Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
CC(=O)Nc1cc(Nc2ccc(I)cc2[N+](=O)[O-])cc(-n2cccc2)c1
InChiKey
ZBYZXYVYIDTGOJ-UHFFFAOYSA-N
Route Signature
de67f6bb40bd5084a879c5c3a90d4b8dfc7ccf6a8dc0f5393f28c83802bc9cd7
Synthesis route with 5 steps (convergent)
Route tree structure (JSON format)
{
"route": {
"id": "sa_e6c5fb4861d53416f76d77eb",
"signature": "de67f6bb40bd5084a879c5c3a90d4b8dfc7ccf6a8dc0f5393f28c83802bc9cd7",
"contentHash": "f5950de1bf6daa128c82bdbc2ccae6bb35cb18d3789793802f536d4671d519c6",
"length": 5,
"isConvergent": true
},
"target": {
"id": "sa_0b8acf9e63abde5435592d53",
"benchmarkSetId": "3895c2909c53593560c5ba610abc7e6df80513dfd8624165c560451735097d36",
"targetId": "n5-01469",
"moleculeId": "sa_140476b2c7a83751233176f0",
"smiles": "CC(=O)Nc1cc(Nc2ccc(I)cc2[N+](=O)[O-])cc(-n2cccc2)c1",
"routeLength": 5,
"isConvergent": true,
"metadata": null,
"molecule": {
"id": "sa_140476b2c7a83751233176f0",
"inchikey": "ZBYZXYVYIDTGOJ-UHFFFAOYSA-N",
"smiles": "CC(=O)Nc1cc(Nc2ccc(I)cc2[N+](=O)[O-])cc(-n2cccc2)c1"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "10220",
"routeId": "sa_e6c5fb4861d53416f76d77eb",
"moleculeId": "sa_140476b2c7a83751233176f0",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_140476b2c7a83751233176f0",
"inchikey": "ZBYZXYVYIDTGOJ-UHFFFAOYSA-N",
"smiles": "CC(=O)Nc1cc(Nc2ccc(I)cc2[N+](=O)[O-])cc(-n2cccc2)c1"
},
"smiles": "CC(=O)Nc1cc(Nc2ccc(I)cc2[N+](=O)[O-])cc(-n2cccc2)c1",
"reactionStepId": "sa_4a13cdc353e78d7d88ac846f",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20150011548A1;0335;1636435\",\"rsmi\":\"F[c:9]1[c:10]([N+:11](=[O:12])[O-:13])[cH:14][c:15]([I:16])[cH:17][cH:18]1.[CH3:1][C:2](=[O:3])[NH:4][c:5]1[cH:6][c:7]([NH2:8])[cH:19][c:20](-[n:21]2[cH:22][cH:23][cH:24][cH:25]2)[cH:26]1>CN(C)C=O.F.[K+]>[CH3:1][C:2](=[O:3])[NH:4][c:5]1[cH:6][c:7]([NH:8][c:9]2[c:10]([N+:11](=[O:12])[O-:13])[cH:14][c:15]([I:16])[cH:17][cH:18]2)[cH:19][c:20](-[n:21]2[cH:22][cH:23][cH:24][cH:25]2)[cH:26]1\"},\"mapped_reaction_smiles\":\"F[c:9]1[c:10]([N+:11](=[O:12])[O-:13])[cH:14][c:15]([I:16])[cH:17][cH:18]1.[CH3:1][C:2](=[O:3])[NH:4][c:5]1[cH:6][c:7]([NH2:8])[cH:19][c:20](-[n:21]2[cH:22][cH:23][cH:24][cH:25]2)[cH:26]1>CN(C)C=O.F.[K+]>[CH3:1][C:2](=[O:3])[NH:4][c:5]1[cH:6][c:7]([NH:8][c:9]2[c:10]([N+:11](=[O:12])[O-:13])[cH:14][c:15]([I:16])[cH:17][cH:18]2)[cH:19][c:20](-[n:21]2[cH:22][cH:23][cH:24][cH:25]2)[cH:26]1\"}",
"reactionStep": {
"id": "sa_4a13cdc353e78d7d88ac846f",
"reactionHash": "fc983c761dabb1cb6a6daffe005c2e46fa3653fa85e019b7c66344a1aad21c3a"
},
"children": [
{
"id": "10221",
