Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
NCCc1ccc(OCc2ccccc2)c(NC=O)c1
InChiKey
DMPYEFKILBFGEP-UHFFFAOYSA-N
Route Signature
bbab1ac5dc07db9d2736acb6dcca30b66dfeb1ff1c707b8ce40ce956b621fd8c
Synthesis route with 7 steps
Route tree structure (JSON format)
{
"route": {
"id": "sa_6bb6f7c5ec24000fcc360297",
"signature": "bbab1ac5dc07db9d2736acb6dcca30b66dfeb1ff1c707b8ce40ce956b621fd8c",
"contentHash": "c92d2e09b157389c4da41035612cfd894e9278ad3815fec584237639cdec7866",
"length": 7,
"isConvergent": false
},
"target": {
"id": "sa_b5cc07f9aa8a87cf5c31e720",
"benchmarkSetId": "61e696668b63e77d7c2a29c0821768e1c383de8313852d6e995224859494442e",
"targetId": "n5-00056",
"moleculeId": "sa_383e76f5543a77baee5b0bc5",
"smiles": "NCCc1ccc(OCc2ccccc2)c(NC=O)c1",
"routeLength": 7,
"isConvergent": false,
"metadata": null,
"molecule": {
"id": "sa_383e76f5543a77baee5b0bc5",
"inchikey": "DMPYEFKILBFGEP-UHFFFAOYSA-N",
"smiles": "NCCc1ccc(OCc2ccccc2)c(NC=O)c1"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "12251",
"routeId": "sa_6bb6f7c5ec24000fcc360297",
"moleculeId": "sa_383e76f5543a77baee5b0bc5",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_383e76f5543a77baee5b0bc5",
"inchikey": "DMPYEFKILBFGEP-UHFFFAOYSA-N",
"smiles": "NCCc1ccc(OCc2ccccc2)c(NC=O)c1"
},
"smiles": "NCCc1ccc(OCc2ccccc2)c(NC=O)c1",
"reactionStepId": "sa_baaa4010de326867a4bfc756",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US04958026;;218704\",\"rsmi\":\"O=[CH:8][OH:9].[NH2:1][CH2:2][CH2:3][c:4]1[cH:5][c:6]([NH2:7])[c:10]([O:11][CH2:12][c:13]2[cH:14][cH:15][cH:16][cH:17][cH:18]2)[cH:19][cH:20]1>CC(=O)OC(C)=O.Cl.ClC(Cl)Cl.O>[NH2:1][CH2:2][CH2:3][c:4]1[cH:5][c:6]([NH:7][CH:8]=[O:9])[c:10]([O:11][CH2:12][c:13]2[cH:14][cH:15][cH:16][cH:17][cH:18]2)[cH:19][cH:20]1\"},\"mapped_reaction_smiles\":\"O=[CH:8][OH:9].[NH2:1][CH2:2][CH2:3][c:4]1[cH:5][c:6]([NH2:7])[c:10]([O:11][CH2:12][c:13]2[cH:14][cH:15][cH:16][cH:17][cH:18]2)[cH:19][cH:20]1>CC(=O)OC(C)=O.Cl.ClC(Cl)Cl.O>[NH2:1][CH2:2][CH2:3][c:4]1[cH:5][c:6]([NH:7][CH:8]=[O:9])[c:10]([O:11][CH2:12][c:13]2[cH:14][cH:15][cH:16][cH:17][cH:18]2)[cH:19][cH:20]1\"}",
"reactionStep": {
"id": "sa_baaa4010de326867a4bfc756",
"reactionHash": "b782577baa4692b19aaa7c00405752dfeb5639d592dcb0c2261e8358d0753268"
},
"children": [
{
"id": "12252",
"routeId": "sa_6bb6f7c5ec24000fcc360297",
"moleculeId": "sa_3bff5ea8042027b95a7e61c6",
"parentId": "12251",
"isLeaf": true,
"molecule": {
"id": "sa_3bff5ea8042027b95a7e61c6",
"inchikey": "BDAGIHXWWSANSR-UHFFFAOYSA-N",
"smiles": "O=CO"
},
"smiles": "O=CO",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "12253",
"routeId": "sa_6bb6f7c5ec24000fcc360297",
"moleculeId": "sa_3e590017968e7acf2082d938",
"parentId": "12251",
"isLeaf": false,
"molecule": {
"id": "sa_3e590017968e7acf2082d938",
