Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
COc1cccc(OC)c1C1CCCC(=O)N1Cc1cnc(OC(F)F)c(Cl)c1
InChiKey
CKHQMMOXQOHIAU-UHFFFAOYSA-N
Route Signature
130b9f3b2387613ebd2cb5d2bbda185d0191727ef09bf4625567902dafd9d7c4
Synthesis route with 3 steps (convergent)
Route tree structure (JSON format)
{
"route": {
"id": "sa_7972bdb44e9624ae6fc41121",
"signature": "130b9f3b2387613ebd2cb5d2bbda185d0191727ef09bf4625567902dafd9d7c4",
"contentHash": "30071f08a361d91d81322f4f5e3c6ebeef75dcffecdf54d52dc91d0eba748ed6",
"length": 3,
"isConvergent": true
},
"target": {
"id": "sa_c27057eab35550c86773b9c2",
"benchmarkSetId": "3895c2909c53593560c5ba610abc7e6df80513dfd8624165c560451735097d36",
"targetId": "n5-02965",
"moleculeId": "sa_f37005da731d09738761fe9f",
"smiles": "COc1cccc(OC)c1C1CCCC(=O)N1Cc1cnc(OC(F)F)c(Cl)c1",
"routeLength": 3,
"isConvergent": true,
"metadata": null,
"molecule": {
"id": "sa_f37005da731d09738761fe9f",
"inchikey": "CKHQMMOXQOHIAU-UHFFFAOYSA-N",
"smiles": "COc1cccc(OC)c1C1CCCC(=O)N1Cc1cnc(OC(F)F)c(Cl)c1"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "10916",
"routeId": "sa_7972bdb44e9624ae6fc41121",
"moleculeId": "sa_f37005da731d09738761fe9f",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_f37005da731d09738761fe9f",
"inchikey": "CKHQMMOXQOHIAU-UHFFFAOYSA-N",
"smiles": "COc1cccc(OC)c1C1CCCC(=O)N1Cc1cnc(OC(F)F)c(Cl)c1"
},
"smiles": "COc1cccc(OC)c1C1CCCC(=O)N1Cc1cnc(OC(F)F)c(Cl)c1",
"reactionStepId": "sa_f2bfb69a4df66a174894084d",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20130237525A1;0838;1419889\",\"rsmi\":\"CO[C:15]([CH2:14][CH2:13][CH2:12][CH:11]([c:10]1[c:3]([O:2][CH3:1])[cH:4][cH:5][cH:6][c:7]1[O:8][CH3:9])[NH2:17])=[O:16].O=[CH:18][c:19]1[cH:20][c:21]([Cl:22])[c:23]([O:24][CH:25]([F:26])[F:27])[n:28][cH:29]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7]([O:8][CH3:9])[c:10]1[CH:11]1[CH2:12][CH2:13][CH2:14][C:15](=[O:16])[N:17]1[CH2:18][c:19]1[cH:20][c:21]([Cl:22])[c:23]([O:24][CH:25]([F:26])[F:27])[n:28][cH:29]1\"},\"mapped_reaction_smiles\":\"CO[C:15]([CH2:14][CH2:13][CH2:12][CH:11]([c:10]1[c:3]([O:2][CH3:1])[cH:4][cH:5][cH:6][c:7]1[O:8][CH3:9])[NH2:17])=[O:16].O=[CH:18][c:19]1[cH:20][c:21]([Cl:22])[c:23]([O:24][CH:25]([F:26])[F:27])[n:28][cH:29]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7]([O:8][CH3:9])[c:10]1[CH:11]1[CH2:12][CH2:13][CH2:14][C:15](=[O:16])[N:17]1[CH2:18][c:19]1[cH:20][c:21]([Cl:22])[c:23]([O:24][CH:25]([F:26])[F:27])[n:28][cH:29]1\"}",
"reactionStep": {
"id": "sa_f2bfb69a4df66a174894084d",
"reactionHash": "3a76fd5efd8567e1c8d7db366d2276b85bc2ed32ecf3f103ac4ee25926fa9fcb"
},
"children": [
{
"id": "10917",
"routeId": "sa_7972bdb44e9624ae6fc41121",
"moleculeId": "sa_f700e4334cee1ac251a7aa08",
"parentId": "10916",
"isLeaf": false,
"molecule": {
"id": "sa_f700e4334cee1ac251a7aa08",
"inchikey": "HQORVZNYERDBKQ-UHFFFAOYSA-N",
