Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
CC(=O)Nc1cc(Oc2ccc(NC(=O)Nc3ccccc3)cc2)ncn1
InChiKey
OOEMGFXLIPOANI-UHFFFAOYSA-N
Route Signature
8b9de7fe7a5f232daa2a76ba00d721ed11795ae6f76f3483508e0e1268212d85
Synthesis route with 5 steps
Route tree structure (JSON format)
{
"route": {
"id": "sa_e5257c752ca2d1651baa5294",
"signature": "8b9de7fe7a5f232daa2a76ba00d721ed11795ae6f76f3483508e0e1268212d85",
"contentHash": "f263b77b3e046c88abf9248a0bad775e7520496c7a2955b55ed1c28dcc0f030e",
"length": 5,
"isConvergent": false
},
"target": {
"id": "sa_1696f9ddc2ef0f9e7ba3e042",
"benchmarkSetId": "f925e688d731a0ad4e3aa6a505df094f6d3ca64ce3facc312bc5f64731921b33",
"targetId": "n5-01593",
"moleculeId": "sa_2904f60424ec8b371520be07",
"smiles": "CC(=O)Nc1cc(Oc2ccc(NC(=O)Nc3ccccc3)cc2)ncn1",
"routeLength": 5,
"isConvergent": false,
"metadata": null,
"molecule": {
"id": "sa_2904f60424ec8b371520be07",
"inchikey": "OOEMGFXLIPOANI-UHFFFAOYSA-N",
"smiles": "CC(=O)Nc1cc(Oc2ccc(NC(=O)Nc3ccccc3)cc2)ncn1"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "5761",
"routeId": "sa_e5257c752ca2d1651baa5294",
"moleculeId": "sa_2904f60424ec8b371520be07",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_2904f60424ec8b371520be07",
"inchikey": "OOEMGFXLIPOANI-UHFFFAOYSA-N",
"smiles": "CC(=O)Nc1cc(Oc2ccc(NC(=O)Nc3ccccc3)cc2)ncn1"
},
"smiles": "CC(=O)Nc1cc(Oc2ccc(NC(=O)Nc3ccccc3)cc2)ncn1",
"reactionStepId": "sa_893247e86d4727b5728d6b25",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20100197911A1;2327;923781\",\"rsmi\":\"CC(=O)O[C:2]([CH3:1])=[O:3].[NH2:4][c:5]1[n:6][cH:7][n:8][c:9]([O:10][c:11]2[cH:12][cH:13][c:14]([NH:15][C:16](=[O:17])[NH:18][c:19]3[cH:20][cH:21][cH:22][cH:23][cH:24]3)[cH:25][cH:26]2)[cH:27]1>O.c1ccncc1>[CH3:1][C:2](=[O:3])[NH:4][c:5]1[n:6][cH:7][n:8][c:9]([O:10][c:11]2[cH:12][cH:13][c:14]([NH:15][C:16](=[O:17])[NH:18][c:19]3[cH:20][cH:21][cH:22][cH:23][cH:24]3)[cH:25][cH:26]2)[cH:27]1\"},\"mapped_reaction_smiles\":\"CC(=O)O[C:2]([CH3:1])=[O:3].[NH2:4][c:5]1[n:6][cH:7][n:8][c:9]([O:10][c:11]2[cH:12][cH:13][c:14]([NH:15][C:16](=[O:17])[NH:18][c:19]3[cH:20][cH:21][cH:22][cH:23][cH:24]3)[cH:25][cH:26]2)[cH:27]1>O.c1ccncc1>[CH3:1][C:2](=[O:3])[NH:4][c:5]1[n:6][cH:7][n:8][c:9]([O:10][c:11]2[cH:12][cH:13][c:14]([NH:15][C:16](=[O:17])[NH:18][c:19]3[cH:20][cH:21][cH:22][cH:23][cH:24]3)[cH:25][cH:26]2)[cH:27]1\"}",
"reactionStep": {
"id": "sa_893247e86d4727b5728d6b25",
"reactionHash": "601a213d72421d8750b60db9a165e101e0af47da7e5e295bbd6206318d38519a"
},
"children": [
{
"id": "5762",
"routeId": "sa_e5257c752ca2d1651baa5294",
"moleculeId": "sa_3defd1eae715c2ec33b23ffb",
"parentId": "5761",
"isLeaf": false,
"molecule": {
"id": "sa_3defd1eae715c2ec33b23ffb",
"inchikey": "GEIMDAARFDIILI-UHFFFAOYSA-N",
"smiles": "Nc1cc(Oc2ccc(NC(=O)Nc3ccccc3)cc2)ncn1"
},
"smiles": "Nc1cc(Oc2ccc(NC(=O)Nc3ccccc3)cc2)ncn1",
