Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
CCNC(=O)c1cc2cc(Cn3cc(C(O)(CC)C(F)(F)F)nn3)ccn2c1-c1ccc(F)cc1
InChiKey
XEXBUBDCYFNUMO-UHFFFAOYSA-N
Route Signature
e8a7580f87b1575dfbb138f06c58df6495d094fb4d233b05ae9e8954eb817c13
Synthesis route with 5 steps (convergent)
Route tree structure (JSON format)
{
"route": {
"id": "sa_6d510c61ea15768625f88b97",
"signature": "e8a7580f87b1575dfbb138f06c58df6495d094fb4d233b05ae9e8954eb817c13",
"contentHash": "33e1daa5baa4dc00853f4c69670d35beb7357fe2eda22c2f03ffc09f613091ce",
"length": 5,
"isConvergent": true
},
"target": {
"id": "sa_1239ced96f8f8566b94efb74",
"benchmarkSetId": "3895c2909c53593560c5ba610abc7e6df80513dfd8624165c560451735097d36",
"targetId": "n5-00430",
"moleculeId": "sa_12990cb3b097d25ab7cbcaef",
"smiles": "CCNC(=O)c1cc2cc(Cn3cc(C(O)(CC)C(F)(F)F)nn3)ccn2c1-c1ccc(F)cc1",
"routeLength": 5,
"isConvergent": true,
"metadata": null,
"molecule": {
"id": "sa_12990cb3b097d25ab7cbcaef",
"inchikey": "XEXBUBDCYFNUMO-UHFFFAOYSA-N",
"smiles": "CCNC(=O)c1cc2cc(Cn3cc(C(O)(CC)C(F)(F)F)nn3)ccn2c1-c1ccc(F)cc1"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "9487",
"routeId": "sa_6d510c61ea15768625f88b97",
"moleculeId": "sa_12990cb3b097d25ab7cbcaef",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_12990cb3b097d25ab7cbcaef",
"inchikey": "XEXBUBDCYFNUMO-UHFFFAOYSA-N",
"smiles": "CCNC(=O)c1cc2cc(Cn3cc(C(O)(CC)C(F)(F)F)nn3)ccn2c1-c1ccc(F)cc1"
},
"smiles": "CCNC(=O)c1cc2cc(Cn3cc(C(O)(CC)C(F)(F)F)nn3)ccn2c1-c1ccc(F)cc1",
"reactionStepId": "sa_96fd7b395879e809e18918cf",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20130005721A1;0600;1317279\",\"rsmi\":\"O[C:4](=[O:5])[c:6]1[c:7](-[c:8]2[cH:9][cH:10][c:11]([F:12])[cH:13][cH:14]2)[n:15]2[cH:16][cH:17][c:18]([CH2:19][n:20]3[cH:21][c:22]([C:23]([OH:24])([CH2:25][CH3:26])[C:27]([F:28])([F:29])[F:30])[n:31][n:32]3)[cH:33][c:34]2[cH:35]1.[CH3:1][CH2:2][NH2:3]>>[CH3:1][CH2:2][NH:3][C:4](=[O:5])[c:6]1[c:7](-[c:8]2[cH:9][cH:10][c:11]([F:12])[cH:13][cH:14]2)[n:15]2[cH:16][cH:17][c:18]([CH2:19][n:20]3[cH:21][c:22]([C:23]([OH:24])([CH2:25][CH3:26])[C:27]([F:28])([F:29])[F:30])[n:31][n:32]3)[cH:33][c:34]2[cH:35]1\"},\"mapped_reaction_smiles\":\"O[C:4](=[O:5])[c:6]1[c:7](-[c:8]2[cH:9][cH:10][c:11]([F:12])[cH:13][cH:14]2)[n:15]2[cH:16][cH:17][c:18]([CH2:19][n:20]3[cH:21][c:22]([C:23]([OH:24])([CH2:25][CH3:26])[C:27]([F:28])([F:29])[F:30])[n:31][n:32]3)[cH:33][c:34]2[cH:35]1.[CH3:1][CH2:2][NH2:3]>>[CH3:1][CH2:2][NH:3][C:4](=[O:5])[c:6]1[c:7](-[c:8]2[cH:9][cH:10][c:11]([F:12])[cH:13][cH:14]2)[n:15]2[cH:16][cH:17][c:18]([CH2:19][n:20]3[cH:21][c:22]([C:23]([OH:24])([CH2:25][CH3:26])[C:27]([F:28])([F:29])[F:30])[n:31][n:32]3)[cH:33][c:34]2[cH:35]1\"}",
"reactionStep": {
"id": "sa_96fd7b395879e809e18918cf",
"reactionHash": "f3f7699e01be9aa03793eb63f4ff06df1eb7e165e08d35fcf19c4032d73f9ae9"
},
"children": [
{
"id": "9488",
"routeId": "sa_6d510c61ea15768625f88b97",
"moleculeId": "sa_ea61da2bbfd62425eabb00e7",
"parentId": "9487",
"isLeaf": false,
"molecule": {
"id": "sa_ea61da2bbfd62425eabb00e7",
