Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
O=C(Cl)C1CCC2CCc3cnc(F)cc3C(=O)N2C1
InChiKey
DCIWOARYGYEKSN-UHFFFAOYSA-N
Route Signature
adc75192ebafe00e6de8ff5b49e521e123cae69da2ad4737adef68317e71aa5d
Synthesis route with 6 steps
Route tree structure (JSON format)
{
"route": {
"id": "sa_31753b431413246a5bc7e46c",
"signature": "adc75192ebafe00e6de8ff5b49e521e123cae69da2ad4737adef68317e71aa5d",
"contentHash": "04a25a05851bdfbe8efd81ba2500ffb61fa447ebeb5f0cc25953bd870b9a0b1d",
"length": 6,
"isConvergent": false
},
"target": {
"id": "sa_0b75c6fa7be1bd056fa8d927",
"benchmarkSetId": "61e696668b63e77d7c2a29c0821768e1c383de8313852d6e995224859494442e",
"targetId": "n5-00577",
"moleculeId": "sa_d208b25346e5b989f77f0154",
"smiles": "O=C(Cl)C1CCC2CCc3cnc(F)cc3C(=O)N2C1",
"routeLength": 6,
"isConvergent": false,
"metadata": null,
"molecule": {
"id": "sa_d208b25346e5b989f77f0154",
"inchikey": "DCIWOARYGYEKSN-UHFFFAOYSA-N",
"smiles": "O=C(Cl)C1CCC2CCc3cnc(F)cc3C(=O)N2C1"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "13508",
"routeId": "sa_31753b431413246a5bc7e46c",
"moleculeId": "sa_d208b25346e5b989f77f0154",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_d208b25346e5b989f77f0154",
"inchikey": "DCIWOARYGYEKSN-UHFFFAOYSA-N",
"smiles": "O=C(Cl)C1CCC2CCc3cnc(F)cc3C(=O)N2C1"
},
"smiles": "O=C(Cl)C1CCC2CCc3cnc(F)cc3C(=O)N2C1",
"reactionStepId": "sa_7ee5004027b4b5d473311f04",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20130210804A1;0307;1406985\",\"rsmi\":\"O=S(Cl)[Cl:3].O[C:2](=[O:1])[CH:4]1[CH2:5][CH2:6][CH:7]2[CH2:8][CH2:9][c:10]3[c:11]([cH:12][c:13]([F:14])[n:15][cH:16]3)[C:17](=[O:18])[N:19]2[CH2:20]1>Cc1ccccc1.ClCCl>[O:1]=[C:2]([Cl:3])[CH:4]1[CH2:5][CH2:6][CH:7]2[CH2:8][CH2:9][c:10]3[c:11]([cH:12][c:13]([F:14])[n:15][cH:16]3)[C:17](=[O:18])[N:19]2[CH2:20]1\"},\"mapped_reaction_smiles\":\"O=S(Cl)[Cl:3].O[C:2](=[O:1])[CH:4]1[CH2:5][CH2:6][CH:7]2[CH2:8][CH2:9][c:10]3[c:11]([cH:12][c:13]([F:14])[n:15][cH:16]3)[C:17](=[O:18])[N:19]2[CH2:20]1>Cc1ccccc1.ClCCl>[O:1]=[C:2]([Cl:3])[CH:4]1[CH2:5][CH2:6][CH:7]2[CH2:8][CH2:9][c:10]3[c:11]([cH:12][c:13]([F:14])[n:15][cH:16]3)[C:17](=[O:18])[N:19]2[CH2:20]1\"}",
"reactionStep": {
"id": "sa_7ee5004027b4b5d473311f04",
"reactionHash": "65403815da346e7d369dce4e68629b946b8f3323d2f0c5899600743fd396362e"
},
"children": [
{
"id": "13509",
"routeId": "sa_31753b431413246a5bc7e46c",
"moleculeId": "sa_6da475caca02f080356f91ff",
"parentId": "13508",
"isLeaf": false,
"molecule": {
"id": "sa_6da475caca02f080356f91ff",
"inchikey": "FRWVMCXAHKBXKJ-UHFFFAOYSA-N",
"smiles": "O=C(O)C1CCC2CCc3cnc(F)cc3C(=O)N2C1"
},
"smiles": "O=C(O)C1CCC2CCc3cnc(F)cc3C(=O)N2C1",