"smiles": "O=Cc1cnc(OC(F)F)c(Cl)c1"
},
"smiles": "O=Cc1cnc(OC(F)F)c(Cl)c1",
"reactionStepId": "sa_635507914552ab1a20efe537",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20130237525A1;0623;1419731\",\"rsmi\":\"[OH:1][CH2:2][c:3]1[cH:4][n:5][c:6]([O:7][CH:8]([F:9])[F:10])[c:11]([Cl:12])[cH:13]1>ClCCl.O=[Mn]=O>[O:1]=[CH:2][c:3]1[cH:4][n:5][c:6]([O:7][CH:8]([F:9])[F:10])[c:11]([Cl:12])[cH:13]1\"},\"mapped_reaction_smiles\":\"[OH:1][CH2:2][c:3]1[cH:4][n:5][c:6]([O:7][CH:8]([F:9])[F:10])[c:11]([Cl:12])[cH:13]1>ClCCl.O=[Mn]=O>[O:1]=[CH:2][c:3]1[cH:4][n:5][c:6]([O:7][CH:8]([F:9])[F:10])[c:11]([Cl:12])[cH:13]1\"}",
"reactionStep": {
"id": "sa_635507914552ab1a20efe537",
"reactionHash": "d98b3cf632babb1c382bc8abc55341249a636e6bf31d85f386e881a9feb4da85"
},
"children": [
{
"id": "10918",
"routeId": "sa_7972bdb44e9624ae6fc41121",
"moleculeId": "sa_f55959db78d03ff24364c647",
"parentId": "10917",
"isLeaf": false,
"molecule": {
"id": "sa_f55959db78d03ff24364c647",
"inchikey": "VZBZNHKSOYUKMG-UHFFFAOYSA-N",
"smiles": "OCc1cnc(OC(F)F)c(Cl)c1"
},
"smiles": "OCc1cnc(OC(F)F)c(Cl)c1",
"reactionStepId": "sa_acc252ef68c60dbff996179b",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20130237525A1;0622;1419730\",\"rsmi\":\"C[O:1][C:2](=O)[c:3]1[cH:4][c:5]([Cl:6])[c:7]([O:8][CH:9]([F:10])[F:11])[n:12][cH:13]1>CC(C)C[AlH]CC(C)C.Cc1ccccc1.O.O=C(O)O.[Na+].[Na+].O>[OH:1][CH2:2][c:3]1[cH:4][c:5]([Cl:6])[c:7]([O:8][CH:9]([F:10])[F:11])[n:12][cH:13]1\"},\"mapped_reaction_smiles\":\"C[O:1][C:2](=O)[c:3]1[cH:4][c:5]([Cl:6])[c:7]([O:8][CH:9]([F:10])[F:11])[n:12][cH:13]1>CC(C)C[AlH]CC(C)C.Cc1ccccc1.O.O=C(O)O.[Na+].[Na+].O>[OH:1][CH2:2][c:3]1[cH:4][c:5]([Cl:6])[c:7]([O:8][CH:9]([F:10])[F:11])[n:12][cH:13]1\"}",
"reactionStep": {
"id": "sa_acc252ef68c60dbff996179b",
"reactionHash": "e5e34e01b183c18fa0b8c430872e6335b63b6d5dd292e489d59a8d040370d060"
},
"children": [
{
"id": "10919",
"routeId": "sa_7972bdb44e9624ae6fc41121",
"moleculeId": "sa_bfa49f1b7bdf6d3925693056",
"parentId": "10918",
"isLeaf": true,
"molecule": {
"id": "sa_bfa49f1b7bdf6d3925693056",
"inchikey": "XGUCLTNCHVUKGN-UHFFFAOYSA-N",
"smiles": "COC(=O)c1cnc(OC(F)F)c(Cl)c1"
},
"smiles": "COC(=O)c1cnc(OC(F)F)c(Cl)c1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
}
]
},
{
"id": "10920",
"routeId": "sa_7972bdb44e9624ae6fc41121",
"moleculeId": "sa_f27df83b7f3d64a03225e9b7",
"parentId": "10916",
"isLeaf": false,
"molecule": {
"id": "sa_f27df83b7f3d64a03225e9b7",
"inchikey": "OMPIVJSMKRJUHN-UHFFFAOYSA-N",
"smiles": "COC(=O)CCCC(N)c1c(OC)cccc1OC"
},
"smiles": "COC(=O)CCCC(N)c1c(OC)cccc1OC",
