Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
COc1cc(C(=O)N2CC(C)OC[C@@H]2[C@@H](C)O)cc2nc(NCc3cc(Cl)ccn3)oc12
InChiKey
RAFSJAPZTDNHRF-CQWUKTPGSA-N
Route Signature
bc539ab9839899eac7758fea86d41356a11d950e16389864287348cd98a8e381
Synthesis route with 4 steps (convergent)
Route tree structure (JSON format)
{
"route": {
"id": "sa_46e5302dea2314ce229905b7",
"signature": "bc539ab9839899eac7758fea86d41356a11d950e16389864287348cd98a8e381",
"contentHash": "e1a96ad9fbc10cbda59f1c02f996a95397fcad5b3095b4b40727b22bcbb19eee",
"length": 4,
"isConvergent": true
},
"target": {
"id": "sa_1164872c46983f4a97e14eb1",
"benchmarkSetId": "3895c2909c53593560c5ba610abc7e6df80513dfd8624165c560451735097d36",
"targetId": "n5-02945",
"moleculeId": "sa_b995ac92ff1c0afeaba6e60d",
"smiles": "COc1cc(C(=O)N2CC(C)OC[C@@H]2[C@@H](C)O)cc2nc(NCc3cc(Cl)ccn3)oc12",
"routeLength": 4,
"isConvergent": true,
"metadata": null,
"molecule": {
"id": "sa_b995ac92ff1c0afeaba6e60d",
"inchikey": "RAFSJAPZTDNHRF-CQWUKTPGSA-N",
"smiles": "COc1cc(C(=O)N2CC(C)OC[C@@H]2[C@@H](C)O)cc2nc(NCc3cc(Cl)ccn3)oc12"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "10907",
"routeId": "sa_46e5302dea2314ce229905b7",
"moleculeId": "sa_b995ac92ff1c0afeaba6e60d",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_b995ac92ff1c0afeaba6e60d",
"inchikey": "RAFSJAPZTDNHRF-CQWUKTPGSA-N",
"smiles": "COc1cc(C(=O)N2CC(C)OC[C@@H]2[C@@H](C)O)cc2nc(NCc3cc(Cl)ccn3)oc12"
},
"smiles": "COc1cc(C(=O)N2CC(C)OC[C@@H]2[C@@H](C)O)cc2nc(NCc3cc(Cl)ccn3)oc12",
"reactionStepId": "sa_bf7f08b1cc497a92846066ce",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20160108027A1;1974;1866942\",\"rsmi\":\"O[C:6]([c:5]1[cH:4][c:3]([O:2][CH3:1])[c:20]2[c:19]([cH:18]1)[n:32][c:22]([NH:23][CH2:24][c:25]1[n:26][cH:27][cH:28][c:29]([Cl:30])[cH:31]1)[o:21]2)=[O:7].[NH:8]1[CH2:9][CH:10]([CH3:11])[O:12][CH2:13][C@@H:14]1[C@@H:15]([CH3:16])[OH:17]>CCN(C(C)C)C(C)C.CN(C)C(On1nnc2cccnc21)=[N+](C)C.CN(C)C=O.F[PH](F)(F)(F)(F)F>[CH3:1][O:2][c:3]1[cH:4][c:5]([C:6](=[O:7])[N:8]2[CH2:9][CH:10]([CH3:11])[O:12][CH2:13][C@@H:14]2[C@@H:15]([CH3:16])[OH:17])[cH:18][c:19]2[c:20]1[o:21][c:22]([NH:23][CH2:24][c:25]1[n:26][cH:27][cH:28][c:29]([Cl:30])[cH:31]1)[n:32]2\"},\"mapped_reaction_smiles\":\"O[C:6]([c:5]1[cH:4][c:3]([O:2][CH3:1])[c:20]2[c:19]([cH:18]1)[n:32][c:22]([NH:23][CH2:24][c:25]1[n:26][cH:27][cH:28][c:29]([Cl:30])[cH:31]1)[o:21]2)=[O:7].[NH:8]1[CH2:9][CH:10]([CH3:11])[O:12][CH2:13][C@@H:14]1[C@@H:15]([CH3:16])[OH:17]>CCN(C(C)C)C(C)C.CN(C)C(On1nnc2cccnc21)=[N+](C)C.CN(C)C=O.F[PH](F)(F)(F)(F)F>[CH3:1][O:2][c:3]1[cH:4][c:5]([C:6](=[O:7])[N:8]2[CH2:9][CH:10]([CH3:11])[O:12][CH2:13][C@@H:14]2[C@@H:15]([CH3:16])[OH:17])[cH:18][c:19]2[c:20]1[o:21][c:22]([NH:23][CH2:24][c:25]1[n:26][cH:27][cH:28][c:29]([Cl:30])[cH:31]1)[n:32]2\"}",
