Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
Cn1cc(Nc2ncc(Cl)c(CCc3ccccc3C(C)(C)C(N)=O)n2)cn1
InChiKey
GGJRNPWQYMGFOS-UHFFFAOYSA-N
Route Signature
282bc4e5e0abf7136363d8b1afa3118c7ba47b243baa11e0ad094d06dc18786d
Synthesis route with 6 steps
Route tree structure (JSON format)
{
"route": {
"id": "sa_715e1bcf1b0e32f51410a414",
"signature": "282bc4e5e0abf7136363d8b1afa3118c7ba47b243baa11e0ad094d06dc18786d",
"contentHash": "4d3995e965a7581c5df1b39ad137d3d80235eec49a60633cd9b262c8d69515e5",
"length": 6,
"isConvergent": false
},
"target": {
"id": "sa_29497ae9c96e916a38e5c48d",
"benchmarkSetId": "f925e688d731a0ad4e3aa6a505df094f6d3ca64ce3facc312bc5f64731921b33",
"targetId": "n5-01186",
"moleculeId": "sa_29a86657e48676749d269b94",
"smiles": "Cn1cc(Nc2ncc(Cl)c(CCc3ccccc3C(C)(C)C(N)=O)n2)cn1",
"routeLength": 6,
"isConvergent": false,
"metadata": null,
"molecule": {
"id": "sa_29a86657e48676749d269b94",
"inchikey": "GGJRNPWQYMGFOS-UHFFFAOYSA-N",
"smiles": "Cn1cc(Nc2ncc(Cl)c(CCc3ccccc3C(C)(C)C(N)=O)n2)cn1"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "5312",
"routeId": "sa_715e1bcf1b0e32f51410a414",
"moleculeId": "sa_29a86657e48676749d269b94",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_29a86657e48676749d269b94",
"inchikey": "GGJRNPWQYMGFOS-UHFFFAOYSA-N",
"smiles": "Cn1cc(Nc2ncc(Cl)c(CCc3ccccc3C(C)(C)C(N)=O)n2)cn1"
},
"smiles": "Cn1cc(Nc2ncc(Cl)c(CCc3ccccc3C(C)(C)C(N)=O)n2)cn1",
"reactionStepId": "sa_1ca685eac631e62033a7aaa4",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20160009686A1;0552;1818313\",\"rsmi\":\"Cl[c:6]1[n:7][cH:8][c:9]([Cl:10])[c:11]([CH2:12][CH2:13][c:14]2[c:15]([C:16]([CH3:17])([CH3:18])[C:19]([NH2:20])=[O:21])[cH:22][cH:23][cH:24][cH:25]2)[n:26]1.[CH3:1][n:2]1[cH:3][c:4]([NH2:5])[cH:27][n:28]1>C1COCCO1.Cc1ccc(S(=O)(=O)O)cc1.O>[CH3:1][n:2]1[cH:3][c:4]([NH:5][c:6]2[n:7][cH:8][c:9]([Cl:10])[c:11]([CH2:12][CH2:13][c:14]3[c:15]([C:16]([CH3:17])([CH3:18])[C:19]([NH2:20])=[O:21])[cH:22][cH:23][cH:24][cH:25]3)[n:26]2)[cH:27][n:28]1\"},\"mapped_reaction_smiles\":\"Cl[c:6]1[n:7][cH:8][c:9]([Cl:10])[c:11]([CH2:12][CH2:13][c:14]2[c:15]([C:16]([CH3:17])([CH3:18])[C:19]([NH2:20])=[O:21])[cH:22][cH:23][cH:24][cH:25]2)[n:26]1.[CH3:1][n:2]1[cH:3][c:4]([NH2:5])[cH:27][n:28]1>C1COCCO1.Cc1ccc(S(=O)(=O)O)cc1.O>[CH3:1][n:2]1[cH:3][c:4]([NH:5][c:6]2[n:7][cH:8][c:9]([Cl:10])[c:11]([CH2:12][CH2:13][c:14]3[c:15]([C:16]([CH3:17])([CH3:18])[C:19]([NH2:20])=[O:21])[cH:22][cH:23][cH:24][cH:25]3)[n:26]2)[cH:27][n:28]1\"}",
"reactionStep": {
"id": "sa_1ca685eac631e62033a7aaa4",
"reactionHash": "77bd74b5e90abb68edd1dafbb07f7d1f9090f3891be63d3c10f948c76876f5b1"
},
"children": [
{
"id": "5313",
"routeId": "sa_715e1bcf1b0e32f51410a414",
"moleculeId": "sa_c47fcbf95e01c1b5483e5d8b",
"parentId": "5312",
