Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
CCn1c(=O)c2c(C)[nH]nc2c2cc(CCCN3CCCC3)ccc21
InChiKey
RZLWUTHZUSVVSB-UHFFFAOYSA-N
Route Signature
9bd5569d659fd8ce110d8bfcf3d9363fd2f816a87ce8618b752e6c1205a2fbcf
Synthesis route with 7 steps
Route tree structure (JSON format)
{
"route": {
"id": "sa_e7f2d1e9a61d7763eae306c8",
"signature": "9bd5569d659fd8ce110d8bfcf3d9363fd2f816a87ce8618b752e6c1205a2fbcf",
"contentHash": "fac31701a43cd0d7d74a24c5ae0fed75175546fa5107cc15da79c6adc47a6a20",
"length": 7,
"isConvergent": false
},
"target": {
"id": "sa_570a6e01f23fffd3a0a98b0c",
"benchmarkSetId": "61e696668b63e77d7c2a29c0821768e1c383de8313852d6e995224859494442e",
"targetId": "n5-00092",
"moleculeId": "sa_3766143b663df7f541d4b386",
"smiles": "CCn1c(=O)c2c(C)[nH]nc2c2cc(CCCN3CCCC3)ccc21",
"routeLength": 7,
"isConvergent": false,
"metadata": null,
"molecule": {
"id": "sa_3766143b663df7f541d4b386",
"inchikey": "RZLWUTHZUSVVSB-UHFFFAOYSA-N",
"smiles": "CCn1c(=O)c2c(C)[nH]nc2c2cc(CCCN3CCCC3)ccc21"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "12387",
"routeId": "sa_e7f2d1e9a61d7763eae306c8",
"moleculeId": "sa_3766143b663df7f541d4b386",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_3766143b663df7f541d4b386",
"inchikey": "RZLWUTHZUSVVSB-UHFFFAOYSA-N",
"smiles": "CCn1c(=O)c2c(C)[nH]nc2c2cc(CCCN3CCCC3)ccc21"
},
"smiles": "CCn1c(=O)c2c(C)[nH]nc2c2cc(CCCN3CCCC3)ccc21",
"reactionStepId": "sa_66db01c9be70486f9ab9c192",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20060035920A1;0458;326678\",\"rsmi\":\"[CH3:1][CH2:2][n:3]1[c:4](=[O:5])[c:6]2[c:7]([CH3:8])[nH:9][n:10][c:11]2[c:12]2[c:13]1[cH:14][cH:15][c:16]([C:17]#[C:18][CH2:19][N:20]1[CH2:21][CH2:22][CH2:23][CH2:24]1)[cH:25]2>CO.[Pd]>[CH3:1][CH2:2][n:3]1[c:4](=[O:5])[c:6]2[c:7]([CH3:8])[nH:9][n:10][c:11]2[c:12]2[c:13]1[cH:14][cH:15][c:16]([CH2:17][CH2:18][CH2:19][N:20]1[CH2:21][CH2:22][CH2:23][CH2:24]1)[cH:25]2\"},\"mapped_reaction_smiles\":\"[CH3:1][CH2:2][n:3]1[c:4](=[O:5])[c:6]2[c:7]([CH3:8])[nH:9][n:10][c:11]2[c:12]2[c:13]1[cH:14][cH:15][c:16]([C:17]#[C:18][CH2:19][N:20]1[CH2:21][CH2:22][CH2:23][CH2:24]1)[cH:25]2>CO.[Pd]>[CH3:1][CH2:2][n:3]1[c:4](=[O:5])[c:6]2[c:7]([CH3:8])[nH:9][n:10][c:11]2[c:12]2[c:13]1[cH:14][cH:15][c:16]([CH2:17][CH2:18][CH2:19][N:20]1[CH2:21][CH2:22][CH2:23][CH2:24]1)[cH:25]2\"}",
"reactionStep": {
"id": "sa_66db01c9be70486f9ab9c192",
"reactionHash": "1f332ac273d7e2fc23fed8ca3cb0e07b33eb7d52ee783358ea59e2c5bcf7418f"
},
"children": [
{
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"routeId": "sa_e7f2d1e9a61d7763eae306c8",
"moleculeId": "sa_db17430ea7f8d00a1b16825b",
"parentId": "12387",
"isLeaf": false,
"molecule": {
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"inchikey": "UVIMWWWWHQPKRN-UHFFFAOYSA-N",
"smiles": "CCn1c(=O)c2c(C)[nH]nc2c2cc(C#CCN3CCCC3)ccc21"