"inchikey": "PCIUVIFUPQAOOH-UHFFFAOYSA-N",
"smiles": "NCCc1ccc(OCc2ccccc2)c(N)c1"
},
"smiles": "NCCc1ccc(OCc2ccccc2)c(N)c1",
"reactionStepId": "sa_4eae30049357b228e348cead",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US04958026;;218682\",\"rsmi\":\"[N:1]#[C:2][CH2:3][c:4]1[cH:5][c:6]([NH2:7])[c:8]([O:9][CH2:10][c:11]2[cH:12][cH:13][cH:14][cH:15][cH:16]2)[cH:17][cH:18]1>N.[Ni]>[NH2:1][CH2:2][CH2:3][c:4]1[cH:5][c:6]([NH2:7])[c:8]([O:9][CH2:10][c:11]2[cH:12][cH:13][cH:14][cH:15][cH:16]2)[cH:17][cH:18]1\"},\"mapped_reaction_smiles\":\"[N:1]#[C:2][CH2:3][c:4]1[cH:5][c:6]([NH2:7])[c:8]([O:9][CH2:10][c:11]2[cH:12][cH:13][cH:14][cH:15][cH:16]2)[cH:17][cH:18]1>N.[Ni]>[NH2:1][CH2:2][CH2:3][c:4]1[cH:5][c:6]([NH2:7])[c:8]([O:9][CH2:10][c:11]2[cH:12][cH:13][cH:14][cH:15][cH:16]2)[cH:17][cH:18]1\"}",
"reactionStep": {
"id": "sa_4eae30049357b228e348cead",
"reactionHash": "f7ffa4468f5de08bb6e4e4857851df67e5ee6df94463ef9524a7d677bcbb95e5"
},
"children": [
{
"id": "12254",
"routeId": "sa_6bb6f7c5ec24000fcc360297",
"moleculeId": "sa_c92521bc7565c754f2237a2a",
"parentId": "12253",
"isLeaf": false,
"molecule": {
"id": "sa_c92521bc7565c754f2237a2a",
"inchikey": "GHMDWGDVQOFDJA-UHFFFAOYSA-N",
"smiles": "N#CCc1ccc(OCc2ccccc2)c(N)c1"
},
"smiles": "N#CCc1ccc(OCc2ccccc2)c(N)c1",
"reactionStepId": "sa_7d1203c1c9fbac9413e4a0d9",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US04958026;;218681\",\"rsmi\":\"O=[N+:7]([O-])[c:6]1[cH:5][c:4]([CH2:3][C:2]#[N:1])[cH:18][cH:17][c:8]1[O:9][CH2:10][c:11]1[cH:12][cH:13][cH:14][cH:15][cH:16]1>CO.[H][H].[Ni]>[N:1]#[C:2][CH2:3][c:4]1[cH:5][c:6]([NH2:7])[c:8]([O:9][CH2:10][c:11]2[cH:12][cH:13][cH:14][cH:15][cH:16]2)[cH:17][cH:18]1\"},\"mapped_reaction_smiles\":\"O=[N+:7]([O-])[c:6]1[cH:5][c:4]([CH2:3][C:2]#[N:1])[cH:18][cH:17][c:8]1[O:9][CH2:10][c:11]1[cH:12][cH:13][cH:14][cH:15][cH:16]1>CO.[H][H].[Ni]>[N:1]#[C:2][CH2:3][c:4]1[cH:5][c:6]([NH2:7])[c:8]([O:9][CH2:10][c:11]2[cH:12][cH:13][cH:14][cH:15][cH:16]2)[cH:17][cH:18]1\"}",
"reactionStep": {
"id": "sa_7d1203c1c9fbac9413e4a0d9",
"reactionHash": "8a245356c5972ecfe57c4fbdbe7136f95b6e8d35c5d3d6b9b76404dfa0e3cccf"
},
"children": [
{
"id": "12255",
"routeId": "sa_6bb6f7c5ec24000fcc360297",
"moleculeId": "sa_fb36f5ab23dfa90ada18e964",
"parentId": "12254",
"isLeaf": false,
"molecule": {
"id": "sa_fb36f5ab23dfa90ada18e964",
"inchikey": "NZYBPPHFWOWHIX-UHFFFAOYSA-N",
"smiles": "N#CCc1ccc(OCc2ccccc2)c([N+](=O)[O-])c1"
},
"smiles": "N#CCc1ccc(OCc2ccccc2)c([N+](=O)[O-])c1",