"isLeaf": false,
"molecule": {
"id": "sa_c47fcbf95e01c1b5483e5d8b",
"inchikey": "DLNIPYOSFPCATM-UHFFFAOYSA-N",
"smiles": "CC(C)(C(N)=O)c1ccccc1CCc1nc(Cl)ncc1Cl"
},
"smiles": "CC(C)(C(N)=O)c1ccccc1CCc1nc(Cl)ncc1Cl",
"reactionStepId": "sa_8d7905aff022d339966b7930",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20160009686A1;0551;1818312\",\"rsmi\":\"[CH3:1][C:2]([CH3:3])([C:4]([NH2:5])=[O:6])[c:7]1[c:8]([C:9]#[C:10][c:11]2[n:12][c:13]([Cl:14])[n:15][cH:16][c:17]2[Cl:18])[cH:19][cH:20][cH:21][cH:22]1>CCOC(C)=O.CN(C)C=O.CO.O=[Pt]=O>[CH3:1][C:2]([CH3:3])([C:4]([NH2:5])=[O:6])[c:7]1[c:8]([CH2:9][CH2:10][c:11]2[n:12][c:13]([Cl:14])[n:15][cH:16][c:17]2[Cl:18])[cH:19][cH:20][cH:21][cH:22]1\"},\"mapped_reaction_smiles\":\"[CH3:1][C:2]([CH3:3])([C:4]([NH2:5])=[O:6])[c:7]1[c:8]([C:9]#[C:10][c:11]2[n:12][c:13]([Cl:14])[n:15][cH:16][c:17]2[Cl:18])[cH:19][cH:20][cH:21][cH:22]1>CCOC(C)=O.CN(C)C=O.CO.O=[Pt]=O>[CH3:1][C:2]([CH3:3])([C:4]([NH2:5])=[O:6])[c:7]1[c:8]([CH2:9][CH2:10][c:11]2[n:12][c:13]([Cl:14])[n:15][cH:16][c:17]2[Cl:18])[cH:19][cH:20][cH:21][cH:22]1\"}",
"reactionStep": {
"id": "sa_8d7905aff022d339966b7930",
"reactionHash": "d0cad1005d5f68994ac701059f5808b1eaa316aa95152df862ee2441ed739d7f"
},
"children": [
{
"id": "5314",
"routeId": "sa_715e1bcf1b0e32f51410a414",
"moleculeId": "sa_2fce62d067e14dc0ee8e3754",
"parentId": "5313",
"isLeaf": false,
"molecule": {
"id": "sa_2fce62d067e14dc0ee8e3754",
"inchikey": "ZKKQRCIKAQPIGX-UHFFFAOYSA-N",
"smiles": "CC(C)(C(N)=O)c1ccccc1C#Cc1nc(Cl)ncc1Cl"
},
"smiles": "CC(C)(C(N)=O)c1ccccc1C#Cc1nc(Cl)ncc1Cl",
"reactionStepId": "sa_735aef931d0dc693d634c09c",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20160009686A1;0550;1818311\",\"rsmi\":\"Cl[c:11]1[n:12][c:13]([Cl:14])[n:15][cH:16][c:17]1[Cl:18].[CH3:1][C:2]([CH3:3])([C:4]([NH2:5])=[O:6])[c:7]1[c:8]([C:9]#[CH:10])[cH:19][cH:20][cH:21][cH:22]1>C1COCCO1.CCN(CC)CC.Cl[Pd](Cl)([PH](c1ccccc1)(c1ccccc1)c1ccccc1)[PH](c1ccccc1)(c1ccccc1)c1ccccc1.[Cu]I>[CH3:1][C:2]([CH3:3])([C:4]([NH2:5])=[O:6])[c:7]1[c:8]([C:9]#[C:10][c:11]2[n:12][c:13]([Cl:14])[n:15][cH:16][c:17]2[Cl:18])[cH:19][cH:20][cH:21][cH:22]1\"},\"mapped_reaction_smiles\":\"Cl[c:11]1[n:12][c:13]([Cl:14])[n:15][cH:16][c:17]1[Cl:18].[CH3:1][C:2]([CH3:3])([C:4]([NH2:5])=[O:6])[c:7]1[c:8]([C:9]#[CH:10])[cH:19][cH:20][cH:21][cH:22]1>C1COCCO1.CCN(CC)CC.Cl[Pd](Cl)([PH](c1ccccc1)(c1ccccc1)c1ccccc1)[PH](c1ccccc1)(c1ccccc1)c1ccccc1.[Cu]I>[CH3:1][C:2]([CH3:3])([C:4]([NH2:5])=[O:6])[c:7]1[c:8]([C:9]#[C:10][c:11]2[n:12][c:13]([Cl:14])[n:15][cH:16][c:17]2[Cl:18])[cH:19][cH:20][cH:21][cH:22]1\"}",
"reactionStep": {
"id": "sa_735aef931d0dc693d634c09c",
"reactionHash": "358f363ef272dc9b08493493c98c7ca9504528fd8f809772a6a98ecc7a35fce2"
},
"children": [
{
"id": "5315",
