Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
CC(C)(C)c1cc(F)c2c(=O)n(Cc3ccc(-c4cc[nH]c(=O)c4)cc3CO)ncc2c1
InChiKey
IMQBHYSXBWWOOO-UHFFFAOYSA-N
Route Signature
90f1f8030e7b1110e81287c3096ebd1c00b57e04bc99379ad8f783e98005fb96
Synthesis route with 5 steps
Route tree structure (JSON format)
{
"route": {
"id": "sa_87a4ce7f3bb6e2cb6e88b55e",
"signature": "90f1f8030e7b1110e81287c3096ebd1c00b57e04bc99379ad8f783e98005fb96",
"contentHash": "e7f5cb16871e9897bacff5898d902e8d372389b3b6a7a4a0da9c476d60502104",
"length": 5,
"isConvergent": false
},
"target": {
"id": "sa_41bbf30d883c069f214bfd5a",
"benchmarkSetId": "f925e688d731a0ad4e3aa6a505df094f6d3ca64ce3facc312bc5f64731921b33",
"targetId": "n5-01548",
"moleculeId": "sa_569471340b52cfd6717faeb6",
"smiles": "CC(C)(C)c1cc(F)c2c(=O)n(Cc3ccc(-c4cc[nH]c(=O)c4)cc3CO)ncc2c1",
"routeLength": 5,
"isConvergent": false,
"metadata": null,
"molecule": {
"id": "sa_569471340b52cfd6717faeb6",
"inchikey": "IMQBHYSXBWWOOO-UHFFFAOYSA-N",
"smiles": "CC(C)(C)c1cc(F)c2c(=O)n(Cc3ccc(-c4cc[nH]c(=O)c4)cc3CO)ncc2c1"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 2
},
"rootNode": {
"id": "5711",
"routeId": "sa_87a4ce7f3bb6e2cb6e88b55e",
"moleculeId": "sa_569471340b52cfd6717faeb6",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_569471340b52cfd6717faeb6",
"inchikey": "IMQBHYSXBWWOOO-UHFFFAOYSA-N",
"smiles": "CC(C)(C)c1cc(F)c2c(=O)n(Cc3ccc(-c4cc[nH]c(=O)c4)cc3CO)ncc2c1"
},
"smiles": "CC(C)(C)c1cc(F)c2c(=O)n(Cc3ccc(-c4cc[nH]c(=O)c4)cc3CO)ncc2c1",
"reactionStepId": "sa_d861f7532aef08eb49852913",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20150291525A1;0339;1767093\",\"rsmi\":\"C[O:23][c:22]1[cH:21][c:20](-[c:19]2[cH:18][c:15]([CH2:16][OH:17])[c:14]([CH2:13][n:12]3[c:10](=[O:11])[c:9]4[c:7]([F:8])[cH:6][c:5]([C:2]([CH3:1])([CH3:3])[CH3:4])[cH:32][c:31]4[cH:30][n:29]3)[cH:28][cH:27]2)[cH:26][cH:25][n:24]1>CC#N.C[Si](C)(C)Cl.O=C(O)O.O=S(O)(O)=S.I.[Na+].[Na+].[Na+].[Na+]>[CH3:1][C:2]([CH3:3])([CH3:4])[c:5]1[cH:6][c:7]([F:8])[c:9]2[c:10](=[O:11])[n:12]([CH2:13][c:14]3[c:15]([CH2:16][OH:17])[cH:18][c:19](-[c:20]4[cH:21][c:22](=[O:23])[nH:24][cH:25][cH:26]4)[cH:27][cH:28]3)[n:29][cH:30][c:31]2[cH:32]1\"},\"mapped_reaction_smiles\":\"C[O:23][c:22]1[cH:21][c:20](-[c:19]2[cH:18][c:15]([CH2:16][OH:17])[c:14]([CH2:13][n:12]3[c:10](=[O:11])[c:9]4[c:7]([F:8])[cH:6][c:5]([C:2]([CH3:1])([CH3:3])[CH3:4])[cH:32][c:31]4[cH:30][n:29]3)[cH:28][cH:27]2)[cH:26][cH:25][n:24]1>CC#N.C[Si](C)(C)Cl.O=C(O)O.O=S(O)(O)=S.I.[Na+].[Na+].[Na+].[Na+]>[CH3:1][C:2]([CH3:3])([CH3:4])[c:5]1[cH:6][c:7]([F:8])[c:9]2[c:10](=[O:11])[n:12]([CH2:13][c:14]3[c:15]([CH2:16][OH:17])[cH:18][c:19](-[c:20]4[cH:21][c:22](=[O:23])[nH:24][cH:25][cH:26]4)[cH:27][cH:28]3)[n:29][cH:30][c:31]2[cH:32]1\"}",