"reactionStep": {
"id": "sa_bf7f08b1cc497a92846066ce",
"reactionHash": "c9b2e7007f848491e8ac2160e2bd0d3a3721dc70e92dd7aad5961943252a0e8c"
},
"children": [
{
"id": "10908",
"routeId": "sa_46e5302dea2314ce229905b7",
"moleculeId": "sa_f46bc5e23890c3e0debfa9d7",
"parentId": "10907",
"isLeaf": false,
"molecule": {
"id": "sa_f46bc5e23890c3e0debfa9d7",
"inchikey": "AKECQURZHKEFAZ-JXBXZBNISA-N",
"smiles": "CC1CN[C@@H]([C@@H](C)O)CO1"
},
"smiles": "CC1CN[C@@H]([C@@H](C)O)CO1",
"reactionStepId": "sa_7206dd5a5e37269efa881534",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20160108027A1;1428;1866839\",\"rsmi\":\"c1ccc(C[N:4]2[CH2:3][CH:2]([CH3:1])[O:10][CH2:9][C@@H:5]2[C@@H:6]([CH3:7])[OH:8])cc1>CCO.O.O.[Pd+2].[Pd]>[CH3:1][CH:2]1[CH2:3][NH:4][C@@H:5]([C@@H:6]([CH3:7])[OH:8])[CH2:9][O:10]1\"},\"mapped_reaction_smiles\":\"c1ccc(C[N:4]2[CH2:3][CH:2]([CH3:1])[O:10][CH2:9][C@@H:5]2[C@@H:6]([CH3:7])[OH:8])cc1>CCO.O.O.[Pd+2].[Pd]>[CH3:1][CH:2]1[CH2:3][NH:4][C@@H:5]([C@@H:6]([CH3:7])[OH:8])[CH2:9][O:10]1\"}",
"reactionStep": {
"id": "sa_7206dd5a5e37269efa881534",
"reactionHash": "a7981b9e00c9e52eb74e3153e62b82f7d6c778ff7f393836df09ed0a09d638ee"
},
"children": [
{
"id": "10909",
"routeId": "sa_46e5302dea2314ce229905b7",
"moleculeId": "sa_87f10b0fa7107056ff43a793",
"parentId": "10908",
"isLeaf": false,
"molecule": {
"id": "sa_87f10b0fa7107056ff43a793",
"inchikey": "ICZLLDGMJNMCAF-JWCMVYSZSA-N",
"smiles": "CC1CN(Cc2ccccc2)[C@@H]([C@@H](C)O)CO1"
},
"smiles": "CC1CN(Cc2ccccc2)[C@@H]([C@@H](C)O)CO1",
"reactionStepId": "sa_3bfd774657b87deec70a488a",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20160108027A1;1424;1866838\",\"rsmi\":\"O=[C:3]1[CH:2]([CH3:1])[O:17][CH2:16][C@H:12]([C@@H:13]([CH3:14])[OH:15])[N:4]1[CH2:5][c:6]1[cH:7][cH:8][cH:9][cH:10][cH:11]1>C1CCOC1.CO>[CH3:1][CH:2]1[CH2:3][N:4]([CH2:5][c:6]2[cH:7][cH:8][cH:9][cH:10][cH:11]2)[C@@H:12]([C@@H:13]([CH3:14])[OH:15])[CH2:16][O:17]1\"},\"mapped_reaction_smiles\":\"O=[C:3]1[CH:2]([CH3:1])[O:17][CH2:16][C@H:12]([C@@H:13]([CH3:14])[OH:15])[N:4]1[CH2:5][c:6]1[cH:7][cH:8][cH:9][cH:10][cH:11]1>C1CCOC1.CO>[CH3:1][CH:2]1[CH2:3][N:4]([CH2:5][c:6]2[cH:7][cH:8][cH:9][cH:10][cH:11]2)[C@@H:12]([C@@H:13]([CH3:14])[OH:15])[CH2:16][O:17]1\"}",
"reactionStep": {
"id": "sa_3bfd774657b87deec70a488a",
"reactionHash": "aee725dd8028592eb070829657912829cb87e3303dcc29dac134f668bec751f2"
},
"children": [
{
"id": "10910",
"routeId": "sa_46e5302dea2314ce229905b7",