"reactionStepId": "sa_966ca24cf93dae97695b176b",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US04958026;;218680\",\"rsmi\":\"Cl[CH2:3][c:4]1[cH:5][c:6]([N+:7](=[O:8])[O-:9])[c:10]([O:11][CH2:12][c:13]2[cH:14][cH:15][cH:16][cH:17][cH:18]2)[cH:19][cH:20]1.[N:1]#[CH:2]>CS(C)=O.[Na+]>[N:1]#[C:2][CH2:3][c:4]1[cH:5][c:6]([N+:7](=[O:8])[O-:9])[c:10]([O:11][CH2:12][c:13]2[cH:14][cH:15][cH:16][cH:17][cH:18]2)[cH:19][cH:20]1\"},\"mapped_reaction_smiles\":\"Cl[CH2:3][c:4]1[cH:5][c:6]([N+:7](=[O:8])[O-:9])[c:10]([O:11][CH2:12][c:13]2[cH:14][cH:15][cH:16][cH:17][cH:18]2)[cH:19][cH:20]1.[N:1]#[CH:2]>CS(C)=O.[Na+]>[N:1]#[C:2][CH2:3][c:4]1[cH:5][c:6]([N+:7](=[O:8])[O-:9])[c:10]([O:11][CH2:12][c:13]2[cH:14][cH:15][cH:16][cH:17][cH:18]2)[cH:19][cH:20]1\"}",
"reactionStep": {
"id": "sa_966ca24cf93dae97695b176b",
"reactionHash": "c012521aced9d8e83150b72abba4ec41d961d8eadb02f4aca6aee5cd6fd090a3"
},
"children": [
{
"id": "12256",
"routeId": "sa_6bb6f7c5ec24000fcc360297",
"moleculeId": "sa_5995aff3aeff665a1f3e984d",
"parentId": "12255",
"isLeaf": true,
"molecule": {
"id": "sa_5995aff3aeff665a1f3e984d",
"inchikey": "LELOWRISYMNNSU-UHFFFAOYSA-N",
"smiles": "C#N"
},
"smiles": "C#N",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "12257",
"routeId": "sa_6bb6f7c5ec24000fcc360297",
"moleculeId": "sa_992e33282d8ce90d0ac79a81",
"parentId": "12255",
"isLeaf": false,
"molecule": {
"id": "sa_992e33282d8ce90d0ac79a81",
"inchikey": "MRZGXESRGMUYBW-UHFFFAOYSA-N",
"smiles": "O=[N+]([O-])c1cc(CCl)ccc1OCc1ccccc1"
},
"smiles": "O=[N+]([O-])c1cc(CCl)ccc1OCc1ccccc1",
"reactionStepId": "sa_2e964275608cdde7baddf5d1",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US04958026;;218679\",\"rsmi\":\"O=S(Cl)[Cl:18].O[CH2:17][c:16]1[cH:15][cH:14][c:5]([O:6][CH2:7][c:8]2[cH:9][cH:10][cH:11][cH:12][cH:13]2)[c:4]([N+:2](=[O:1])[O-:3])[cH:19]1>>[O:1]=[N+:2]([O-:3])[c:4]1[c:5]([O:6][CH2:7][c:8]2[cH:9][cH:10][cH:11][cH:12][cH:13]2)[cH:14][cH:15][c:16]([CH2:17][Cl:18])[cH:19]1\"},\"mapped_reaction_smiles\":\"O=S(Cl)[Cl:18].O[CH2:17][c:16]1[cH:15][cH:14][c:5]([O:6][CH2:7][c:8]2[cH:9][cH:10][cH:11][cH:12][cH:13]2)[c:4]([N+:2](=[O:1])[O-:3])[cH:19]1>>[O:1]=[N+:2]([O-:3])[c:4]1[c:5]([O:6][CH2:7][c:8]2[cH:9][cH:10][cH:11][cH:12][cH:13]2)[cH:14][cH:15][c:16]([CH2:17][Cl:18])[cH:19]1\"}",
"reactionStep": {
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"reactionHash": "984d94e41c8b35d8388a89ef8f5fb8596cb77c65e573a09d76e1e507edb63fce"
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"children": [
{
"id": "12258",
"routeId": "sa_6bb6f7c5ec24000fcc360297",
"moleculeId": "sa_cd67ce42f230ef1a4063353c",
"parentId": "12257",
"isLeaf": true,
"molecule": {
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"inchikey": "FYSNRJHAOHDILO-UHFFFAOYSA-N",
"smiles": "O=S(Cl)Cl"
},
"smiles": "O=S(Cl)Cl",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "12259",
"routeId": "sa_6bb6f7c5ec24000fcc360297",
"moleculeId": "sa_c8a67776604c454fe004efaa",
"parentId": "12257",
"isLeaf": false,
"molecule": {
"id": "sa_c8a67776604c454fe004efaa",
"inchikey": "OSTBLDHANBUNQO-UHFFFAOYSA-N",
"smiles": "O=[N+]([O-])c1cc(CO)ccc1OCc1ccccc1"
