Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
O=C(Nc1cccnn1)N1CCC(=Cc2cccc(Oc3ccc(N4CCCC4)cn3)c2)CC1
InChiKey
CPKSBJNUCZLOOE-UHFFFAOYSA-N
Route Signature
5a9d63ead22c91db61a70030a37a9a1db3fa4390dd3af07768b0f1acc857e0b6
Synthesis route with 5 steps (convergent)
Route tree structure (JSON format)
{
"route": {
"id": "sa_df458d4141682a428fabd962",
"signature": "5a9d63ead22c91db61a70030a37a9a1db3fa4390dd3af07768b0f1acc857e0b6",
"contentHash": "a3afcc345c439d6998d15b3da9f80439f8882d42783082fb34bd588cfc4ae9ed",
"length": 5,
"isConvergent": true
},
"target": {
"id": "sa_11e7ad5d0688254fed9f50f0",
"benchmarkSetId": "3895c2909c53593560c5ba610abc7e6df80513dfd8624165c560451735097d36",
"targetId": "n5-00421",
"moleculeId": "sa_2a4535677dc060c4d9980db7",
"smiles": "O=C(Nc1cccnn1)N1CCC(=Cc2cccc(Oc3ccc(N4CCCC4)cn3)c2)CC1",
"routeLength": 5,
"isConvergent": true,
"metadata": null,
"molecule": {
"id": "sa_2a4535677dc060c4d9980db7",
"inchikey": "CPKSBJNUCZLOOE-UHFFFAOYSA-N",
"smiles": "O=C(Nc1cccnn1)N1CCC(=Cc2cccc(Oc3ccc(N4CCCC4)cn3)c2)CC1"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "9475",
"routeId": "sa_df458d4141682a428fabd962",
"moleculeId": "sa_2a4535677dc060c4d9980db7",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_2a4535677dc060c4d9980db7",
"inchikey": "CPKSBJNUCZLOOE-UHFFFAOYSA-N",
"smiles": "O=C(Nc1cccnn1)N1CCC(=Cc2cccc(Oc3ccc(N4CCCC4)cn3)c2)CC1"
},
"smiles": "O=C(Nc1cccnn1)N1CCC(=Cc2cccc(Oc3ccc(N4CCCC4)cn3)c2)CC1",
"reactionStepId": "sa_f7f320de2ee6b9910f01b8fc",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20080261941A1;0403;622242\",\"rsmi\":\"[NH:10]1[CH2:11][CH2:12][C:13](=[CH:14][c:15]2[cH:16][c:17]([O:18][c:19]3[n:20][cH:21][c:22]([N:23]4[CH2:24][CH2:25][CH2:26][CH2:27]4)[cH:28][cH:29]3)[cH:30][cH:31][cH:32]2)[CH2:33][CH2:34]1.c1ccc(O[C:2](=[O:1])[NH:3][c:4]2[cH:5][cH:6][cH:7][n:8][n:9]2)cc1>CCN(CC)CC.CS(C)=O.O>[O:1]=[C:2]([NH:3][c:4]1[cH:5][cH:6][cH:7][n:8][n:9]1)[N:10]1[CH2:11][CH2:12][C:13](=[CH:14][c:15]2[cH:16][c:17]([O:18][c:19]3[n:20][cH:21][c:22]([N:23]4[CH2:24][CH2:25][CH2:26][CH2:27]4)[cH:28][cH:29]3)[cH:30][cH:31][cH:32]2)[CH2:33][CH2:34]1\"},\"mapped_reaction_smiles\":\"[NH:10]1[CH2:11][CH2:12][C:13](=[CH:14][c:15]2[cH:16][c:17]([O:18][c:19]3[n:20][cH:21][c:22]([N:23]4[CH2:24][CH2:25][CH2:26][CH2:27]4)[cH:28][cH:29]3)[cH:30][cH:31][cH:32]2)[CH2:33][CH2:34]1.c1ccc(O[C:2](=[O:1])[NH:3][c:4]2[cH:5][cH:6][cH:7][n:8][n:9]2)cc1>CCN(CC)CC.CS(C)=O.O>[O:1]=[C:2]([NH:3][c:4]1[cH:5][cH:6][cH:7][n:8][n:9]1)[N:10]1[CH2:11][CH2:12][C:13](=[CH:14][c:15]2[cH:16][c:17]([O:18][c:19]3[n:20][cH:21][c:22]([N:23]4[CH2:24][CH2:25][CH2:26][CH2:27]4)[cH:28][cH:29]3)[cH:30][cH:31][cH:32]2)[CH2:33][CH2:34]1\"}",