"moleculeId": "sa_baf572d31e17f36253f5b9a0",
"parentId": "10909",
"isLeaf": false,
"molecule": {
"id": "sa_baf572d31e17f36253f5b9a0",
"inchikey": "FWACCFWSVNOACY-IAUSTGCCSA-N",
"smiles": "CC1OC[C@H]([C@@H](C)O)N(Cc2ccccc2)C1=O"
},
"smiles": "CC1OC[C@H]([C@@H](C)O)N(Cc2ccccc2)C1=O",
"reactionStepId": "sa_b41ab835d9ab78e43b051e85",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20160108027A1;1421;1866837\",\"rsmi\":\"CC(C)(C)[Si](C)(C)[O:8][C@@H:6]([C@H:5]1[CH2:4][O:3][CH:2]([CH3:1])[C:17](=[O:18])[N:9]1[CH2:10][c:11]1[cH:12][cH:13][cH:14][cH:15][cH:16]1)[CH3:7]>C1CCOC1.CCCC[N+](CCCC)(CCCC)CCCC.F>[CH3:1][CH:2]1[O:3][CH2:4][C@H:5]([C@@H:6]([CH3:7])[OH:8])[N:9]([CH2:10][c:11]2[cH:12][cH:13][cH:14][cH:15][cH:16]2)[C:17]1=[O:18]\"},\"mapped_reaction_smiles\":\"CC(C)(C)[Si](C)(C)[O:8][C@@H:6]([C@H:5]1[CH2:4][O:3][CH:2]([CH3:1])[C:17](=[O:18])[N:9]1[CH2:10][c:11]1[cH:12][cH:13][cH:14][cH:15][cH:16]1)[CH3:7]>C1CCOC1.CCCC[N+](CCCC)(CCCC)CCCC.F>[CH3:1][CH:2]1[O:3][CH2:4][C@H:5]([C@@H:6]([CH3:7])[OH:8])[N:9]([CH2:10][c:11]2[cH:12][cH:13][cH:14][cH:15][cH:16]2)[C:17]1=[O:18]\"}",
"reactionStep": {
"id": "sa_b41ab835d9ab78e43b051e85",
"reactionHash": "00cf95b6bc07ed2c44d0f45333fa2c09f63e9d040db06316e77619e4aaa5ba9c"
},
"children": [
{
"id": "10911",
"routeId": "sa_46e5302dea2314ce229905b7",
"moleculeId": "sa_5e17bb0b0d5c9768ee37c989",
"parentId": "10910",
"isLeaf": true,
"molecule": {
"id": "sa_5e17bb0b0d5c9768ee37c989",
"inchikey": "VVCFIVRSQWBYKX-IFJNFQAOSA-N",
"smiles": "CC1OC[C@H]([C@@H](C)O[Si](C)(C)C(C)(C)C)N(Cc2ccccc2)C1=O"
},
"smiles": "CC1OC[C@H]([C@@H](C)O[Si](C)(C)C(C)(C)C)N(Cc2ccccc2)C1=O",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
}
]
}
]
},
{
"id": "10912",
"routeId": "sa_46e5302dea2314ce229905b7",
"moleculeId": "sa_478b207148c2db3ddd3a9660",
"parentId": "10907",
"isLeaf": false,
"molecule": {
"id": "sa_478b207148c2db3ddd3a9660",
"inchikey": "DANOHUSMTFDBGU-UHFFFAOYSA-N",
"smiles": "COc1cc(C(=O)O)cc2nc(NCc3cc(Cl)ccn3)oc12"
},
"smiles": "COc1cc(C(=O)O)cc2nc(NCc3cc(Cl)ccn3)oc12",
"reactionStepId": "sa_a33c112d817813cc1c98bbb6",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20160108027A1;0763;1866690\",\"rsmi\":\"C[O:8][C:6]([c:5]1[cH:4][c:3]([O:2][CH3:1])[c:11]2[c:10]([cH:9]1)[n:23][c:13]([NH:14][CH2:15][c:16]1[n:17][cH:18][cH:19][c:20]([Cl:21])[cH:22]1)[o:12]2)=[O:7]>C1COCCO1.[Na+].O>[CH3:1][O:2][c:3]1[cH:4][c:5]([C:6](=[O:7])[OH:8])[cH:9][c:10]2[c:11]1[o:12][c:13]([NH:14][CH2:15][c:16]1[n:17][cH:18][cH:19][c:20]([Cl:21])[cH:22]1)[n:23]2\"},\"mapped_reaction_smiles\":\"C[O:8][C:6]([c:5]1[cH:4][c:3]([O:2][CH3:1])[c:11]2[c:10]([cH:9]1)[n:23][c:13]([NH:14][CH2:15][c:16]1[n:17][cH:18][cH:19][c:20]([Cl:21])[cH:22]1)[o:12]2)=[O:7]>C1COCCO1.[Na+].O>[CH3:1][O:2][c:3]1[cH:4][c:5]([C:6](=[O:7])[OH:8])[cH:9][c:10]2[c:11]1[o:12][c:13]([NH:14][CH2:15][c:16]1[n:17][cH:18][cH:19][c:20]([Cl:21])[cH:22]1)[n:23]2\"}",
