Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
CS(=O)(=O)N1CC[C@@H](Oc2ccc(-c3cccn4nc(NC(=O)C5CC5)cc34)cc2)C1
InChiKey
KYZJUTKZOKDMTA-GOSISDBHSA-N
Route Signature
9563e43583c5c1341f784b26d2b8e7bc949c734dc300614a08bf3239a5f8476f
Synthesis route with 5 steps (convergent)
Route tree structure (JSON format)
{
"route": {
"id": "sa_97f11daf4cf2355c584ec351",
"signature": "9563e43583c5c1341f784b26d2b8e7bc949c734dc300614a08bf3239a5f8476f",
"contentHash": "ea820be1b6ccabedc977b4f0d6cfeeaed58bb546f69826e07ab993929ccae6ee",
"length": 5,
"isConvergent": true
},
"target": {
"id": "sa_aa5e6bfdf7290bd38e830b8d",
"benchmarkSetId": "3895c2909c53593560c5ba610abc7e6df80513dfd8624165c560451735097d36",
"targetId": "n5-00701",
"moleculeId": "sa_7602ad347901fad4b4655cd5",
"smiles": "CS(=O)(=O)N1CC[C@@H](Oc2ccc(-c3cccn4nc(NC(=O)C5CC5)cc34)cc2)C1",
"routeLength": 5,
"isConvergent": true,
"metadata": null,
"molecule": {
"id": "sa_7602ad347901fad4b4655cd5",
"inchikey": "KYZJUTKZOKDMTA-GOSISDBHSA-N",
"smiles": "CS(=O)(=O)N1CC[C@@H](Oc2ccc(-c3cccn4nc(NC(=O)C5CC5)cc34)cc2)C1"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "1106",
"routeId": "sa_97f11daf4cf2355c584ec351",
"moleculeId": "sa_7602ad347901fad4b4655cd5",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_7602ad347901fad4b4655cd5",
"inchikey": "KYZJUTKZOKDMTA-GOSISDBHSA-N",
"smiles": "CS(=O)(=O)N1CC[C@@H](Oc2ccc(-c3cccn4nc(NC(=O)C5CC5)cc34)cc2)C1"
},
"smiles": "CS(=O)(=O)N1CC[C@@H](Oc2ccc(-c3cccn4nc(NC(=O)C5CC5)cc34)cc2)C1",
"reactionStepId": "sa_b5206b35fc965e26b546f960",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20140051677A1;0395;1490000\",\"rsmi\":\"Cl[S:2]([CH3:1])(=[O:3])=[O:4].[NH:5]1[CH2:6][CH2:7][C@@H:8]([O:9][c:10]2[cH:11][cH:12][c:13](-[c:14]3[cH:15][cH:16][cH:17][n:18]4[n:19][c:20]([NH:21][C:22](=[O:23])[CH:24]5[CH2:25][CH2:26]5)[cH:27][c:28]34)[cH:29][cH:30]2)[CH2:31]1>CCN(CC)CC.ClCCl>[CH3:1][S:2](=[O:3])(=[O:4])[N:5]1[CH2:6][CH2:7][C@@H:8]([O:9][c:10]2[cH:11][cH:12][c:13](-[c:14]3[cH:15][cH:16][cH:17][n:18]4[n:19][c:20]([NH:21][C:22](=[O:23])[CH:24]5[CH2:25][CH2:26]5)[cH:27][c:28]34)[cH:29][cH:30]2)[CH2:31]1\"},\"mapped_reaction_smiles\":\"Cl[S:2]([CH3:1])(=[O:3])=[O:4].[NH:5]1[CH2:6][CH2:7][C@@H:8]([O:9][c:10]2[cH:11][cH:12][c:13](-[c:14]3[cH:15][cH:16][cH:17][n:18]4[n:19][c:20]([NH:21][C:22](=[O:23])[CH:24]5[CH2:25][CH2:26]5)[cH:27][c:28]34)[cH:29][cH:30]2)[CH2:31]1>CCN(CC)CC.ClCCl>[CH3:1][S:2](=[O:3])(=[O:4])[N:5]1[CH2:6][CH2:7][C@@H:8]([O:9][c:10]2[cH:11][cH:12][c:13](-[c:14]3[cH:15][cH:16][cH:17][n:18]4[n:19][c:20]([NH:21][C:22](=[O:23])[CH:24]5[CH2:25][CH2:26]5)[cH:27][c:28]34)[cH:29][cH:30]2)[CH2:31]1\"}",
"reactionStep": {
"id": "sa_b5206b35fc965e26b546f960",
"reactionHash": "3a84653a6a45ea0b52a077b9e0e6ba0ab2db1d45f214cbca897344f007523d4a"
},
"children": [
{
"id": "1107",
"routeId": "sa_97f11daf4cf2355c584ec351",
"moleculeId": "sa_df3242d11c55090e080f8a02",
"parentId": "1106",
"isLeaf": false,
"molecule": {
"id": "sa_df3242d11c55090e080f8a02",
"inchikey": "AEYLZACNTAZLDS-QGZVFWFLSA-N",
"smiles": "O=C(Nc1cc2c(-c3ccc(O[C@@H]4CCNC4)cc3)cccn2n1)C1CC1"
},
