Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
COC(=O)N1c2ccc(-c3csc(C4(O)CCNCC4)n3)c(OC3CCC3)c2CC[C@@H]1C
InChiKey
APXPYZBGCWNWTK-HNNXBMFYSA-N
Route Signature
1645334051a4edea346f8f20741eae271095991da80d39010b50da70649b3852
Synthesis route with 3 steps (convergent)
Route tree structure (JSON format)
{
"route": {
"id": "sa_3dae6c5a752a6aa9f6bbe6f3",
"signature": "1645334051a4edea346f8f20741eae271095991da80d39010b50da70649b3852",
"contentHash": "fbdcdca5d2d60a3ba32850d4434c97d8c578ae363dee1b3fa023849a318fca30",
"length": 3,
"isConvergent": true
},
"target": {
"id": "sa_0ec3b34e3e47ef2c23706239",
"benchmarkSetId": "3895c2909c53593560c5ba610abc7e6df80513dfd8624165c560451735097d36",
"targetId": "n5-05299",
"moleculeId": "sa_cb6bd615effe6477e2ab9baf",
"smiles": "COC(=O)N1c2ccc(-c3csc(C4(O)CCNCC4)n3)c(OC3CCC3)c2CC[C@@H]1C",
"routeLength": 3,
"isConvergent": true,
"metadata": null,
"molecule": {
"id": "sa_cb6bd615effe6477e2ab9baf",
"inchikey": "APXPYZBGCWNWTK-HNNXBMFYSA-N",
"smiles": "COC(=O)N1c2ccc(-c3csc(C4(O)CCNCC4)n3)c(OC3CCC3)c2CC[C@@H]1C"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "11403",
"routeId": "sa_3dae6c5a752a6aa9f6bbe6f3",
"moleculeId": "sa_cb6bd615effe6477e2ab9baf",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_cb6bd615effe6477e2ab9baf",
"inchikey": "APXPYZBGCWNWTK-HNNXBMFYSA-N",
"smiles": "COC(=O)N1c2ccc(-c3csc(C4(O)CCNCC4)n3)c(OC3CCC3)c2CC[C@@H]1C"
},
"smiles": "COC(=O)N1c2ccc(-c3csc(C4(O)CCNCC4)n3)c(OC3CCC3)c2CC[C@@H]1C",
"reactionStepId": "sa_df1ddde65b8016ee6ca9ecab",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20150232445A1;1639;1739631\",\"rsmi\":\"CC(C)(C)OC(=O)[N:18]1[CH2:17][CH2:16][C:14]([c:13]2[s:12][cH:11][c:10](-[c:9]3[cH:8][cH:7][c:6]4[c:28]([c:22]3[O:23][CH:24]3[CH2:25][CH2:26][CH2:27]3)[CH2:29][CH2:30][C@H:31]([CH3:32])[N:5]4[C:3]([O:2][CH3:1])=[O:4])[n:21]2)([OH:15])[CH2:20][CH2:19]1>C1COCCO1.Cl>[CH3:1][O:2][C:3](=[O:4])[N:5]1[c:6]2[cH:7][cH:8][c:9](-[c:10]3[cH:11][s:12][c:13]([C:14]4([OH:15])[CH2:16][CH2:17][NH:18][CH2:19][CH2:20]4)[n:21]3)[c:22]([O:23][CH:24]3[CH2:25][CH2:26][CH2:27]3)[c:28]2[CH2:29][CH2:30][C@@H:31]1[CH3:32]\"},\"mapped_reaction_smiles\":\"CC(C)(C)OC(=O)[N:18]1[CH2:17][CH2:16][C:14]([c:13]2[s:12][cH:11][c:10](-[c:9]3[cH:8][cH:7][c:6]4[c:28]([c:22]3[O:23][CH:24]3[CH2:25][CH2:26][CH2:27]3)[CH2:29][CH2:30][C@H:31]([CH3:32])[N:5]4[C:3]([O:2][CH3:1])=[O:4])[n:21]2)([OH:15])[CH2:20][CH2:19]1>C1COCCO1.Cl>[CH3:1][O:2][C:3](=[O:4])[N:5]1[c:6]2[cH:7][cH:8][c:9](-[c:10]3[cH:11][s:12][c:13]([C:14]4([OH:15])[CH2:16][CH2:17][NH:18][CH2:19][CH2:20]4)[n:21]3)[c:22]([O:23][CH:24]3[CH2:25][CH2:26][CH2:27]3)[c:28]2[CH2:29][CH2:30][C@@H:31]1[CH3:32]\"}",
