Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
C[C@@H]1CCc2ncnc(C3CCN(C(=O)[C@@H](c4ccc(Cl)cc4)[C@@H]4CCC(C)(C)N4C(=O)OC(C)(C)C)CC3)c21
InChiKey
PTRPUHSJXDNTNR-RAHIQWLESA-N
Route Signature
7a6bf8f2bc2d4998f8e25ffc07200b61c39820dce3cc1d3ff0b3b8b9c1ff77a6
Synthesis route with 6 steps
Route tree structure (JSON format)
{
"route": {
"id": "sa_5f4ba5a42d884815beaa9dae",
"signature": "7a6bf8f2bc2d4998f8e25ffc07200b61c39820dce3cc1d3ff0b3b8b9c1ff77a6",
"contentHash": "7942d5dcba7d5b0865213f96af60c22ca74635c67666a0fbcf5396d0b6415932",
"length": 6,
"isConvergent": false
},
"target": {
"id": "sa_99731880c56f2aba7bd50899",
"benchmarkSetId": "61e696668b63e77d7c2a29c0821768e1c383de8313852d6e995224859494442e",
"targetId": "n5-00810",
"moleculeId": "sa_58bf4df6aa9bac6482347b96",
"smiles": "C[C@@H]1CCc2ncnc(C3CCN(C(=O)[C@@H](c4ccc(Cl)cc4)[C@@H]4CCC(C)(C)N4C(=O)OC(C)(C)C)CC3)c21",
"routeLength": 6,
"isConvergent": false,
"metadata": null,
"molecule": {
"id": "sa_58bf4df6aa9bac6482347b96",
"inchikey": "PTRPUHSJXDNTNR-RAHIQWLESA-N",
"smiles": "C[C@@H]1CCc2ncnc(C3CCN(C(=O)[C@@H](c4ccc(Cl)cc4)[C@@H]4CCC(C)(C)N4C(=O)OC(C)(C)C)CC3)c21"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "13811",
"routeId": "sa_5f4ba5a42d884815beaa9dae",
"moleculeId": "sa_58bf4df6aa9bac6482347b96",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_58bf4df6aa9bac6482347b96",
"inchikey": "PTRPUHSJXDNTNR-RAHIQWLESA-N",
"smiles": "C[C@@H]1CCc2ncnc(C3CCN(C(=O)[C@@H](c4ccc(Cl)cc4)[C@@H]4CCC(C)(C)N4C(=O)OC(C)(C)C)CC3)c21"
},
"smiles": "C[C@@H]1CCc2ncnc(C3CCN(C(=O)[C@@H](c4ccc(Cl)cc4)[C@@H]4CCC(C)(C)N4C(=O)OC(C)(C)C)CC3)c21",
"reactionStepId": "sa_fc6bfd6ec893f654b94f1acb",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20150266852A1;0343;1755493\",\"rsmi\":\"O[C:12](=[O:13])[C@@H:14]([c:15]1[cH:16][cH:17][c:18]([Cl:19])[cH:20][cH:21]1)[C@@H:22]1[CH2:23][CH2:24][C:25]([CH3:26])([CH3:27])[N:28]1[C:29](=[O:30])[O:31][C:32]([CH3:33])([CH3:34])[CH3:35].[CH3:1][C@@H:2]1[CH2:3][CH2:4][c:5]2[c:6]1[c:7]([CH:8]1[CH2:9][CH2:10][NH:11][CH2:36][CH2:37]1)[n:38][cH:39][n:40]2>CCN(C(C)C)C(C)C.CN(C)C(On1nnc2ccccc21)=[N+](C)C.ClCCl.F[PH](F)(F)(F)(F)F>[CH3:1][C@@H:2]1[CH2:3][CH2:4][c:5]2[c:6]1[c:7]([CH:8]1[CH2:9][CH2:10][N:11]([C:12](=[O:13])[C@@H:14]([c:15]3[cH:16][cH:17][c:18]([Cl:19])[cH:20][cH:21]3)[C@@H:22]3[CH2:23][CH2:24][C:25]([CH3:26])([CH3:27])[N:28]3[C:29](=[O:30])[O:31][C:32]([CH3:33])([CH3:34])[CH3:35])[CH2:36][CH2:37]1)[n:38][cH:39][n:40]2\"},\"mapped_reaction_smiles\":\"O[C:12](=[O:13])[C@@H:14]([c:15]1[cH:16][cH:17][c:18]([Cl:19])[cH:20][cH:21]1)[C@@H:22]1[CH2:23][CH2:24][C:25]([CH3:26])([CH3:27])[N:28]1[C:29](=[O:30])[O:31][C:32]([CH3:33])([CH3:34])[CH3:35].