"smiles": "O=C(Nc1cc2c(-c3ccc(O[C@@H]4CCNC4)cc3)cccn2n1)C1CC1",
"reactionStepId": "sa_d2583fe6e12a537972605f68",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20140051677A1;0394;1489999\",\"rsmi\":\"CC(C)(C)OC(=O)[N:19]1[CH2:18][CH2:17][C@@H:16]([O:15][c:14]2[cH:13][cH:12][c:11](-[c:10]3[cH:9][cH:8][cH:7][n:6]4[n:5][c:4]([NH:3][C:2](=[O:1])[CH:25]5[CH2:26][CH2:27]5)[cH:24][c:23]43)[cH:22][cH:21]2)[CH2:20]1>ClCCl.O=C(O)C(F)(F)F>[O:1]=[C:2]([NH:3][c:4]1[n:5][n:6]2[cH:7][cH:8][cH:9][c:10](-[c:11]3[cH:12][cH:13][c:14]([O:15][C@@H:16]4[CH2:17][CH2:18][NH:19][CH2:20]4)[cH:21][cH:22]3)[c:23]2[cH:24]1)[CH:25]1[CH2:26][CH2:27]1\"},\"mapped_reaction_smiles\":\"CC(C)(C)OC(=O)[N:19]1[CH2:18][CH2:17][C@@H:16]([O:15][c:14]2[cH:13][cH:12][c:11](-[c:10]3[cH:9][cH:8][cH:7][n:6]4[n:5][c:4]([NH:3][C:2](=[O:1])[CH:25]5[CH2:26][CH2:27]5)[cH:24][c:23]43)[cH:22][cH:21]2)[CH2:20]1>ClCCl.O=C(O)C(F)(F)F>[O:1]=[C:2]([NH:3][c:4]1[n:5][n:6]2[cH:7][cH:8][cH:9][c:10](-[c:11]3[cH:12][cH:13][c:14]([O:15][C@@H:16]4[CH2:17][CH2:18][NH:19][CH2:20]4)[cH:21][cH:22]3)[c:23]2[cH:24]1)[CH:25]1[CH2:26][CH2:27]1\"}",
"reactionStep": {
"id": "sa_d2583fe6e12a537972605f68",
"reactionHash": "3ee4d8e5192bb45711745883d2fd0bc22a75cfb269f642039f491a6b51f4b9ab"
},
"children": [
{
"id": "1108",
"routeId": "sa_97f11daf4cf2355c584ec351",
"moleculeId": "sa_d79324249cf01e3e1d01be00",
"parentId": "1107",
"isLeaf": false,
"molecule": {
"id": "sa_d79324249cf01e3e1d01be00",
"inchikey": "RMUMCXQRIKCFNW-HXUWFJFHSA-N",
"smiles": "CC(C)(C)OC(=O)N1CC[C@@H](Oc2ccc(-c3cccn4nc(NC(=O)C5CC5)cc34)cc2)C1"
},
"smiles": "CC(C)(C)OC(=O)N1CC[C@@H](Oc2ccc(-c3cccn4nc(NC(=O)C5CC5)cc34)cc2)C1",
"reactionStepId": "sa_93825d63ceea4c147d7ba7f2",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20140051677A1;0393;1489998\",\"rsmi\":\"Br[c:17]1[cH:18][cH:19][cH:20][n:21]2[n:22][c:23]([NH:24][C:25](=[O:26])[CH:27]3[CH2:28][CH2:29]3)[cH:30][c:31]12.CC1(C)OB([c:16]2[cH:15][cH:14][c:13]([O:12][C@@H:11]3[CH2:10][CH2:9][N:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:34]3)[cH:33][cH:32]2)OC1(C)C>C1COCCO1.O.O=C(O)O.[Na+].[Na+]>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][C@@H:11]([O:12][c:13]2[cH:14][cH:15][c:16](-[c:17]3[cH:18][cH:19][cH:20][n:21]4[n:22][c:23]([NH:24][C:25](=[O:26])[CH:27]5[CH2:28][CH2:29]5)[cH:30][c:31]34)[cH:32][cH:33]2)[CH2:34]1\"},\"mapped_reaction_smiles\":\"Br[c:17]1[cH:18][cH:19][cH:20][n:21]2[n:22][c:23]([NH:24][C:25](=[O:26])[CH:27]3[CH2:28][CH2:29]3)[cH:30][c:31]12.CC1(C)OB([c:16]2[cH:15][cH:14][c:13]([O:12][C@@H:11]3[CH2:10][CH2:9][N:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:34]3)[cH:33][cH:32]2)OC1(C)C>C1COCCO1.O.O=C(O)O.[Na+].[Na+]>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][C@@H:11]([O:12][c:13]2[cH:14][cH:15][c:16](-[c:17]3[cH:18][cH:19][cH:20][n:21]4[n:22][c:23]([NH:24][C:25](=[O:26])[CH:27]5[CH2:28][CH2:29]5)[cH:30][c:31]34)[cH:32][cH:33]2)[CH2:34]1\"}",
"reactionStep": {
"id": "sa_93825d63ceea4c147d7ba7f2",
"reactionHash": "b151fc5995ffc2940be8cc4f6dbb07a39690174e819e485f6e0c24039125895e"
},
"children": [
{
"id": "1109",
"routeId": "sa_97f11daf4cf2355c584ec351",