"reactionStep": {
"id": "sa_f7f320de2ee6b9910f01b8fc",
"reactionHash": "032ab34860eb478914402728e8950b342bf1e18d3fa9121bd27c3ce92b7b545b"
},
"children": [
{
"id": "9476",
"routeId": "sa_df458d4141682a428fabd962",
"moleculeId": "sa_44f6ed9b21463035f97267f8",
"parentId": "9475",
"isLeaf": false,
"molecule": {
"id": "sa_44f6ed9b21463035f97267f8",
"inchikey": "QPZCSARPVJAGQW-UHFFFAOYSA-N",
"smiles": "O=C(N=c1cccn[nH]1)Oc1ccccc1"
},
"smiles": "O=C(Nc1cccnn1)Oc1ccccc1",
"reactionStepId": "sa_997cc1dfa735e7600162371e",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20080261941A1;0279;622127\",\"rsmi\":\"Cl[C:2](=[O:1])[O:10][c:11]1[cH:12][cH:13][cH:14][cH:15][cH:16]1.[NH2:3][c:4]1[cH:5][cH:6][cH:7][n:8][n:9]1>C1CCOC1.CC#N.c1ccncc1>[O:1]=[C:2]([NH:3][c:4]1[cH:5][cH:6][cH:7][n:8][n:9]1)[O:10][c:11]1[cH:12][cH:13][cH:14][cH:15][cH:16]1\"},\"mapped_reaction_smiles\":\"Cl[C:2](=[O:1])[O:10][c:11]1[cH:12][cH:13][cH:14][cH:15][cH:16]1.[NH2:3][c:4]1[cH:5][cH:6][cH:7][n:8][n:9]1>C1CCOC1.CC#N.c1ccncc1>[O:1]=[C:2]([NH:3][c:4]1[cH:5][cH:6][cH:7][n:8][n:9]1)[O:10][c:11]1[cH:12][cH:13][cH:14][cH:15][cH:16]1\"}",
"reactionStep": {
"id": "sa_997cc1dfa735e7600162371e",
"reactionHash": "9d6737fa27eef3a185ebf19a423b45344d05db9a2ff8ddf1f00ce3d14a15b8e4"
},
"children": [
{
"id": "9477",
"routeId": "sa_df458d4141682a428fabd962",
"moleculeId": "sa_c3f902b5f9863db0f23f1ee5",
"parentId": "9476",
"isLeaf": true,
"molecule": {
"id": "sa_c3f902b5f9863db0f23f1ee5",
"inchikey": "AHWALFGBDFAJAI-UHFFFAOYSA-N",
"smiles": "O=C(Cl)Oc1ccccc1"
},
"smiles": "O=C(Cl)Oc1ccccc1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "9478",
"routeId": "sa_df458d4141682a428fabd962",
"moleculeId": "sa_0b85d039756591b2e781ea75",
"parentId": "9476",
"isLeaf": true,
"molecule": {
"id": "sa_0b85d039756591b2e781ea75",
"inchikey": "LETVJWLLIMJADE-UHFFFAOYSA-N",
"smiles": "N=c1cccn[nH]1"
},
"smiles": "Nc1cccnn1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
},
{
"id": "9479",
"routeId": "sa_df458d4141682a428fabd962",
"moleculeId": "sa_3b62175eb3e471cd449baa23",
"parentId": "9475",
"isLeaf": false,
"molecule": {
"id": "sa_3b62175eb3e471cd449baa23",
"inchikey": "WXLQMYHGBBADLK-UHFFFAOYSA-N",
"smiles": "C(=C1CCNCC1)c1cccc(Oc2ccc(N3CCCC3)cn2)c1"
