Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
Cc1nc(N2CCN(CC(C)C)C2=O)sc1C(N)=O
InChiKey
IHRQCNPXTUDNMD-UHFFFAOYSA-N
Route Signature
e5a9031c9b6ae128fae7af1193613d0618e9d313ec17f1b046bb9282de0679cc
Synthesis route with 4 steps (convergent)
Route tree structure (JSON format)
{
"route": {
"id": "sa_7ec8e1538e30ce48ec8ae55f",
"signature": "e5a9031c9b6ae128fae7af1193613d0618e9d313ec17f1b046bb9282de0679cc",
"contentHash": "c9de667f4f36be8cf73489aeff3dcfe830113ee2637a4a36c5c7fab71d69702d",
"length": 4,
"isConvergent": true
},
"target": {
"id": "sa_e310e4b54c4a7d4b11a409a0",
"benchmarkSetId": "3895c2909c53593560c5ba610abc7e6df80513dfd8624165c560451735097d36",
"targetId": "n5-01295",
"moleculeId": "sa_bd1e58758a19cc16ada5b043",
"smiles": "Cc1nc(N2CCN(CC(C)C)C2=O)sc1C(N)=O",
"routeLength": 4,
"isConvergent": true,
"metadata": null,
"molecule": {
"id": "sa_bd1e58758a19cc16ada5b043",
"inchikey": "IHRQCNPXTUDNMD-UHFFFAOYSA-N",
"smiles": "Cc1nc(N2CCN(CC(C)C)C2=O)sc1C(N)=O"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "10065",
"routeId": "sa_7ec8e1538e30ce48ec8ae55f",
"moleculeId": "sa_bd1e58758a19cc16ada5b043",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_bd1e58758a19cc16ada5b043",
"inchikey": "IHRQCNPXTUDNMD-UHFFFAOYSA-N",
"smiles": "Cc1nc(N2CCN(CC(C)C)C2=O)sc1C(N)=O"
},
"smiles": "Cc1nc(N2CCN(CC(C)C)C2=O)sc1C(N)=O",
"reactionStepId": "sa_ab2e96ccd29e62bdec1844b6",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US08318949B2;0666;1255394\",\"rsmi\":\"Cc1nc(-n2c[n:5]n(Cc3ccc(F)cc3)c2=O)sc1C(=O)O.O[C:4]([c:3]1[c:2]([CH3:1])[n:19][c:8]([N:9]2[CH2:10][CH2:11][N:12]([CH2:13][CH:14]([CH3:15])[CH3:16])[C:17]2=[O:18])[s:7]1)=[O:6]>>[CH3:1][c:2]1[c:3]([C:4]([NH2:5])=[O:6])[s:7][c:8]([N:9]2[CH2:10][CH2:11][N:12]([CH2:13][CH:14]([CH3:15])[CH3:16])[C:17]2=[O:18])[n:19]1\"},\"mapped_reaction_smiles\":\"Cc1nc(-n2c[n:5]n(Cc3ccc(F)cc3)c2=O)sc1C(=O)O.O[C:4]([c:3]1[c:2]([CH3:1])[n:19][c:8]([N:9]2[CH2:10][CH2:11][N:12]([CH2:13][CH:14]([CH3:15])[CH3:16])[C:17]2=[O:18])[s:7]1)=[O:6]>>[CH3:1][c:2]1[c:3]([C:4]([NH2:5])=[O:6])[s:7][c:8]([N:9]2[CH2:10][CH2:11][N:12]([CH2:13][CH:14]([CH3:15])[CH3:16])[C:17]2=[O:18])[n:19]1\"}",
"reactionStep": {
"id": "sa_ab2e96ccd29e62bdec1844b6",
"reactionHash": "8629d31ab052d634b8fb3e468d7d556d1baeee30cc36a001b3c1280e87db4145"
},
"children": [
{
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"moleculeId": "sa_f7c741515806708616b5f48f",
"parentId": "10065",
"isLeaf": false,
"molecule": {
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"inchikey": "LLZNNNVBKGONSG-UHFFFAOYSA-N",
"smiles": "Cc1nc(N2CCN(CC(C)C)C2=O)sc1C(=O)O"
},
"smiles": "Cc1nc(N2CCN(CC(C)C)C2=O)sc1C(=O)O",
"reactionStepId": "sa_60e011812700991cdd9dea4f",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US08318949B2;0627;1255374\",\"rsmi\":\"CC[O:6][C:4]([c:3]1[c:2]([CH3:1])[n:19][c:8]([N:9]2[CH2:10][CH2:11][N:12]([CH2:13][CH:14]([CH3:15])[CH3:16])[C:17]2=[O:18])[s:7]1)=[O:5]>CCOC(=O)c1sc(N2CCN(CC3CC3(F)F)C2=O)nc1C>[CH3:1][c:2]1[c:3]([C:4](=[O:5])[OH:6])[s:7][c:8]([N:9]2[CH2:10][CH2:11][N:12]([CH2:13][CH:14]([CH3:15])[CH3:16])[C:17]2=[O:18])[n:19]1\"},\"mapped_reaction_smiles\":\"CC[O:6][C:4]([c:3]1[c:2]([CH3:1])[n:19][c:8]([N:9]2[CH2:10][CH2:11][N:12]([CH2:13][CH:14]([CH3:15])[CH3:16])[C:17]2=[O:18])[s:7]1)=[O:5]>CCOC(=O)c1sc(N2CCN(CC3CC3(F)F)C2=O)nc1C>[CH3:1][c:2]1[c:3]([C:4](=[O:5])[OH:6])[s:7][c:8]([N:9]2[CH2:10][CH2:11][N:12]([CH2:13][CH:14]([CH3:15])[CH3:16])[C:17]2=[O:18])[n:19]1\"}",
"reactionStep": {