"reactionStep": {
"id": "sa_df1ddde65b8016ee6ca9ecab",
"reactionHash": "838962a3bb734b0152f9d632cd85b69ca03ffac00ada055d1a6281c84b4c898f"
},
"children": [
{
"id": "11404",
"routeId": "sa_3dae6c5a752a6aa9f6bbe6f3",
"moleculeId": "sa_aa05fb4c79c19dee112a3b07",
"parentId": "11403",
"isLeaf": false,
"molecule": {
"id": "sa_aa05fb4c79c19dee112a3b07",
"inchikey": "SXKLZMTVNRIPOC-SFHVURJKSA-N",
"smiles": "COC(=O)N1c2ccc(-c3csc(C4(O)CCN(C(=O)OC(C)(C)C)CC4)n3)c(OC3CCC3)c2CC[C@@H]1C"
},
"smiles": "COC(=O)N1c2ccc(-c3csc(C4(O)CCN(C(=O)OC(C)(C)C)CC4)n3)c(OC3CCC3)c2CC[C@@H]1C",
"reactionStepId": "sa_952b9c5eb05784a7885b9b1f",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20150232445A1;1638;1739630\",\"rsmi\":\"Br[c:10]1[cH:11][s:12][c:13]([C:14]2([OH:15])[CH2:16][CH2:17][N:18]([C:19](=[O:20])[O:21][C:22]([CH3:23])([CH3:24])[CH3:25])[CH2:26][CH2:27]2)[n:28]1.CC1(C)OB([c:9]2[cH:8][cH:7][c:6]3[c:35]([c:29]2[O:30][CH:31]2[CH2:32][CH2:33][CH2:34]2)[CH2:36][CH2:37][C@H:38]([CH3:39])[N:5]3[C:3]([O:2][CH3:1])=[O:4])OC1(C)C>C1COCCO1.CC(C)c1cc(C(C)C)c(-c2cccc(P(C3CCCCC3)C3CCCCC3)c2)c(C(C)C)c1.Cl[Pd+].Nc1ccccc1-c1ccccc1.O.O=C(O)O.[Cs+].[Cs+]>[CH3:1][O:2][C:3](=[O:4])[N:5]1[c:6]2[cH:7][cH:8][c:9](-[c:10]3[cH:11][s:12][c:13]([C:14]4([OH:15])[CH2:16][CH2:17][N:18]([C:19](=[O:20])[O:21][C:22]([CH3:23])([CH3:24])[CH3:25])[CH2:26][CH2:27]4)[n:28]3)[c:29]([O:30][CH:31]3[CH2:32][CH2:33][CH2:34]3)[c:35]2[CH2:36][CH2:37][C@@H:38]1[CH3:39]\"},\"mapped_reaction_smiles\":\"Br[c:10]1[cH:11][s:12][c:13]([C:14]2([OH:15])[CH2:16][CH2:17][N:18]([C:19](=[O:20])[O:21][C:22]([CH3:23])([CH3:24])[CH3:25])[CH2:26][CH2:27]2)[n:28]1.CC1(C)OB([c:9]2[cH:8][cH:7][c:6]3[c:35]([c:29]2[O:30][CH:31]2[CH2:32][CH2:33][CH2:34]2)[CH2:36][CH2:37][C@H:38]([CH3:39])[N:5]3[C:3]([O:2][CH3:1])=[O:4])OC1(C)C>C1COCCO1.CC(C)c1cc(C(C)C)c(-c2cccc(P(C3CCCCC3)C3CCCCC3)c2)c(C(C)C)c1.Cl[Pd+].Nc1ccccc1-c1ccccc1.O.O=C(O)O.[Cs+].[Cs+]>[CH3:1][O:2][C:3](=[O:4])[N:5]1[c:6]2[cH:7][cH:8][c:9](-[c:10]3[cH:11][s:12][c:13]([C:14]4([OH:15])[CH2:16][CH2:17][N:18]([C:19](=[O:20])[O:21][C:22]([CH3:23])([CH3:24])[CH3:25])[CH2:26][CH2:27]4)[n:28]3)[c:29]([O:30][CH:31]3[CH2:32][CH2:33][CH2:34]3)[c:35]2[CH2:36][CH2:37][C@@H:38]1[CH3:39]\"}",
