Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
COC(=O)N1CCC(c2ccc(-c3cc4c(C(=O)O)c[nH]c4cc3Cl)cc2)C1
InChiKey
GFKWGTIEMRZGTL-UHFFFAOYSA-N
Route Signature
3f6d6862b3f280356136b09b350df2f630961ca3a8894db1d2187ac412dd07bd
Synthesis route with 4 steps (convergent)
Route tree structure (JSON format)
{
"route": {
"id": "sa_ad62db45bcb96c12f1f1a124",
"signature": "3f6d6862b3f280356136b09b350df2f630961ca3a8894db1d2187ac412dd07bd",
"contentHash": "f5d62b4c46086f0ddad8ee58e8193fae4a7bee3709823b2054c62bdde53bbe29",
"length": 4,
"isConvergent": true
},
"target": {
"id": "sa_4e9c54b55bb0d032d27579d2",
"benchmarkSetId": "3895c2909c53593560c5ba610abc7e6df80513dfd8624165c560451735097d36",
"targetId": "n5-06188",
"moleculeId": "sa_f353b14a25e1da3af52eb021",
"smiles": "COC(=O)N1CCC(c2ccc(-c3cc4c(C(=O)O)c[nH]c4cc3Cl)cc2)C1",
"routeLength": 4,
"isConvergent": true,
"metadata": null,
"molecule": {
"id": "sa_f353b14a25e1da3af52eb021",
"inchikey": "GFKWGTIEMRZGTL-UHFFFAOYSA-N",
"smiles": "COC(=O)N1CCC(c2ccc(-c3cc4c(C(=O)O)c[nH]c4cc3Cl)cc2)C1"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "11529",
"routeId": "sa_ad62db45bcb96c12f1f1a124",
"moleculeId": "sa_f353b14a25e1da3af52eb021",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_f353b14a25e1da3af52eb021",
"inchikey": "GFKWGTIEMRZGTL-UHFFFAOYSA-N",
"smiles": "COC(=O)N1CCC(c2ccc(-c3cc4c(C(=O)O)c[nH]c4cc3Cl)cc2)C1"
},
"smiles": "COC(=O)N1CCC(c2ccc(-c3cc4c(C(=O)O)c[nH]c4cc3Cl)cc2)C1",
"reactionStepId": "sa_c81dc46e6c65fe330db0196a",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20150038484A1;0770;1649240\",\"rsmi\":\"O=P(O)(O)[OH:23].[CH3:1][O:2][C:3](=[O:4])[N:5]1[CH2:6][CH2:7][CH:8]([c:9]2[cH:10][cH:11][c:12](-[c:13]3[c:14]([Cl:15])[cH:16][c:17]4[nH:18][cH:19][c:20]([CH:21]=[O:22])[c:24]4[cH:25]3)[cH:26][cH:27]2)[CH2:28]1>CC#N.CC(C)(C)O.CC=C(C)C.O.O.O.[Na+].[Na+].[O-][Cl+]O>[CH3:1][O:2][C:3](=[O:4])[N:5]1[CH2:6][CH2:7][CH:8]([c:9]2[cH:10][cH:11][c:12](-[c:13]3[c:14]([Cl:15])[cH:16][c:17]4[nH:18][cH:19][c:20]([C:21](=[O:22])[OH:23])[c:24]4[cH:25]3)[cH:26][cH:27]2)[CH2:28]1\"},\"mapped_reaction_smiles\":\"O=P(O)(O)[OH:23].[CH3:1][O:2][C:3](=[O:4])[N:5]1[CH2:6][CH2:7][CH:8]([c:9]2[cH:10][cH:11][c:12](-[c:13]3[c:14]([Cl:15])[cH:16][c:17]4[nH:18][cH:19][c:20]([CH:21]=[O:22])[c:24]4[cH:25]3)[cH:26][cH:27]2)[CH2:28]1>CC#N.CC(C)(C)O.CC=C(C)C.O.O.O.[Na+].[Na+].[O-][Cl+]O>[CH3:1][O:2][C:3](=[O:4])[N:5]1[CH2:6][CH2:7][CH:8]([c:9]2[cH:10][cH:11][c:12](-[c:13]3[c:14]([Cl:15])[cH:16][c:17]4[nH:18][cH:19][c:20]([C:21](=[O:22])[OH:23])[c:24]4[cH:25]3)[cH:26][cH:27]2)[CH2:28]1\"}",
