Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
CC1CC(c2ccccc2)(c2cc(OCc3ccc4cc(F)ccc4n3)ccc2C(=O)CN=[N+]=[N-])C1
InChiKey
QLPSUSHPBWSOKI-UHFFFAOYSA-N
Route Signature
01e113cd6347b8d60db09a93280610079fda7946fe07ac3a76ba2d00ac242314
Synthesis route with 4 steps
Route tree structure (JSON format)
{
"route": {
"id": "sa_1327abdabd235b17710d3a73",
"signature": "01e113cd6347b8d60db09a93280610079fda7946fe07ac3a76ba2d00ac242314",
"contentHash": "0a84ddc6be96bf2f2800872dccf7e82ad7214fd43e849a3d31d10723640d2844",
"length": 4,
"isConvergent": false
},
"target": {
"id": "sa_631c67ff87e21de70d77e356",
"benchmarkSetId": "61e696668b63e77d7c2a29c0821768e1c383de8313852d6e995224859494442e",
"targetId": "n5-06396",
"moleculeId": "sa_a008dfba96dcb04873a4038e",
"smiles": "CC1CC(c2ccccc2)(c2cc(OCc3ccc4cc(F)ccc4n3)ccc2C(=O)CN=[N+]=[N-])C1",
"routeLength": 4,
"isConvergent": false,
"metadata": null,
"molecule": {
"id": "sa_a008dfba96dcb04873a4038e",
"inchikey": "QLPSUSHPBWSOKI-UHFFFAOYSA-N",
"smiles": "CC1CC(c2ccccc2)(c2cc(OCc3ccc4cc(F)ccc4n3)ccc2C(=O)CN=[N+]=[N-])C1"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "15920",
"routeId": "sa_1327abdabd235b17710d3a73",
"moleculeId": "sa_a008dfba96dcb04873a4038e",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_a008dfba96dcb04873a4038e",
"inchikey": "QLPSUSHPBWSOKI-UHFFFAOYSA-N",
"smiles": "CC1CC(c2ccccc2)(c2cc(OCc3ccc4cc(F)ccc4n3)ccc2C(=O)CN=[N+]=[N-])C1"
},
"smiles": "CC1CC(c2ccccc2)(c2cc(OCc3ccc4cc(F)ccc4n3)ccc2C(=O)CN=[N+]=[N-])C1",
"reactionStepId": "sa_cc58c350624224671d03f5f5",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20090197883A1;0265;745809\",\"rsmi\":\"Br[CH2:15][C:13]([c:12]1[c:11]([C:4]2([c:5]3[cH:6][cH:7][cH:8][cH:9][cH:10]3)[CH2:3][CH:2]([CH3:1])[CH2:36]2)[cH:35][c:21]([O:22][CH2:23][c:24]2[n:25][c:26]3[cH:27][cH:28][c:29]([F:30])[cH:31][c:32]3[cH:33][cH:34]2)[cH:20][cH:19]1)=[O:14].[N-:16]=[N+:17]=[N-:18]>CN(C)C=O.O.[Na+]>[CH3:1][CH:2]1[CH2:3][C:4]([c:5]2[cH:6][cH:7][cH:8][cH:9][cH:10]2)([c:11]2[c:12]([C:13](=[O:14])[CH2:15][N:16]=[N+:17]=[N-:18])[cH:19][cH:20][c:21]([O:22][CH2:23][c:24]3[n:25][c:26]4[cH:27][cH:28][c:29]([F:30])[cH:31][c:32]4[cH:33][cH:34]3)[cH:35]2)[CH2:36]1\"},\"mapped_reaction_smiles\":\"Br[CH2:15][C:13]([c:12]1[c:11]([C:4]2([c:5]3[cH:6][cH:7][cH:8][cH:9][cH:10]3)[CH2:3][CH:2]([CH3:1])[CH2:36]2)[cH:35][c:21]([O:22][CH2:23][c:24]2[n:25][c:26]3[cH:27][cH:28][c:29]([F:30])[cH:31][c:32]3[cH:33][cH:34]2)[cH:20][cH:19]1)=[O:14].