"reactionStepId": "sa_6e5c83da82a44751cc4d168b",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20100197911A1;2318;923777\",\"rsmi\":\"[C:11](=[O:12])=[N:13][c:14]1[cH:15][cH:16][cH:17][cH:18][cH:19]1.[NH2:1][c:2]1[cH:3][c:4]([O:5][c:6]2[cH:7][cH:8][c:9]([NH2:10])[cH:20][cH:21]2)[n:22][cH:23][n:24]1>CCCCCC.CCOC(C)=O.CN(C)C=O.O>[NH2:1][c:2]1[cH:3][c:4]([O:5][c:6]2[cH:7][cH:8][c:9]([NH:10][C:11](=[O:12])[NH:13][c:14]3[cH:15][cH:16][cH:17][cH:18][cH:19]3)[cH:20][cH:21]2)[n:22][cH:23][n:24]1\"},\"mapped_reaction_smiles\":\"[C:11](=[O:12])=[N:13][c:14]1[cH:15][cH:16][cH:17][cH:18][cH:19]1.[NH2:1][c:2]1[cH:3][c:4]([O:5][c:6]2[cH:7][cH:8][c:9]([NH2:10])[cH:20][cH:21]2)[n:22][cH:23][n:24]1>CCCCCC.CCOC(C)=O.CN(C)C=O.O>[NH2:1][c:2]1[cH:3][c:4]([O:5][c:6]2[cH:7][cH:8][c:9]([NH:10][C:11](=[O:12])[NH:13][c:14]3[cH:15][cH:16][cH:17][cH:18][cH:19]3)[cH:20][cH:21]2)[n:22][cH:23][n:24]1\"}",
"reactionStep": {
"id": "sa_6e5c83da82a44751cc4d168b",
"reactionHash": "73c37eaa17a9d3ceb18edbeef1993454a628b05c9e46353c18c002a2c713e94c"
},
"children": [
{
"id": "5763",
"routeId": "sa_e5257c752ca2d1651baa5294",
"moleculeId": "sa_f86e5cd2eb956136a6a638a0",
"parentId": "5762",
"isLeaf": true,
"molecule": {
"id": "sa_f86e5cd2eb956136a6a638a0",
"inchikey": "DGTNSSLYPYDJGL-UHFFFAOYSA-N",
"smiles": "O=C=Nc1ccccc1"
},
"smiles": "O=C=Nc1ccccc1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "5764",
"routeId": "sa_e5257c752ca2d1651baa5294",
"moleculeId": "sa_bd9605839c48c232ad8b3cd9",
"parentId": "5762",
"isLeaf": false,
"molecule": {
"id": "sa_bd9605839c48c232ad8b3cd9",
"inchikey": "KVLGPVUVQGKLDH-UHFFFAOYSA-N",
"smiles": "Nc1ccc(Oc2cc(N)ncn2)cc1"
},
"smiles": "Nc1ccc(Oc2cc(N)ncn2)cc1",
"reactionStepId": "sa_98301965476f71f79a921015",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20100197911A1;2325;923780\",\"rsmi\":\"O=[N+:1]([O-])[c:2]1[cH:3][cH:4][c:5]([O:6][c:7]2[cH:8][c:9]([NH2:10])[n:11][cH:12][n:13]2)[cH:14][cH:15]1>CCO.O.Cl.[Fe].N>[NH2:1][c:2]1[cH:3][cH:4][c:5]([O:6][c:7]2[cH:8][c:9]([NH2:10])[n:11][cH:12][n:13]2)[cH:14][cH:15]1\"},\"mapped_reaction_smiles\":\"O=[N+:1]([O-])[c:2]1[cH:3][cH:4][c:5]([O:6][c:7]2[cH:8][c:9]([NH2:10])[n:11][cH:12][n:13]2)[cH:14][cH:15]1>CCO.O.Cl.[Fe].N>[NH2:1][c:2]1[cH:3][cH:4][c:5]([O:6][c:7]2[cH:8][c:9]([NH2:10])[n:11][cH:12][n:13]2)[cH:14][cH:15]1\"}",
"reactionStep": {
"id": "sa_98301965476f71f79a921015",
"reactionHash": "9910d264002fc3452082fa380af4ac69c6024dd3919b9313d347e795bfd64c8c"
},
"children": [
{
"id": "5765",
"routeId": "sa_e5257c752ca2d1651baa5294",
"moleculeId": "sa_79dc7b5e0d7ddc3bad70d039",
"parentId": "5764",
"isLeaf": false,
"molecule": {
"id": "sa_79dc7b5e0d7ddc3bad70d039",
"inchikey": "ASLMCNIFOSOQPE-UHFFFAOYSA-N",
"smiles": "Nc1cc(Oc2ccc([N+](=O)[O-])cc2)ncn1"
},
"smiles": "Nc1cc(Oc2ccc([N+](=O)[O-])cc2)ncn1",
"reactionStepId": "sa_5092597dd179d9ae6f146783",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20100197911A1;2323;923779\",\"rsmi\":\"Cl[c:2]1[n:3][cH:4][n:5][c:6]([O:7][c:8]2[cH:9][cH:10][c:11]([N+:12](=[O:13])[O-:14])[cH:15][cH:16]2)[cH:17]1.[NH3:1]>CCCCCC.CCO.CCOC(C)=O.O>[NH2:1][c:2]1[n:3][cH:4][n:5][c:6]([O:7][c:8]2[cH:9][cH:10][c:11]([N+:12](=[O:13])[O-:14])[cH:15][cH:16]2)[cH:17]1\"},\"mapped_reaction_smiles\":\"Cl[c:2]1[n:3][cH:4][n:5][c:6]([O:7][c:8]2[cH:9][cH:10][c:11]([N+:12](=[O:13])[O-:14])[cH:15][cH:16]2)[cH:17]1.[NH3:1]>CCCCCC.CCO.CCOC(C)=O.O>[NH2:1][c:2]1[n:3][cH:4][n:5][c:6]([O:7][c:8]2[cH:9][cH:10][c:11]([N+:12](=[O:13])[O-:14])[cH:15][cH:16]2)[cH:17]1\"}",