},
"smiles": "C(=C1CCNCC1)c1cccc(Oc2ccc(N3CCCC3)cn2)c1",
"reactionStepId": "sa_87857abeba4d690c2c5d78b5",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20080261941A1;0402;622241\",\"rsmi\":\"CC(C)(C)OC(=O)[N:22]1[CH2:21][CH2:20][C:19](=[CH:18][c:17]2[cH:16][c:3]([O:4][c:5]3[n:6][cH:7][c:8]([N:9]4[CH2:10][CH2:11][CH2:12][CH2:13]4)[cH:14][cH:15]3)[cH:2][cH:1][cH:25]2)[CH2:24][CH2:23]1>ClCCl.O=C(O)C(F)(F)F>[cH:1]1[cH:2][c:3]([O:4][c:5]2[n:6][cH:7][c:8]([N:9]3[CH2:10][CH2:11][CH2:12][CH2:13]3)[cH:14][cH:15]2)[cH:16][c:17]([CH:18]=[C:19]2[CH2:20][CH2:21][NH:22][CH2:23][CH2:24]2)[cH:25]1\"},\"mapped_reaction_smiles\":\"CC(C)(C)OC(=O)[N:22]1[CH2:21][CH2:20][C:19](=[CH:18][c:17]2[cH:16][c:3]([O:4][c:5]3[n:6][cH:7][c:8]([N:9]4[CH2:10][CH2:11][CH2:12][CH2:13]4)[cH:14][cH:15]3)[cH:2][cH:1][cH:25]2)[CH2:24][CH2:23]1>ClCCl.O=C(O)C(F)(F)F>[cH:1]1[cH:2][c:3]([O:4][c:5]2[n:6][cH:7][c:8]([N:9]3[CH2:10][CH2:11][CH2:12][CH2:13]3)[cH:14][cH:15]2)[cH:16][c:17]([CH:18]=[C:19]2[CH2:20][CH2:21][NH:22][CH2:23][CH2:24]2)[cH:25]1\"}",
"reactionStep": {
"id": "sa_87857abeba4d690c2c5d78b5",
"reactionHash": "530d2bc2feda037ddfc052735a4f4741455fddd0628bd5e1a8150dfdc0c0de9c"
},
"children": [
{
"id": "9480",
"routeId": "sa_df458d4141682a428fabd962",
"moleculeId": "sa_ef45270eaaca3751cc61fb3e",
"parentId": "9479",
"isLeaf": false,
"molecule": {
"id": "sa_ef45270eaaca3751cc61fb3e",
"inchikey": "COFCVNNTSQUBNJ-UHFFFAOYSA-N",
"smiles": "CC(C)(C)OC(=O)N1CCC(=Cc2cccc(Oc3ccc(N4CCCC4)cn3)c2)CC1"
},
"smiles": "CC(C)(C)OC(=O)N1CCC(=Cc2cccc(Oc3ccc(N4CCCC4)cn3)c2)CC1",
"reactionStepId": "sa_73da0dfb917046a672cd378c",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20080261941A1;0401;622240\",\"rsmi\":\"Br[c:20]1[cH:19][n:18][c:17]([O:16][c:15]2[cH:14][c:13]([CH:12]=[C:11]3[CH2:10][CH2:9][N:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:32][CH2:31]3)[cH:30][cH:29][cH:28]2)[cH:27][cH:26]1.[NH:21]1[CH2:22][CH2:23][CH2:24][CH2:25]1>CC(=O)O.CC(=O)O.CC(C)(C)P(c1ccccc1-c1ccccc1)C(C)(C)C.CC(C)(C)O.Cc1ccccc1.[Na+].[Pd+2]>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][C:11](=[CH:12][c:13]2[cH:14][c:15]([O:16][c:17]3[n:18][cH:19][c:20]([N:21]4[CH2:22][CH2:23][CH2:24][CH2:25]4)[cH:26][cH:27]3)[cH:28][cH:29][cH:30]2)[CH2:31][CH2:32]1\"},\"mapped_reaction_smiles\":\"Br[c:20]1[cH:19][n:18][c:17]([O:16][c:15]2[cH:14][c:13]([CH:12]=[C:11]3[CH2:10][CH2:9][N:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:32][CH2:31]3)[cH:30][cH:29][cH:28]2)[cH:27][cH:26]1.