[N-:16]=[N+:17]=[N-:18]>CN(C)C=O.O.[Na+]>[CH3:1][CH:2]1[CH2:3][C:4]([c:5]2[cH:6][cH:7][cH:8][cH:9][cH:10]2)([c:11]2[c:12]([C:13](=[O:14])[CH2:15][N:16]=[N+:17]=[N-:18])[cH:19][cH:20][c:21]([O:22][CH2:23][c:24]3[n:25][c:26]4[cH:27][cH:28][c:29]([F:30])[cH:31][c:32]4[cH:33][cH:34]3)[cH:35]2)[CH2:36]1\"}",
"reactionStep": {
"id": "sa_cc58c350624224671d03f5f5",
"reactionHash": "f63400583c0d63153a9c39e454aa753aac4ce3ef905e68cf4a3e715e90f8ee02"
},
"children": [
{
"id": "15921",
"routeId": "sa_1327abdabd235b17710d3a73",
"moleculeId": "sa_50a8f83dd89c267fbada1205",
"parentId": "15920",
"isLeaf": true,
"molecule": {
"id": "sa_50a8f83dd89c267fbada1205",
"inchikey": "IVRMZWNICZWHMI-UHFFFAOYSA-N",
"smiles": "[N]N=[N-]"
},
"smiles": "[N-]=[N+]=[N-]",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "15922",
"routeId": "sa_1327abdabd235b17710d3a73",
"moleculeId": "sa_f670f03c2c47f7f1831963a1",
"parentId": "15920",
"isLeaf": false,
"molecule": {
"id": "sa_f670f03c2c47f7f1831963a1",
"inchikey": "JHTJMEQDGMBKLF-UHFFFAOYSA-N",
"smiles": "CC1CC(c2ccccc2)(c2cc(OCc3ccc4cc(F)ccc4n3)ccc2C(=O)CBr)C1"
},
"smiles": "CC1CC(c2ccccc2)(c2cc(OCc3ccc4cc(F)ccc4n3)ccc2C(=O)CBr)C1",
"reactionStepId": "sa_5100737b02e7ab3f1dd76578",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20090197883A1;0258;745807\",\"rsmi\":\"[CH3:1][CH:2]1[CH2:3][C:4]([c:5]2[cH:6][cH:7][cH:8][cH:9][cH:10]2)([c:11]2[c:12]([C:13](=[O:14])[CH3:15])[cH:17][cH:18][c:19]([O:20][CH2:21][c:22]3[n:23][c:24]4[cH:25][cH:26][c:27]([F:28])[cH:29][c:30]4[cH:31][cH:32]3)[cH:33]2)[CH2:34]1>C1CCOC1.O=C(O)O.O=C1CCCN1.[Na+]>[CH3:1][CH:2]1[CH2:3][C:4]([c:5]2[cH:6][cH:7][cH:8][cH:9][cH:10]2)([c:11]2[c:12]([C:13](=[O:14])[CH2:15][Br:16])[cH:17][cH:18][c:19]([O:20][CH2:21][c:22]3[n:23][c:24]4[cH:25][cH:26][c:27]([F:28])[cH:29][c:30]4[cH:31][cH:32]3)[cH:33]2)[CH2:34]1\"},\"mapped_reaction_smiles\":\"[CH3:1][CH:2]1[CH2:3][C:4]([c:5]2[cH:6][cH:7][cH:8][cH:9][cH:10]2)([c:11]2[c:12]([C:13](=[O:14])[CH3:15])[cH:17][cH:18][c:19]([O:20][CH2:21][c:22]3[n:23][c:24]4[cH:25][cH:26][c:27]([F:28])[cH:29][c:30]4[cH:31][cH:32]3)[cH:33]2)[CH2:34]1>C1CCOC1.O=C(O)O.O=C1CCCN1.[Na+]>[CH3:1][CH:2]1[CH2:3][C:4]([c:5]2[cH:6][cH:7][cH:8][cH:9][cH:10]2)([c:11]2[c:12]([C:13](=[O:14])[CH2:15][Br:16])[cH:17][cH:18][c:19]([O:20][CH2:21][c:22]3[n:23][c:24]4[cH:25][cH:26][c:27]([F:28])[cH:29][c:30]4[cH:31][cH:32]3)[cH:33]2)[CH2:34]1\"}",