"reactionStep": {
"id": "sa_c81dc46e6c65fe330db0196a",
"reactionHash": "edbe9f01b63500d810f8474cd27cbe5d89368e61cc11a4c937a92ac7847fca2c"
},
"children": [
{
"id": "11530",
"routeId": "sa_ad62db45bcb96c12f1f1a124",
"moleculeId": "sa_da349ac9eae26ee586907c7c",
"parentId": "11529",
"isLeaf": false,
"molecule": {
"id": "sa_da349ac9eae26ee586907c7c",
"inchikey": "CCOHORONIVSVPS-UHFFFAOYSA-N",
"smiles": "COC(=O)N1CCC(c2ccc(-c3cc4c(C=O)c[nH]c4cc3Cl)cc2)C1"
},
"smiles": "COC(=O)N1CCC(c2ccc(-c3cc4c(C=O)c[nH]c4cc3Cl)cc2)C1",
"reactionStepId": "sa_5067adcef508afba8a808bf8",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20150038484A1;0769;1649239\",\"rsmi\":\"Br[c:13]1[c:14]([Cl:15])[cH:16][c:17]2[nH:18][cH:19][c:20]([CH:21]=[O:22])[c:23]2[cH:24]1.CC1(C)COB([c:12]2[cH:11][cH:10][c:9]([CH:8]3[CH2:7][CH2:6][N:5]([C:3]([O:2][CH3:1])=[O:4])[CH2:27]3)[cH:26][cH:25]2)OC1>CCO.Cc1ccccc1.Cl[Pd]Cl.O=C(O)O.[Fe+2].[K+].[K+]>[CH3:1][O:2][C:3](=[O:4])[N:5]1[CH2:6][CH2:7][CH:8]([c:9]2[cH:10][cH:11][c:12](-[c:13]3[c:14]([Cl:15])[cH:16][c:17]4[nH:18][cH:19][c:20]([CH:21]=[O:22])[c:23]4[cH:24]3)[cH:25][cH:26]2)[CH2:27]1\"},\"mapped_reaction_smiles\":\"Br[c:13]1[c:14]([Cl:15])[cH:16][c:17]2[nH:18][cH:19][c:20]([CH:21]=[O:22])[c:23]2[cH:24]1.CC1(C)COB([c:12]2[cH:11][cH:10][c:9]([CH:8]3[CH2:7][CH2:6][N:5]([C:3]([O:2][CH3:1])=[O:4])[CH2:27]3)[cH:26][cH:25]2)OC1>CCO.Cc1ccccc1.Cl[Pd]Cl.O=C(O)O.[Fe+2].[K+].[K+]>[CH3:1][O:2][C:3](=[O:4])[N:5]1[CH2:6][CH2:7][CH:8]([c:9]2[cH:10][cH:11][c:12](-[c:13]3[c:14]([Cl:15])[cH:16][c:17]4[nH:18][cH:19][c:20]([CH:21]=[O:22])[c:23]4[cH:24]3)[cH:25][cH:26]2)[CH2:27]1\"}",
"reactionStep": {
"id": "sa_5067adcef508afba8a808bf8",
"reactionHash": "824c6cb775ec7f865aa19955496d0215bd6a5c1c6ccf19652f3916e9ce9d6373"
},
"children": [
{
"id": "11531",
"routeId": "sa_ad62db45bcb96c12f1f1a124",
"moleculeId": "sa_97fd698712fb4eee0016bfe2",
"parentId": "11530",
"isLeaf": false,
"molecule": {
"id": "sa_97fd698712fb4eee0016bfe2",
"inchikey": "ISNMSGBNFQGRLG-UHFFFAOYSA-N",
"smiles": "O=Cc1c[nH]c2cc(Cl)c(Br)cc12"
},
"smiles": "O=Cc1c[nH]c2cc(Cl)c(Br)cc12",
"reactionStepId": "sa_3f630ab48ae66d0ba2198d75",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20150038484A1;0695;1649189\",\"rsmi\":\"CN(C)[CH:2]=[O:1].[cH:3]1[cH:4][nH:5][c:6]2[cH:7][c:8]([Cl:9])[c:10]([Br:11])[cH:12][c:13]12>O.O=P(Cl)(Cl)Cl.[Na+].O>[O:1]=[CH:2][c:3]1[cH:4][nH:5][c:6]2[cH:7][c:8]([Cl:9])[c:10]([Br:11])[cH:12][c:13]12\"},\"mapped_reaction_smiles\":\"CN(C)[CH:2]=[O:1].[cH:3]1[cH:4][nH:5][c:6]2[cH:7][c:8]([Cl:9])[c:10]([Br:11])[cH:12][c:13]12>O.O=P(Cl)(Cl)Cl.[Na+].O>[O:1]=[CH:2][c:3]1[cH:4][nH:5][c:6]2[cH:7][c:8]([Cl:9])[c:10]([Br:11])[cH:12][c:13]12\"}",