"inchikey": "NXQNUYBJLANZPK-UHFFFAOYSA-N",
"smiles": "CCC(O)(c1cn(Cc2ccn3c(-c4ccc(F)cc4)c(C(=O)O)cc3c2)nn1)C(F)(F)F"
},
"smiles": "CCC(O)(c1cn(Cc2ccn3c(-c4ccc(F)cc4)c(C(=O)O)cc3c2)nn1)C(F)(F)F",
"reactionStepId": "sa_5a3634a715353d4ca0eead3e",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20130005721A1;0427;1317219\",\"rsmi\":\"CC[O:16][C:14]([c:13]1[cH:12][c:11]2[cH:10][c:9]([CH2:8][n:7]3[cH:6][c:5]([C:3]([CH2:2][CH3:1])([OH:4])[C:30]([F:31])([F:32])[F:33])[n:29][n:28]3)[cH:27][cH:26][n:25]2[c:17]1-[c:18]1[cH:19][cH:20][c:21]([F:22])[cH:23][cH:24]1)=[O:15]>CO.[Li+].O>[CH3:1][CH2:2][C:3]([OH:4])([c:5]1[cH:6][n:7]([CH2:8][c:9]2[cH:10][c:11]3[cH:12][c:13]([C:14](=[O:15])[OH:16])[c:17](-[c:18]4[cH:19][cH:20][c:21]([F:22])[cH:23][cH:24]4)[n:25]3[cH:26][cH:27]2)[n:28][n:29]1)[C:30]([F:31])([F:32])[F:33]\"},\"mapped_reaction_smiles\":\"CC[O:16][C:14]([c:13]1[cH:12][c:11]2[cH:10][c:9]([CH2:8][n:7]3[cH:6][c:5]([C:3]([CH2:2][CH3:1])([OH:4])[C:30]([F:31])([F:32])[F:33])[n:29][n:28]3)[cH:27][cH:26][n:25]2[c:17]1-[c:18]1[cH:19][cH:20][c:21]([F:22])[cH:23][cH:24]1)=[O:15]>CO.[Li+].O>[CH3:1][CH2:2][C:3]([OH:4])([c:5]1[cH:6][n:7]([CH2:8][c:9]2[cH:10][c:11]3[cH:12][c:13]([C:14](=[O:15])[OH:16])[c:17](-[c:18]4[cH:19][cH:20][c:21]([F:22])[cH:23][cH:24]4)[n:25]3[cH:26][cH:27]2)[n:28][n:29]1)[C:30]([F:31])([F:32])[F:33]\"}",
"reactionStep": {
"id": "sa_5a3634a715353d4ca0eead3e",
"reactionHash": "aa7f2b4a64ac6aaa17b7dbff7dbb6e7af7d9fd9a8f5968f6786560c76db5d4bf"
},
"children": [
{
"id": "9489",
"routeId": "sa_6d510c61ea15768625f88b97",
"moleculeId": "sa_0633c1bf0b264f15fcbef910",
"parentId": "9488",
"isLeaf": false,
"molecule": {
"id": "sa_0633c1bf0b264f15fcbef910",
"inchikey": "NNVNUBTXLCFNKH-UHFFFAOYSA-N",
"smiles": "CCOC(=O)c1cc2cc(Cn3cc(C(O)(CC)C(F)(F)F)nn3)ccn2c1-c1ccc(F)cc1"
},
"smiles": "CCOC(=O)c1cc2cc(Cn3cc(C(O)(CC)C(F)(F)F)nn3)ccn2c1-c1ccc(F)cc1",
"reactionStepId": "sa_797f092d3b34ad7eb302d7d1",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20130005721A1;0414;1317212\",\"rsmi\":\"[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[c:7](-[c:8]2[cH:9][cH:10][c:11]([F:12])[cH:13][cH:14]2)[n:15]2[cH:16][cH:17][c:18]([CH2:19][N:20]=[N+:32]=[N-:31])[cH:33][c:34]2[cH:35]1.[CH:21]#[C:22][C:23]([OH:24])([CH2:25][CH3:26])[C:27]([F:28])([F:29])[F:30]>C1CCOC1.CCN(C(C)C)C(C)C.CCOC(C)=O.I[Cu]I>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[c:7](-[c:8]2[cH:9][cH:10][c:11]([F:12])[cH:13][cH:14]2)[n:15]2[cH:16][cH:17][c:18]([CH2:19][n:20]3[cH:21][c:22]([C:23]([OH:24])([CH2:25][CH3:26])[C:27]([F:28])([F:29])[F:30])[n:31][n:32]3)[cH:33][c:34]2[cH:35]1\"},\"mapped_reaction_smiles\":\"[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[c:7](-[c:8]2[cH:9][cH:10][c:11]([F:12])[cH:13][cH:14]2)[n:15]2[cH:16][cH:17][c:18]([CH2:19][N:20]=[N+:32]=[N-:31])[cH:33][c:34]2[cH:35]1.[CH:21]#[C:22][C:23]([OH:24])([CH2:25][CH3:26])[C:27]([F:28])([F:29])[F:30]>C1CCOC1.CCN(C(C)C)C(C)C.CCOC(C)=O.I[Cu]I>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[c:7](-[c:8]2[cH:9][cH:10][c:11]([F:12])[cH:13][cH:14]2)[n:15]2[cH:16][cH:17][c:18]([CH2:19][n:20]3[cH:21][c:22]([C:23]([OH:24])([CH2:25][CH3:26])[C:27]([F:28])([F:29])[F:30])[n:31][n:32]3)[cH:33][c:34]2[cH:35]1\"}",