[NH:21]1[CH2:22][CH2:23][CH2:24][CH2:25]1>CC(=O)O.CC(=O)O.CC(C)(C)P(c1ccccc1-c1ccccc1)C(C)(C)C.CC(C)(C)O.Cc1ccccc1.[Na+].[Pd+2]>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][C:11](=[CH:12][c:13]2[cH:14][c:15]([O:16][c:17]3[n:18][cH:19][c:20]([N:21]4[CH2:22][CH2:23][CH2:24][CH2:25]4)[cH:26][cH:27]3)[cH:28][cH:29][cH:30]2)[CH2:31][CH2:32]1\"}",
"reactionStep": {
"id": "sa_73da0dfb917046a672cd378c",
"reactionHash": "3559eb625653d835cb1f87dbeb6477c9bd53345dbb1ca91ba092fb062bb63d0a"
},
"children": [
{
"id": "9481",
"routeId": "sa_df458d4141682a428fabd962",
"moleculeId": "sa_ab1f3e4f505868589094bfe7",
"parentId": "9480",
"isLeaf": false,
"molecule": {
"id": "sa_ab1f3e4f505868589094bfe7",
"inchikey": "LROZQLDTXPGSNN-UHFFFAOYSA-N",
"smiles": "CC(C)(C)OC(=O)N1CCC(=Cc2cccc(Oc3ccc(Br)cn3)c2)CC1"
},
"smiles": "CC(C)(C)OC(=O)N1CCC(=Cc2cccc(Oc3ccc(Br)cn3)c2)CC1",
"reactionStepId": "sa_e9d8527828ac808c8aac9bea",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20080261941A1;0263;622113\",\"rsmi\":\"CCOP(=O)(OCC)[CH2:12][c:13]1[cH:14][c:15]([O:16][c:17]2[n:18][cH:19][c:20]([Br:21])[cH:22][cH:23]2)[cH:24][cH:25][cH:26]1.O=[C:11]1[CH2:10][CH2:9][N:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:28][CH2:27]1>C1CCOC1.C1COCCOCCOCCOCCO1.O.[HH].[Na+]>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][C:11](=[CH:12][c:13]2[cH:14][c:15]([O:16][c:17]3[n:18][cH:19][c:20]([Br:21])[cH:22][cH:23]3)[cH:24][cH:25][cH:26]2)[CH2:27][CH2:28]1\"},\"mapped_reaction_smiles\":\"CCOP(=O)(OCC)[CH2:12][c:13]1[cH:14][c:15]([O:16][c:17]2[n:18][cH:19][c:20]([Br:21])[cH:22][cH:23]2)[cH:24][cH:25][cH:26]1.O=[C:11]1[CH2:10][CH2:9][N:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:28][CH2:27]1>C1CCOC1.C1COCCOCCOCCOCCO1.O.[HH].[Na+]>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][C:11](=[CH:12][c:13]2[cH:14][c:15]([O:16][c:17]3[n:18][cH:19][c:20]([Br:21])[cH:22][cH:23]3)[cH:24][cH:25][cH:26]2)[CH2:27][CH2:28]1\"}",
"reactionStep": {
"id": "sa_e9d8527828ac808c8aac9bea",
"reactionHash": "9a2ce908b998d701b47e03220100b280d6214dac05d934c5f1a0b9976341714f"
},
"children": [
{
"id": "9482",
"routeId": "sa_df458d4141682a428fabd962",
"moleculeId": "sa_eb6dd176df2613ced83b818b",
"parentId": "9481",
"isLeaf": false,
"molecule": {
"id": "sa_eb6dd176df2613ced83b818b",
"inchikey": "FEUYRHDNSQLVJW-UHFFFAOYSA-N",
"smiles": "CCOP(=O)(Cc1cccc(Oc2ccc(Br)cn2)c1)OCC"
},