"reactionStep": {
"id": "sa_d861f7532aef08eb49852913",
"reactionHash": "89fe3aa2cd358dd463a79c09324e8e3b1e4b358b2aed9403846d2d4d6efef577"
},
"children": [
{
"id": "5712",
"routeId": "sa_87a4ce7f3bb6e2cb6e88b55e",
"moleculeId": "sa_2768e8cbf81d77c13c2b88b0",
"parentId": "5711",
"isLeaf": false,
"molecule": {
"id": "sa_2768e8cbf81d77c13c2b88b0",
"inchikey": "XBOVLNVMHKZUSA-UHFFFAOYSA-N",
"smiles": "COc1cc(-c2ccc(Cn3ncc4cc(C(C)(C)C)cc(F)c4c3=O)c(CO)c2)ccn1"
},
"smiles": "COc1cc(-c2ccc(Cn3ncc4cc(C(C)(C)C)cc(F)c4c3=O)c(CO)c2)ccn1",
"reactionStepId": "sa_efd6d58d53a0dfec02b5a9ac",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20150291525A1;0337;1767092\",\"rsmi\":\"Br[c:8]1[cH:9][c:10]([CH2:11][OH:12])[c:13]([CH2:14][n:15]2[n:16][cH:17][c:18]3[cH:19][c:20]([C:21]([CH3:22])([CH3:23])[CH3:24])[cH:25][c:26]([F:27])[c:28]3[c:29]2=[O:30])[cH:31][cH:32]1.OB(O)[c:7]1[cH:6][cH:5][n:4][c:3]([O:2][CH3:1])[cH:33]1>C1CCC(P(C2CCCCC2)C2CCCCC2)CC1.C1COCCO1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(O)O.[K+].[K+].[Pd].[Pd]>[CH3:1][O:2][c:3]1[n:4][cH:5][cH:6][c:7](-[c:8]2[cH:9][c:10]([CH2:11][OH:12])[c:13]([CH2:14][n:15]3[n:16][cH:17][c:18]4[cH:19][c:20]([C:21]([CH3:22])([CH3:23])[CH3:24])[cH:25][c:26]([F:27])[c:28]4[c:29]3=[O:30])[cH:31][cH:32]2)[cH:33]1\"},\"mapped_reaction_smiles\":\"Br[c:8]1[cH:9][c:10]([CH2:11][OH:12])[c:13]([CH2:14][n:15]2[n:16][cH:17][c:18]3[cH:19][c:20]([C:21]([CH3:22])([CH3:23])[CH3:24])[cH:25][c:26]([F:27])[c:28]3[c:29]2=[O:30])[cH:31][cH:32]1.OB(O)[c:7]1[cH:6][cH:5][n:4][c:3]([O:2][CH3:1])[cH:33]1>C1CCC(P(C2CCCCC2)C2CCCCC2)CC1.C1COCCO1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(O)O.[K+].[K+].[Pd].[Pd]>[CH3:1][O:2][c:3]1[n:4][cH:5][cH:6][c:7](-[c:8]2[cH:9][c:10]([CH2:11][OH:12])[c:13]([CH2:14][n:15]3[n:16][cH:17][c:18]4[cH:19][c:20]([C:21]([CH3:22])([CH3:23])[CH3:24])[cH:25][c:26]([F:27])[c:28]4[c:29]3=[O:30])[cH:31][cH:32]2)[cH:33]1\"}",
"reactionStep": {
"id": "sa_efd6d58d53a0dfec02b5a9ac",
"reactionHash": "3868a1598f8befab3bbce0ce61dd4de7fe59261d9090eedc402e5a23f84f554f"
},
"children": [
{
"id": "5713",
"routeId": "sa_87a4ce7f3bb6e2cb6e88b55e",
"moleculeId": "sa_0d01a119519941174dbd88df",
"parentId": "5712",
"isLeaf": false,
"molecule": {
"id": "sa_0d01a119519941174dbd88df",
"inchikey": "BCBSLWJOLQIYDQ-UHFFFAOYSA-N",
