Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
Cc1ccc(O)c(N2CCC3(CC2)CCN(c2ccc(OC(F)(F)F)cc2)C3=O)c1
InChiKey
QJPQCPCFRNQINL-UHFFFAOYSA-N
Route Signature
8896c526812e1d03958376a7dae83dee9911803e85a8b4011b31a6b5281d492d
Synthesis route with 5 steps
Route tree structure (JSON format)
{
"route": {
"id": "sa_68ef3ccbfcc4bbc49cbe5e65",
"signature": "8896c526812e1d03958376a7dae83dee9911803e85a8b4011b31a6b5281d492d",
"contentHash": "11ca9e5aa3524d85fad531b4d510d55827bcbde4eafd2482f844267d2db13251",
"length": 5,
"isConvergent": false
},
"target": {
"id": "sa_2457b081fa2279c66fe988c2",
"benchmarkSetId": "f925e688d731a0ad4e3aa6a505df094f6d3ca64ce3facc312bc5f64731921b33",
"targetId": "n5-02543",
"moleculeId": "sa_ecb2c2b8c1df607ec9a10fb2",
"smiles": "Cc1ccc(O)c(N2CCC3(CC2)CCN(c2ccc(OC(F)(F)F)cc2)C3=O)c1",
"routeLength": 5,
"isConvergent": false,
"metadata": null,
"molecule": {
"id": "sa_ecb2c2b8c1df607ec9a10fb2",
"inchikey": "QJPQCPCFRNQINL-UHFFFAOYSA-N",
"smiles": "Cc1ccc(O)c(N2CCC3(CC2)CCN(c2ccc(OC(F)(F)F)cc2)C3=O)c1"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "6409",
"routeId": "sa_68ef3ccbfcc4bbc49cbe5e65",
"moleculeId": "sa_ecb2c2b8c1df607ec9a10fb2",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_ecb2c2b8c1df607ec9a10fb2",
"inchikey": "QJPQCPCFRNQINL-UHFFFAOYSA-N",
"smiles": "Cc1ccc(O)c(N2CCC3(CC2)CCN(c2ccc(OC(F)(F)F)cc2)C3=O)c1"
},
"smiles": "Cc1ccc(O)c(N2CCC3(CC2)CCN(c2ccc(OC(F)(F)F)cc2)C3=O)c1",
"reactionStepId": "sa_48433f39f2f38c8bd29d684c",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20150148363A1;0158;1694545\",\"rsmi\":\"C[O:28][c:27]1[c:4]([N:5]2[CH2:6][CH2:7][C:8]3([CH2:9][CH2:10]2)[CH2:11][CH2:12][N:13]([c:14]2[cH:15][cH:16][c:17]([O:18][C:19]([F:20])([F:21])[F:22])[cH:23][cH:24]2)[C:25]3=[O:26])[cH:3][c:2]([CH3:1])[cH:30][cH:29]1>BrB(Br)Br>[CH3:1][c:2]1[cH:3][c:4]([N:5]2[CH2:6][CH2:7][C:8]3([CH2:9][CH2:10]2)[CH2:11][CH2:12][N:13]([c:14]2[cH:15][cH:16][c:17]([O:18][C:19]([F:20])([F:21])[F:22])[cH:23][cH:24]2)[C:25]3=[O:26])[c:27]([OH:28])[cH:29][cH:30]1\"},\"mapped_reaction_smiles\":\"C[O:28][c:27]1[c:4]([N:5]2[CH2:6][CH2:7][C:8]3([CH2:9][CH2:10]2)[CH2:11][CH2:12][N:13]([c:14]2[cH:15][cH:16][c:17]([O:18][C:19]([F:20])([F:21])[F:22])[cH:23][cH:24]2)[C:25]3=[O:26])[cH:3][c:2]([CH3:1])[cH:30][cH:29]1>BrB(Br)Br>[CH3:1][c:2]1[cH:3][c:4]([N:5]2[CH2:6][CH2:7][C:8]3([CH2:9][CH2:10]2)[CH2:11][CH2:12][N:13]([c:14]2[cH:15][cH:16][c:17]([O:18][C:19]([F:20])([F:21])[F:22])[cH:23][cH:24]2)[C:25]3=[O:26])[c:27]([OH:28])[cH:29][cH:30]1\"}",
"reactionStep": {
"id": "sa_48433f39f2f38c8bd29d684c",