"routeId": "sa_e6c5fb4861d53416f76d77eb",
"moleculeId": "sa_e2fd3c49efd22f497da9ba6b",
"parentId": "10220",
"isLeaf": false,
"molecule": {
"id": "sa_e2fd3c49efd22f497da9ba6b",
"inchikey": "AOEYWYQJWTYHMU-UHFFFAOYSA-N",
"smiles": "CC(=O)Nc1cc(N)cc(-n2cccc2)c1"
},
"smiles": "CC(=O)Nc1cc(N)cc(-n2cccc2)c1",
"reactionStepId": "sa_174e91b024e49db0df049391",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20150011548A1;0317;1636430\",\"rsmi\":\"O=[N+:8]([O-])[c:7]1[cH:6][c:5]([NH:4][C:2]([CH3:1])=[O:3])[cH:16][c:10](-[n:11]2[cH:12][cH:13][cH:14][cH:15]2)[cH:9]1>CCO.O.[Ca+2].Cl.Cl.[Fe]>[CH3:1][C:2](=[O:3])[NH:4][c:5]1[cH:6][c:7]([NH2:8])[cH:9][c:10](-[n:11]2[cH:12][cH:13][cH:14][cH:15]2)[cH:16]1\"},\"mapped_reaction_smiles\":\"O=[N+:8]([O-])[c:7]1[cH:6][c:5]([NH:4][C:2]([CH3:1])=[O:3])[cH:16][c:10](-[n:11]2[cH:12][cH:13][cH:14][cH:15]2)[cH:9]1>CCO.O.[Ca+2].Cl.Cl.[Fe]>[CH3:1][C:2](=[O:3])[NH:4][c:5]1[cH:6][c:7]([NH2:8])[cH:9][c:10](-[n:11]2[cH:12][cH:13][cH:14][cH:15]2)[cH:16]1\"}",
"reactionStep": {
"id": "sa_174e91b024e49db0df049391",
"reactionHash": "b59c8c7c8803f41b289f80c0ed3c99c14db50342664247c78580ff8ed643c9af"
},
"children": [
{
"id": "10222",
"routeId": "sa_e6c5fb4861d53416f76d77eb",
"moleculeId": "sa_a45d56a750311fcf6d201f69",
"parentId": "10221",
"isLeaf": false,
"molecule": {
"id": "sa_a45d56a750311fcf6d201f69",
"inchikey": "DRGOFJJTSMPBBE-UHFFFAOYSA-N",
"smiles": "CC(=O)Nc1cc(-n2cccc2)cc([N+](=O)[O-])c1"
},
"smiles": "CC(=O)Nc1cc(-n2cccc2)cc([N+](=O)[O-])c1",
"reactionStepId": "sa_a600942051ea3906919c1099",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20150011548A1;0316;1636429\",\"rsmi\":\"CC(=O)O[C:2]([CH3:1])=[O:3].[NH2:4][c:5]1[cH:6][c:7]([N+:8](=[O:9])[O-:10])[cH:11][c:12](-[n:13]2[cH:14][cH:15][cH:16][cH:17]2)[cH:18]1>>[CH3:1][C:2](=[O:3])[NH:4][c:5]1[cH:6][c:7]([N+:8](=[O:9])[O-:10])[cH:11][c:12](-[n:13]2[cH:14][cH:15][cH:16][cH:17]2)[cH:18]1\"},\"mapped_reaction_smiles\":\"CC(=O)O[C:2]([CH3:1])=[O:3].[NH2:4][c:5]1[cH:6][c:7]([N+:8](=[O:9])[O-:10])[cH:11][c:12](-[n:13]2[cH:14][cH:15][cH:16][cH:17]2)[cH:18]1>>[CH3:1][C:2](=[O:3])[NH:4][c:5]1[cH:6][c:7]([N+:8](=[O:9])[O-:10])[cH:11][c:12](-[n:13]2[cH:14][cH:15][cH:16][cH:17]2)[cH:18]1\"}",
"reactionStep": {
"id": "sa_a600942051ea3906919c1099",
"reactionHash": "e4dbe5b992d84acbf2b6acd45aaaff40b8a971c775b498e33efe554cfc5e3d58"
},
"children": [
{
"id": "10223",
"routeId": "sa_e6c5fb4861d53416f76d77eb",
"moleculeId": "sa_15ec52bd7d8e55094c889d27",
"parentId": "10222",
"isLeaf": false,
"molecule": {
"id": "sa_15ec52bd7d8e55094c889d27",
"inchikey": "PNTYKNLEOHYPRG-UHFFFAOYSA-N",