"reactionStep": {
"id": "sa_5100737b02e7ab3f1dd76578",
"reactionHash": "9680a737ba60efe09aa9b5ad8a05b367587f4a2de65c0320b4792f760502dd84"
},
"children": [
{
"id": "15923",
"routeId": "sa_1327abdabd235b17710d3a73",
"moleculeId": "sa_cd5de501a5658013c41d5127",
"parentId": "15922",
"isLeaf": false,
"molecule": {
"id": "sa_cd5de501a5658013c41d5127",
"inchikey": "VSEUCFUTPDEGQE-UHFFFAOYSA-N",
"smiles": "CC(=O)c1ccc(OCc2ccc3cc(F)ccc3n2)cc1C1(c2ccccc2)CC(C)C1"
},
"smiles": "CC(=O)c1ccc(OCc2ccc3cc(F)ccc3n2)cc1C1(c2ccccc2)CC(C)C1",
"reactionStepId": "sa_4d57880b68c440716786c87f",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20090197883A1;0246;745806\",\"rsmi\":\"[CH3:1][CH:2]([OH:3])[c:4]1[c:5]([C:6]2([c:7]3[cH:8][cH:9][cH:10][cH:11][cH:12]3)[CH2:13][CH:14]([CH3:15])[CH2:16]2)[cH:17][c:18]([O:19][CH2:20][c:21]2[n:22][c:23]3[cH:24][cH:25][c:26]([F:27])[cH:28][c:29]3[cH:30][cH:31]2)[cH:32][cH:33]1>Cc1ccccc1.[Mn+4].[O-2].[O-2]>[CH3:1][C:2](=[O:3])[c:4]1[c:5]([C:6]2([c:7]3[cH:8][cH:9][cH:10][cH:11][cH:12]3)[CH2:13][CH:14]([CH3:15])[CH2:16]2)[cH:17][c:18]([O:19][CH2:20][c:21]2[n:22][c:23]3[cH:24][cH:25][c:26]([F:27])[cH:28][c:29]3[cH:30][cH:31]2)[cH:32][cH:33]1\"},\"mapped_reaction_smiles\":\"[CH3:1][CH:2]([OH:3])[c:4]1[c:5]([C:6]2([c:7]3[cH:8][cH:9][cH:10][cH:11][cH:12]3)[CH2:13][CH:14]([CH3:15])[CH2:16]2)[cH:17][c:18]([O:19][CH2:20][c:21]2[n:22][c:23]3[cH:24][cH:25][c:26]([F:27])[cH:28][c:29]3[cH:30][cH:31]2)[cH:32][cH:33]1>Cc1ccccc1.[Mn+4].[O-2].[O-2]>[CH3:1][C:2](=[O:3])[c:4]1[c:5]([C:6]2([c:7]3[cH:8][cH:9][cH:10][cH:11][cH:12]3)[CH2:13][CH:14]([CH3:15])[CH2:16]2)[cH:17][c:18]([O:19][CH2:20][c:21]2[n:22][c:23]3[cH:24][cH:25][c:26]([F:27])[cH:28][c:29]3[cH:30][cH:31]2)[cH:32][cH:33]1\"}",
"reactionStep": {
"id": "sa_4d57880b68c440716786c87f",
"reactionHash": "2859345d65a312db948ec4c2666d590f4b0cd7dc039cf36cce76dc112851648f"
},
"children": [
{
"id": "15924",
"routeId": "sa_1327abdabd235b17710d3a73",
"moleculeId": "sa_df5d8938b839675c7661185e",
"parentId": "15923",
"isLeaf": false,
"molecule": {