"routeId": "sa_715e1bcf1b0e32f51410a414",
"moleculeId": "sa_fde86ac4eaa353047ff34d33",
"parentId": "5314",
"isLeaf": true,
"molecule": {
"id": "sa_fde86ac4eaa353047ff34d33",
"inchikey": "GIKMWFAAEIACRF-UHFFFAOYSA-N",
"smiles": "Clc1ncc(Cl)c(Cl)n1"
},
"smiles": "Clc1ncc(Cl)c(Cl)n1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "5316",
"routeId": "sa_715e1bcf1b0e32f51410a414",
"moleculeId": "sa_09435da74f01797d209528c4",
"parentId": "5314",
"isLeaf": false,
"molecule": {
"id": "sa_09435da74f01797d209528c4",
"inchikey": "YEOJGWGWOPKRNN-UHFFFAOYSA-N",
"smiles": "C#Cc1ccccc1C(C)(C)C(N)=O"
},
"smiles": "C#Cc1ccccc1C(C)(C)C(N)=O",
"reactionStepId": "sa_952133b0816df327ba1ca93e",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20160009686A1;0549;1818310\",\"rsmi\":\"CC[Si](CC)(CC)[C:1]#[C:2][c:3]1[c:4]([C:5]([CH3:6])([CH3:7])[C:8]([NH2:9])=[O:10])[cH:11][cH:12][cH:13][cH:14]1>C1CCOC1.CCCC[N+](CCCC)(CCCC)CCCC.O=C(O)O.F.[Na+]>[CH:1]#[C:2][c:3]1[c:4]([C:5]([CH3:6])([CH3:7])[C:8]([NH2:9])=[O:10])[cH:11][cH:12][cH:13][cH:14]1\"},\"mapped_reaction_smiles\":\"CC[Si](CC)(CC)[C:1]#[C:2][c:3]1[c:4]([C:5]([CH3:6])([CH3:7])[C:8]([NH2:9])=[O:10])[cH:11][cH:12][cH:13][cH:14]1>C1CCOC1.CCCC[N+](CCCC)(CCCC)CCCC.O=C(O)O.F.[Na+]>[CH:1]#[C:2][c:3]1[c:4]([C:5]([CH3:6])([CH3:7])[C:8]([NH2:9])=[O:10])[cH:11][cH:12][cH:13][cH:14]1\"}",
"reactionStep": {
"id": "sa_952133b0816df327ba1ca93e",
"reactionHash": "7e08327130229ab0b179e501352f4c614163a780f25f14e5b170be9c2d64f7bb"
},
"children": [
{
"id": "5317",
"routeId": "sa_715e1bcf1b0e32f51410a414",
"moleculeId": "sa_138dd9bbf259cddad3e677af",
"parentId": "5316",
"isLeaf": false,
"molecule": {
"id": "sa_138dd9bbf259cddad3e677af",
"inchikey": "CODHDFOTERCRAY-UHFFFAOYSA-N",
"smiles": "CC[Si](C#Cc1ccccc1C(C)(C)C(N)=O)(CC)CC"
},
"smiles": "CC[Si](C#Cc1ccccc1C(C)(C)C(N)=O)(CC)CC",
"reactionStepId": "sa_eb05ea3bbf341545c0ea9732",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20160009686A1;0548;1818309\",\"rsmi\":\"Br[c:6]1[c:7]([C:8]([CH3:9])([CH3:10])[C:11]([NH2:12])=[O:13])[cH:14][cH:15][cH:16][cH:17]1.[CH3:1][CH2:2][Si:3]([C:4]#[CH:5])([CH2:18][CH3:19])[CH2:20][CH3:21]>CC(C)(C)P(C(C)(C)C)C(C)(C)C.CN(C)C=O.Cl[Pd](Cl)([PH](c1ccccc1)(c1ccccc1)c1ccccc1)[PH](c1ccccc1)(c1ccccc1)c1ccccc1.F[B-](F)(F)F.[Cu]I>[CH3:1][CH2:2][Si:3]([C:4]#[C:5][c:6]1[c:7]([C:8]([CH3:9])([CH3:10])[C:11]([NH2:12])=[O:13])[cH:14][cH:15][cH:16][cH:17]1)([CH2:18][CH3:19])[CH2:20][CH3:21]\"},\"mapped_reaction_smiles\":\"Br[c:6]1[c:7]([C:8]([CH3:9])([CH3:10])[C:11]([NH2:12])=[O:13])[cH:14][cH:15][cH:16][cH:17]1.[CH3:1][CH2:2][Si:3]([C:4]#[CH:5])([CH2:18][CH3:19])[CH2:20][CH3:21]>CC(C)(C)P(C(C)(C)C)C(C)(C)C.CN(C)C=O.Cl[Pd](Cl)([PH](c1ccccc1)(c1ccccc1)c1ccccc1)[PH](c1ccccc1)(c1ccccc1)c1ccccc1.F[B-](F)(F)F.[Cu]I>[CH3:1][CH2:2][Si:3]([C:4]#[C:5][c:6]1[c:7]([C:8]([CH3:9])([CH3:10])[C:11]([NH2:12])=[O:13])[cH:14][cH:15][cH:16][cH:17]1)([CH2:18][CH3:19])[CH2:20][CH3:21]\"}",