"reactionHash": "dffb5f9c00ce373ce6d70232a98b25badf4b70ada9fd198737f5479168d7f6e1"
},
"children": [
{
"id": "6410",
"routeId": "sa_68ef3ccbfcc4bbc49cbe5e65",
"moleculeId": "sa_45e08c7f862b3af1c9c4df21",
"parentId": "6409",
"isLeaf": false,
"molecule": {
"id": "sa_45e08c7f862b3af1c9c4df21",
"inchikey": "YBQIFUIMTUIAQW-UHFFFAOYSA-N",
"smiles": "COc1ccc(C)cc1N1CCC2(CC1)CCN(c1ccc(OC(F)(F)F)cc1)C2=O"
},
"smiles": "COc1ccc(C)cc1N1CCC2(CC1)CCN(c1ccc(OC(F)(F)F)cc1)C2=O",
"reactionStepId": "sa_503ce1cce5525730425955b0",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20150148363A1;0146;1694539\",\"rsmi\":\"Br[c:4]1[c:3]([O:2][CH3:1])[cH:31][cH:30][c:28]([CH3:29])[cH:27]1.[NH:5]1[CH2:6][CH2:7][C:8]2([CH2:9][CH2:10]1)[CH2:11][CH2:12][N:13]([c:14]1[cH:15][cH:16][c:17]([O:18][C:19]([F:20])([F:21])[F:22])[cH:23][cH:24]1)[C:25]2=[O:26]>>[CH3:1][O:2][c:3]1[c:4]([N:5]2[CH2:6][CH2:7][C:8]3([CH2:9][CH2:10]2)[CH2:11][CH2:12][N:13]([c:14]2[cH:15][cH:16][c:17]([O:18][C:19]([F:20])([F:21])[F:22])[cH:23][cH:24]2)[C:25]3=[O:26])[cH:27][c:28]([CH3:29])[cH:30][cH:31]1\"},\"mapped_reaction_smiles\":\"Br[c:4]1[c:3]([O:2][CH3:1])[cH:31][cH:30][c:28]([CH3:29])[cH:27]1.[NH:5]1[CH2:6][CH2:7][C:8]2([CH2:9][CH2:10]1)[CH2:11][CH2:12][N:13]([c:14]1[cH:15][cH:16][c:17]([O:18][C:19]([F:20])([F:21])[F:22])[cH:23][cH:24]1)[C:25]2=[O:26]>>[CH3:1][O:2][c:3]1[c:4]([N:5]2[CH2:6][CH2:7][C:8]3([CH2:9][CH2:10]2)[CH2:11][CH2:12][N:13]([c:14]2[cH:15][cH:16][c:17]([O:18][C:19]([F:20])([F:21])[F:22])[cH:23][cH:24]2)[C:25]3=[O:26])[cH:27][c:28]([CH3:29])[cH:30][cH:31]1\"}",
"reactionStep": {
"id": "sa_503ce1cce5525730425955b0",
"reactionHash": "ac0ea1a50ec03b66dac2d0142b85d8399b1c7203ba0abeb41485311e98e5b9f2"
},
"children": [
{
"id": "6411",
"routeId": "sa_68ef3ccbfcc4bbc49cbe5e65",
"moleculeId": "sa_13a8bfc099cb6a9182d00b7c",
"parentId": "6410",
"isLeaf": true,
"molecule": {
"id": "sa_13a8bfc099cb6a9182d00b7c",
"inchikey": "DHPUIKWBNXTXOB-UHFFFAOYSA-N",
"smiles": "COc1ccc(C)cc1Br"
},
"smiles": "COc1ccc(C)cc1Br",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "6412",
"routeId": "sa_68ef3ccbfcc4bbc49cbe5e65",
"moleculeId": "sa_9bc18022fb778e49d919fde7",
"parentId": "6410",
"isLeaf": false,
"molecule": {
"id": "sa_9bc18022fb778e49d919fde7",
"inchikey": "FRJFQVAADRNWND-UHFFFAOYSA-N",
"smiles": "O=C1N(c2ccc(OC(F)(F)F)cc2)CCC12CCNCC2"
},
"smiles": "O=C1N(c2ccc(OC(F)(F)F)cc2)CCC12CCNCC2",