"id": "sa_df5d8938b839675c7661185e",
"inchikey": "DRCHPSYBNOQOJC-UHFFFAOYSA-N",
"smiles": "CC1CC(c2ccccc2)(c2cc(OCc3ccc4cc(F)ccc4n3)ccc2C(C)O)C1"
},
"smiles": "CC1CC(c2ccccc2)(c2cc(OCc3ccc4cc(F)ccc4n3)ccc2C(C)O)C1",
"reactionStepId": "sa_d9c22794345fbbb6c36b2695",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20090197883A1;0245;745805\",\"rsmi\":\"Br[Mg][CH3:14].[CH3:1][CH:2]1[CH2:3][C:4]([c:5]2[cH:6][cH:7][cH:8][cH:9][cH:10]2)([c:11]2[c:12]([CH:13]=[O:15])[cH:16][cH:17][c:18]([O:19][CH2:20][c:21]3[n:22][c:23]4[cH:24][cH:25][c:26]([F:27])[cH:28][c:29]4[cH:30][cH:31]3)[cH:32]2)[CH2:33]1>C1CCOC1>[CH3:1][CH:2]1[CH2:3][C:4]([c:5]2[cH:6][cH:7][cH:8][cH:9][cH:10]2)([c:11]2[c:12]([CH:13]([CH3:14])[OH:15])[cH:16][cH:17][c:18]([O:19][CH2:20][c:21]3[n:22][c:23]4[cH:24][cH:25][c:26]([F:27])[cH:28][c:29]4[cH:30][cH:31]3)[cH:32]2)[CH2:33]1\"},\"mapped_reaction_smiles\":\"Br[Mg][CH3:14].[CH3:1][CH:2]1[CH2:3][C:4]([c:5]2[cH:6][cH:7][cH:8][cH:9][cH:10]2)([c:11]2[c:12]([CH:13]=[O:15])[cH:16][cH:17][c:18]([O:19][CH2:20][c:21]3[n:22][c:23]4[cH:24][cH:25][c:26]([F:27])[cH:28][c:29]4[cH:30][cH:31]3)[cH:32]2)[CH2:33]1>C1CCOC1>[CH3:1][CH:2]1[CH2:3][C:4]([c:5]2[cH:6][cH:7][cH:8][cH:9][cH:10]2)([c:11]2[c:12]([CH:13]([CH3:14])[OH:15])[cH:16][cH:17][c:18]([O:19][CH2:20][c:21]3[n:22][c:23]4[cH:24][cH:25][c:26]([F:27])[cH:28][c:29]4[cH:30][cH:31]3)[cH:32]2)[CH2:33]1\"}",
"reactionStep": {
"id": "sa_d9c22794345fbbb6c36b2695",
"reactionHash": "27940b3edfa91159f2f3b706a9801b5ad7a793a809b600f8742797e3dfc86408"
},
"children": [
{
"id": "15925",
"routeId": "sa_1327abdabd235b17710d3a73",
"moleculeId": "sa_1f49d1fc04ca53874d94e458",
"parentId": "15924",
"isLeaf": true,
"molecule": {
"id": "sa_1f49d1fc04ca53874d94e458",
"inchikey": "AVFUHBJCUUTGCD-UHFFFAOYSA-M",
"smiles": "[CH3][Mg][Br]"
},
"smiles": "[CH3][Mg][Br]",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "15926",
"routeId": "sa_1327abdabd235b17710d3a73",
"moleculeId": "sa_445bdf4d4ab074868a3fe912",
"parentId": "15924",
"isLeaf": true,
"molecule": {
"id": "sa_445bdf4d4ab074868a3fe912",
"inchikey": "KPVXGFNUFOIMQN-UHFFFAOYSA-N",
"smiles": "CC1CC(c2ccccc2)(c2cc(OCc3ccc4cc(F)ccc4n3)ccc2C=O)C1"
},
"smiles": "CC1CC(c2ccccc2)(c2cc(OCc3ccc4cc(F)ccc4n3)ccc2C=O)C1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
}
]
}
]
}
]
}
}