"id": "sa_60e011812700991cdd9dea4f",
"reactionHash": "86919ef5030c52cdbf3569587697865add7a15792eb00bfc68805cf0b11aa64e"
},
"children": [
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"molecule": {
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"inchikey": "RTGVGPWFKZTUTK-UHFFFAOYSA-N",
"smiles": "CCOC(=O)c1sc(N2CCN(CC(C)C)C2=O)nc1C"
},
"smiles": "CCOC(=O)c1sc(N2CCN(CC(C)C)C2=O)nc1C",
"reactionStepId": "sa_55c8eab69c6254bdc8c7dec2",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US08318949B2;0607;1255364\",\"rsmi\":\"Br[CH2:15][CH:16]([CH3:17])[CH3:18].[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[c:7]([CH3:8])[n:9][c:10]([N:11]2[CH2:12][CH2:13][NH:14][C:19]2=[O:20])[s:21]1>FC1(F)CC1CBr>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[c:7]([CH3:8])[n:9][c:10]([N:11]2[CH2:12][CH2:13][N:14]([CH2:15][CH:16]([CH3:17])[CH3:18])[C:19]2=[O:20])[s:21]1\"},\"mapped_reaction_smiles\":\"Br[CH2:15][CH:16]([CH3:17])[CH3:18].[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[c:7]([CH3:8])[n:9][c:10]([N:11]2[CH2:12][CH2:13][NH:14][C:19]2=[O:20])[s:21]1>FC1(F)CC1CBr>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[c:7]([CH3:8])[n:9][c:10]([N:11]2[CH2:12][CH2:13][N:14]([CH2:15][CH:16]([CH3:17])[CH3:18])[C:19]2=[O:20])[s:21]1\"}",
"reactionStep": {
"id": "sa_55c8eab69c6254bdc8c7dec2",
"reactionHash": "f22beae5b9df1a863d79e01654040fe30d211c224a6295ffc4ca2f7d30b343e6"
},
"children": [
{
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"moleculeId": "sa_28a2ec6b7af9ccb3438680cd",
"parentId": "10067",
"isLeaf": false,
"molecule": {
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"inchikey": "DKAUQWJNSZRYMD-UHFFFAOYSA-N",
"smiles": "CCOC(=O)c1sc(N2CCNC2=O)nc1C"
},
"smiles": "CCOC(=O)c1sc(N2CCNC2=O)nc1C",
"reactionStepId": "sa_b8b08e9ca3db8aa178873063",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US08318949B2;0589;1255355\",\"rsmi\":\"Cl[CH2:12][CH2:13][N:14]=[C:15]=[O:16].[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[c:7]([CH3:8])[n:9][c:10]([NH2:11])[s:17]1>C1CCOC1.CCCC[N+](CCCC)(CCCC)CCCC.O=C(O)O.I.[K+].[K+]>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[c:7]([CH3:8])[n:9][c:10]([N:11]2[CH2:12][CH2:13][NH:14][C:15]2=[O:16])[s:17]1\"},\"mapped_reaction_smiles\":\"Cl[CH2:12][CH2:13][N:14]=[C:15]=[O:16].[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[c:7]([CH3:8])[n:9][c:10]([NH2:11])[s:17]1>C1CCOC1.CCCC[N+](CCCC)(CCCC)CCCC.O=C(O)O.I.[K+].[K+]>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[c:7]([CH3:8])[n:9][c:10]([N:11]2[CH2:12][CH2:13][NH:14][C:15]2=[O:16])[s:17]1\"}",
"reactionStep": {
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"reactionHash": "50e4ae5d0901f5c47b3c5a7a161661874ae7302b5fcf8547549bd5a088e8393e"
},
"children": [
{
"id": "10069",
"routeId": "sa_7ec8e1538e30ce48ec8ae55f",
"moleculeId": "sa_9892fc63675aa20069047c01",
"parentId": "10068",
"isLeaf": true,
"molecule": {
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"inchikey": "BCMYXYHEMGPZJN-UHFFFAOYSA-N",
"smiles": "O=C=NCCCl"
},
"smiles": "O=C=NCCCl",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "10070",
"routeId": "sa_7ec8e1538e30ce48ec8ae55f",
"moleculeId": "sa_6c25c4857a25aa8da647e8f1",
"parentId": "10068",
"isLeaf": true,
"molecule": {
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"inchikey": "WZHUPCREDVWLKC-UHFFFAOYSA-N",
"smiles": "CCOC(=O)c1sc(=N)[nH]c1C"
},
"smiles": "CCOC(=O)c1sc(N)nc1C",
"reactionStepId": null,
"template": null,