},
"smiles": "CCn1c(=O)c2c(C)[nH]nc2c2cc(C#CCN3CCCC3)ccc21",
"reactionStepId": "sa_7fbb156425d29c61c9b91d78",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20060035920A1;0372;326669\",\"rsmi\":\"C1CCC([n:9]2[c:7]([CH3:8])[c:6]3[c:4](=[O:5])[n:3]([CH2:2][CH3:1])[c:13]4[c:12]([c:11]3[n:10]2)[cH:25][c:16]([C:17]#[C:18][CH2:19][N:20]2[CH2:21][CH2:22][CH2:23][CH2:24]2)[cH:15][cH:14]4)OC1>CO.Cl>[CH3:1][CH2:2][n:3]1[c:4](=[O:5])[c:6]2[c:7]([CH3:8])[nH:9][n:10][c:11]2[c:12]2[c:13]1[cH:14][cH:15][c:16]([C:17]#[C:18][CH2:19][N:20]1[CH2:21][CH2:22][CH2:23][CH2:24]1)[cH:25]2\"},\"mapped_reaction_smiles\":\"C1CCC([n:9]2[c:7]([CH3:8])[c:6]3[c:4](=[O:5])[n:3]([CH2:2][CH3:1])[c:13]4[c:12]([c:11]3[n:10]2)[cH:25][c:16]([C:17]#[C:18][CH2:19][N:20]2[CH2:21][CH2:22][CH2:23][CH2:24]2)[cH:15][cH:14]4)OC1>CO.Cl>[CH3:1][CH2:2][n:3]1[c:4](=[O:5])[c:6]2[c:7]([CH3:8])[nH:9][n:10][c:11]2[c:12]2[c:13]1[cH:14][cH:15][c:16]([C:17]#[C:18][CH2:19][N:20]1[CH2:21][CH2:22][CH2:23][CH2:24]1)[cH:25]2\"}",
"reactionStep": {
"id": "sa_7fbb156425d29c61c9b91d78",
"reactionHash": "375f25a74dee71f4a3b7034ef45721501c8bdc14a9f6374ed234cc3b5ee92e72"
},
"children": [
{
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"moleculeId": "sa_e37a47ef9d2fda9e33565137",
"parentId": "12388",
"isLeaf": false,
"molecule": {
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"inchikey": "JZVQFPWCHUYAMP-UHFFFAOYSA-N",
"smiles": "CCn1c(=O)c2c(C)n(C3CCCCO3)nc2c2cc(C#CCN3CCCC3)ccc21"
},
"smiles": "CCn1c(=O)c2c(C)n(C3CCCCO3)nc2c2cc(C#CCN3CCCC3)ccc21",
"reactionStepId": "sa_cccf0b406d245df404cd5cad",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20060035920A1;0371;326668\",\"rsmi\":\"I[c:22]1[cH:21][cH:20][c:19]2[n:3]([CH2:2][CH3:1])[c:4](=[O:5])[c:6]3[c:7]([CH3:8])[n:9]([CH:10]4[CH2:11][CH2:12][CH2:13][CH2:14][O:15]4)[n:16][c:17]3[c:18]2[cH:31]1.[CH:23]#[C:24][CH2:25][N:26]1[CH2:27][CH2:28][CH2:29][CH2:30]1>CCN(CC)CC.CCOC(C)=O.CN(C)C=O.Cl[Pd](Cl)([PH](c1ccccc1)(c1ccccc1)c1ccccc1)[PH](c1ccccc1)(c1ccccc1)c1ccccc1.I[Cu]I.O>[CH3:1][CH2:2][n:3]1[c:4](=[O:5])[c:6]2[c:7]([CH3:8])[n:9]([CH:10]3[CH2:11][CH2:12][CH2:13][CH2:14][O:15]3)[n:16][c:17]2[c:18]2[c:19]1[cH:20][cH:21][c:22]([C:23]#[C:24][CH2:25][N:26]1[CH2:27][CH2:28][CH2:29][CH2:30]1)[cH:31]2\"},\"mapped_reaction_smiles\":\"I[c:22]1[cH:21][cH:20][c:19]2[n:3]([CH2:2][CH3:1])[c:4](=[O:5])[c:6]3[c:7]([CH3:8])[n:9]([CH:10]4[CH2:11][CH2:12][CH2:13][CH2:14][O:15]4)[n:16][c:17]3[c:18]2[cH:31]1.[CH:23]#[C:24][CH2:25][N:26]1[CH2:27][CH2:28][CH2:29][CH2:30]1>CCN(CC)CC.CCOC(C)=O.CN(C)C=O.Cl[Pd](Cl)([PH](c1ccccc1)(c1ccccc1)c1ccccc1)[PH](c1ccccc1)(c1ccccc1)c1ccccc1.I[Cu]I.O>[CH3:1][CH2:2][n:3]1[c:4](=[O:5])[c:6]2[c:7]([CH3:8])[n:9]([CH:10]3[CH2:11][CH2:12][CH2:13][CH2:14][O:15]3)[n:16][c:17]2[c:18]2[c:19]1[cH:20][cH:21][c:22]([C:23]#[C:24][CH2:25][N:26]1[CH2:27][CH2:28][CH2:29][CH2:30]1)[cH:31]2\"}",
