Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
CC(NC(=O)OC(C)(C)C)c1nc2ccc(F)cc2c(C(=O)NCC2CC2)c1-c1ccccc1
InChiKey
PLIWADNSCZVCEG-UHFFFAOYSA-N
Route Signature
1a9da004e51258db822b3f9d64c7b9ead0e76df9339ea31b1634328241d21c3f
Synthesis route with 6 steps
Route tree structure (JSON format)
{
"route": {
"id": "sa_9685436a03e520147a86647b",
"signature": "1a9da004e51258db822b3f9d64c7b9ead0e76df9339ea31b1634328241d21c3f",
"contentHash": "b0ec52ab8e23b36ef12605aa3e7c969353e2d825d3b1366b71fa95de1f96f292",
"length": 6,
"isConvergent": false
},
"target": {
"id": "sa_43ee64434c43f09d3f4d12e7",
"benchmarkSetId": "61e696668b63e77d7c2a29c0821768e1c383de8313852d6e995224859494442e",
"targetId": "n5-00564",
"moleculeId": "sa_7129ee1c270c0ceddbc0335b",
"smiles": "CC(NC(=O)OC(C)(C)C)c1nc2ccc(F)cc2c(C(=O)NCC2CC2)c1-c1ccccc1",
"routeLength": 6,
"isConvergent": false,
"metadata": null,
"molecule": {
"id": "sa_7129ee1c270c0ceddbc0335b",
"inchikey": "PLIWADNSCZVCEG-UHFFFAOYSA-N",
"smiles": "CC(NC(=O)OC(C)(C)C)c1nc2ccc(F)cc2c(C(=O)NCC2CC2)c1-c1ccccc1"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "13485",
"routeId": "sa_9685436a03e520147a86647b",
"moleculeId": "sa_7129ee1c270c0ceddbc0335b",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_7129ee1c270c0ceddbc0335b",
"inchikey": "PLIWADNSCZVCEG-UHFFFAOYSA-N",
"smiles": "CC(NC(=O)OC(C)(C)C)c1nc2ccc(F)cc2c(C(=O)NCC2CC2)c1-c1ccccc1"
},
"smiles": "CC(NC(=O)OC(C)(C)C)c1nc2ccc(F)cc2c(C(=O)NCC2CC2)c1-c1ccccc1",
"reactionStepId": "sa_286d26b140d266dc13c040e2",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20100331306A1;0528;995428\",\"rsmi\":\"O[C:21]([c:20]1[c:19]2[c:13]([n:12][c:11]([CH:2]([CH3:1])[NH:3][C:4](=[O:5])[O:6][C:7]([CH3:8])([CH3:9])[CH3:10])[c:28]1-[c:29]1[cH:30][cH:31][cH:32][cH:33][cH:34]1)[cH:14][cH:15][c:16]([F:17])[cH:18]2)=[O:22].[NH2:23][CH2:24][CH:25]1[CH2:26][CH2:27]1>CCN(C(C)C)C(C)C.CCOC(C)=O.CN(C)C(On1nnc2cccnc21)=[N+](C)C.CN(C)C=O.F[PH](F)(F)(F)(F)F>[CH3:1][CH:2]([NH:3][C:4](=[O:5])[O:6][C:7]([CH3:8])([CH3:9])[CH3:10])[c:11]1[n:12][c:13]2[cH:14][cH:15][c:16]([F:17])[cH:18][c:19]2[c:20]([C:21](=[O:22])[NH:23][CH2:24][CH:25]2[CH2:26][CH2:27]2)[c:28]1-[c:29]1[cH:30][cH:31][cH:32][cH:33][cH:34]1\"},\"mapped_reaction_smiles\":\"O[C:21]([c:20]1[c:19]2[c:13]([n:12][c:11]([CH:2]([CH3:1])[NH:3][C:4](=[O:5])[O:6][C:7]([CH3:8])([CH3:9])[CH3:10])[c:28]1-[c:29]1[cH:30][cH:31][cH:32][cH:33][cH:34]1)[cH:14][cH:15][c:16]([F:17])[cH:18]2)=[O:22].[NH2:23][CH2:24][CH:25]1[CH2:26][CH2:27]1>CCN(C(C)C)C(C)C.CCOC(C)=O.CN(C)C(On1nnc2cccnc21)=[N+](C)C.CN(C)C=O.F[PH](F)(F)(F)(F)F>[CH3:1][CH:2]([NH:3][C:4](=[O:5])[O:6][C:7]([CH3:8])([CH3:9])[CH3:10])[c:11]1[n:12][c:13]2[cH:14][cH:15][c:16]([F:17])[cH:18][c:19]2[c:20]([C:21](=[O:22])[NH:23][CH2:24][CH:25]2[CH2:26][CH2:27]2)[c:28]1-[c:29]1[cH:30][cH:31][cH:32][cH:33][cH:34]1\"}",
"reactionStep": {
"id": "sa_286d26b140d266dc13c040e2",
"reactionHash": "7f99d40c25a4ab057df59c2f1a4900677ccf445c562d9ad21e577af6de98bd24"