"reactionStep": {
"id": "sa_797f092d3b34ad7eb302d7d1",
"reactionHash": "88057647391b05f7b20297b492e65349ddd14304f17818eba11322bef30c32b2"
},
"children": [
{
"id": "9490",
"routeId": "sa_6d510c61ea15768625f88b97",
"moleculeId": "sa_09d08064efc7e23876b45d2b",
"parentId": "9489",
"isLeaf": false,
"molecule": {
"id": "sa_09d08064efc7e23876b45d2b",
"inchikey": "GRDZDJKDTAVDCQ-UHFFFAOYSA-N",
"smiles": "C#CC(O)(CC)C(F)(F)F"
},
"smiles": "C#CC(O)(CC)C(F)(F)F",
"reactionStepId": "sa_8be56d04ddd97d3dee66d3fd",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20130005721A1;0413;1317211\",\"rsmi\":\"C[Si](C)(C)[C:1]#[C:2][C:3]([OH:4])([CH2:5][CH3:6])[C:7]([F:8])([F:9])[F:10]>CC#N.CCOCC.[Cs+].F>[CH:1]#[C:2][C:3]([OH:4])([CH2:5][CH3:6])[C:7]([F:8])([F:9])[F:10]\"},\"mapped_reaction_smiles\":\"C[Si](C)(C)[C:1]#[C:2][C:3]([OH:4])([CH2:5][CH3:6])[C:7]([F:8])([F:9])[F:10]>CC#N.CCOCC.[Cs+].F>[CH:1]#[C:2][C:3]([OH:4])([CH2:5][CH3:6])[C:7]([F:8])([F:9])[F:10]\"}",
"reactionStep": {
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"reactionHash": "9f001beb2820505125be75c752ec9b1a753c8b599ae94bff8295d3f94ceff55d"
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"children": [
{
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"moleculeId": "sa_077a1c0e887f070df3db8dde",
"parentId": "9490",
"isLeaf": true,
"molecule": {
"id": "sa_077a1c0e887f070df3db8dde",
"inchikey": "BHSIFDRRYFYCQG-UHFFFAOYSA-N",
"smiles": "CCC(O)(C#C[Si](C)(C)C)C(F)(F)F"
},
"smiles": "CCC(O)(C#C[Si](C)(C)C)C(F)(F)F",
"reactionStepId": null,
"template": null,
"metadata": null,
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}
]
},
{
"id": "9492",
"routeId": "sa_6d510c61ea15768625f88b97",
"moleculeId": "sa_0598705b03f33b4d98d971c4",
"parentId": "9489",
"isLeaf": false,
"molecule": {
"id": "sa_0598705b03f33b4d98d971c4",
"inchikey": "WAKARWGHVBXMOG-UHFFFAOYSA-N",
"smiles": "CCOC(=O)c1cc2cc(CN=[N+]=[N-])ccn2c1-c1ccc(F)cc1"
},
"smiles": "CCOC(=O)c1cc2cc(CN=[N+]=[N-])ccn2c1-c1ccc(F)cc1",
"reactionStepId": "sa_3202f42f246251749d82bc2a",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20130005721A1;0411;1317209\",\"rsmi\":\"CS(=O)(=O)O[CH2:19][c:18]1[cH:17][cH:16][n:15]2[c:7](-[c:8]3[cH:9][cH:10][c:11]([F:12])[cH:13][cH:14]3)[c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[cH:25][c:24]2[cH:23]1.[N-:20]=[N+:21]=[N-:22]>CCOC(C)=O.CN(C)C=O.[Na+]>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[c:7](-[c:8]2[cH:9][cH:10][c:11]([F:12])[cH:13][cH:14]2)[n:15]2[cH:16][cH:17][c:18]([CH2:19][N:20]=[N+:21]=[N-:22])[cH:23][c:24]2[cH:25]1\"},\"mapped_reaction_smiles\":\"CS(=O)(=O)O[CH2:19][c:18]1[cH:17][cH:16][n:15]2[c:7](-[c:8]3[cH:9][cH:10][c:11]([F:12])[cH:13][cH:14]3)[c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[cH:25][c:24]2[cH:23]1.[N-:20]=[N+:21]=[N-:22]>CCOC(C)=O.CN(C)C=O.[Na+]>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[c:7](-[c:8]2[cH:9][cH:10][c:11]([F:12])[cH:13][cH:14]2)[n:15]2[cH:16][cH:17][c:18]([CH2:19][N:20]=[N+:21]=[N-:22])[cH:23][c:24]2[cH:25]1\"}",