"moleculeId": "sa_e6e446adf5e9522a1562c88b",
"parentId": "1108",
"isLeaf": false,
"molecule": {
"id": "sa_e6e446adf5e9522a1562c88b",
"inchikey": "MQJBPZNMSOLKSN-UHFFFAOYSA-N",
"smiles": "O=C(Nc1cc2c(Br)cccn2n1)C1CC1"
},
"smiles": "O=C(Nc1cc2c(Br)cccn2n1)C1CC1",
"reactionStepId": "sa_e816f4285c7f3415d8be4357",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20140051677A1;0295;1489971\",\"rsmi\":\"Cl[C:2](=[O:1])[CH:14]1[CH2:15][CH2:16]1.[NH2:3][c:4]1[n:5][n:6]2[cH:7][cH:8][cH:9][c:10]([Br:11])[c:12]2[cH:13]1>CC#N.CCN(CC)CC>[O:1]=[C:2]([NH:3][c:4]1[n:5][n:6]2[cH:7][cH:8][cH:9][c:10]([Br:11])[c:12]2[cH:13]1)[CH:14]1[CH2:15][CH2:16]1\"},\"mapped_reaction_smiles\":\"Cl[C:2](=[O:1])[CH:14]1[CH2:15][CH2:16]1.[NH2:3][c:4]1[n:5][n:6]2[cH:7][cH:8][cH:9][c:10]([Br:11])[c:12]2[cH:13]1>CC#N.CCN(CC)CC>[O:1]=[C:2]([NH:3][c:4]1[n:5][n:6]2[cH:7][cH:8][cH:9][c:10]([Br:11])[c:12]2[cH:13]1)[CH:14]1[CH2:15][CH2:16]1\"}",
"reactionStep": {
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"reactionHash": "966f1861352ddefecb1ce3adb2b1c250169c94115221b9c8e93ceeb4ae4ad3fa"
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"children": [
{
"id": "1110",
"routeId": "sa_97f11daf4cf2355c584ec351",
"moleculeId": "sa_ed290cda3c914c97b7b80221",
"parentId": "1109",
"isLeaf": true,
"molecule": {
"id": "sa_ed290cda3c914c97b7b80221",
"inchikey": "MMMBISQBDZHRTI-UHFFFAOYSA-N",
"smiles": "Nc1cc2c(Br)cccn2n1"
},
"smiles": "Nc1cc2c(Br)cccn2n1",
"reactionStepId": null,
"template": null,
"metadata": null,
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},
{
"id": "1111",
"routeId": "sa_97f11daf4cf2355c584ec351",
"moleculeId": "sa_533af856f6df3abb2d70c000",
"parentId": "1109",
"isLeaf": true,
"molecule": {
"id": "sa_533af856f6df3abb2d70c000",
"inchikey": "ZOOSILUVXHVRJE-UHFFFAOYSA-N",
"smiles": "O=C(Cl)C1CC1"
},
"smiles": "O=C(Cl)C1CC1",
"reactionStepId": null,
"template": null,
"metadata": null,
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}
]
},
{
"id": "1112",
"routeId": "sa_97f11daf4cf2355c584ec351",
"moleculeId": "sa_d749054099ef33671aaa1387",
"parentId": "1108",
"isLeaf": false,
"molecule": {
"id": "sa_d749054099ef33671aaa1387",
"inchikey": "SGHPXNIINLLSMV-QGZVFWFLSA-N",
"smiles": "CC(C)(C)OC(=O)N1CC[C@@H](Oc2ccc(B3OC(C)(C)C(C)(C)O3)cc2)C1"
},
"smiles": "CC(C)(C)OC(=O)N1CC[C@@H](Oc2ccc(B3OC(C)(C)C(C)(C)O3)cc2)C1",
"reactionStepId": "sa_f4a676691c757ec8ef54cbfe",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20140051677A1;0392;1489997\",\"rsmi\":\"CS(=O)(=O)O[C@H:11]1[CH2:10][CH2:9][N:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:28]1.[OH:12][c:13]1[cH:14][cH:15][c:16]([B:17]2[O:18][C:19]([CH3:20])([CH3:21])[C:22]([CH3:23])([CH3:24])[O:25]2)[cH:26][cH:27]1>CN(C)C=O.O=C(O)O.[K+].[K+]>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][C@@H:11]([O:12][c:13]2[cH:14][cH:15][c:16]([B:17]3[O:18][C:19]([CH3:20])([CH3:21])[C:22]([CH3:23])([CH3:24])[O:25]3)[cH:26][cH:27]2)[CH2:28]1\"},\"mapped_reaction_smiles\":\"CS(=O)(=O)O[C@H:11]1[CH2:10][CH2:9][N:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:28]1.[OH:12][c:13]1[cH:14][cH:15][c:16]([B:17]2[O:18][C:19]([CH3:20])([CH3:21])[C:22]([CH3:23])([CH3:24])[O:25]2)[cH:26][cH:27]1>CN(C)C=O.O=C(O)O.[K+].[K+]>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][C@@H:11]([O:12][c:13]2[cH:14][cH:15][c:16]([B:17]3[O:18][C:19]([CH3:20])([CH3:21])[C:22]([CH3:23])([CH3:24])[O:25]3)[cH:26][cH:27]2)[CH2:28]1\"}",