"reactionStep": {
"id": "sa_a33c112d817813cc1c98bbb6",
"reactionHash": "e5fcc26c50a2b794610018c2d181b8c5831ed12128d7774e2155ad0c0a8db2d2"
},
"children": [
{
"id": "10913",
"routeId": "sa_46e5302dea2314ce229905b7",
"moleculeId": "sa_1e648eccecbc9c025286a6b0",
"parentId": "10912",
"isLeaf": false,
"molecule": {
"id": "sa_1e648eccecbc9c025286a6b0",
"inchikey": "SFYBDKKRAXMLLT-UHFFFAOYSA-N",
"smiles": "COC(=O)c1cc(OC)c2oc(NCc3cc(Cl)ccn3)nc2c1"
},
"smiles": "COC(=O)c1cc(OC)c2oc(NCc3cc(Cl)ccn3)nc2c1",
"reactionStepId": "sa_b965e22e778919dd07d36649",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20160108027A1;0760;1866689\",\"rsmi\":\"Cl[c:10]1[o:9][c:8]2[c:7]([cH:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[cH:24][c:21]2[O:22][CH3:23])[n:20]1.[NH2:11][CH2:12][c:13]1[n:14][cH:15][cH:16][c:17]([Cl:18])[cH:19]1>C1COCCO1.CCN(C(C)C)C(C)C.Cl.Cl>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]2[c:8]([o:9][c:10]([NH:11][CH2:12][c:13]3[n:14][cH:15][cH:16][c:17]([Cl:18])[cH:19]3)[n:20]2)[c:21]([O:22][CH3:23])[cH:24]1\"},\"mapped_reaction_smiles\":\"Cl[c:10]1[o:9][c:8]2[c:7]([cH:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[cH:24][c:21]2[O:22][CH3:23])[n:20]1.[NH2:11][CH2:12][c:13]1[n:14][cH:15][cH:16][c:17]([Cl:18])[cH:19]1>C1COCCO1.CCN(C(C)C)C(C)C.Cl.Cl>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]2[c:8]([o:9][c:10]([NH:11][CH2:12][c:13]3[n:14][cH:15][cH:16][c:17]([Cl:18])[cH:19]3)[n:20]2)[c:21]([O:22][CH3:23])[cH:24]1\"}",
"reactionStep": {
"id": "sa_b965e22e778919dd07d36649",
"reactionHash": "46e8193c4174f6695714affa0c49969b63389a37d0ac65b0fc54cd892d83df0e"
},
"children": [
{
"id": "10914",
"routeId": "sa_46e5302dea2314ce229905b7",
"moleculeId": "sa_619b4434f0f51b7aa871e8c5",
"parentId": "10913",
"isLeaf": true,
"molecule": {
"id": "sa_619b4434f0f51b7aa871e8c5",
"inchikey": "FZCYDUZIHRNWSQ-UHFFFAOYSA-N",
"smiles": "NCc1cc(Cl)ccn1"
},
"smiles": "NCc1cc(Cl)ccn1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "10915",
"routeId": "sa_46e5302dea2314ce229905b7",
"moleculeId": "sa_a887470840854bb4ed221345",
"parentId": "10913",
"isLeaf": true,
"molecule": {
"id": "sa_a887470840854bb4ed221345",
"inchikey": "ULFAAGQMQWPCSV-UHFFFAOYSA-N",
"smiles": "COC(=O)c1cc(OC)c2oc(Cl)nc2c1"
},
"smiles": "COC(=O)c1cc(OC)c2oc(Cl)nc2c1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
}
]
}
]
}
}