"reactionStep": {
"id": "sa_eb05ea3bbf341545c0ea9732",
"reactionHash": "788117889f6fec8e2347ebb32321991462f254f94fceb276ffc091d037175caf"
},
"children": [
{
"id": "5318",
"routeId": "sa_715e1bcf1b0e32f51410a414",
"moleculeId": "sa_050cd2a9a5bbd7142d455936",
"parentId": "5317",
"isLeaf": true,
"molecule": {
"id": "sa_050cd2a9a5bbd7142d455936",
"inchikey": "FWSPXZXVNVQHIF-UHFFFAOYSA-N",
"smiles": "C#C[Si](CC)(CC)CC"
},
"smiles": "C#C[Si](CC)(CC)CC",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "5319",
"routeId": "sa_715e1bcf1b0e32f51410a414",
"moleculeId": "sa_a33c88baf0dc3538c41cd3de",
"parentId": "5317",
"isLeaf": false,
"molecule": {
"id": "sa_a33c88baf0dc3538c41cd3de",
"inchikey": "XJVQCOZVLGPMGE-UHFFFAOYSA-N",
"smiles": "CC(C)(C(N)=O)c1ccccc1Br"
},
"smiles": "CC(C)(C(N)=O)c1ccccc1Br",
"reactionStepId": "sa_86a834d04d4663330bfedaf4",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20160009686A1;0547;1818308\",\"rsmi\":\"[CH3:1][C:2]([CH3:3])([C:4]#[N:5])[c:7]1[c:8]([Br:9])[cH:10][cH:11][cH:12][cH:13]1.[OH2:6]>CC(C)(C)O.ClCCl.[Na+]>[CH3:1][C:2]([CH3:3])([C:4]([NH2:5])=[O:6])[c:7]1[c:8]([Br:9])[cH:10][cH:11][cH:12][cH:13]1\"},\"mapped_reaction_smiles\":\"[CH3:1][C:2]([CH3:3])([C:4]#[N:5])[c:7]1[c:8]([Br:9])[cH:10][cH:11][cH:12][cH:13]1.[OH2:6]>CC(C)(C)O.ClCCl.[Na+]>[CH3:1][C:2]([CH3:3])([C:4]([NH2:5])=[O:6])[c:7]1[c:8]([Br:9])[cH:10][cH:11][cH:12][cH:13]1\"}",
"reactionStep": {
"id": "sa_86a834d04d4663330bfedaf4",
"reactionHash": "d7deb705c0e4e9090d41b009a9452079338e1fcd25a93d6f665ce0b1b67fe80e"
},
"children": [
{
"id": "5320",
"routeId": "sa_715e1bcf1b0e32f51410a414",
"moleculeId": "sa_106b35b8a76bbe73829a0a69",
"parentId": "5319",
"isLeaf": true,
"molecule": {
"id": "sa_106b35b8a76bbe73829a0a69",
"inchikey": "XLYOFNOQVPJJNP-UHFFFAOYSA-N",
"smiles": "O"
},
"smiles": "O",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "5321",
"routeId": "sa_715e1bcf1b0e32f51410a414",
"moleculeId": "sa_ce621760d53a24ef02aae1e0",
"parentId": "5319",
"isLeaf": true,
"molecule": {
"id": "sa_ce621760d53a24ef02aae1e0",
"inchikey": "YTUDHLARHDCOIR-UHFFFAOYSA-N",
"smiles": "CC(C)(C#N)c1ccccc1Br"
},
"smiles": "CC(C)(C#N)c1ccccc1Br",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
}
]
}
]
}
]
}
]
},
{
"id": "5322",
"routeId": "sa_715e1bcf1b0e32f51410a414",
"moleculeId": "sa_9610bc0988f037b26565c330",
"parentId": "5312",
"isLeaf": true,
"molecule": {
"id": "sa_9610bc0988f037b26565c330",
"inchikey": "LBGSWBJURUFGLR-UHFFFAOYSA-N",
"smiles": "Cn1cc(N)cn1"
},
"smiles": "Cn1cc(N)cn1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
}
}