"smiles": "Nc1cc(-n2cccc2)cc([N+](=O)[O-])c1"
},
"smiles": "Nc1cc(-n2cccc2)cc([N+](=O)[O-])c1",
"reactionStepId": "sa_efc042587b17d55aa24e8966",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20150011548A1;0315;1636428\",\"rsmi\":\"O=[N+:1]([O-])[c:2]1[cH:3][c:4]([N+:5](=[O:6])[O-:7])[cH:8][c:9](-[n:10]2[cH:11][cH:12][cH:13][cH:14]2)[cH:15]1>CCO.O.c1ccncc1>[NH2:1][c:2]1[cH:3][c:4]([N+:5](=[O:6])[O-:7])[cH:8][c:9](-[n:10]2[cH:11][cH:12][cH:13][cH:14]2)[cH:15]1\"},\"mapped_reaction_smiles\":\"O=[N+:1]([O-])[c:2]1[cH:3][c:4]([N+:5](=[O:6])[O-:7])[cH:8][c:9](-[n:10]2[cH:11][cH:12][cH:13][cH:14]2)[cH:15]1>CCO.O.c1ccncc1>[NH2:1][c:2]1[cH:3][c:4]([N+:5](=[O:6])[O-:7])[cH:8][c:9](-[n:10]2[cH:11][cH:12][cH:13][cH:14]2)[cH:15]1\"}",
"reactionStep": {
"id": "sa_efc042587b17d55aa24e8966",
"reactionHash": "4f4f6cc60d53742ceacd5cec82219420d96ba01a11b007dcef5008c20e509bad"
},
"children": [
{
"id": "10224",
"routeId": "sa_e6c5fb4861d53416f76d77eb",
"moleculeId": "sa_45cbd5d28795b1a3f0e971e4",
"parentId": "10223",
"isLeaf": false,
"molecule": {
"id": "sa_45cbd5d28795b1a3f0e971e4",
"inchikey": "NXFBNYABTSUFNB-UHFFFAOYSA-N",
"smiles": "O=[N+]([O-])c1cc(-n2cccc2)cc([N+](=O)[O-])c1"
},
"smiles": "O=[N+]([O-])c1cc(-n2cccc2)cc([N+](=O)[O-])c1",
"reactionStepId": "sa_b62ef9be048090c02da1a734",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20150011548A1;0314;1636427\",\"rsmi\":\"CO[CH:8]1O[CH:11](OC)[CH2:10][CH2:9]1.[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][c:6]([NH2:7])[cH:12][c:13]([N+:14](=[O:15])[O-:16])[cH:17]1>CC(=O)O>[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][c:6](-[n:7]2[cH:8][cH:9][cH:10][cH:11]2)[cH:12][c:13]([N+:14](=[O:15])[O-:16])[cH:17]1\"},\"mapped_reaction_smiles\":\"CO[CH:8]1O[CH:11](OC)[CH2:10][CH2:9]1.[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][c:6]([NH2:7])[cH:12][c:13]([N+:14](=[O:15])[O-:16])[cH:17]1>CC(=O)O>[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][c:6](-[n:7]2[cH:8][cH:9][cH:10][cH:11]2)[cH:12][c:13]([N+:14](=[O:15])[O-:16])[cH:17]1\"}",
"reactionStep": {
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"reactionHash": "1acef3e8fc3c65dec51a429c1227b35a3934e3189bd65b75ebb4e257e7953cd6"
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"children": [
{
"id": "10225",
"routeId": "sa_e6c5fb4861d53416f76d77eb",
"moleculeId": "sa_82c8fc97524a7e97d97a27a3",
"parentId": "10224",
"isLeaf": true,
"molecule": {
"id": "sa_82c8fc97524a7e97d97a27a3",
"inchikey": "GFISDBXSWQMOND-UHFFFAOYSA-N",
"smiles": "COC1CCC(OC)O1"
},
"smiles": "COC1CCC(OC)O1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "10226",
