Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
CC(C)(C)OC(=O)NC1CCOCC1COc1ccc(-c2ccc(Cl)cn2)cc1F
InChiKey
KKDIBMFYYRBCBW-UHFFFAOYSA-N
Route Signature
cb4f1b61c150a2b08a5c53f82b74f76b41ed919eca41e741d7b91b336c953a15
Synthesis route with 4 steps (convergent)
Route tree structure (JSON format)
{
"route": {
"id": "sa_eaf9c55e9f8dbcd44799676b",
"signature": "cb4f1b61c150a2b08a5c53f82b74f76b41ed919eca41e741d7b91b336c953a15",
"contentHash": "5ec10f4df7bae6643314a4acdaa02f4b90e9ae2ed23e3358096f9ae4bed3a796",
"length": 4,
"isConvergent": true
},
"target": {
"id": "sa_479e57368ff77a280861d70f",
"benchmarkSetId": "3895c2909c53593560c5ba610abc7e6df80513dfd8624165c560451735097d36",
"targetId": "n5-02879",
"moleculeId": "sa_b4fe3cfb6dac7a2b868a88f0",
"smiles": "CC(C)(C)OC(=O)NC1CCOCC1COc1ccc(-c2ccc(Cl)cn2)cc1F",
"routeLength": 4,
"isConvergent": true,
"metadata": null,
"molecule": {
"id": "sa_b4fe3cfb6dac7a2b868a88f0",
"inchikey": "KKDIBMFYYRBCBW-UHFFFAOYSA-N",
"smiles": "CC(C)(C)OC(=O)NC1CCOCC1COc1ccc(-c2ccc(Cl)cn2)cc1F"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "10872",
"routeId": "sa_eaf9c55e9f8dbcd44799676b",
"moleculeId": "sa_b4fe3cfb6dac7a2b868a88f0",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_b4fe3cfb6dac7a2b868a88f0",
"inchikey": "KKDIBMFYYRBCBW-UHFFFAOYSA-N",
"smiles": "CC(C)(C)OC(=O)NC1CCOCC1COc1ccc(-c2ccc(Cl)cn2)cc1F"
},
"smiles": "CC(C)(C)OC(=O)NC1CCOCC1COc1ccc(-c2ccc(Cl)cn2)cc1F",
"reactionStepId": "sa_22ebc44087c912e98fa9f603",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20140024650A1;1295;1476355\",\"rsmi\":\"O[c:17]1[c:18]([F:19])[cH:20][c:21](-[c:22]2[n:23][cH:24][c:25]([Cl:26])[cH:27][cH:28]2)[cH:29][cH:30]1.[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][CH:9]1[CH2:10][CH2:11][O:12][CH2:13][CH:14]1[CH2:15][OH:16]>CCCCP(CCCC)CCCC.O=C(N=NC(=O)N1CCCCC1)N1CCCCC1.[Na+].O>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][CH:9]1[CH2:10][CH2:11][O:12][CH2:13][CH:14]1[CH2:15][O:16][c:17]1[c:18]([F:19])[cH:20][c:21](-[c:22]2[n:23][cH:24][c:25]([Cl:26])[cH:27][cH:28]2)[cH:29][cH:30]1\"},\"mapped_reaction_smiles\":\"O[c:17]1[c:18]([F:19])[cH:20][c:21](-[c:22]2[n:23][cH:24][c:25]([Cl:26])[cH:27][cH:28]2)[cH:29][cH:30]1.[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][CH:9]1[CH2:10][CH2:11][O:12][CH2:13][CH:14]1[CH2:15][OH:16]>CCCCP(CCCC)CCCC.O=C(N=NC(=O)N1CCCCC1)N1CCCCC1.[Na+].O>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][CH:9]1[CH2:10][CH2:11][O:12][CH2:13][CH:14]1[CH2:15][O:16][c:17]1[c:18]([F:19])[cH:20][c:21](-[c:22]2[n:23][cH:24][c:25]([Cl:26])[cH:27][cH:28]2)[cH:29][cH:30]1\"}",
"reactionStep": {
"id": "sa_22ebc44087c912e98fa9f603",