},
"children": [
{
"id": "13486",
"routeId": "sa_9685436a03e520147a86647b",
"moleculeId": "sa_49f5427df14e97396563aaad",
"parentId": "13485",
"isLeaf": false,
"molecule": {
"id": "sa_49f5427df14e97396563aaad",
"inchikey": "FUGMSMXSMLCKHL-UHFFFAOYSA-N",
"smiles": "CC(NC(=O)OC(C)(C)C)c1nc2ccc(F)cc2c(C(=O)O)c1-c1ccccc1"
},
"smiles": "CC(NC(=O)OC(C)(C)C)c1nc2ccc(F)cc2c(C(=O)O)c1-c1ccccc1",
"reactionStepId": "sa_6b8b9234ff4734c9851721ec",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20100331306A1;0496;995411\",\"rsmi\":\"C[O:23][C:21]([c:20]1[c:19]2[c:13]([n:12][c:11]([CH:2]([CH3:1])[NH:3][C:4](=[O:5])[O:6][C:7]([CH3:8])([CH3:9])[CH3:10])[c:24]1-[c:25]1[cH:26][cH:27][cH:28][cH:29][cH:30]1)[cH:14][cH:15][c:16]([F:17])[cH:18]2)=[O:22]>C1CCOC1.CO.Cl.O.[Li+].O>[CH3:1][CH:2]([NH:3][C:4](=[O:5])[O:6][C:7]([CH3:8])([CH3:9])[CH3:10])[c:11]1[n:12][c:13]2[cH:14][cH:15][c:16]([F:17])[cH:18][c:19]2[c:20]([C:21](=[O:22])[OH:23])[c:24]1-[c:25]1[cH:26][cH:27][cH:28][cH:29][cH:30]1\"},\"mapped_reaction_smiles\":\"C[O:23][C:21]([c:20]1[c:19]2[c:13]([n:12][c:11]([CH:2]([CH3:1])[NH:3][C:4](=[O:5])[O:6][C:7]([CH3:8])([CH3:9])[CH3:10])[c:24]1-[c:25]1[cH:26][cH:27][cH:28][cH:29][cH:30]1)[cH:14][cH:15][c:16]([F:17])[cH:18]2)=[O:22]>C1CCOC1.CO.Cl.O.[Li+].O>[CH3:1][CH:2]([NH:3][C:4](=[O:5])[O:6][C:7]([CH3:8])([CH3:9])[CH3:10])[c:11]1[n:12][c:13]2[cH:14][cH:15][c:16]([F:17])[cH:18][c:19]2[c:20]([C:21](=[O:22])[OH:23])[c:24]1-[c:25]1[cH:26][cH:27][cH:28][cH:29][cH:30]1\"}",
"reactionStep": {
"id": "sa_6b8b9234ff4734c9851721ec",
"reactionHash": "1dab226da22c81c327916dd013c54c2c3ca0ab497d711d5b1844f7c296d7fb5d"
},
"children": [
{
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"routeId": "sa_9685436a03e520147a86647b",
"moleculeId": "sa_7ff0c918b19aa66501031818",
"parentId": "13486",
"isLeaf": false,
"molecule": {
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"inchikey": "YWCIAJVATHHODI-UHFFFAOYSA-N",
"smiles": "COC(=O)c1c(-c2ccccc2)c(C(C)NC(=O)OC(C)(C)C)nc2ccc(F)cc12"
},
"smiles": "COC(=O)c1c(-c2ccccc2)c(C(C)NC(=O)OC(C)(C)C)nc2ccc(F)cc12",
"reactionStepId": "sa_5133986041b9089409efdf88",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20100331306A1;0496;995410\",\"rsmi\":\"CC(C)(C)OC(=O)O[C:17](=[O:18])[O:19][C:20]([CH3:21])([CH3:22])[CH3:23].[CH3:1][O:2][C:3](=[O:4])[c:5]1[c:6](-[c:7]2[cH:8][cH:9][cH:10][cH:11][cH:12]2)[c:13]([CH:14]([CH3:15])[NH2:16])[n:24][c:25]2[cH:26][cH:27][c:28]([F:29])[cH:30][c:31]12>C1CCOC1.CCN(CC)CC>[CH3:1][O:2][C:3](=[O:4])[c:5]1[c:6](-[c:7]2[cH:8][cH:9][cH:10][cH:11][cH:12]2)[c:13]([CH:14]([CH3:15])[NH:16][C:17](=[O:18])[O:19][C:20]([CH3:21])([CH3:22])[CH3:23])[n:24][c:25]2[cH:26][cH:27][c:28]([F:29])[cH:30][c:31]12\"},\"mapped_reaction_smiles\":\"CC(C)(C)OC(=O)O[C:17](=[O:18])[O:19][C:20]([CH3:21])([CH3:22])[CH3:23].[CH3:1][O:2][C:3](=[O:4])[c:5]1[c:6](-[c:7]2[cH:8][cH:9][cH:10][cH:11][cH:12]2)[c:13]([CH:14]([CH3:15])[NH2:16])[n:24][c:25]2[cH:26][cH:27][c:28]([F:29])[cH:30][c:31]12>C1CCOC1.CCN(CC)CC>[CH3:1][O:2][C:3](=[O:4])[c:5]1[c:6](-[c:7]2[cH:8][cH:9][cH:10][cH:11][cH:12]2)[c:13]([CH:14]([CH3:15])[NH:16][C:17](=[O:18])[O:19][C:20]([CH3:21])([CH3:22])[CH3:23])[n:24][c:25]2[cH:26][cH:27][c:28]([F:29])[cH:30][c:31]12\"}",