"smiles": "CCOP(=O)(Cc1cccc(Oc2ccc(Br)cn2)c1)OCC",
"reactionStepId": "sa_c09791ce50999b850e2df79f",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20080261941A1;0262;622112\",\"rsmi\":\"CC[O:5][P:4]([O:3][CH2:2][CH3:1])[O:21][CH2:22][CH3:23].Cl[CH2:6][c:7]1[cH:8][c:9]([O:10][c:11]2[n:12][cH:13][c:14]([Br:15])[cH:16][cH:17]2)[cH:18][cH:19][cH:20]1>CCCCCCC>[CH3:1][CH2:2][O:3][P:4](=[O:5])([CH2:6][c:7]1[cH:8][c:9]([O:10][c:11]2[n:12][cH:13][c:14]([Br:15])[cH:16][cH:17]2)[cH:18][cH:19][cH:20]1)[O:21][CH2:22][CH3:23]\"},\"mapped_reaction_smiles\":\"CC[O:5][P:4]([O:3][CH2:2][CH3:1])[O:21][CH2:22][CH3:23].Cl[CH2:6][c:7]1[cH:8][c:9]([O:10][c:11]2[n:12][cH:13][c:14]([Br:15])[cH:16][cH:17]2)[cH:18][cH:19][cH:20]1>CCCCCCC>[CH3:1][CH2:2][O:3][P:4](=[O:5])([CH2:6][c:7]1[cH:8][c:9]([O:10][c:11]2[n:12][cH:13][c:14]([Br:15])[cH:16][cH:17]2)[cH:18][cH:19][cH:20]1)[O:21][CH2:22][CH3:23]\"}",
"reactionStep": {
"id": "sa_c09791ce50999b850e2df79f",
"reactionHash": "0bf9cf65ef79be9cec3bb775f0fcd341a9e05b12587ee6b2f7c6748afe38f89d"
},
"children": [
{
"id": "9483",
"routeId": "sa_df458d4141682a428fabd962",
"moleculeId": "sa_89f1484a9c859438eeae3e6a",
"parentId": "9482",
"isLeaf": true,
"molecule": {
"id": "sa_89f1484a9c859438eeae3e6a",
"inchikey": "BDZBKCUKTQZUTL-UHFFFAOYSA-N",
"smiles": "CCOP(OCC)OCC"
},
"smiles": "CCOP(OCC)OCC",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "9484",
"routeId": "sa_df458d4141682a428fabd962",
"moleculeId": "sa_8c336a2ab5c08cd0c0469fc7",
"parentId": "9482",
"isLeaf": true,
"molecule": {
"id": "sa_8c336a2ab5c08cd0c0469fc7",
"inchikey": "KVYCOPBONROTDE-UHFFFAOYSA-N",
"smiles": "ClCc1cccc(Oc2ccc(Br)cn2)c1"
},
"smiles": "ClCc1cccc(Oc2ccc(Br)cn2)c1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
},
{
"id": "9485",
"routeId": "sa_df458d4141682a428fabd962",
"moleculeId": "sa_806e424090667321a5b9727c",
"parentId": "9481",
"isLeaf": true,
"molecule": {
"id": "sa_806e424090667321a5b9727c",
"inchikey": "ROUYFJUVMYHXFJ-UHFFFAOYSA-N",
"smiles": "CC(C)(C)OC(=O)N1CCC(=O)CC1"
},
"smiles": "CC(C)(C)OC(=O)N1CCC(=O)CC1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
},
{
"id": "9486",
"routeId": "sa_df458d4141682a428fabd962",
"moleculeId": "sa_62377f86fd21f04e8ff496ef",
"parentId": "9480",
"isLeaf": true,
"molecule": {
"id": "sa_62377f86fd21f04e8ff496ef",
"inchikey": "RWRDLPDLKQPQOW-UHFFFAOYSA-N",
"smiles": "C1CCNC1"
},
"smiles": "C1CCNC1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
}
]
}
]
}
}