"metadata": null,
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}
]
},
{
"id": "10071",
"routeId": "sa_7ec8e1538e30ce48ec8ae55f",
"moleculeId": "sa_e3e6f1570a7440e1d651c18a",
"parentId": "10067",
"isLeaf": true,
"molecule": {
"id": "sa_e3e6f1570a7440e1d651c18a",
"inchikey": "HLVFKOKELQSXIQ-UHFFFAOYSA-N",
"smiles": "CC(C)CBr"
},
"smiles": "CC(C)CBr",
"reactionStepId": null,
"template": null,
"metadata": null,
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"children": []
}
]
}
]
},
{
"id": "10072",
"routeId": "sa_7ec8e1538e30ce48ec8ae55f",
"moleculeId": "sa_56149c18171867ff21672c6a",
"parentId": "10065",
"isLeaf": false,
"molecule": {
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"inchikey": "SKMPJGFSQCNRGQ-UHFFFAOYSA-N",
"smiles": "Cc1nc(-n2cnn(Cc3ccc(F)cc3)c2=O)sc1C(=O)O"
},
"smiles": "Cc1nc(-n2cnn(Cc3ccc(F)cc3)c2=O)sc1C(=O)O",
"reactionStepId": "sa_f5759b91b7b31a42af2210af",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US08318949B2;0615;1255368\",\"rsmi\":\"CC[O:6][C:4]([c:3]1[c:2]([CH3:1])[n:23][c:8](-[n:9]2[cH:10][n:11][n:12]([CH2:13][c:14]3[cH:15][cH:16][c:17]([F:18])[cH:19][cH:20]3)[c:21]2=[O:22])[s:7]1)=[O:5]>CCOC(=O)c1sc(N2CCN(CC3CC3(F)F)C2=O)nc1C>[CH3:1][c:2]1[c:3]([C:4](=[O:5])[OH:6])[s:7][c:8](-[n:9]2[cH:10][n:11][n:12]([CH2:13][c:14]3[cH:15][cH:16][c:17]([F:18])[cH:19][cH:20]3)[c:21]2=[O:22])[n:23]1\"},\"mapped_reaction_smiles\":\"CC[O:6][C:4]([c:3]1[c:2]([CH3:1])[n:23][c:8](-[n:9]2[cH:10][n:11][n:12]([CH2:13][c:14]3[cH:15][cH:16][c:17]([F:18])[cH:19][cH:20]3)[c:21]2=[O:22])[s:7]1)=[O:5]>CCOC(=O)c1sc(N2CCN(CC3CC3(F)F)C2=O)nc1C>[CH3:1][c:2]1[c:3]([C:4](=[O:5])[OH:6])[s:7][c:8](-[n:9]2[cH:10][n:11][n:12]([CH2:13][c:14]3[cH:15][cH:16][c:17]([F:18])[cH:19][cH:20]3)[c:21]2=[O:22])[n:23]1\"}",
"reactionStep": {
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"children": [
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"moleculeId": "sa_44d29c21af1f86ca16dd6c0f",
"parentId": "10072",
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"molecule": {
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"smiles": "CCOC(=O)c1sc(-n2cnn(Cc3ccc(F)cc3)c2=O)nc1C"
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"smiles": "CCOC(=O)c1sc(-n2cnn(Cc3ccc(F)cc3)c2=O)nc1C",
"reactionStepId": "sa_81474ab88e34e7a64f5f30b5",
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"metadata": "{\"annotations\":{\"ID\":\"US08318949B2;0597;1255359\",\"rsmi\":\"Br[CH2:15][c:16]1[cH:17][cH:18][c:19]([F:20])[cH:21][cH:22]1.[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[c:7]([CH3:8])[n:9][c:10](-[n:11]2[cH:12][n:13][nH:14][c:23]2=[O:24])[s:25]1>FC1(F)CC1CBr>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[c:7]([CH3:8])[n:9][c:10](-[n:11]2[cH:12][n:13][n:14]([CH2:15][c:16]3[cH:17][cH:18][c:19]([F:20])[cH:21][cH:22]3)[c:23]2=[O:24])[s:25]1\"},\"mapped_reaction_smiles\":\"Br[CH2:15][c:16]1[cH:17][cH:18][c:19]([F:20])[cH:21][cH:22]1.[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[c:7]([CH3:8])[n:9][c:10](-[n:11]2[cH:12][n:13][nH:14][c:23]2=[O:24])[s:25]1>FC1(F)CC1CBr>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[c:7]([CH3:8])[n:9][c:10](-[n:11]2[cH:12][n:13][n:14]([CH2:15][c:16]3[cH:17][cH:18][c:19]([F:20])[cH:21][cH:22]3)[c:23]2=[O:24])[s:25]1\"}",
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"children": [
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},
"smiles": "CCOC(=O)c1sc(-n2cn[nH]c2=O)nc1C",
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]
}
}