"smiles": "CC(C)(C)c1cc(F)c2c(=O)n(Cc3ccc(Br)cc3CO)ncc2c1"
},
"smiles": "CC(C)(C)c1cc(F)c2c(=O)n(Cc3ccc(Br)cc3CO)ncc2c1",
"reactionStepId": "sa_fb49ccaeb7019353eafcf14b",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20150291525A1;0335;1767091\",\"rsmi\":\"Br[CH2:13][c:14]1[c:15]([CH2:16][OH:17])[cH:18][c:19]([Br:20])[cH:21][cH:22]1.[CH3:1][C:2]([CH3:3])([CH3:4])[c:5]1[cH:6][c:7]([F:8])[c:9]2[c:10](=[O:11])[nH:12][n:23][cH:24][c:25]2[cH:26]1>CN(C)C=O.[HH].[Na+]>[CH3:1][C:2]([CH3:3])([CH3:4])[c:5]1[cH:6][c:7]([F:8])[c:9]2[c:10](=[O:11])[n:12]([CH2:13][c:14]3[c:15]([CH2:16][OH:17])[cH:18][c:19]([Br:20])[cH:21][cH:22]3)[n:23][cH:24][c:25]2[cH:26]1\"},\"mapped_reaction_smiles\":\"Br[CH2:13][c:14]1[c:15]([CH2:16][OH:17])[cH:18][c:19]([Br:20])[cH:21][cH:22]1.[CH3:1][C:2]([CH3:3])([CH3:4])[c:5]1[cH:6][c:7]([F:8])[c:9]2[c:10](=[O:11])[nH:12][n:23][cH:24][c:25]2[cH:26]1>CN(C)C=O.[HH].[Na+]>[CH3:1][C:2]([CH3:3])([CH3:4])[c:5]1[cH:6][c:7]([F:8])[c:9]2[c:10](=[O:11])[n:12]([CH2:13][c:14]3[c:15]([CH2:16][OH:17])[cH:18][c:19]([Br:20])[cH:21][cH:22]3)[n:23][cH:24][c:25]2[cH:26]1\"}",
"reactionStep": {
"id": "sa_fb49ccaeb7019353eafcf14b",
"reactionHash": "423881961e9b0959df44bf9c3d0689e2a85ee6fa6766f85180787ee035826c72"
},
"children": [
{
"id": "5714",
"routeId": "sa_87a4ce7f3bb6e2cb6e88b55e",
"moleculeId": "sa_21bf88946658101257503b6a",
"parentId": "5713",
"isLeaf": false,
"molecule": {
"id": "sa_21bf88946658101257503b6a",
"inchikey": "PAFPIHMSXJSSJT-UHFFFAOYSA-N",
"smiles": "OCc1cc(Br)ccc1CBr"
},
"smiles": "OCc1cc(Br)ccc1CBr",
"reactionStepId": "sa_35946437dde001c3295e8895",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20150291525A1;0333;1767090\",\"rsmi\":\"C[O:1][C:2](=O)[c:3]1[c:4]([CH2:5][Br:6])[cH:7][cH:8][c:9]([Br:10])[cH:11]1>CC(C)C[AlH]CC(C)C.Cc1ccccc1.Cl>[OH:1][CH2:2][c:3]1[c:4]([CH2:5][Br:6])[cH:7][cH:8][c:9]([Br:10])[cH:11]1\"},\"mapped_reaction_smiles\":\"C[O:1][C:2](=O)[c:3]1[c:4]([CH2:5][Br:6])[cH:7][cH:8][c:9]([Br:10])[cH:11]1>CC(C)C[AlH]CC(C)C.Cc1ccccc1.Cl>[OH:1][CH2:2][c:3]1[c:4]([CH2:5][Br:6])[cH:7][cH:8][c:9]([Br:10])[cH:11]1\"}",
"reactionStep": {
"id": "sa_35946437dde001c3295e8895",
"reactionHash": "8aa3c76de90cba52637a3ada8667a8e38081027d7351162ba9bf394f7d8cc997"
},
"children": [
{
"id": "5715",
"routeId": "sa_87a4ce7f3bb6e2cb6e88b55e",
"moleculeId": "sa_a4b810a09d077a796df2ebd5",
"parentId": "5714",
"isLeaf": false,
"molecule": {
"id": "sa_a4b810a09d077a796df2ebd5",
"inchikey": "UVIJBFVFEGZZLQ-UHFFFAOYSA-N",