"reactionHash": "cd914a7034278366c9a56c62a8343fea79dbc4740e7bdad46bcad82d47aec9d8"
},
"children": [
{
"id": "10873",
"routeId": "sa_eaf9c55e9f8dbcd44799676b",
"moleculeId": "sa_c70fb680fd676326dacb2ae4",
"parentId": "10872",
"isLeaf": false,
"molecule": {
"id": "sa_c70fb680fd676326dacb2ae4",
"inchikey": "FRDGZGPPARLECT-UHFFFAOYSA-N",
"smiles": "CC(C)(C)OC(=O)NC1CCOCC1CO"
},
"smiles": "CC(C)(C)OC(=O)NC1CCOCC1CO",
"reactionStepId": "sa_071a3583d2754b0424747726",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20140024650A1;0958;1476258\",\"rsmi\":\"CCO[C:15]([CH:14]1[CH:9]([NH:8][C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:10][CH2:11][O:12][CH2:13]1)=[O:16]>C1CCOC1.CCOC(C)=O.O.O=S(=O)(O)O.[Al+3].[HH].[HH].[HH].[HH].[Li+].[Mg+2]>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][CH:9]1[CH2:10][CH2:11][O:12][CH2:13][CH:14]1[CH2:15][OH:16]\"},\"mapped_reaction_smiles\":\"CCO[C:15]([CH:14]1[CH:9]([NH:8][C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:10][CH2:11][O:12][CH2:13]1)=[O:16]>C1CCOC1.CCOC(C)=O.O.O=S(=O)(O)O.[Al+3].[HH].[HH].[HH].[HH].[Li+].[Mg+2]>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][CH:9]1[CH2:10][CH2:11][O:12][CH2:13][CH:14]1[CH2:15][OH:16]\"}",
"reactionStep": {
"id": "sa_071a3583d2754b0424747726",
"reactionHash": "9b9f480c8a7b71698631ffbc3e8ac44f0d5588f2d726b41d75ddea07290b5cb8"
},
"children": [
{
"id": "10874",
"routeId": "sa_eaf9c55e9f8dbcd44799676b",
"moleculeId": "sa_663674f22c62bbba1db2badb",
"parentId": "10873",
"isLeaf": false,
"molecule": {
"id": "sa_663674f22c62bbba1db2badb",
"inchikey": "MSXNNAPQKFRZSN-UHFFFAOYSA-N",
"smiles": "CCOC(=O)C1COCCC1NC(=O)OC(C)(C)C"
},
"smiles": "CCOC(=O)C1COCCC1NC(=O)OC(C)(C)C",
"reactionStepId": "sa_98a8b67f88a3936603a3b939",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20140024650A1;0956;1476257\",\"rsmi\":\"CC(C)(C)OC(=O)O[C:13](=[O:14])[O:15][C:16]([CH3:17])([CH3:18])[CH3:19].[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]1[CH2:7][O:8][CH2:9][CH2:10][CH:11]1[NH2:12]>CCN(CC)CC>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]1[CH2:7][O:8][CH2:9][CH2:10][CH:11]1[NH:12][C:13](=[O:14])[O:15][C:16]([CH3:17])([CH3:18])[CH3:19]\"},\"mapped_reaction_smiles\":\"CC(C)(C)OC(=O)O[C:13](=[O:14])[O:15][C:16]([CH3:17])([CH3:18])[CH3:19].[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]1[CH2:7][O:8][CH2:9][CH2:10][CH:11]1[NH2:12]>CCN(CC)CC>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]1[CH2:7][O:8][CH2:9][CH2:10][CH:11]1[NH:12][C:13](=[O:14])[O:15][C:16]([CH3:17])([CH3:18])[CH3:19]\"}",
"reactionStep": {
"id": "sa_98a8b67f88a3936603a3b939",
"reactionHash": "d7cb4d5dc3ce0a128942ca6d9f6080f538f750fbd16f53883f446b3b80ecac9f"