"reactionStepId": "sa_5fae27321ace559aa654cee2",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20130210804A1;0306;1406984\",\"rsmi\":\"C[O:3][C:2](=[O:1])[CH:4]1[CH2:5][CH2:6][CH:7]2[CH2:8][CH2:9][c:10]3[c:11]([cH:12][c:13]([F:14])[n:15][cH:16]3)[C:17](=[O:18])[N:19]2[CH2:20]1>C1CCOC1.Cl.O.[Li+].O>[O:1]=[C:2]([OH:3])[CH:4]1[CH2:5][CH2:6][CH:7]2[CH2:8][CH2:9][c:10]3[c:11]([cH:12][c:13]([F:14])[n:15][cH:16]3)[C:17](=[O:18])[N:19]2[CH2:20]1\"},\"mapped_reaction_smiles\":\"C[O:3][C:2](=[O:1])[CH:4]1[CH2:5][CH2:6][CH:7]2[CH2:8][CH2:9][c:10]3[c:11]([cH:12][c:13]([F:14])[n:15][cH:16]3)[C:17](=[O:18])[N:19]2[CH2:20]1>C1CCOC1.Cl.O.[Li+].O>[O:1]=[C:2]([OH:3])[CH:4]1[CH2:5][CH2:6][CH:7]2[CH2:8][CH2:9][c:10]3[c:11]([cH:12][c:13]([F:14])[n:15][cH:16]3)[C:17](=[O:18])[N:19]2[CH2:20]1\"}",
"reactionStep": {
"id": "sa_5fae27321ace559aa654cee2",
"reactionHash": "4ff8bd9864371396a2f8b43d2f1abc04537532a312ccb86627d31170a2bdfd9f"
},
"children": [
{
"id": "13510",
"routeId": "sa_31753b431413246a5bc7e46c",
"moleculeId": "sa_82b4bceb789012b810115e74",
"parentId": "13509",
"isLeaf": false,
"molecule": {
"id": "sa_82b4bceb789012b810115e74",
"inchikey": "STCHPTJJNLDXSL-UHFFFAOYSA-N",
"smiles": "COC(=O)C1CCC2CCc3cnc(F)cc3C(=O)N2C1"
},
"smiles": "COC(=O)C1CCC2CCc3cnc(F)cc3C(=O)N2C1",
"reactionStepId": "sa_608ec8d246007a84299b2779",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20130210804A1;0305;1406983\",\"rsmi\":\"N[c:14]1[cH:13][c:12]2[c:11]([cH:17][n:16]1)[CH2:10][CH2:9][CH:8]1[CH2:7][CH2:6][CH:5]([C:3]([O:2][CH3:1])=[O:4])[CH2:21][N:20]1[C:18]2=[O:19].[FH:15]>O.O=NO.N.[Na+].O.c1ccncc1>[CH3:1][O:2][C:3](=[O:4])[CH:5]1[CH2:6][CH2:7][CH:8]2[CH2:9][CH2:10][c:11]3[c:12]([cH:13][c:14]([F:15])[n:16][cH:17]3)[C:18](=[O:19])[N:20]2[CH2:21]1\"},\"mapped_reaction_smiles\":\"N[c:14]1[cH:13][c:12]2[c:11]([cH:17][n:16]1)[CH2:10][CH2:9][CH:8]1[CH2:7][CH2:6][CH:5]([C:3]([O:2][CH3:1])=[O:4])[CH2:21][N:20]1[C:18]2=[O:19].[FH:15]>O.O=NO.N.[Na+].O.c1ccncc1>[CH3:1][O:2][C:3](=[O:4])[CH:5]1[CH2:6][CH2:7][CH:8]2[CH2:9][CH2:10][c:11]3[c:12]([cH:13][c:14]([F:15])[n:16][cH:17]3)[C:18](=[O:19])[N:20]2[CH2:21]1\"}",
"reactionStep": {
"id": "sa_608ec8d246007a84299b2779",
"reactionHash": "a689f7f5fad8dc6900df37547c22e50a7cc2950ee9807b6f583621cf551aec6d"
},
"children": [
{
"id": "13511",
"routeId": "sa_31753b431413246a5bc7e46c",
"moleculeId": "sa_9581507e839422691fec597a",
"parentId": "13510",
"isLeaf": false,
"molecule": {
"id": "sa_9581507e839422691fec597a",
"inchikey": "IQTUAPAQMGIGBB-UHFFFAOYSA-N",
"smiles": "COC(=O)C1CCC2CCc3cnc(N)cc3C(=O)N2C1"
},
"smiles": "COC(=O)C1CCC2CCc3cnc(N)cc3C(=O)N2C1",