"smiles": "COC(=O)c1cc(Br)ccc1CBr"
},
"smiles": "COC(=O)c1cc(Br)ccc1CBr",
"reactionStepId": "sa_94d8a906fdae145dc80c9dbb",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20150291525A1;0331;1767089\",\"rsmi\":\"O=C1CCC(=O)N1[Br:8].[CH3:1][O:2][C:3](=[O:4])[c:5]1[c:6]([CH3:7])[cH:9][cH:10][c:11]([Br:12])[cH:13]1>CC(C)(C#N)N=NC(C)(C)C#N.ClC(Cl)(Cl)Cl.O=S(O)(O)=S.[Na+].[Na+]>[CH3:1][O:2][C:3](=[O:4])[c:5]1[c:6]([CH2:7][Br:8])[cH:9][cH:10][c:11]([Br:12])[cH:13]1\"},\"mapped_reaction_smiles\":\"O=C1CCC(=O)N1[Br:8].[CH3:1][O:2][C:3](=[O:4])[c:5]1[c:6]([CH3:7])[cH:9][cH:10][c:11]([Br:12])[cH:13]1>CC(C)(C#N)N=NC(C)(C)C#N.ClC(Cl)(Cl)Cl.O=S(O)(O)=S.[Na+].[Na+]>[CH3:1][O:2][C:3](=[O:4])[c:5]1[c:6]([CH2:7][Br:8])[cH:9][cH:10][c:11]([Br:12])[cH:13]1\"}",
"reactionStep": {
"id": "sa_94d8a906fdae145dc80c9dbb",
"reactionHash": "afc8409bbd47e19ba947dd1a87f051c960d2a27697714103795db60f67f84eca"
},
"children": [
{
"id": "5716",
"routeId": "sa_87a4ce7f3bb6e2cb6e88b55e",
"moleculeId": "sa_ce0750880ac49962765bd30c",
"parentId": "5715",
"isLeaf": true,
"molecule": {
"id": "sa_ce0750880ac49962765bd30c",
"inchikey": "FDCYLMYCHALQJR-UHFFFAOYSA-N",
"smiles": "COC(=O)c1cc(Br)ccc1C"
},
"smiles": "COC(=O)c1cc(Br)ccc1C",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "5717",
"routeId": "sa_87a4ce7f3bb6e2cb6e88b55e",
"moleculeId": "sa_ccdcf23ac83e7a68bfa4f2e5",
"parentId": "5715",
"isLeaf": true,
"molecule": {
"id": "sa_ccdcf23ac83e7a68bfa4f2e5",
"inchikey": "PCLIMKBDDGJMGD-UHFFFAOYSA-N",
"smiles": "O=C1CCC(=O)N1Br"
},
"smiles": "O=C1CCC(=O)N1Br",
"reactionStepId": null,
"template": null,
"metadata": null,
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"children": []
}
]
}
]
},
{
"id": "5718",
"routeId": "sa_87a4ce7f3bb6e2cb6e88b55e",
"moleculeId": "sa_ff5d9169c710d659ece8ffa8",
"parentId": "5713",
"isLeaf": true,
"molecule": {
"id": "sa_ff5d9169c710d659ece8ffa8",
"inchikey": "UQLKXNSVRRFDGE-UHFFFAOYSA-N",
"smiles": "CC(C)(C)c1cc(F)c2c(=O)[nH]ncc2c1"
},
"smiles": "CC(C)(C)c1cc(F)c2c(=O)[nH]ncc2c1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
},
{
"id": "5719",
"routeId": "sa_87a4ce7f3bb6e2cb6e88b55e",
"moleculeId": "sa_9cec135f712c742e08122ecb",
"parentId": "5712",
"isLeaf": true,
"molecule": {
"id": "sa_9cec135f712c742e08122ecb",
"inchikey": "DHQMUJSACXTPEA-UHFFFAOYSA-N",
"smiles": "COc1cc(B(O)O)ccn1"
},
"smiles": "COc1cc(B(O)O)ccn1",
"reactionStepId": null,
"template": null,
"metadata": null,
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"children": []
}
]
}
]
}
}