"routeId": "sa_e6c5fb4861d53416f76d77eb",
"moleculeId": "sa_4fd624b080c715373e0800aa",
"parentId": "10224",
"isLeaf": true,
"molecule": {
"id": "sa_4fd624b080c715373e0800aa",
"inchikey": "MPBZUKLDHPOCLS-UHFFFAOYSA-N",
"smiles": "Nc1cc([N+](=O)[O-])cc([N+](=O)[O-])c1"
},
"smiles": "Nc1cc([N+](=O)[O-])cc([N+](=O)[O-])c1",
"reactionStepId": null,
"template": null,
"metadata": null,
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}
]
}
]
},
{
"id": "10227",
"routeId": "sa_e6c5fb4861d53416f76d77eb",
"moleculeId": "sa_a7893fcf81826693d9b4bed4",
"parentId": "10222",
"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": []
}
]
}
]
},
{
"id": "10228",
"routeId": "sa_e6c5fb4861d53416f76d77eb",
"moleculeId": "sa_0bfb72673e87a4965dd0a319",
"parentId": "10220",
"isLeaf": false,
"molecule": {
"id": "sa_0bfb72673e87a4965dd0a319",
"inchikey": "KUJTZQXHTBKAMO-UHFFFAOYSA-N",
"smiles": "O=[N+]([O-])c1cc(I)ccc1F"
},
"smiles": "O=[N+]([O-])c1cc(I)ccc1F",
"reactionStepId": "sa_e122d9505674f0c8a9fc8189",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20150011548A1;0132;1636364\",\"rsmi\":\"O=C1CCC(=O)N1[I:10].[O:1]=[N+:2]([O-:3])[c:4]1[c:5]([F:6])[cH:7][cH:8][cH:9][cH:11]1>O=S(=O)(O)C(F)(F)F>[O:1]=[N+:2]([O-:3])[c:4]1[c:5]([F:6])[cH:7][cH:8][c:9]([I:10])[cH:11]1\"},\"mapped_reaction_smiles\":\"O=C1CCC(=O)N1[I:10].[O:1]=[N+:2]([O-:3])[c:4]1[c:5]([F:6])[cH:7][cH:8][cH:9][cH:11]1>O=S(=O)(O)C(F)(F)F>[O:1]=[N+:2]([O-:3])[c:4]1[c:5]([F:6])[cH:7][cH:8][c:9]([I:10])[cH:11]1\"}",
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"reactionHash": "9d84ed4bc61d441d950ecf31c48ae027feace4ea89547c9da259bd5b439ac734"
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"children": [
{
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"moleculeId": "sa_e0a6dc663dcf837255678d0a",
"parentId": "10228",
"isLeaf": true,
"molecule": {
"id": "sa_e0a6dc663dcf837255678d0a",
"inchikey": "LQZMLBORDGWNPD-UHFFFAOYSA-N",
"smiles": "O=C1CCC(=O)N1I"
},
"smiles": "O=C1CCC(=O)N1I",
"reactionStepId": null,
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"metadata": null,
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{
"id": "10230",
"routeId": "sa_e6c5fb4861d53416f76d77eb",
"moleculeId": "sa_c6e28a8931be15ef857ac2d5",
"parentId": "10228",
"isLeaf": true,
"molecule": {
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"inchikey": "PWKNBLFSJAVFAB-UHFFFAOYSA-N",
"smiles": "O=[N+]([O-])c1ccccc1F"
},
"smiles": "O=[N+]([O-])c1ccccc1F",
"reactionStepId": null,
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]
}
]
}
}