"reactionStepId": "sa_c42aadbdb9ce41ffa422790a",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20130210804A1;0304;1406982\",\"rsmi\":\"CC(C)(C)[NH:15][c:14]1[cH:13][c:12]2[c:11]([cH:17][n:16]1)[CH2:10][CH2:9][CH:8]1[CH2:7][CH2:6][CH:5]([C:3]([O:2][CH3:1])=[O:4])[CH2:21][N:20]1[C:18]2=[O:19]>O=C(O)C(F)(F)F>[CH3:1][O:2][C:3](=[O:4])[CH:5]1[CH2:6][CH2:7][CH:8]2[CH2:9][CH2:10][c:11]3[c:12]([cH:13][c:14]([NH2:15])[n:16][cH:17]3)[C:18](=[O:19])[N:20]2[CH2:21]1\"},\"mapped_reaction_smiles\":\"CC(C)(C)[NH:15][c:14]1[cH:13][c:12]2[c:11]([cH:17][n:16]1)[CH2:10][CH2:9][CH:8]1[CH2:7][CH2:6][CH:5]([C:3]([O:2][CH3:1])=[O:4])[CH2:21][N:20]1[C:18]2=[O:19]>O=C(O)C(F)(F)F>[CH3:1][O:2][C:3](=[O:4])[CH:5]1[CH2:6][CH2:7][CH:8]2[CH2:9][CH2:10][c:11]3[c:12]([cH:13][c:14]([NH2:15])[n:16][cH:17]3)[C:18](=[O:19])[N:20]2[CH2:21]1\"}",
"reactionStep": {
"id": "sa_c42aadbdb9ce41ffa422790a",
"reactionHash": "16b8a3af0d0ce41deb1e1aee3051787d4b797b0722ccb92152c8d55be48d7cba"
},
"children": [
{
"id": "13512",
"routeId": "sa_31753b431413246a5bc7e46c",
"moleculeId": "sa_4c392bb712f3d5f1401091b3",
"parentId": "13511",
"isLeaf": false,
"molecule": {
"id": "sa_4c392bb712f3d5f1401091b3",
"inchikey": "NNIWYQZLQIBLCC-UHFFFAOYSA-N",
"smiles": "COC(=O)C1CCC2CCc3cnc(NC(C)(C)C)cc3C(=O)N2C1"
},
"smiles": "COC(=O)C1CCC2CCc3cnc(NC(C)(C)C)cc3C(=O)N2C1",
"reactionStepId": "sa_7b37c19e46234559f1406bf7",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20130210804A1;0303;1406981\",\"rsmi\":\"[NH2:15][C:16]([CH3:17])([CH3:18])[CH3:19].[O-][n+:20]1[cH:14][cH:13][c:12]2[c:11]([cH:21]1)[CH2:10][CH2:9][CH:8]1[CH2:7][CH2:6][CH:5]([C:3]([O:2][CH3:1])=[O:4])[CH2:25][N:24]1[C:22]2=[O:23]>C1CCOC1.CCCCCC.Cc1ccc(S(=O)(=O)OS(=O)(=O)c2ccc(C)cc2)cc1.FC(F)(F)c1ccccc1>[CH3:1][O:2][C:3](=[O:4])[CH:5]1[CH2:6][CH2:7][CH:8]2[CH2:9][CH2:10][c:11]3[c:12]([cH:13][c:14]([NH:15][C:16]([CH3:17])([CH3:18])[CH3:19])[n:20][cH:21]3)[C:22](=[O:23])[N:24]2[CH2:25]1\"},\"mapped_reaction_smiles\":\"[NH2:15][C:16]([CH3:17])([CH3:18])[CH3:19].[O-][n+:20]1[cH:14][cH:13][c:12]2[c:11]([cH:21]1)[CH2:10][CH2:9][CH:8]1[CH2:7][CH2:6][CH:5]([C:3]([O:2][CH3:1])=[O:4])[CH2:25][N:24]1[C:22]2=[O:23]>C1CCOC1.CCCCCC.Cc1ccc(S(=O)(=O)OS(=O)(=O)c2ccc(C)cc2)cc1.FC(F)(F)c1ccccc1>[CH3:1][O:2][C:3](=[O:4])[CH:5]1[CH2:6][CH2:7][CH:8]2[CH2:9][CH2:10][c:11]3[c:12]([cH:13][c:14]([NH:15][C:16]([CH3:17])([CH3:18])[CH3:19])[n:20][cH:21]3)[C:22](=[O:23])[N:24]2[CH2:25]1\"}",
"reactionStep": {
"id": "sa_7b37c19e46234559f1406bf7",
"reactionHash": "9f6e0511485426718679186383f59a82da50f21836037a088b8db469f61be97f"
},
"children": [
{
"id": "13513",
"routeId": "sa_31753b431413246a5bc7e46c",
"moleculeId": "sa_665c99364b7c3b288e7fe8f3",
"parentId": "13512",
"isLeaf": false,
"molecule": {
"id": "sa_665c99364b7c3b288e7fe8f3",
"inchikey": "OJEMPUWACBDUBV-UHFFFAOYSA-N",
"smiles": "COC(=O)C1CCC2CCc3c[n+]([O-])ccc3C(=O)N2C1"
},
"smiles": "COC(=O)C1CCC2CCc3c[n+]([O-])ccc3C(=O)N2C1",