},
"smiles": "O=[N+]([O-])c1cc(CO)ccc1OCc1ccccc1",
"reactionStepId": "sa_d4661d091695b1f94932714c",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US04958026;;218678\",\"rsmi\":\"[O:1]=[N+:2]([O-:3])[c:4]1[c:5]([O:6][CH2:7][c:8]2[cH:9][cH:10][cH:11][cH:12][cH:13]2)[cH:14][cH:15][c:16]([CH:17]=[O:18])[cH:19]1>CO.Cl.B.[Na+]>[O:1]=[N+:2]([O-:3])[c:4]1[c:5]([O:6][CH2:7][c:8]2[cH:9][cH:10][cH:11][cH:12][cH:13]2)[cH:14][cH:15][c:16]([CH2:17][OH:18])[cH:19]1\"},\"mapped_reaction_smiles\":\"[O:1]=[N+:2]([O-:3])[c:4]1[c:5]([O:6][CH2:7][c:8]2[cH:9][cH:10][cH:11][cH:12][cH:13]2)[cH:14][cH:15][c:16]([CH:17]=[O:18])[cH:19]1>CO.Cl.B.[Na+]>[O:1]=[N+:2]([O-:3])[c:4]1[c:5]([O:6][CH2:7][c:8]2[cH:9][cH:10][cH:11][cH:12][cH:13]2)[cH:14][cH:15][c:16]([CH2:17][OH:18])[cH:19]1\"}",
"reactionStep": {
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"children": [
{
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"routeId": "sa_6bb6f7c5ec24000fcc360297",
"moleculeId": "sa_1594c291aec5cdde2214b22c",
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"molecule": {
"id": "sa_1594c291aec5cdde2214b22c",
"inchikey": "VJANVDWJMIGNFW-UHFFFAOYSA-N",
"smiles": "O=Cc1ccc(OCc2ccccc2)c([N+](=O)[O-])c1"
},
"smiles": "O=Cc1ccc(OCc2ccccc2)c([N+](=O)[O-])c1",
"reactionStepId": "sa_ea12bf9d6e36515c316723c7",
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"metadata": "{\"annotations\":{\"ID\":\"US04958026;;218677\",\"rsmi\":\"Cl[CH2:11][c:12]1[cH:13][cH:14][cH:15][cH:16][cH:17]1.[O:1]=[CH:2][c:3]1[cH:4][c:5]([N+:6](=[O:7])[O-:8])[c:9]([OH:10])[cH:18][cH:19]1>CN(C)C=O.O.O=C(O)O.[K+].[K+]>[O:1]=[CH:2][c:3]1[cH:4][c:5]([N+:6](=[O:7])[O-:8])[c:9]([O:10][CH2:11][c:12]2[cH:13][cH:14][cH:15][cH:16][cH:17]2)[cH:18][cH:19]1\"},\"mapped_reaction_smiles\":\"Cl[CH2:11][c:12]1[cH:13][cH:14][cH:15][cH:16][cH:17]1.[O:1]=[CH:2][c:3]1[cH:4][c:5]([N+:6](=[O:7])[O-:8])[c:9]([OH:10])[cH:18][cH:19]1>CN(C)C=O.O.O=C(O)O.[K+].[K+]>[O:1]=[CH:2][c:3]1[cH:4][c:5]([N+:6](=[O:7])[O-:8])[c:9]([O:10][CH2:11][c:12]2[cH:13][cH:14][cH:15][cH:16][cH:17]2)[cH:18][cH:19]1\"}",
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"children": [
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"molecule": {
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"inchikey": "KCXMKQUNVWSEMD-UHFFFAOYSA-N",
"smiles": "ClCc1ccccc1"
},
"smiles": "ClCc1ccccc1",
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{
"id": "12262",
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"molecule": {
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"inchikey": "YTHJCZRFJGXPTL-UHFFFAOYSA-N",
"smiles": "O=Cc1ccc(O)c([N+](=O)[O-])c1"
},
"smiles": "O=Cc1ccc(O)c([N+](=O)[O-])c1",
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}
]
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]
}
]
}
]
}
]
}
]
}
]
}
}