"reactionStepId": "sa_60c8bc9b0c4424dd04a69ff9",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20150148363A1;0129;1694531\",\"rsmi\":\"c1ccc(C[N:20]2[CH2:19][CH2:18][C:17]3([C:2](=[O:1])[N:3]([c:4]4[cH:5][cH:6][c:7]([O:8][C:9]([F:10])([F:11])[F:12])[cH:13][cH:14]4)[CH2:15][CH2:16]3)[CH2:22][CH2:21]2)cc1>CC(=O)O.CO.O.O.[Pd+2]>[O:1]=[C:2]1[N:3]([c:4]2[cH:5][cH:6][c:7]([O:8][C:9]([F:10])([F:11])[F:12])[cH:13][cH:14]2)[CH2:15][CH2:16][C:17]12[CH2:18][CH2:19][NH:20][CH2:21][CH2:22]2\"},\"mapped_reaction_smiles\":\"c1ccc(C[N:20]2[CH2:19][CH2:18][C:17]3([C:2](=[O:1])[N:3]([c:4]4[cH:5][cH:6][c:7]([O:8][C:9]([F:10])([F:11])[F:12])[cH:13][cH:14]4)[CH2:15][CH2:16]3)[CH2:22][CH2:21]2)cc1>CC(=O)O.CO.O.O.[Pd+2]>[O:1]=[C:2]1[N:3]([c:4]2[cH:5][cH:6][c:7]([O:8][C:9]([F:10])([F:11])[F:12])[cH:13][cH:14]2)[CH2:15][CH2:16][C:17]12[CH2:18][CH2:19][NH:20][CH2:21][CH2:22]2\"}",
"reactionStep": {
"id": "sa_60c8bc9b0c4424dd04a69ff9",
"reactionHash": "37c711702d929589c9464d1d957c18ff7c9f133aecae7ac01a752311113fe427"
},
"children": [
{
"id": "6413",
"routeId": "sa_68ef3ccbfcc4bbc49cbe5e65",
"moleculeId": "sa_0db1e0d84d9177e9a3530b12",
"parentId": "6412",
"isLeaf": false,
"molecule": {
"id": "sa_0db1e0d84d9177e9a3530b12",
"inchikey": "RUWYMWZXKVQOBZ-UHFFFAOYSA-N",
"smiles": "O=C1N(c2ccc(OC(F)(F)F)cc2)CCC12CCN(Cc1ccccc1)CC2"
},
"smiles": "O=C1N(c2ccc(OC(F)(F)F)cc2)CCC12CCN(Cc1ccccc1)CC2",
"reactionStepId": "sa_ca66911cab5658cf7a3e0d28",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20150148363A1;0127;1694530\",\"rsmi\":\"CCO[C:2](=[O:1])[C:17]1([CH2:16][CH2:15]OC)[CH2:18][CH2:19][N:20]([CH2:21][c:22]2[cH:23][cH:24][cH:25][cH:26][cH:27]2)[CH2:28][CH2:29]1.[NH2:3][c:4]1[cH:5][cH:6][c:7]([O:8][C:9]([F:10])([F:11])[F:12])[cH:13][cH:14]1>C[Al+]C.Cc1ccccc1.Cl>[O:1]=[C:2]1[N:3]([c:4]2[cH:5][cH:6][c:7]([O:8][C:9]([F:10])([F:11])[F:12])[cH:13][cH:14]2)[CH2:15][CH2:16][C:17]12[CH2:18][CH2:19][N:20]([CH2:21][c:22]1[cH:23][cH:24][cH:25][cH:26][cH:27]1)[CH2:28][CH2:29]2\"},\"mapped_reaction_smiles\":\"CCO[C:2](=[O:1])[C:17]1([CH2:16][CH2:15]OC)[CH2:18][CH2:19][N:20]([CH2:21][c:22]2[cH:23][cH:24][cH:25][cH:26][cH:27]2)[CH2:28][CH2:29]1.[NH2:3][c:4]1[cH:5][cH:6][c:7]([O:8][C:9]([F:10])([F:11])[F:12])[cH:13][cH:14]1>C[Al+]C.Cc1ccccc1.Cl>[O:1]=[C:2]1[N:3]([c:4]2[cH:5][cH:6][c:7]([O:8][C:9]([F:10])([F:11])[F:12])[cH:13][cH:14]2)[CH2:15][CH2:16][C:17]12[CH2:18][CH2:19][N:20]([CH2:21][c:22]1[cH:23][cH:24][cH:25][cH:26][cH:27]1)[CH2:28][CH2:29]2\"}",
"reactionStep": {
"id": "sa_ca66911cab5658cf7a3e0d28",
"reactionHash": "06df409fc4fab6aa652702f5592143ff52273aab14ba4079a4b04443b797d691"
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"children": [
{
"id": "6414",
"routeId": "sa_68ef3ccbfcc4bbc49cbe5e65",
"moleculeId": "sa_8f079a9eb75fc1701eede5ec",
"parentId": "6413",
"isLeaf": false,
"molecule": {
"id": "sa_8f079a9eb75fc1701eede5ec",