},
"children": [
{
"id": "10875",
"routeId": "sa_eaf9c55e9f8dbcd44799676b",
"moleculeId": "sa_b273d4d4546165bca2b249b5",
"parentId": "10874",
"isLeaf": true,
"molecule": {
"id": "sa_b273d4d4546165bca2b249b5",
"inchikey": "DYHSDKLCOJIUFX-UHFFFAOYSA-N",
"smiles": "CC(C)(C)OC(=O)OC(=O)OC(C)(C)C"
},
"smiles": "CC(C)(C)OC(=O)OC(=O)OC(C)(C)C",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "10876",
"routeId": "sa_eaf9c55e9f8dbcd44799676b",
"moleculeId": "sa_eb21eaed09bed8a7912baf2f",
"parentId": "10874",
"isLeaf": false,
"molecule": {
"id": "sa_eb21eaed09bed8a7912baf2f",
"inchikey": "WMJOASBTWYDSDT-UHFFFAOYSA-N",
"smiles": "CCOC(=O)C1COCCC1N"
},
"smiles": "CCOC(=O)C1COCCC1N",
"reactionStepId": "sa_9dbf666e0c99606943bf05ca",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20140024650A1;0953;1476256\",\"rsmi\":\"c1ccc(C[NH:12][CH:11]2[CH:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[CH2:7][O:8][CH2:9][CH2:10]2)cc1>CCO>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]1[CH2:7][O:8][CH2:9][CH2:10][CH:11]1[NH2:12]\"},\"mapped_reaction_smiles\":\"c1ccc(C[NH:12][CH:11]2[CH:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[CH2:7][O:8][CH2:9][CH2:10]2)cc1>CCO>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]1[CH2:7][O:8][CH2:9][CH2:10][CH:11]1[NH2:12]\"}",
"reactionStep": {
"id": "sa_9dbf666e0c99606943bf05ca",
"reactionHash": "43161861bfa1d741a6a6f96be130f97b077ecd841509469a314da9ae6197035d"
},
"children": [
{
"id": "10877",
"routeId": "sa_eaf9c55e9f8dbcd44799676b",
"moleculeId": "sa_d13943b95c18d0fe5e92376f",
"parentId": "10876",
"isLeaf": true,
"molecule": {
"id": "sa_d13943b95c18d0fe5e92376f",
"inchikey": "YQRBPIGRTWUYGR-UHFFFAOYSA-N",
"smiles": "CCOC(=O)C1COCCC1NCc1ccccc1"
},
"smiles": "CCOC(=O)C1COCCC1NCc1ccccc1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
}
]
}
]
},
{
"id": "10878",
"routeId": "sa_eaf9c55e9f8dbcd44799676b",
"moleculeId": "sa_fecab28ef8ddd095b62de55d",
"parentId": "10872",
"isLeaf": false,
"molecule": {
"id": "sa_fecab28ef8ddd095b62de55d",
"inchikey": "PFSTVSMFKPYFNU-UHFFFAOYSA-N",
"smiles": "Oc1ccc(-c2ccc(Cl)cn2)cc1F"
},
"smiles": "Oc1ccc(-c2ccc(Cl)cn2)cc1F",
"reactionStepId": "sa_4a04a37b59a41fb27a34ade9",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20140024650A1;1293;1476354\",\"rsmi\":\"C[O:1][c:2]1[c:3]([F:4])[cH:5][c:6](-[c:7]2[n:8][cH:9][c:10]([Cl:11])[cH:12][cH:13]2)[cH:14][cH:15]1>CCCCCCCCCCCCS.Cc1ccccc1.[Al+3].Cl.Cl.Cl>[OH:1][c:2]1[c:3]([F:4])[cH:5][c:6](-[c:7]2[n:8][cH:9][c:10]([Cl:11])[cH:12][cH:13]2)[cH:14][cH:15]1\"},\"mapped_reaction_smiles\":\"C[O:1][c:2]1[c:3]([F:4])[cH:5][c:6](-[c:7]2[n:8][cH:9][c:10]([Cl:11])[cH:12][cH:13]2)[cH:14][cH:15]1>CCCCCCCCCCCCS.Cc1ccccc1.[Al+3].Cl.Cl.Cl>[OH:1][c:2]1[c:3]([F:4])[cH:5][c:6](-[c:7]2[n:8][cH:9][c:10]([Cl:11])[cH:12][cH:13]2)[cH:14][cH:15]1\"}",