"reactionStep": {
"id": "sa_cccf0b406d245df404cd5cad",
"reactionHash": "6f2f3794604064fc5b6a8a7fafe06a1038f4566a9afda84427a547cc48fe887f"
},
"children": [
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"moleculeId": "sa_e02f1f4b9fa55c7a1380657a",
"parentId": "12389",
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"molecule": {
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"smiles": "CCn1c(=O)c2c(C)n(C3CCCCO3)nc2c2cc(I)ccc21"
},
"smiles": "CCn1c(=O)c2c(C)n(C3CCCCO3)nc2c2cc(I)ccc21",
"reactionStepId": "sa_c42a1c35f9e15c9bd2ff9353",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20060035920A1;0370;326667\",\"rsmi\":\"I[CH2:2][CH3:1].[nH:3]1[c:4](=[O:5])[c:6]2[c:7]([CH3:8])[n:9]([CH:10]3[CH2:11][CH2:12][CH2:13][CH2:14][O:15]3)[n:16][c:17]2[c:18]2[c:19]1[cH:20][cH:21][c:22]([I:23])[cH:24]2>CN(C)C=O.O=C(O)O.[Cs+].[Cs+]>[CH3:1][CH2:2][n:3]1[c:4](=[O:5])[c:6]2[c:7]([CH3:8])[n:9]([CH:10]3[CH2:11][CH2:12][CH2:13][CH2:14][O:15]3)[n:16][c:17]2[c:18]2[c:19]1[cH:20][cH:21][c:22]([I:23])[cH:24]2\"},\"mapped_reaction_smiles\":\"I[CH2:2][CH3:1].[nH:3]1[c:4](=[O:5])[c:6]2[c:7]([CH3:8])[n:9]([CH:10]3[CH2:11][CH2:12][CH2:13][CH2:14][O:15]3)[n:16][c:17]2[c:18]2[c:19]1[cH:20][cH:21][c:22]([I:23])[cH:24]2>CN(C)C=O.O=C(O)O.[Cs+].[Cs+]>[CH3:1][CH2:2][n:3]1[c:4](=[O:5])[c:6]2[c:7]([CH3:8])[n:9]([CH:10]3[CH2:11][CH2:12][CH2:13][CH2:14][O:15]3)[n:16][c:17]2[c:18]2[c:19]1[cH:20][cH:21][c:22]([I:23])[cH:24]2\"}",
"reactionStep": {
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"reactionHash": "51dd7ec99a7d2abeed554154edc63124f5231ad7bac521d0f502f848cd72f012"
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"parentId": "12390",
"isLeaf": true,
"molecule": {
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"inchikey": "HVTICUPFWKNHNG-UHFFFAOYSA-N",
"smiles": "CCI"
},
"smiles": "CCI",
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{
"id": "12392",
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"molecule": {
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"inchikey": "SPFBIFRCEJZDSG-UHFFFAOYSA-N",
"smiles": "Cc1c2c(=O)[nH]c3ccc(I)cc3c2nn1C1CCCCO1"
},
"smiles": "Cc1c2c(=O)[nH]c3ccc(I)cc3c2nn1C1CCCCO1",
"reactionStepId": "sa_c81414271cc3e09a5fc50dbb",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20060035920A1;0369;326666\",\"rsmi\":\"[CH2:17]1[CH2:18][CH2:19][CH:20]=[CH:21][O:22]1.[CH3:1][c:2]1[c:3]2[c:4](=[O:5])[nH:6][c:7]3[c:8]([cH:9][c:10]([I:11])[cH:12][cH:13]3)[c:14]2[n:15][nH:16]1>Cc1ccc(S(=O)(=O)O)cc1>[CH3:1][c:2]1[c:3]2[c:4](=[O:5])[nH:6][c:7]3[c:8]([cH:9][c:10]([I:11])[cH:12][cH:13]3)[c:14]2[n:15][n:16]1[CH:17]1[CH2:18][CH2:19][CH2:20][CH2:21][O:22]1\"},\"mapped_reaction_smiles\":\"[CH2:17]1[CH2:18][CH2:19][CH:20]=[CH:21][O:22]1.[CH3:1][c:2]1[c:3]2[c:4](=[O:5])[nH:6][c:7]3[c:8]([cH:9][c:10]([I:11])[cH:12][cH:13]3)[c:14]2[n:15][nH:16]1>Cc1ccc(S(=O)(=O)O)cc1>[CH3:1][c:2]1[c:3]2[c:4](=[O:5])[nH:6][c:7]3[c:8]([cH:9][c:10]([I:11])[cH:12][cH:13]3)[c:14]2[n:15][n:16]1[CH:17]1[CH2:18][CH2:19][CH2:20][CH2:21][O:22]1\"}",