"reactionStepId": "sa_3517ce55a03fbe6ba0d38057",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20130210804A1;0302;1406980\",\"rsmi\":\"O=C(O[OH:16])c1cccc(Cl)c1.[CH3:1][O:2][C:3](=[O:4])[CH:5]1[CH2:6][CH2:7][CH:8]2[CH2:9][CH2:10][c:11]3[c:12]([cH:13][cH:14][n:15][cH:17]3)[C:18](=[O:19])[N:20]2[CH2:21]1>ClCCl>[CH3:1][O:2][C:3](=[O:4])[CH:5]1[CH2:6][CH2:7][CH:8]2[CH2:9][CH2:10][c:11]3[c:12]([cH:13][cH:14][n+:15]([O-:16])[cH:17]3)[C:18](=[O:19])[N:20]2[CH2:21]1\"},\"mapped_reaction_smiles\":\"O=C(O[OH:16])c1cccc(Cl)c1.[CH3:1][O:2][C:3](=[O:4])[CH:5]1[CH2:6][CH2:7][CH:8]2[CH2:9][CH2:10][c:11]3[c:12]([cH:13][cH:14][n:15][cH:17]3)[C:18](=[O:19])[N:20]2[CH2:21]1>ClCCl>[CH3:1][O:2][C:3](=[O:4])[CH:5]1[CH2:6][CH2:7][CH:8]2[CH2:9][CH2:10][c:11]3[c:12]([cH:13][cH:14][n+:15]([O-:16])[cH:17]3)[C:18](=[O:19])[N:20]2[CH2:21]1\"}",
"reactionStep": {
"id": "sa_3517ce55a03fbe6ba0d38057",
"reactionHash": "b637900ff62844187fa0fc6729906cc187e324b9a0d900500c3777bf37679ad3"
},
"children": [
{
"id": "13514",
"routeId": "sa_31753b431413246a5bc7e46c",
"moleculeId": "sa_a666cc61416a1e187c1abeab",
"parentId": "13513",
"isLeaf": true,
"molecule": {
"id": "sa_a666cc61416a1e187c1abeab",
"inchikey": "MAFGSMUHCYJBSZ-UHFFFAOYSA-N",
"smiles": "COC(=O)C1CCC2CCc3cnccc3C(=O)N2C1"
},
"smiles": "COC(=O)C1CCC2CCc3cnccc3C(=O)N2C1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "13515",
"routeId": "sa_31753b431413246a5bc7e46c",
"moleculeId": "sa_292aab804b3670e84ce954f3",
"parentId": "13513",
"isLeaf": true,
"molecule": {
"id": "sa_292aab804b3670e84ce954f3",
"inchikey": "NHQDETIJWKXCTC-UHFFFAOYSA-N",
"smiles": "O=C(OO)c1cccc(Cl)c1"
},
"smiles": "O=C(OO)c1cccc(Cl)c1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
},
{
"id": "13516",
"routeId": "sa_31753b431413246a5bc7e46c",
"moleculeId": "sa_8413f5aed68586ea647bdeb5",
"parentId": "13512",
"isLeaf": true,
"molecule": {
"id": "sa_8413f5aed68586ea647bdeb5",
"inchikey": "YBRBMKDOPFTVDT-UHFFFAOYSA-N",
"smiles": "CC(C)(C)N"
},
"smiles": "CC(C)(C)N",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
}
]
},
{
"id": "13517",
"routeId": "sa_31753b431413246a5bc7e46c",
"moleculeId": "sa_c4cf09586582aa4d31b7a2d1",
"parentId": "13510",
"isLeaf": true,
"molecule": {
"id": "sa_c4cf09586582aa4d31b7a2d1",
"inchikey": "KRHYYFGTRYWZRS-UHFFFAOYSA-N",
"smiles": "F"
},
"smiles": "F",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
}
]
},
{
"id": "13518",
"routeId": "sa_31753b431413246a5bc7e46c",
"moleculeId": "sa_cd67ce42f230ef1a4063353c",
"parentId": "13508",
"isLeaf": true,
"molecule": {
"id": "sa_cd67ce42f230ef1a4063353c",
"inchikey": "FYSNRJHAOHDILO-UHFFFAOYSA-N",
"smiles": "O=S(Cl)Cl"
},
"smiles": "O=S(Cl)Cl",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
}
}