"reactionStep": {
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"reactionHash": "45978417f82287b3601cf9bc2604b24a4279360749401a5b5195220524ef7f08"
},
"children": [
{
"id": "10879",
"routeId": "sa_eaf9c55e9f8dbcd44799676b",
"moleculeId": "sa_2d6e86d7299f83b2d234b093",
"parentId": "10878",
"isLeaf": false,
"molecule": {
"id": "sa_2d6e86d7299f83b2d234b093",
"inchikey": "HMDKLYSDXDBULU-UHFFFAOYSA-N",
"smiles": "COc1ccc(-c2ccc(Cl)cn2)cc1F"
},
"smiles": "COc1ccc(-c2ccc(Cl)cn2)cc1F",
"reactionStepId": "sa_a89035c8c7a020cb75417292",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20140024650A1;1291;1476353\",\"rsmi\":\"Br[c:8]1[n:9][cH:10][c:11]([Cl:12])[cH:13][cH:14]1.OB(O)[c:7]1[cH:6][c:4]([F:5])[c:3]([O:2][CH3:1])[cH:16][cH:15]1>COCCOC.O.O=C(O)O.[Na+].[Na+].c1ccc([PH](c2ccccc2)(c2ccccc2)[Pd]([PH](c2ccccc2)(c2ccccc2)c2ccccc2)([PH](c2ccccc2)(c2ccccc2)c2ccccc2)[PH](c2ccccc2)(c2ccccc2)c2ccccc2)cc1>[CH3:1][O:2][c:3]1[c:4]([F:5])[cH:6][c:7](-[c:8]2[n:9][cH:10][c:11]([Cl:12])[cH:13][cH:14]2)[cH:15][cH:16]1\"},\"mapped_reaction_smiles\":\"Br[c:8]1[n:9][cH:10][c:11]([Cl:12])[cH:13][cH:14]1.OB(O)[c:7]1[cH:6][c:4]([F:5])[c:3]([O:2][CH3:1])[cH:16][cH:15]1>COCCOC.O.O=C(O)O.[Na+].[Na+].c1ccc([PH](c2ccccc2)(c2ccccc2)[Pd]([PH](c2ccccc2)(c2ccccc2)c2ccccc2)([PH](c2ccccc2)(c2ccccc2)c2ccccc2)[PH](c2ccccc2)(c2ccccc2)c2ccccc2)cc1>[CH3:1][O:2][c:3]1[c:4]([F:5])[cH:6][c:7](-[c:8]2[n:9][cH:10][c:11]([Cl:12])[cH:13][cH:14]2)[cH:15][cH:16]1\"}",
"reactionStep": {
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"reactionHash": "2b1665294907132a8dab1c71cf9288145a4bd49c14a8b94ef852e5028f681782"
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"children": [
{
"id": "10880",
"routeId": "sa_eaf9c55e9f8dbcd44799676b",
"moleculeId": "sa_9f75996028c627668581a38c",
"parentId": "10879",
"isLeaf": true,
"molecule": {
"id": "sa_9f75996028c627668581a38c",
"inchikey": "BZUUVQCSPHPUQA-UHFFFAOYSA-N",
"smiles": "Clc1ccc(Br)nc1"
},
"smiles": "Clc1ccc(Br)nc1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "10881",
"routeId": "sa_eaf9c55e9f8dbcd44799676b",
"moleculeId": "sa_873ff6c80df33a405dc8b329",
"parentId": "10879",
"isLeaf": true,
"molecule": {
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"inchikey": "IILGLPAJXQMKGQ-UHFFFAOYSA-N",
"smiles": "COc1ccc(B(O)O)cc1F"
},
"smiles": "COc1ccc(B(O)O)cc1F",
"reactionStepId": null,
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"metadata": null,
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"children": []
}
]
}
]
}
]
}
}