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"molecule": {
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"inchikey": "BUDQDWGNQVEFAC-UHFFFAOYSA-N",
"smiles": "C1=COCCC1"
},
"smiles": "C1=COCCC1",
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{
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"molecule": {
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"inchikey": "CGYAWOXPWQTLGC-UHFFFAOYSA-N",
"smiles": "Cc1[nH]nc2c1c(=O)[nH]c1ccc(I)cc12"
},
"smiles": "Cc1[nH]nc2c1c(=O)[nH]c1ccc(I)cc12",
"reactionStepId": "sa_cbfd6b9aa1a3c6b252e13de0",
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"metadata": "{\"annotations\":{\"ID\":\"US20060035920A1;0368;326665\",\"rsmi\":\"O=[C:2]([CH3:1])[c:3]1[c:4](=[O:5])[nH:6][c:7]2[c:8]([cH:9][c:10]([I:11])[cH:12][cH:13]2)[c:14]1O.[NH2:15][NH2:16]>CN(C)C=O.O>[CH3:1][c:2]1[c:3]2[c:4](=[O:5])[nH:6][c:7]3[c:8]([cH:9][c:10]([I:11])[cH:12][cH:13]3)[c:14]2[n:15][nH:16]1\"},\"mapped_reaction_smiles\":\"O=[C:2]([CH3:1])[c:3]1[c:4](=[O:5])[nH:6][c:7]2[c:8]([cH:9][c:10]([I:11])[cH:12][cH:13]2)[c:14]1O.[NH2:15][NH2:16]>CN(C)C=O.O>[CH3:1][c:2]1[c:3]2[c:4](=[O:5])[nH:6][c:7]3[c:8]([cH:9][c:10]([I:11])[cH:12][cH:13]3)[c:14]2[n:15][nH:16]1\"}",
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{
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"smiles": "CC(=O)c1c(O)c2cc(I)ccc2[nH]c1=O",
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"metadata": "{\"annotations\":{\"ID\":\"US20060035920A1;0367;326664\",\"rsmi\":\"CO[C:5](=[O:6])[c:7]1[cH:8][c:9]([I:10])[cH:11][cH:12][c:13]1[NH:14][C:15]([CH2:4][C:2]([CH3:1])=[O:3])=[O:16]>CO.CO[Na].Cl>[CH3:1][C:2](=[O:3])[c:4]1[c:5]([OH:6])[c:7]2[cH:8][c:9]([I:10])[cH:11][cH:12][c:13]2[nH:14][c:15]1=[O:16]\"},\"mapped_reaction_smiles\":\"CO[C:5](=[O:6])[c:7]1[cH:8][c:9]([I:10])[cH:11][cH:12][c:13]1[NH:14][C:15]([CH2:4][C:2]([CH3:1])=[O:3])=[O:16]>CO.CO[Na].Cl>[CH3:1][C:2](=[O:3])[c:4]1[c:5]([OH:6])[c:7]2[cH:8][c:9]([I:10])[cH:11][cH:12][c:13]2[nH:14][c:15]1=[O:16]\"}",
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},
"smiles": "COC(=O)c1cc(I)ccc1NC(=O)CC(C)=O",
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}
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]
}
]
},
{
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"molecule": {
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"smiles": "C#CCN1CCCC1"
},
"smiles": "C#CCN1CCCC1",
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"children": []
}
]
}
]
}
]
}
}