"reactionStep": {
"id": "sa_3f630ab48ae66d0ba2198d75",
"reactionHash": "d16e6d7dc766423f7627252c3670ce4ca781f838d42a62ae0938146b38f9959d"
},
"children": [
{
"id": "11532",
"routeId": "sa_ad62db45bcb96c12f1f1a124",
"moleculeId": "sa_fb41824392d522dc6a273179",
"parentId": "11531",
"isLeaf": true,
"molecule": {
"id": "sa_fb41824392d522dc6a273179",
"inchikey": "SMZUROGBNBCCPT-UHFFFAOYSA-N",
"smiles": "Clc1cc2[nH]ccc2cc1Br"
},
"smiles": "Clc1cc2[nH]ccc2cc1Br",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "11533",
"routeId": "sa_ad62db45bcb96c12f1f1a124",
"moleculeId": "sa_e0b5e93d36242e79e81ef68c",
"parentId": "11531",
"isLeaf": true,
"molecule": {
"id": "sa_e0b5e93d36242e79e81ef68c",
"inchikey": "ZMXDDKWLCZADIW-UHFFFAOYSA-N",
"smiles": "CN(C)C=O"
},
"smiles": "CN(C)C=O",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
},
{
"id": "11534",
"routeId": "sa_ad62db45bcb96c12f1f1a124",
"moleculeId": "sa_318c6d762e5282004735c899",
"parentId": "11530",
"isLeaf": false,
"molecule": {
"id": "sa_318c6d762e5282004735c899",
"inchikey": "MAVHFFXVPNVJID-UHFFFAOYSA-N",
"smiles": "COC(=O)N1CCC(c2ccc(B3OCC(C)(C)CO3)cc2)C1"
},
"smiles": "COC(=O)N1CCC(c2ccc(B3OCC(C)(C)CO3)cc2)C1",
"reactionStepId": "sa_dbcd8343e567e87f29f6bd1e",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20150038484A1;0768;1649238\",\"rsmi\":\"Br[c:12]1[cH:11][cH:10][c:9]([CH:8]2[CH2:7][CH2:6][N:5]([C:3]([O:2][CH3:1])=[O:4])[CH2:23]2)[cH:22][cH:21]1.CC1(C)COB([B:13]2[O:14][CH2:15][C:16]([CH3:17])([CH3:18])[CH2:19][O:20]2)OC1>C1COCCO1.CC(=O)O.Cl[Pd]Cl.[Fe+2].[K+]>[CH3:1][O:2][C:3](=[O:4])[N:5]1[CH2:6][CH2:7][CH:8]([c:9]2[cH:10][cH:11][c:12]([B:13]3[O:14][CH2:15][C:16]([CH3:17])([CH3:18])[CH2:19][O:20]3)[cH:21][cH:22]2)[CH2:23]1\"},\"mapped_reaction_smiles\":\"Br[c:12]1[cH:11][cH:10][c:9]([CH:8]2[CH2:7][CH2:6][N:5]([C:3]([O:2][CH3:1])=[O:4])[CH2:23]2)[cH:22][cH:21]1.CC1(C)COB([B:13]2[O:14][CH2:15][C:16]([CH3:17])([CH3:18])[CH2:19][O:20]2)OC1>C1COCCO1.CC(=O)O.Cl[Pd]Cl.[Fe+2].[K+]>[CH3:1][O:2][C:3](=[O:4])[N:5]1[CH2:6][CH2:7][CH:8]([c:9]2[cH:10][cH:11][c:12]([B:13]3[O:14][CH2:15][C:16]([CH3:17])([CH3:18])[CH2:19][O:20]3)[cH:21][cH:22]2)[CH2:23]1\"}",
"reactionStep": {
"id": "sa_dbcd8343e567e87f29f6bd1e",
"reactionHash": "a6894dfcde4e9ce4b6d2f41c3a5f0b44d9e47e00b7d1be06d133ca5390bf43a9"
},
"children": [
{
"id": "11535",
