Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
CCOC(=O)c1sc(N2CC[C@H](NC(=O)c3nc(Cl)c(CC)[nH]3)[C@H](N(C)C)C2)nc1C
InChiKey
PESTZLKDIJPHMB-UONOGXRCSA-N
Route Signature
575061d82d6ebf4d9c2abf3a2ec4aa53e788268fe242ba357f9c917aeeb5848f
Synthesis route with 4 steps (convergent)
Route tree structure (JSON format)
{
"route": {
"id": "sa_767af59ab07a851f47a83139",
"signature": "575061d82d6ebf4d9c2abf3a2ec4aa53e788268fe242ba357f9c917aeeb5848f",
"contentHash": "c8e00d71f743806f9eef193de460105c5021fc2ebb6076e1d3259a482d5ca7da",
"length": 4,
"isConvergent": true
},
"target": {
"id": "sa_f2a097101b56dfe5aad837ce",
"benchmarkSetId": "7390a9c2522b1c81605e80a42a8de7c7ad9a5797d028633b54904bc78f091bb8",
"targetId": "n5-01338",
"moleculeId": "sa_600688b69b5dfd154495a550",
"smiles": "CCOC(=O)c1sc(N2CC[C@H](NC(=O)c3nc(Cl)c(CC)[nH]3)[C@H](N(C)C)C2)nc1C",
"routeLength": 4,
"isConvergent": true,
"metadata": null,
"molecule": {
"id": "sa_600688b69b5dfd154495a550",
"inchikey": "PESTZLKDIJPHMB-UONOGXRCSA-N",
"smiles": "CCOC(=O)c1sc(N2CC[C@H](NC(=O)c3nc(Cl)c(CC)[nH]3)[C@H](N(C)C)C2)nc1C"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "1486",
"routeId": "sa_767af59ab07a851f47a83139",
"moleculeId": "sa_600688b69b5dfd154495a550",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_600688b69b5dfd154495a550",
"inchikey": "PESTZLKDIJPHMB-UONOGXRCSA-N",
"smiles": "CCOC(=O)c1sc(N2CC[C@H](NC(=O)c3nc(Cl)c(CC)[nH]3)[C@H](N(C)C)C2)nc1C"
},
"smiles": "CCOC(=O)c1sc(N2CC[C@H](NC(=O)c3nc(Cl)c(CC)[nH]3)[C@H](N(C)C)C2)nc1C",
"reactionStepId": "sa_fe49b66df601a872b485217e",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20140073622A1;2062;1500321\",\"rsmi\":\"Br[c:10]1[n:9][c:7]([CH3:8])[c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[s:31]1.CC(C)(C)OC(=O)[N:11]1[CH2:12][CH2:13][C@H:14]([NH:15][C:16](=[O:17])[c:18]2[n:19][c:20]([Cl:21])[c:22]([CH2:23][CH3:24])[nH:25]2)[C@H:26]([N:27]([CH3:28])[CH3:29])[CH2:30]1>C1COCCO1.Cl.O=C(O)O.[Na+].[Na+]>[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][C@H:14]([NH:15][C:16](=[O:17])[c:18]3[n:19][c:20]([Cl:21])[c:22]([CH2:23][CH3:24])[nH:25]3)[C@H:26]([N:27]([CH3:28])[CH3:29])[CH2:30]2)[s:31]1\"},\"mapped_reaction_smiles\":\"Br[c:10]1[n:9][c:7]([CH3:8])[c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[s:31]1.CC(C)(C)OC(=O)[N:11]1[CH2:12][CH2:13][C@H:14]([NH:15][C:16](=[O:17])[c:18]2[n:19][c:20]([Cl:21])[c:22]([CH2:23][CH3:24])[nH:25]2)[C@H:26]([N:27]([CH3:28])[CH3:29])[CH2:30]1>C1COCCO1.Cl.O=C(O)O.[Na+].[Na+]>[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][C@H:14]([NH:15][C:16](=[O:17])[c:18]3[n:19][c:20]([Cl:21])[c:22]([CH2:23][CH3:24])[nH:25]3)[C@H:26]([N:27]([CH3:28])[CH3:29])[CH2:30]2)[s:31]1\"}",
"reactionStep": {
"id": "sa_fe49b66df601a872b485217e",