"reactionStep": {
"id": "sa_952b9c5eb05784a7885b9b1f",
"reactionHash": "aa3d92f192d9a9fdef9b9d0ca4287792abb87e690225b810050591d5237cd6cc"
},
"children": [
{
"id": "11405",
"routeId": "sa_3dae6c5a752a6aa9f6bbe6f3",
"moleculeId": "sa_6f2fca3ce1e73fdcea414261",
"parentId": "11404",
"isLeaf": false,
"molecule": {
"id": "sa_6f2fca3ce1e73fdcea414261",
"inchikey": "JGTNMIQSBBWYDN-UHFFFAOYSA-N",
"smiles": "CC(C)(C)OC(=O)N1CCC(O)(c2nc(Br)cs2)CC1"
},
"smiles": "CC(C)(C)OC(=O)N1CCC(O)(c2nc(Br)cs2)CC1",
"reactionStepId": "sa_b6488d1eb345b0e2ffd39412",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20150232445A1;1636;1739628\",\"rsmi\":\"Br[c:13]1[n:14][c:15]([Br:16])[cH:17][s:18]1.[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][C:11](=[O:12])[CH2:19][CH2:20]1>ClCCl.[Li]CCCC>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][C:11]([OH:12])([c:13]2[n:14][c:15]([Br:16])[cH:17][s:18]2)[CH2:19][CH2:20]1\"},\"mapped_reaction_smiles\":\"Br[c:13]1[n:14][c:15]([Br:16])[cH:17][s:18]1.[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][C:11](=[O:12])[CH2:19][CH2:20]1>ClCCl.[Li]CCCC>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][C:11]([OH:12])([c:13]2[n:14][c:15]([Br:16])[cH:17][s:18]2)[CH2:19][CH2:20]1\"}",
"reactionStep": {
"id": "sa_b6488d1eb345b0e2ffd39412",
"reactionHash": "5030d72d675052902736d88347baa24a6a64607cf62117484de3cf9dcf59c9c7"
},
"children": [
{
"id": "11406",
"routeId": "sa_3dae6c5a752a6aa9f6bbe6f3",
"moleculeId": "sa_fd1a492179d6a4ac7c6238e0",
"parentId": "11405",
"isLeaf": true,
"molecule": {
"id": "sa_fd1a492179d6a4ac7c6238e0",
"inchikey": "MKEJZKKVVUZXIS-UHFFFAOYSA-N",
"smiles": "Brc1csc(Br)n1"
},
"smiles": "Brc1csc(Br)n1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "11407",
"routeId": "sa_3dae6c5a752a6aa9f6bbe6f3",
"moleculeId": "sa_806e424090667321a5b9727c",
"parentId": "11405",
"isLeaf": true,
"molecule": {
"id": "sa_806e424090667321a5b9727c",
"inchikey": "ROUYFJUVMYHXFJ-UHFFFAOYSA-N",
"smiles": "CC(C)(C)OC(=O)N1CCC(=O)CC1"
},
"smiles": "CC(C)(C)OC(=O)N1CCC(=O)CC1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
},
{
"id": "11408",
"routeId": "sa_3dae6c5a752a6aa9f6bbe6f3",
"moleculeId": "sa_70c1c6e53770ebbdde231dc3",
"parentId": "11404",
"isLeaf": false,
"molecule": {
"id": "sa_70c1c6e53770ebbdde231dc3",