"routeId": "sa_ad62db45bcb96c12f1f1a124",
"moleculeId": "sa_1127e753c784ae00c70b637a",
"parentId": "11534",
"isLeaf": true,
"molecule": {
"id": "sa_1127e753c784ae00c70b637a",
"inchikey": "MDNDJMCSXOXBFZ-UHFFFAOYSA-N",
"smiles": "CC1(C)COB(B2OCC(C)(C)CO2)OC1"
},
"smiles": "CC1(C)COB(B2OCC(C)(C)CO2)OC1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "11536",
"routeId": "sa_ad62db45bcb96c12f1f1a124",
"moleculeId": "sa_b886a71002068e7b43d4d7d5",
"parentId": "11534",
"isLeaf": false,
"molecule": {
"id": "sa_b886a71002068e7b43d4d7d5",
"inchikey": "NKIUXUFQTFHOCG-UHFFFAOYSA-N",
"smiles": "COC(=O)N1CCC(c2ccc(Br)cc2)C1"
},
"smiles": "COC(=O)N1CCC(c2ccc(Br)cc2)C1",
"reactionStepId": "sa_52ef0ce72b994df43820ff44",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20150038484A1;0767;1649237\",\"rsmi\":\"Cl[C:3]([O:2][CH3:1])=[O:4].[NH:5]1[CH2:6][CH2:7][CH:8]([c:9]2[cH:10][cH:11][c:12]([Br:13])[cH:14][cH:15]2)[CH2:16]1>C1CCOC1.CCN(CC)CC.Cl.O>[CH3:1][O:2][C:3](=[O:4])[N:5]1[CH2:6][CH2:7][CH:8]([c:9]2[cH:10][cH:11][c:12]([Br:13])[cH:14][cH:15]2)[CH2:16]1\"},\"mapped_reaction_smiles\":\"Cl[C:3]([O:2][CH3:1])=[O:4].[NH:5]1[CH2:6][CH2:7][CH:8]([c:9]2[cH:10][cH:11][c:12]([Br:13])[cH:14][cH:15]2)[CH2:16]1>C1CCOC1.CCN(CC)CC.Cl.O>[CH3:1][O:2][C:3](=[O:4])[N:5]1[CH2:6][CH2:7][CH:8]([c:9]2[cH:10][cH:11][c:12]([Br:13])[cH:14][cH:15]2)[CH2:16]1\"}",
"reactionStep": {
"id": "sa_52ef0ce72b994df43820ff44",
"reactionHash": "ad937c3fe14ea81ace3c8e1ebc605ddaa891ca0168a3b01ea5dcc03c2717cc9c"
},
"children": [
{
"id": "11537",
"routeId": "sa_ad62db45bcb96c12f1f1a124",
"moleculeId": "sa_44cbc99115490ff6662309e3",
"parentId": "11536",
"isLeaf": true,
"molecule": {
"id": "sa_44cbc99115490ff6662309e3",
"inchikey": "HXTSCISDZDBQEK-UHFFFAOYSA-N",
"smiles": "Brc1ccc(C2CCNC2)cc1"
},
"smiles": "Brc1ccc(C2CCNC2)cc1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "11538",
"routeId": "sa_ad62db45bcb96c12f1f1a124",
"moleculeId": "sa_786c6159be77bb31e43bff8a",
"parentId": "11536",
"isLeaf": true,
"molecule": {
"id": "sa_786c6159be77bb31e43bff8a",
"inchikey": "XMJHPCRAQCTCFT-UHFFFAOYSA-N",
"smiles": "COC(=O)Cl"
},
"smiles": "COC(=O)Cl",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
}
]
}
]
},
{
"id": "11539",
"routeId": "sa_ad62db45bcb96c12f1f1a124",
"moleculeId": "sa_2727b39ca20bd50996471dcf",
"parentId": "11529",
"isLeaf": true,
"molecule": {
"id": "sa_2727b39ca20bd50996471dcf",
"inchikey": "NBIIXXVUZAFLBC-UHFFFAOYSA-N",
"smiles": "O=P(O)(O)O"
},
"smiles": "O=P(O)(O)O",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
}
}