"reactionHash": "6be1dd63d6aff1bd168d443c9741dfb3d30bad82e588faa593cbc24abc8c8886"
},
"children": [
{
"id": "1487",
"routeId": "sa_767af59ab07a851f47a83139",
"moleculeId": "sa_4b9da5a78605e2a143631a3e",
"parentId": "1486",
"isLeaf": true,
"molecule": {
"id": "sa_4b9da5a78605e2a143631a3e",
"inchikey": "CFBIOWPDDZPIDP-UHFFFAOYSA-N",
"smiles": "CCOC(=O)c1sc(Br)nc1C"
},
"smiles": "CCOC(=O)c1sc(Br)nc1C",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "1488",
"routeId": "sa_767af59ab07a851f47a83139",
"moleculeId": "sa_493ee2acc95a698f16738d9b",
"parentId": "1486",
"isLeaf": false,
"molecule": {
"id": "sa_493ee2acc95a698f16738d9b",
"inchikey": "FZRBSAWKWBWSSX-QWHCGFSZSA-N",
"smiles": "CCc1[nH]c(C(=O)N[C@H]2CCN(C(=O)OC(C)(C)C)C[C@H]2N(C)C)nc1Cl"
},
"smiles": "CCc1[nH]c(C(=O)N[C@H]2CCN(C(=O)OC(C)(C)C)C[C@H]2N(C)C)nc1Cl",
"reactionStepId": "sa_eec46b417966a319c3e38bdf",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20140073622A1;2059;1500320\",\"rsmi\":\"O[C:8]([c:7]1[n:6][c:4]([Cl:5])[c:3]([CH2:2][CH3:1])[nH:27]1)=[O:9].[NH2:10][C@H:11]1[CH2:12][CH2:13][N:14]([C:15](=[O:16])[O:17][C:18]([CH3:19])([CH3:20])[CH3:21])[CH2:22][C@H:23]1[N:24]([CH3:25])[CH3:26]>CCN(CC)CC.CCN=C=NCCCN(C)C.Cl.O.On1nnc2ccccc21>[CH3:1][CH2:2][c:3]1[c:4]([Cl:5])[n:6][c:7]([C:8](=[O:9])[NH:10][C@H:11]2[CH2:12][CH2:13][N:14]([C:15](=[O:16])[O:17][C:18]([CH3:19])([CH3:20])[CH3:21])[CH2:22][C@H:23]2[N:24]([CH3:25])[CH3:26])[nH:27]1\"},\"mapped_reaction_smiles\":\"O[C:8]([c:7]1[n:6][c:4]([Cl:5])[c:3]([CH2:2][CH3:1])[nH:27]1)=[O:9].[NH2:10][C@H:11]1[CH2:12][CH2:13][N:14]([C:15](=[O:16])[O:17][C:18]([CH3:19])([CH3:20])[CH3:21])[CH2:22][C@H:23]1[N:24]([CH3:25])[CH3:26]>CCN(CC)CC.CCN=C=NCCCN(C)C.Cl.O.On1nnc2ccccc21>[CH3:1][CH2:2][c:3]1[c:4]([Cl:5])[n:6][c:7]([C:8](=[O:9])[NH:10][C@H:11]2[CH2:12][CH2:13][N:14]([C:15](=[O:16])[O:17][C:18]([CH3:19])([CH3:20])[CH3:21])[CH2:22][C@H:23]2[N:24]([CH3:25])[CH3:26])[nH:27]1\"}",
"reactionStep": {
"id": "sa_eec46b417966a319c3e38bdf",
"reactionHash": "60c5a6b4cab2792a878c6f43f1d446fe9cf8118b80375f51f1c57aa7362ddfef"
},
"children": [
{
"id": "1489",
"routeId": "sa_767af59ab07a851f47a83139",
"moleculeId": "sa_26d066dc1e952b50ebd5a55f",
"parentId": "1488",
"isLeaf": false,
"molecule": {
"id": "sa_26d066dc1e952b50ebd5a55f",
"inchikey": "FABGLFBEEVHDHN-VHSXEESVSA-N",
"smiles": "CN(C)[C@@H]1CN(C(=O)OC(C)(C)C)CC[C@@H]1N"
},
"smiles": "CN(C)[C@@H]1CN(C(=O)OC(C)(C)C)CC[C@@H]1N",
