC)CC.ClCCl>[F:1][c:2]1[cH:3][c:4]([F:5])[c:6]([CH2:7][N:8]2[CH2:9][CH2:10][N:11]([c:12]3[c:13]([Cl:14])[n:15][c:16]4[cH:17][n:18][cH:19][cH:20][c:21]4[n:22]3)[CH2:23][CH2:24]2)[cH:25][cH:26]1\"},\"mapped_reaction_smiles\":\"Cl[c:12]1[c:13]([Cl:14])[n:15][c:16]2[cH:17][n:18][cH:19][cH:20][c:21]2[n:22]1.[F:1][c:2]1[cH:3][c:4]([F:5])[c:6]([CH2:7][N:8]2[CH2:9][CH2:10][NH:11][CH2:23][CH2:24]2)[cH:25][cH:26]1>CCN(CC)CC.ClCCl>[F:1][c:2]1[cH:3][c:4]([F:5])[c:6]([CH2:7][N:8]2[CH2:9][CH2:10][N:11]([c:12]3[c:13]([Cl:14])[n:15][c:16]4[cH:17][n:18][cH:19][cH:20][c:21]4[n:22]3)[CH2:23][CH2:24]2)[cH:25][cH:26]1\"}",
"reactionStep": {
"id": "sa_3a6387f92af8f67c0cab429f",
"reactionHash": "9d39c6e8e52990c8c640910ed37eeb75b82dc01f70131d59793b457304e957ce"
},
"children": [
{
"id": "3864",
"routeId": "sa_031b608886c549a5bddddf0b",
"moleculeId": "sa_b49693d099ef0719609f3555",
"parentId": "3863",
"isLeaf": false,
"molecule": {
"id": "sa_b49693d099ef0719609f3555",
"inchikey": "GGARUFCQRZCXHK-UHFFFAOYSA-N",
"smiles": "Fc1ccc(CN2CCNCC2)c(F)c1"
},
"smiles": "Fc1ccc(CN2CCNCC2)c(F)c1",
"reactionStepId": "sa_c99686f4cfc409a473a4905e",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20160031881A1;0202;1832652\",\"rsmi\":\"Cl[CH2:7][c:6]1[c:4]([F:5])[cH:3][c:2]([F:1])[cH:15][cH:14]1.[NH:8]1[CH2:9][CH2:10][NH:11][CH2:12][CH2:13]1>C1CCOC1>[F:1][c:2]1[cH:3][c:4]([F:5])[c:6]([CH2:7][N:8]2[CH2:9][CH2:10][NH:11][CH2:12][CH2:13]2)[cH:14][cH:15]1\"},\"mapped_reaction_smiles\":\"Cl[CH2:7][c:6]1[c:4]([F:5])[cH:3][c:2]([F:1])[cH:15][cH:14]1.[NH:8]1[CH2:9][CH2:10][NH:11][CH2:12][CH2:13]1>C1CCOC1>[F:1][c:2]1[cH:3][c:4]([F:5])[c:6]([CH2:7][N:8]2[CH2:9][CH2:10][NH:11][CH2:12][CH2:13]2)[cH:14][cH:15]1\"}",
"reactionStep": {
"id": "sa_c99686f4cfc409a473a4905e",
"reactionHash": "fc772a5e78a51d9a7bb1c58f57f0568d763d62598af69457068148259d20c9f0"
},
"children": [
{
"id": "3865",
"routeId": "sa_031b608886c549a5bddddf0b",
"moleculeId": "sa_330bd414c5d4211e41bcaa1a",
"parentId": "3864",
"isLeaf": true,
"molecule": {
"id": "sa_330bd414c5d4211e41bcaa1a",
"inchikey": "GLUUGHFHXGJENI-UHFFFAOYSA-N",
"smiles": "C1CNCCN1"
},
"smiles": "C1CNCCN1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "3866",
"routeId": "sa_031b608886c549a5bddddf0b",
"moleculeId": "sa_bcd6bb2b93e3fd8f4d1a4ea2",
"parentId": "3864",
"isLeaf": true,
"molecule": {
"id": "sa_bcd6bb2b93e3fd8f4d1a4ea2",
"inchikey": "XPGHWBDZNQUUQD-UHFFFAOYSA-N",
"smiles": "Fc1ccc(CCl)c(F)c1"
},
"smiles": "Fc1ccc(CCl)c(F)c1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
},
{
"id": "3867",
"routeId": "sa_031b608886c549a5bddddf0b",
"moleculeId": "sa_b723fd586baa71779c9e70cc",
"parentId": "3863",
"isLeaf": true,
"molecule": {
"id": "sa_b723fd586baa71779c9e70cc",
"inchikey": "GZTHKSLJDQQAGP-UHFFFAOYSA-N",
"smiles": "Clc1nc2ccncc2nc1Cl"
},
"smiles": "Clc1nc2ccncc2nc1Cl",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
}
]
}
]
}
]
}
]
}
}