[CH3:1][C@@H:2]1[CH2:3][CH2:4][c:5]2[c:6]1[c:7]([CH:8]1[CH2:9][CH2:10][NH:11][CH2:36][CH2:37]1)[n:38][cH:39][n:40]2>CCN(C(C)C)C(C)C.CN(C)C(On1nnc2ccccc21)=[N+](C)C.ClCCl.F[PH](F)(F)(F)(F)F>[CH3:1][C@@H:2]1[CH2:3][CH2:4][c:5]2[c:6]1[c:7]([CH:8]1[CH2:9][CH2:10][N:11]([C:12](=[O:13])[C@@H:14]([c:15]3[cH:16][cH:17][c:18]([Cl:19])[cH:20][cH:21]3)[C@@H:22]3[CH2:23][CH2:24][C:25]([CH3:26])([CH3:27])[N:28]3[C:29](=[O:30])[O:31][C:32]([CH3:33])([CH3:34])[CH3:35])[CH2:36][CH2:37]1)[n:38][cH:39][n:40]2\"}",
"reactionStep": {
"id": "sa_fc6bfd6ec893f654b94f1acb",
"reactionHash": "2ba814066985afa1e3e3a5a3eada73bfd1efb75968f0b6baedbee190ab5dbb4f"
},
"children": [
{
"id": "13812",
"routeId": "sa_5f4ba5a42d884815beaa9dae",
"moleculeId": "sa_88f6275863d1fe4fdf2c3b5a",
"parentId": "13811",
"isLeaf": true,
"molecule": {
"id": "sa_88f6275863d1fe4fdf2c3b5a",
"inchikey": "FYUMTDCFUZDBGP-GJZGRUSLSA-N",
"smiles": "CC(C)(C)OC(=O)N1[C@H]([C@@H](C(=O)O)c2ccc(Cl)cc2)CCC1(C)C"
},
"smiles": "CC(C)(C)OC(=O)N1[C@H]([C@@H](C(=O)O)c2ccc(Cl)cc2)CCC1(C)C",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "13813",
"routeId": "sa_5f4ba5a42d884815beaa9dae",
"moleculeId": "sa_5cd08020ae485bdf061ef7b0",
"parentId": "13811",
"isLeaf": false,
"molecule": {
"id": "sa_5cd08020ae485bdf061ef7b0",
"inchikey": "REWGOOHNCMENKC-SECBINFHSA-N",
"smiles": "C[C@@H]1CCc2ncnc(C3CCNCC3)c21"
},
"smiles": "C[C@@H]1CCc2ncnc(C3CCNCC3)c21",
"reactionStepId": "sa_3d69db39e5c0a80ba954f4a0",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20150266852A1;0342;1755492\",\"rsmi\":\"CC(C)(C)OC(=O)[N:11]1[CH2:10][CH2:9][CH:8]([c:7]2[c:6]3[c:5]([n:16][cH:15][n:14]2)[CH2:4][CH2:3][C@H:2]3[CH3:1])[CH2:13][CH2:12]1>ClCCl.O=C(O)C(F)(F)F>[CH3:1][C@@H:2]1[CH2:3][CH2:4][c:5]2[c:6]1[c:7]([CH:8]1[CH2:9][CH2:10][NH:11][CH2:12][CH2:13]1)[n:14][cH:15][n:16]2\"},\"mapped_reaction_smiles\":\"CC(C)(C)OC(=O)[N:11]1[CH2:10][CH2:9][CH:8]([c:7]2[c:6]3[c:5]([n:16][cH:15][n:14]2)[CH2:4][CH2:3][C@H:2]3[CH3:1])[CH2:13][CH2:12]1>ClCCl.O=C(O)C(F)(F)F>[CH3:1][C@@H:2]1[CH2:3][CH2:4][c:5]2[c:6]1[c:7]([CH:8]1[CH2:9][CH2:10][NH:11][CH2:12][CH2:13]1)[n:14][cH:15][n:16]2\"}",
"reactionStep": {
"id": "sa_3d69db39e5c0a80ba954f4a0",
"reactionHash": "cc32921c37dde9ee6d93314af9ab23267f63b147044046fa017fbe24fddebc4d"
},
"children": [
{
"id": "13814",
"routeId": "sa_5f4ba5a42d884815beaa9dae",
"moleculeId": "sa_af23a1cd32ce2837105650fe",
"parentId": "13813",
"isLeaf": false,
"molecule": {
"id": "sa_af23a1cd32ce2837105650fe",
"inchikey": "QQVRGMQIQURPAB-GFCCVEGCSA-N",
"smiles": "C[C@@H]1CCc2ncnc(C3CCN(C(=O)OC(C)(C)C)CC3)c21"
},
"smiles": "C[C@@H]1CCc2ncnc(C3CCN(C(=O)OC(C)(C)C)CC3)c21",