"reactionStepId": "sa_ad50139e5b2c7868a5b7e75e",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20140073622A1;2056;1500319\",\"rsmi\":\"O=C(OCc1ccccc1)[NH:17][C@@H:16]1[C@H:4]([N:2]([CH3:1])[CH3:3])[CH2:5][N:6]([C:7](=[O:8])[O:9][C:10]([CH3:11])([CH3:12])[CH3:13])[CH2:14][CH2:15]1>CO.[H][H].O.O.[Pd+2]>[CH3:1][N:2]([CH3:3])[C@@H:4]1[CH2:5][N:6]([C:7](=[O:8])[O:9][C:10]([CH3:11])([CH3:12])[CH3:13])[CH2:14][CH2:15][C@@H:16]1[NH2:17]\"},\"mapped_reaction_smiles\":\"O=C(OCc1ccccc1)[NH:17][C@@H:16]1[C@H:4]([N:2]([CH3:1])[CH3:3])[CH2:5][N:6]([C:7](=[O:8])[O:9][C:10]([CH3:11])([CH3:12])[CH3:13])[CH2:14][CH2:15]1>CO.[H][H].O.O.[Pd+2]>[CH3:1][N:2]([CH3:3])[C@@H:4]1[CH2:5][N:6]([C:7](=[O:8])[O:9][C:10]([CH3:11])([CH3:12])[CH3:13])[CH2:14][CH2:15][C@@H:16]1[NH2:17]\"}",
"reactionStep": {
"id": "sa_ad50139e5b2c7868a5b7e75e",
"reactionHash": "378bb678ac3c4d7439a4025c78100c0f68fd1305a515d71dd4f7c8a6621e9cbb"
},
"children": [
{
"id": "1490",
"routeId": "sa_767af59ab07a851f47a83139",
"moleculeId": "sa_622ac6d796f531ee76e9106e",
"parentId": "1489",
"isLeaf": false,
"molecule": {
"id": "sa_622ac6d796f531ee76e9106e",
"inchikey": "WFCFIZGGVJKOLC-DLBZAZTESA-N",
"smiles": "CN(C)[C@@H]1CN(C(=O)OC(C)(C)C)CC[C@@H]1NC(=O)OCc1ccccc1"
},
"smiles": "CN(C)[C@@H]1CN(C(=O)OC(C)(C)C)CC[C@@H]1NC(=O)OCc1ccccc1",
"reactionStepId": "sa_cad0481306ed9b1beb6553a8",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20140073622A1;2053;1500318\",\"rsmi\":\"O=[CH2:1].O[CH3:3].[NH2:2][C@@H:4]1[CH2:5][N:6]([C:7](=[O:8])[O:9][C:10]([CH3:11])([CH3:12])[CH3:13])[CH2:14][CH2:15][C@@H:16]1[NH:17][C:18](=[O:19])[O:20][CH2:21][c:22]1[cH:23][cH:24][cH:25][cH:26][cH:27]1>C1CCOC1.CC(=O)O.BC#N.[Na+]>[CH3:1][N:2]([CH3:3])[C@@H:4]1[CH2:5][N:6]([C:7](=[O:8])[O:9][C:10]([CH3:11])([CH3:12])[CH3:13])[CH2:14][CH2:15][C@@H:16]1[NH:17][C:18](=[O:19])[O:20][CH2:21][c:22]1[cH:23][cH:24][cH:25][cH:26][cH:27]1\"},\"mapped_reaction_smiles\":\"O=[CH2:1].O[CH3:3].[NH2:2][C@@H:4]1[CH2:5][N:6]([C:7](=[O:8])[O:9][C:10]([CH3:11])([CH3:12])[CH3:13])[CH2:14][CH2:15][C@@H:16]1[NH:17][C:18](=[O:19])[O:20][CH2:21][c:22]1[cH:23][cH:24][cH:25][cH:26][cH:27]1>C1CCOC1.CC(=O)O.BC#N.[Na+]>[CH3:1][N:2]([CH3:3])[C@@H:4]1[CH2:5][N:6]([C:7](=[O:8])[O:9][C:10]([CH3:11])([CH3:12])[CH3:13])[CH2:14][CH2:15][C@@H:16]1[NH:17][C:18](=[O:19])[O:20][CH2:21][c:22]1[cH:23][cH:24][cH:25][cH:26][cH:27]1\"}",
"reactionStep": {
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"reactionHash": "e34318ad94132213a73dc782df797adea17e2d68be36e7b7ad19bbf343927bcc"
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"children": [
{
"id": "1491",
"routeId": "sa_767af59ab07a851f47a83139",
"moleculeId": "sa_061a3efbe4d30c2cc87d48e7",
"parentId": "1490",
"isLeaf": true,
"molecule": {
"id": "sa_061a3efbe4d30c2cc87d48e7",
"inchikey": "OKKJLVBELUTLKV-UHFFFAOYSA-N",
"smiles": "CO"
},
"smiles": "CO",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "1492",
"routeId": "sa_767af59ab07a851f47a83139",
"moleculeId": "sa_c247abe7247984cd2a9035cf",
"parentId": "1490",
"isLeaf": true,
"molecule": {
"id": "sa_c247abe7247984cd2a9035cf",
"inchikey": "RBQHRSMMDLWGKF-CABCVRRESA-N",