"reactionStep": {
"id": "sa_5092597dd179d9ae6f146783",
"reactionHash": "253ea08d07ee6a99a65e371a2f274fcd9e150843483feea10c4cf7a54ca00e4d"
},
"children": [
{
"id": "5766",
"routeId": "sa_e5257c752ca2d1651baa5294",
"moleculeId": "sa_c9679fdd876f32f86b77fb69",
"parentId": "5765",
"isLeaf": true,
"molecule": {
"id": "sa_c9679fdd876f32f86b77fb69",
"inchikey": "QGZKDVFQNNGYKY-UHFFFAOYSA-N",
"smiles": "N"
},
"smiles": "N",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "5767",
"routeId": "sa_e5257c752ca2d1651baa5294",
"moleculeId": "sa_12cec431b4bc67fe0743c65c",
"parentId": "5765",
"isLeaf": false,
"molecule": {
"id": "sa_12cec431b4bc67fe0743c65c",
"inchikey": "TZXIWIUCQFFQDT-UHFFFAOYSA-N",
"smiles": "O=[N+]([O-])c1ccc(Oc2cc(Cl)ncn2)cc1"
},
"smiles": "O=[N+]([O-])c1ccc(Oc2cc(Cl)ncn2)cc1",
"reactionStepId": "sa_995c6531c273c9612a1bb0d5",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20100197911A1;0471;923494\",\"rsmi\":\"Cl[c:9]1[n:10][cH:11][n:12][c:13]([Cl:14])[cH:15]1.[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][cH:6][c:7]([OH:8])[cH:16][cH:17]1>O.Cl.[HH].[Na+].[Na+]>[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][cH:6][c:7]([O:8][c:9]2[n:10][cH:11][n:12][c:13]([Cl:14])[cH:15]2)[cH:16][cH:17]1\"},\"mapped_reaction_smiles\":\"Cl[c:9]1[n:10][cH:11][n:12][c:13]([Cl:14])[cH:15]1.[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][cH:6][c:7]([OH:8])[cH:16][cH:17]1>O.Cl.[HH].[Na+].[Na+]>[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][cH:6][c:7]([O:8][c:9]2[n:10][cH:11][n:12][c:13]([Cl:14])[cH:15]2)[cH:16][cH:17]1\"}",
"reactionStep": {
"id": "sa_995c6531c273c9612a1bb0d5",
"reactionHash": "7b7f29941925868b29735b3e79f1574d37baa23aff21e9a9837255c56296afde"
},
"children": [
{
"id": "5768",
"routeId": "sa_e5257c752ca2d1651baa5294",
"moleculeId": "sa_147b4db36ece2bc0cf54b265",
"parentId": "5767",
"isLeaf": true,
"molecule": {
"id": "sa_147b4db36ece2bc0cf54b265",
"inchikey": "BTJIUGUIPKRLHP-UHFFFAOYSA-N",
"smiles": "O=[N+]([O-])c1ccc(O)cc1"
},
"smiles": "O=[N+]([O-])c1ccc(O)cc1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "5769",
"routeId": "sa_e5257c752ca2d1651baa5294",
"moleculeId": "sa_db8aea1103296dc9b89dfb68",
"parentId": "5767",
"isLeaf": true,
"molecule": {
"id": "sa_db8aea1103296dc9b89dfb68",
"inchikey": "XJPZKYIHCLDXST-UHFFFAOYSA-N",
"smiles": "Clc1cc(Cl)ncn1"
},
"smiles": "Clc1cc(Cl)ncn1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
}
]
}
]
}
]
},
{
"id": "5770",
"routeId": "sa_e5257c752ca2d1651baa5294",
"moleculeId": "sa_a7893fcf81826693d9b4bed4",
"parentId": "5761",
"isLeaf": true,
"molecule": {
"id": "sa_a7893fcf81826693d9b4bed4",
"inchikey": "WFDIJRYMOXRFFG-UHFFFAOYSA-N",
"smiles": "CC(=O)OC(C)=O"
},
"smiles": "CC(=O)OC(C)=O",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
}
}