"reactionStepId": "sa_eb815863ae88d52468a93aa8",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20150266852A1;0341;1755491\",\"rsmi\":\"[CH3:1][C@@H:2]1[CH2:3][CH2:4][c:5]2[c:6]1[c:7]([C:8]1=[CH:9][CH2:10][N:11]([C:12](=[O:13])[O:14][C:15]([CH3:16])([CH3:17])[CH3:18])[CH2:19][CH2:20]1)[n:21][cH:22][n:23]2>CCOC(C)=O.[Pd]>[CH3:1][C@@H:2]1[CH2:3][CH2:4][c:5]2[c:6]1[c:7]([CH:8]1[CH2:9][CH2:10][N:11]([C:12](=[O:13])[O:14][C:15]([CH3:16])([CH3:17])[CH3:18])[CH2:19][CH2:20]1)[n:21][cH:22][n:23]2\"},\"mapped_reaction_smiles\":\"[CH3:1][C@@H:2]1[CH2:3][CH2:4][c:5]2[c:6]1[c:7]([C:8]1=[CH:9][CH2:10][N:11]([C:12](=[O:13])[O:14][C:15]([CH3:16])([CH3:17])[CH3:18])[CH2:19][CH2:20]1)[n:21][cH:22][n:23]2>CCOC(C)=O.[Pd]>[CH3:1][C@@H:2]1[CH2:3][CH2:4][c:5]2[c:6]1[c:7]([CH:8]1[CH2:9][CH2:10][N:11]([C:12](=[O:13])[O:14][C:15]([CH3:16])([CH3:17])[CH3:18])[CH2:19][CH2:20]1)[n:21][cH:22][n:23]2\"}",
"reactionStep": {
"id": "sa_eb815863ae88d52468a93aa8",
"reactionHash": "481dc200bdcb820432cdbd0dad57e7b6ddac4d9d3f5f4f0645f6a7bfcf448745"
},
"children": [
{
"id": "13815",
"routeId": "sa_5f4ba5a42d884815beaa9dae",
"moleculeId": "sa_8b3a37dc1498eb40904b3341",
"parentId": "13814",
"isLeaf": false,
"molecule": {
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"inchikey": "FCECLRDWWKWEMH-GFCCVEGCSA-N",
"smiles": "C[C@@H]1CCc2ncnc(C3=CCN(C(=O)OC(C)(C)C)CC3)c21"
},
"smiles": "C[C@@H]1CCc2ncnc(C3=CCN(C(=O)OC(C)(C)C)CC3)c21",
"reactionStepId": "sa_1ce4ed7d7f696672446ffdf4",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20150266852A1;0340;1755490\",\"rsmi\":\"CC1(C)OB([C:8]2=[CH:9][CH2:10][N:11]([C:12](=[O:13])[O:14][C:15]([CH3:16])([CH3:17])[CH3:18])[CH2:19][CH2:20]2)OC1(C)C.Cl[c:7]1[c:6]2[c:5]([n:23][cH:22][n:21]1)[CH2:4][CH2:3][C@H:2]2[CH3:1]>C1COCCO1.Cl[Pd](Cl)([PH](c1ccccc1)(c1ccccc1)c1ccccc1)[PH](c1ccccc1)(c1ccccc1)c1ccccc1.O.O=C(O)O.[Na+].[Na+]>[CH3:1][C@@H:2]1[CH2:3][CH2:4][c:5]2[c:6]1[c:7]([C:8]1=[CH:9][CH2:10][N:11]([C:12](=[O:13])[O:14][C:15]([CH3:16])([CH3:17])[CH3:18])[CH2:19][CH2:20]1)[n:21][cH:22][n:23]2\"},\"mapped_reaction_smiles\":\"CC1(C)OB([C:8]2=[CH:9][CH2:10][N:11]([C:12](=[O:13])[O:14][C:15]([CH3:16])([CH3:17])[CH3:18])[CH2:19][CH2:20]2)OC1(C)C.Cl[c:7]1[c:6]2[c:5]([n:23][cH:22][n:21]1)[CH2:4][CH2:3][C@H:2]2[CH3:1]>C1COCCO1.Cl[Pd](Cl)([PH](c1ccccc1)(c1ccccc1)c1ccccc1)[PH](c1ccccc1)(c1ccccc1)c1ccccc1.O.O=C(O)O.[Na+].[Na+]>[CH3:1][C@@H:2]1[CH2:3][CH2:4][c:5]2[c:6]1[c:7]([C:8]1=[CH:9][CH2:10][N:11]([C:12](=[O:13])[O:14][C:15]([CH3:16])([CH3:17])[CH3:18])[CH2:19][CH2:20]1)[n:21][cH:22][n:23]2\"}",
"reactionStep": {
"id": "sa_1ce4ed7d7f696672446ffdf4",
"reactionHash": "19f67f1d3a11091bd7e05fbe7ea8334875b1182b3cc3c0e14de57211863ae687"