"smiles": "CC(C)(C)OC(=O)N1CC[C@H](NC(=O)OCc2ccccc2)[C@H](N)C1"
},
"smiles": "CC(C)(C)OC(=O)N1CC[C@H](NC(=O)OCc2ccccc2)[C@H](N)C1",
"reactionStepId": null,
"template": null,
"metadata": null,
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{
"id": "1493",
"routeId": "sa_767af59ab07a851f47a83139",
"moleculeId": "sa_fa48b0311f9ecb906b2132fe",
"parentId": "1490",
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"molecule": {
"id": "sa_fa48b0311f9ecb906b2132fe",
"inchikey": "WSFSSNUMVMOOMR-UHFFFAOYSA-N",
"smiles": "C=O"
},
"smiles": "C=O",
"reactionStepId": null,
"template": null,
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]
},
{
"id": "1494",
"routeId": "sa_767af59ab07a851f47a83139",
"moleculeId": "sa_9bc8b08abdf7525102dd4467",
"parentId": "1488",
"isLeaf": false,
"molecule": {
"id": "sa_9bc8b08abdf7525102dd4467",
"inchikey": "WBRFPIVOPOBICF-UHFFFAOYSA-N",
"smiles": "CCc1[nH]c(C(=O)O)nc1Cl"
},
"smiles": "CCc1[nH]c(C(=O)O)nc1Cl",
"reactionStepId": "sa_f145be2dbb2bb8ad8b26d359",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20140073622A1;0254;1499906\",\"rsmi\":\"CC[O:10][C:8]([c:7]1[n:6][c:4]([Cl:5])[c:3]([CH2:2][CH3:1])[nH:11]1)=[O:9]>CO.ClCCl.[Li+].O>[CH3:1][CH2:2][c:3]1[c:4]([Cl:5])[n:6][c:7]([C:8](=[O:9])[OH:10])[nH:11]1\"},\"mapped_reaction_smiles\":\"CC[O:10][C:8]([c:7]1[n:6][c:4]([Cl:5])[c:3]([CH2:2][CH3:1])[nH:11]1)=[O:9]>CO.ClCCl.[Li+].O>[CH3:1][CH2:2][c:3]1[c:4]([Cl:5])[n:6][c:7]([C:8](=[O:9])[OH:10])[nH:11]1\"}",
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"children": [
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"molecule": {
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"inchikey": "KNQZWWOAZXSMTG-UHFFFAOYSA-N",
"smiles": "CCOC(=O)c1nc(Cl)c(CC)[nH]1"
},
"smiles": "CCOC(=O)c1nc(Cl)c(CC)[nH]1",
"reactionStepId": "sa_9add913b41fde2dc06ad7c95",
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"metadata": "{\"annotations\":{\"ID\":\"US20140073622A1;0252;1499905\",\"rsmi\":\"O=C1CCC(=O)N1[Cl:9].[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[n:7][cH:8][c:10]([CH2:11][CH3:12])[nH:13]1>ClC(Cl)Cl.O=C(O)O.[Na+]>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[n:7][c:8]([Cl:9])[c:10]([CH2:11][CH3:12])[nH:13]1\"},\"mapped_reaction_smiles\":\"O=C1CCC(=O)N1[Cl:9].[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[n:7][cH:8][c:10]([CH2:11][CH3:12])[nH:13]1>ClC(Cl)Cl.O=C(O)O.[Na+]>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[n:7][c:8]([Cl:9])[c:10]([CH2:11][CH3:12])[nH:13]1\"}",
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{
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},
"smiles": "CCOC(=O)c1ncc(CC)[nH]1",
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}
]
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]
}
]
}
]
}
}