"reactionStepId": "sa_e443342b5dbee39d323c339e",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20130237525A1;0699;1419797\",\"rsmi\":\"CC(C)(C)S(=O)[NH:9][CH:8]([CH2:7][CH2:6][CH2:5][C:3]([O:2][CH3:1])=[O:4])[c:10]1[c:11]([O:12][CH3:13])[cH:14][cH:15][cH:16][c:17]1[O:18][CH3:19]>C1COCCO1.CO.Cl>[CH3:1][O:2][C:3](=[O:4])[CH2:5][CH2:6][CH2:7][CH:8]([NH2:9])[c:10]1[c:11]([O:12][CH3:13])[cH:14][cH:15][cH:16][c:17]1[O:18][CH3:19]\"},\"mapped_reaction_smiles\":\"CC(C)(C)S(=O)[NH:9][CH:8]([CH2:7][CH2:6][CH2:5][C:3]([O:2][CH3:1])=[O:4])[c:10]1[c:11]([O:12][CH3:13])[cH:14][cH:15][cH:16][c:17]1[O:18][CH3:19]>C1COCCO1.CO.Cl>[CH3:1][O:2][C:3](=[O:4])[CH2:5][CH2:6][CH2:7][CH:8]([NH2:9])[c:10]1[c:11]([O:12][CH3:13])[cH:14][cH:15][cH:16][c:17]1[O:18][CH3:19]\"}",
"reactionStep": {
"id": "sa_e443342b5dbee39d323c339e",
"reactionHash": "7cd29119ac918d23b04cded7d336f7a022cfc5a738e82597ecb4c36a6ab03746"
},
"children": [
{
"id": "10921",
"routeId": "sa_7972bdb44e9624ae6fc41121",
"moleculeId": "sa_0ca1b420157d494af9fcdf77",
"parentId": "10920",
"isLeaf": false,
"molecule": {
"id": "sa_0ca1b420157d494af9fcdf77",
"inchikey": "BWKYAXLNBMFIOS-UHFFFAOYSA-N",
"smiles": "COC(=O)CCCC(NS(=O)C(C)(C)C)c1c(OC)cccc1OC"
},
"smiles": "COC(=O)CCCC(NS(=O)C(C)(C)C)c1c(OC)cccc1OC",
"reactionStepId": "sa_e29c6564ab2007f1413ab32b",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20130237525A1;0698;1419796\",\"rsmi\":\"I[c:16]1[c:17]([O:18][CH3:19])[cH:20][cH:21][cH:22][c:23]1[O:24][CH3:25].[CH3:1][O:2][C:3](=[O:4])[CH2:5][CH2:6][CH2:7][CH:8]=[N:9][S:10](=[O:11])[C:12]([CH3:13])([CH3:14])[CH3:15]>C1CCOC1.CCOCC.O.Cl.[Li]CCCC.N>[CH3:1][O:2][C:3](=[O:4])[CH2:5][CH2:6][CH2:7][CH:8]([NH:9][S:10](=[O:11])[C:12]([CH3:13])([CH3:14])[CH3:15])[c:16]1[c:17]([O:18][CH3:19])[cH:20][cH:21][cH:22][c:23]1[O:24][CH3:25]\"},\"mapped_reaction_smiles\":\"I[c:16]1[c:17]([O:18][CH3:19])[cH:20][cH:21][cH:22][c:23]1[O:24][CH3:25].[CH3:1][O:2][C:3](=[O:4])[CH2:5][CH2:6][CH2:7][CH:8]=[N:9][S:10](=[O:11])[C:12]([CH3:13])([CH3:14])[CH3:15]>C1CCOC1.CCOCC.O.Cl.[Li]CCCC.N>[CH3:1][O:2][C:3](=[O:4])[CH2:5][CH2:6][CH2:7][CH:8]([NH:9][S:10](=[O:11])[C:12]([CH3:13])([CH3:14])[CH3:15])[c:16]1[c:17]([O:18][CH3:19])[cH:20][cH:21][cH:22][c:23]1[O:24][CH3:25]\"}",
"reactionStep": {
"id": "sa_e29c6564ab2007f1413ab32b",
"reactionHash": "0a6044e6941cb6187b06590425b384fc806983f1142531aae42ea3f4571fbfcf"
},
"children": [
{
"id": "10922",
"routeId": "sa_7972bdb44e9624ae6fc41121",
"moleculeId": "sa_cf0921d1e31cfe887a6c2986",
"parentId": "10921",
"isLeaf": true,
"molecule": {
"id": "sa_cf0921d1e31cfe887a6c2986",
"inchikey": "VVWNLAOXPFRGRT-UHFFFAOYSA-N",
"smiles": "COC(=O)CCCC=NS(=O)C(C)(C)C"
},
"smiles": "COC(=O)CCCC=NS(=O)C(C)(C)C",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "10923",
"routeId": "sa_7972bdb44e9624ae6fc41121",
"moleculeId": "sa_5df8b88b94a0be2394a8e275",
"parentId": "10921",
"isLeaf": true,
"molecule": {
"id": "sa_5df8b88b94a0be2394a8e275",
"inchikey": "WCYZALIKRBYPOM-UHFFFAOYSA-N",
"smiles": "COc1cccc(OC)c1I"
},
"smiles": "COc1cccc(OC)c1I",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
}
]
}
]
}
}