"reactionStep": {
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"reactionHash": "8b6c0455b5a7529ef958ebc2c85b28910457b84650418d25ea0624d6aa6e1b9b"
},
"children": [
{
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"routeId": "sa_97f11daf4cf2355c584ec351",
"moleculeId": "sa_8abfda130f58505f511e73c7",
"parentId": "1112",
"isLeaf": true,
"molecule": {
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"inchikey": "BICZJRAGTCRORZ-UHFFFAOYSA-N",
"smiles": "CC1(C)OB(c2ccc(O)cc2)OC1(C)C"
},
"smiles": "CC1(C)OB(c2ccc(O)cc2)OC1(C)C",
"reactionStepId": null,
"template": null,
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},
{
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"molecule": {
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"inchikey": "KWQRKOSMSFLBTJ-QMMMGPOBSA-N",
"smiles": "CC(C)(C)OC(=O)N1CC[C@H](OS(C)(=O)=O)C1"
},
"smiles": "CC(C)(C)OC(=O)N1CC[C@H](OS(C)(=O)=O)C1",
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"metadata": "{\"annotations\":{\"ID\":\"US20140051677A1;0391;1489996\",\"rsmi\":\"Cl[S:13]([CH3:14])(=[O:15])=[O:16].[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][C@H:11]([OH:12])[CH2:17]1>CCN(CC)CC.ClCCl>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][C@H:11]([O:12][S:13]([CH3:14])(=[O:15])=[O:16])[CH2:17]1\"},\"mapped_reaction_smiles\":\"Cl[S:13]([CH3:14])(=[O:15])=[O:16].[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][C@H:11]([OH:12])[CH2:17]1>CCN(CC)CC.ClCCl>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][C@H:11]([O:12][S:13]([CH3:14])(=[O:15])=[O:16])[CH2:17]1\"}",
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"children": [
{
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"parentId": "1114",
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"molecule": {
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"inchikey": "APCBTRDHCDOPNY-ZETCQYMHSA-N",
"smiles": "CC(C)(C)OC(=O)N1CC[C@H](O)C1"
},
"smiles": "CC(C)(C)OC(=O)N1CC[C@H](O)C1",
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},
{
"id": "1116",
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"molecule": {
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"inchikey": "QARBMVPHQWIHKH-UHFFFAOYSA-N",
"smiles": "CS(=O)(=O)Cl"
},
"smiles": "CS(=O)(=O)Cl",
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}
]
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]
}
]
}
]
},
{
"id": "1117",
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"moleculeId": "sa_d2a31ea58046b00856f61ca5",
"parentId": "1106",
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"molecule": {
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"inchikey": "QARBMVPHQWIHKH-UHFFFAOYSA-N",
"smiles": "CS(=O)(=O)Cl"
},
"smiles": "CS(=O)(=O)Cl",
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}
]
}
}