"reactionStep": {
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"reactionHash": "514241b3fa5f8dad93409a4b653053101d11acac96288c68623d0b30d21df45f"
},
"children": [
{
"id": "13488",
"routeId": "sa_9685436a03e520147a86647b",
"moleculeId": "sa_b273d4d4546165bca2b249b5",
"parentId": "13487",
"isLeaf": true,
"molecule": {
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"inchikey": "DYHSDKLCOJIUFX-UHFFFAOYSA-N",
"smiles": "CC(C)(C)OC(=O)OC(=O)OC(C)(C)C"
},
"smiles": "CC(C)(C)OC(=O)OC(=O)OC(C)(C)C",
"reactionStepId": null,
"template": null,
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},
{
"id": "13489",
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"molecule": {
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"inchikey": "NOKYKJVLLVQQKX-UHFFFAOYSA-N",
"smiles": "COC(=O)c1c(-c2ccccc2)c(C(C)N)nc2ccc(F)cc12"
},
"smiles": "COC(=O)c1c(-c2ccccc2)c(C(C)N)nc2ccc(F)cc12",
"reactionStepId": "sa_1f3f5aa294c51838cc293de4",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20100331306A1;0490;995407\",\"rsmi\":\"[N-]=[N+]=[N:16][CH:14]([c:13]1[c:6](-[c:7]2[cH:8][cH:9][cH:10][cH:11][cH:12]2)[c:5]([C:3]([O:2][CH3:1])=[O:4])[c:24]2[c:18]([n:17]1)[cH:19][cH:20][c:21]([F:22])[cH:23]2)[CH3:15]>CO.[Pd]>[CH3:1][O:2][C:3](=[O:4])[c:5]1[c:6](-[c:7]2[cH:8][cH:9][cH:10][cH:11][cH:12]2)[c:13]([CH:14]([CH3:15])[NH2:16])[n:17][c:18]2[cH:19][cH:20][c:21]([F:22])[cH:23][c:24]12\"},\"mapped_reaction_smiles\":\"[N-]=[N+]=[N:16][CH:14]([c:13]1[c:6](-[c:7]2[cH:8][cH:9][cH:10][cH:11][cH:12]2)[c:5]([C:3]([O:2][CH3:1])=[O:4])[c:24]2[c:18]([n:17]1)[cH:19][cH:20][c:21]([F:22])[cH:23]2)[CH3:15]>CO.[Pd]>[CH3:1][O:2][C:3](=[O:4])[c:5]1[c:6](-[c:7]2[cH:8][cH:9][cH:10][cH:11][cH:12]2)[c:13]([CH:14]([CH3:15])[NH2:16])[n:17][c:18]2[cH:19][cH:20][c:21]([F:22])[cH:23][c:24]12\"}",
"reactionStep": {
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"reactionHash": "fa0ca2a02585353d51bc84cf4484d810fd4ca801e9fe8d20b1a0d7be5d61a093"
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"children": [
{
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"molecule": {
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"inchikey": "XCIZXBBUSVBSFI-UHFFFAOYSA-N",
"smiles": "COC(=O)c1c(-c2ccccc2)c(C(C)N=[N+]=[N-])nc2ccc(F)cc12"
},
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"reactionStepId": "sa_97cbd36e4ec157de7f4b8f48",