"inchikey": "WQQLLDOWHMZMGR-AWEZNQCLSA-N",
"smiles": "COC(=O)N1c2ccc(B3OC(C)(C)C(C)(C)O3)c(OC3CCC3)c2CC[C@@H]1C"
},
"smiles": "COC(=O)N1c2ccc(B3OC(C)(C)C(C)(C)O3)c(OC3CCC3)c2CC[C@@H]1C",
"reactionStepId": "sa_3a2175967bb8a43d8f0228e0",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20150232445A1;1637;1739629\",\"rsmi\":\"Br[c:9]1[cH:8][cH:7][c:6]2[c:25]([c:19]1[O:20][CH:21]1[CH2:22][CH2:23][CH2:24]1)[CH2:26][CH2:27][C@H:28]([CH3:29])[N:5]2[C:3]([O:2][CH3:1])=[O:4].CC1(C)OB([B:10]2[O:11][C:12]([CH3:13])([CH3:14])[C:15]([CH3:16])([CH3:17])[O:18]2)OC1(C)C>C1COCCO1.CC(=O)O.ClCCl.Cl[Pd]Cl.[Fe+2].[K+]>[CH3:1][O:2][C:3](=[O:4])[N:5]1[c:6]2[cH:7][cH:8][c:9]([B:10]3[O:11][C:12]([CH3:13])([CH3:14])[C:15]([CH3:16])([CH3:17])[O:18]3)[c:19]([O:20][CH:21]3[CH2:22][CH2:23][CH2:24]3)[c:25]2[CH2:26][CH2:27][C@@H:28]1[CH3:29]\"},\"mapped_reaction_smiles\":\"Br[c:9]1[cH:8][cH:7][c:6]2[c:25]([c:19]1[O:20][CH:21]1[CH2:22][CH2:23][CH2:24]1)[CH2:26][CH2:27][C@H:28]([CH3:29])[N:5]2[C:3]([O:2][CH3:1])=[O:4].CC1(C)OB([B:10]2[O:11][C:12]([CH3:13])([CH3:14])[C:15]([CH3:16])([CH3:17])[O:18]2)OC1(C)C>C1COCCO1.CC(=O)O.ClCCl.Cl[Pd]Cl.[Fe+2].[K+]>[CH3:1][O:2][C:3](=[O:4])[N:5]1[c:6]2[cH:7][cH:8][c:9]([B:10]3[O:11][C:12]([CH3:13])([CH3:14])[C:15]([CH3:16])([CH3:17])[O:18]3)[c:19]([O:20][CH:21]3[CH2:22][CH2:23][CH2:24]3)[c:25]2[CH2:26][CH2:27][C@@H:28]1[CH3:29]\"}",
"reactionStep": {
"id": "sa_3a2175967bb8a43d8f0228e0",
"reactionHash": "9ad9de089f62a28f97c268a8eae85f0511af52fee0efe6621d00a5b3167e85a8"
},
"children": [
{
"id": "11409",
"routeId": "sa_3dae6c5a752a6aa9f6bbe6f3",
"moleculeId": "sa_eaec232f36dbe616633722f1",
"parentId": "11408",
"isLeaf": true,
"molecule": {
"id": "sa_eaec232f36dbe616633722f1",
"inchikey": "CHZIGXDUYDDVHV-JTQLQIEISA-N",
"smiles": "COC(=O)N1c2ccc(Br)c(OC3CCC3)c2CC[C@@H]1C"
},
"smiles": "COC(=O)N1c2ccc(Br)c(OC3CCC3)c2CC[C@@H]1C",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "11410",
"routeId": "sa_3dae6c5a752a6aa9f6bbe6f3",
"moleculeId": "sa_e6c301388ac142801d4af5a2",
"parentId": "11408",
"isLeaf": true,
"molecule": {
"id": "sa_e6c301388ac142801d4af5a2",
"inchikey": "IPWKHHSGDUIRAH-UHFFFAOYSA-N",
"smiles": "CC1(C)OB(B2OC(C)(C)C(C)(C)O2)OC1(C)C"
},
"smiles": "CC1(C)OB(B2OC(C)(C)C(C)(C)O2)OC1(C)C",
"reactionStepId": null,
"template": null,
"metadata": null,
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"children": []
}
]
}
]
}
]
}
}