"reactionStep": {
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"reactionHash": "141ed161535fcf9a6a3c08202843d78f11e32325f9ff3b5746f331f04a643c7d"
},
"children": [
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"parentId": "9492",
"isLeaf": true,
"molecule": {
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"inchikey": "IVRMZWNICZWHMI-UHFFFAOYSA-N",
"smiles": "[N]N=[N-]"
},
"smiles": "[N-]=[N+]=[N-]",
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"metadata": null,
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{
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"moleculeId": "sa_a11f2c3112b0956f0b04a79e",
"parentId": "9492",
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"molecule": {
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"inchikey": "MIFNSZLPBVFOJU-UHFFFAOYSA-N",
"smiles": "CCOC(=O)c1cc2cc(COS(C)(=O)=O)ccn2c1-c1ccc(F)cc1"
},
"smiles": "CCOC(=O)c1cc2cc(COS(C)(=O)=O)ccn2c1-c1ccc(F)cc1",
"reactionStepId": "sa_d73f43b654203febef517008",
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"metadata": "{\"annotations\":{\"ID\":\"US20130005721A1;0410;1317208\",\"rsmi\":\"Cl[S:21]([CH3:22])(=[O:23])=[O:24].[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[c:7](-[c:8]2[cH:9][cH:10][c:11]([F:12])[cH:13][cH:14]2)[n:15]2[cH:16][cH:17][c:18]([CH2:19][OH:20])[cH:25][c:26]2[cH:27]1>CCN(CC)CC.ClCCl>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[c:7](-[c:8]2[cH:9][cH:10][c:11]([F:12])[cH:13][cH:14]2)[n:15]2[cH:16][cH:17][c:18]([CH2:19][O:20][S:21]([CH3:22])(=[O:23])=[O:24])[cH:25][c:26]2[cH:27]1\"},\"mapped_reaction_smiles\":\"Cl[S:21]([CH3:22])(=[O:23])=[O:24].[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[c:7](-[c:8]2[cH:9][cH:10][c:11]([F:12])[cH:13][cH:14]2)[n:15]2[cH:16][cH:17][c:18]([CH2:19][OH:20])[cH:25][c:26]2[cH:27]1>CCN(CC)CC.ClCCl>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[c:7](-[c:8]2[cH:9][cH:10][c:11]([F:12])[cH:13][cH:14]2)[n:15]2[cH:16][cH:17][c:18]([CH2:19][O:20][S:21]([CH3:22])(=[O:23])=[O:24])[cH:25][c:26]2[cH:27]1\"}",
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},
"smiles": "CS(=O)(=O)Cl",
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},
{
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"molecule": {
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"smiles": "CCOC(=O)c1cc2cc(CO)ccn2c1-c1ccc(F)cc1"
},
"smiles": "CCOC(=O)c1cc2cc(CO)ccn2c1-c1ccc(F)cc1",
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}
]
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]
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]
}
]
},
{
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"molecule": {
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"inchikey": "QUSNBJAOOMFDIB-UHFFFAOYSA-N",
"smiles": "CCN"
},
"smiles": "CCN",
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"children": []
}
]
}
}