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"metadata": "{\"annotations\":{\"ID\":\"US20100331306A1;0490;995406\",\"rsmi\":\"Br[CH:14]([c:13]1[c:6](-[c:7]2[cH:8][cH:9][cH:10][cH:11][cH:12]2)[c:5]([C:3]([O:2][CH3:1])=[O:4])[c:26]2[c:20]([n:19]1)[cH:21][cH:22][c:23]([F:24])[cH:25]2)[CH3:15].[N-:16]=[N+:17]=[N-:18]>CN(C)C=O.O.[Na+]>[CH3:1][O:2][C:3](=[O:4])[c:5]1[c:6](-[c:7]2[cH:8][cH:9][cH:10][cH:11][cH:12]2)[c:13]([CH:14]([CH3:15])[N:16]=[N+:17]=[N-:18])[n:19][c:20]2[cH:21][cH:22][c:23]([F:24])[cH:25][c:26]12\"},\"mapped_reaction_smiles\":\"Br[CH:14]([c:13]1[c:6](-[c:7]2[cH:8][cH:9][cH:10][cH:11][cH:12]2)[c:5]([C:3]([O:2][CH3:1])=[O:4])[c:26]2[c:20]([n:19]1)[cH:21][cH:22][c:23]([F:24])[cH:25]2)[CH3:15].[N-:16]=[N+:17]=[N-:18]>CN(C)C=O.O.[Na+]>[CH3:1][O:2][C:3](=[O:4])[c:5]1[c:6](-[c:7]2[cH:8][cH:9][cH:10][cH:11][cH:12]2)[c:13]([CH:14]([CH3:15])[N:16]=[N+:17]=[N-:18])[n:19][c:20]2[cH:21][cH:22][c:23]([F:24])[cH:25][c:26]12\"}",
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"children": [
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"parentId": "13490",
"isLeaf": false,
"molecule": {
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"inchikey": "DUTJSRIRKRTSCO-UHFFFAOYSA-N",
"smiles": "COC(=O)c1c(-c2ccccc2)c(C(C)Br)nc2ccc(F)cc12"
},
"smiles": "COC(=O)c1c(-c2ccccc2)c(C(C)Br)nc2ccc(F)cc12",
"reactionStepId": "sa_636e08592a2e804d51466302",
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"metadata": "{\"annotations\":{\"ID\":\"US20100331306A1;0490;995405\",\"rsmi\":\"CC1(C)C(=O)N(Br)C(=O)N1[Br:16].[CH3:1][O:2][C:3](=[O:4])[c:5]1[c:6](-[c:7]2[cH:8][cH:9][cH:10][cH:11][cH:12]2)[c:13]([CH2:14][CH3:15])[n:17][c:18]2[cH:19][cH:20][c:21]([F:22])[cH:23][c:24]12>ClC(Cl)(Cl)Cl.O=C(OOC(=O)c1ccccc1)c1ccccc1.O=C(O)O.[Na+]>[CH3:1][O:2][C:3](=[O:4])[c:5]1[c:6](-[c:7]2[cH:8][cH:9][cH:10][cH:11][cH:12]2)[c:13]([CH:14]([CH3:15])[Br:16])[n:17][c:18]2[cH:19][cH:20][c:21]([F:22])[cH:23][c:24]12\"},\"mapped_reaction_smiles\":\"CC1(C)C(=O)N(Br)C(=O)N1[Br:16].[CH3:1][O:2][C:3](=[O:4])[c:5]1[c:6](-[c:7]2[cH:8][cH:9][cH:10][cH:11][cH:12]2)[c:13]([CH2:14][CH3:15])[n:17][c:18]2[cH:19][cH:20][c:21]([F:22])[cH:23][c:24]12>ClC(Cl)(Cl)Cl.O=C(OOC(=O)c1ccccc1)c1ccccc1.O=C(O)O.[Na+]>[CH3:1][O:2][C:3](=[O:4])[c:5]1[c:6](-[c:7]2[cH:8][cH:9][cH:10][cH:11][cH:12]2)[c:13]([CH:14]([CH3:15])[Br:16])[n:17][c:18]2[cH:19][cH:20][c:21]([F:22])[cH:23][c:24]12\"}",
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},
"smiles": "CCc1nc2ccc(F)cc2c(C(=O)OC)c1-c1ccccc1",
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{
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"molecule": {
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},
"smiles": "CC1(C)C(=O)N(Br)C(=O)N1Br",
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}
]
},
{
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"smiles": "[N]N=[N-]"
},
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}
]
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}
]
},
{
"id": "13495",
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"molecule": {
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"smiles": "NCC1CC1"
},
"smiles": "NCC1CC1",
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}
]
}
}