"inchikey": "MJNSQBGZEVRNQO-UHFFFAOYSA-N",
"smiles": "CCOC(=O)C1(CCOC)CCN(Cc2ccccc2)CC1"
},
"smiles": "CCOC(=O)C1(CCOC)CCN(Cc2ccccc2)CC1",
"reactionStepId": "sa_02f752b877c4083efe234f8d",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20150148363A1;0125;1694529\",\"rsmi\":\"Br[CH2:7][CH2:8][O:9][CH3:10].[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]1[CH2:11][CH2:12][N:13]([CH2:14][c:15]2[cH:16][cH:17][cH:18][cH:19][cH:20]2)[CH2:21][CH2:22]1>C1CCOC1.CC(C)NC(C)C.CCCCCC.CCOC(C)=O>[CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6]1([CH2:7][CH2:8][O:9][CH3:10])[CH2:11][CH2:12][N:13]([CH2:14][c:15]2[cH:16][cH:17][cH:18][cH:19][cH:20]2)[CH2:21][CH2:22]1\"},\"mapped_reaction_smiles\":\"Br[CH2:7][CH2:8][O:9][CH3:10].[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]1[CH2:11][CH2:12][N:13]([CH2:14][c:15]2[cH:16][cH:17][cH:18][cH:19][cH:20]2)[CH2:21][CH2:22]1>C1CCOC1.CC(C)NC(C)C.CCCCCC.CCOC(C)=O>[CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6]1([CH2:7][CH2:8][O:9][CH3:10])[CH2:11][CH2:12][N:13]([CH2:14][c:15]2[cH:16][cH:17][cH:18][cH:19][cH:20]2)[CH2:21][CH2:22]1\"}",
"reactionStep": {
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"reactionHash": "7a58da19be197059b645e8677bbe9403db08bf4df624b3948c47088a29f3ac45"
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"children": [
{
"id": "6415",
"routeId": "sa_68ef3ccbfcc4bbc49cbe5e65",
"moleculeId": "sa_8922431b155a6ef7ce93280f",
"parentId": "6414",
"isLeaf": true,
"molecule": {
"id": "sa_8922431b155a6ef7ce93280f",
"inchikey": "ASQCOPJFYLJCGD-UHFFFAOYSA-N",
"smiles": "CCOC(=O)C1CCN(Cc2ccccc2)CC1"
},
"smiles": "CCOC(=O)C1CCN(Cc2ccccc2)CC1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "6416",
"routeId": "sa_68ef3ccbfcc4bbc49cbe5e65",
"moleculeId": "sa_1d500dd023c3a4d81d60b398",
"parentId": "6414",
"isLeaf": true,
"molecule": {
"id": "sa_1d500dd023c3a4d81d60b398",
"inchikey": "YZUPZGFPHUVJKC-UHFFFAOYSA-N",
"smiles": "COCCBr"
},
"smiles": "COCCBr",
"reactionStepId": null,
"template": null,
"metadata": null,
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"children": []
}
]
},
{
"id": "6417",
"routeId": "sa_68ef3ccbfcc4bbc49cbe5e65",
"moleculeId": "sa_092084762c3a51ea022a4811",
"parentId": "6413",
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"molecule": {
"id": "sa_092084762c3a51ea022a4811",
"inchikey": "XUJFOSLZQITUOI-UHFFFAOYSA-N",
"smiles": "Nc1ccc(OC(F)(F)F)cc1"
},
"smiles": "Nc1ccc(OC(F)(F)F)cc1",
"reactionStepId": null,
"template": null,
"metadata": null,
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"children": []
}
]
}
]
}
]
}
]
}
}