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"children": [
{
"id": "13816",
"routeId": "sa_5f4ba5a42d884815beaa9dae",
"moleculeId": "sa_3fe24a64120b53883c3a173a",
"parentId": "13815",
"isLeaf": false,
"molecule": {
"id": "sa_3fe24a64120b53883c3a173a",
"inchikey": "AUMBWDKTDZHUNN-RXMQYKEDSA-N",
"smiles": "C[C@@H]1CCc2ncnc(Cl)c21"
},
"smiles": "C[C@@H]1CCc2ncnc(Cl)c21",
"reactionStepId": "sa_266fe6bb21faba9751aae825",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20150266852A1;0261;1755449\",\"rsmi\":\"O=P(Cl)(Cl)[Cl:8].O[c:7]1[c:6]2[c:5]([n:11][cH:10][n:9]1)[CH2:4][CH2:3][C@H:2]2[CH3:1]>>[CH3:1][C@@H:2]1[CH2:3][CH2:4][c:5]2[c:6]1[c:7]([Cl:8])[n:9][cH:10][n:11]2\"},\"mapped_reaction_smiles\":\"O=P(Cl)(Cl)[Cl:8].O[c:7]1[c:6]2[c:5]([n:11][cH:10][n:9]1)[CH2:4][CH2:3][C@H:2]2[CH3:1]>>[CH3:1][C@@H:2]1[CH2:3][CH2:4][c:5]2[c:6]1[c:7]([Cl:8])[n:9][cH:10][n:11]2\"}",
"reactionStep": {
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"children": [
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"molecule": {
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"smiles": "C[C@@H]1CCc2ncnc(O)c21"
},
"smiles": "C[C@@H]1CCc2ncnc(O)c21",
"reactionStepId": "sa_001866db9373e8211e74c35d",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20150266852A1;0257;1755446\",\"rsmi\":\"S[c:10]1[n:9][c:7]([OH:8])[c:6]2[c:5]([n:11]1)[CH2:4][CH2:3][C@H:2]2[CH3:1]>O.N.[Ni].O>[CH3:1][C@@H:2]1[CH2:3][CH2:4][c:5]2[c:6]1[c:7]([OH:8])[n:9][cH:10][n:11]2\"},\"mapped_reaction_smiles\":\"S[c:10]1[n:9][c:7]([OH:8])[c:6]2[c:5]([n:11]1)[CH2:4][CH2:3][C@H:2]2[CH3:1]>O.N.[Ni].O>[CH3:1][C@@H:2]1[CH2:3][CH2:4][c:5]2[c:6]1[c:7]([OH:8])[n:9][cH:10][n:11]2\"}",
"reactionStep": {
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"children": [
{
"id": "13818",
"routeId": "sa_5f4ba5a42d884815beaa9dae",
"moleculeId": "sa_49261ba2663b43f895b6b8e4",
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"smiles": "C[C@@H]1CCc2nc(S)nc(O)c21",
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}
]
},
{
"id": "13819",
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"moleculeId": "sa_312a7cd3d48a055e9bc98180",
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"molecule": {
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"inchikey": "XHXFXVLFKHQFAL-UHFFFAOYSA-N",
"smiles": "O=P(Cl)(Cl)Cl"
},
"smiles": "O=P(Cl)(Cl)Cl",
"reactionStepId": null,
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},
{
"id": "13820",
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"molecule": {
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},
"smiles": "CC(C)(C)OC(=O)N1CC=C(B2OC(C)(C)C(C)(C)O2)CC1",
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}
]
}
]
}
}