Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
Cc1cc(Cl)ccc1C(NC(=O)Cc1ccc2oc(-c3c(C)ccnc3C)nc2c1)c1ccccc1
InChiKey
DCRHRRLAMHNDBW-UHFFFAOYSA-N
Route Signature
e709b6094c14da00ecf96b5b8fae47da4c91f5d812f4e7b69cb6081b96699b98
Synthesis route with 5 steps (convergent)
Route tree structure (JSON format)
{
"route": {
"id": "sa_e3d22058420221efece96f28",
"signature": "e709b6094c14da00ecf96b5b8fae47da4c91f5d812f4e7b69cb6081b96699b98",
"contentHash": "b9e93a6d9bcfafd7ee11e21dbfb5ac8151911609d8d289aaaa4a5da94e9e5f2a",
"length": 5,
"isConvergent": true
},
"target": {
"id": "sa_5c478a2887e2f372089f72ef",
"benchmarkSetId": "7390a9c2522b1c81605e80a42a8de7c7ad9a5797d028633b54904bc78f091bb8",
"targetId": "n5-00775",
"moleculeId": "sa_e95c8cf478b7e9008cb33099",
"smiles": "Cc1cc(Cl)ccc1C(NC(=O)Cc1ccc2oc(-c3c(C)ccnc3C)nc2c1)c1ccccc1",
"routeLength": 5,
"isConvergent": true,
"metadata": null,
"molecule": {
"id": "sa_e95c8cf478b7e9008cb33099",
"inchikey": "DCRHRRLAMHNDBW-UHFFFAOYSA-N",
"smiles": "Cc1cc(Cl)ccc1C(NC(=O)Cc1ccc2oc(-c3c(C)ccnc3C)nc2c1)c1ccccc1"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 2
},
"rootNode": {
"id": "1166",
"routeId": "sa_e3d22058420221efece96f28",
"moleculeId": "sa_e95c8cf478b7e9008cb33099",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_e95c8cf478b7e9008cb33099",
"inchikey": "DCRHRRLAMHNDBW-UHFFFAOYSA-N",
"smiles": "Cc1cc(Cl)ccc1C(NC(=O)Cc1ccc2oc(-c3c(C)ccnc3C)nc2c1)c1ccccc1"
},
"smiles": "Cc1cc(Cl)ccc1C(NC(=O)Cc1ccc2oc(-c3c(C)ccnc3C)nc2c1)c1ccccc1",
"reactionStepId": "sa_96ade445cdc165782f150894",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20140315881A1;0902;1601172\",\"rsmi\":\"O=[C:9]([c:8]1[c:2]([CH3:1])[n:3][cH:4][cH:5][c:6]1[CH3:7])[NH:10][c:11]1[c:12]([OH:36])[cH:13][cH:14][c:15]([CH2:16][C:17](=[O:18])[NH:19][CH:20]([c:21]2[cH:22][cH:23][cH:24][cH:25][cH:26]2)[c:27]2[c:28]([CH3:29])[cH:30][c:31]([Cl:32])[cH:33][cH:34]2)[cH:35]1>C1COCCO1.Cc1ccc(S(=O)(=O)O)cc1.O>[CH3:1][c:2]1[n:3][cH:4][cH:5][c:6]([CH3:7])[c:8]1-[c:9]1[n:10][c:11]2[c:12]([cH:13][cH:14][c:15]([CH2:16][C:17](=[O:18])[NH:19][CH:20]([c:21]3[cH:22][cH:23][cH:24][cH:25][cH:26]3)[c:27]3[c:28]([CH3:29])[cH:30][c:31]([Cl:32])[cH:33][cH:34]3)[cH:35]2)[o:36]1\"},\"mapped_reaction_smiles\":\"O=[C:9]([c:8]1[c:2]([CH3:1])[n:3][cH:4][cH:5][c:6]1[CH3:7])[NH:10][c:11]1[c:12]([OH:36])[cH:13][cH:14][c:15]([CH2:16][C:17](=[O:18])[NH:19][CH:20]([c:21]2[cH:22][cH:23][cH:24][cH:25][cH:26]2)[c:27]2[c:28]([CH3:29])[cH:30][c:31]([Cl:32])[cH:33][cH:34]2)[cH:35]1>C1COCCO1.Cc1ccc(S(=O)(=O)O)cc1.O>[CH3:1][c:2]1[n:3][cH:4][cH:5][c:6]([CH3:7])[c:8]1-[c:9]1[n:10][c:11]2[c:12]([cH:13][cH:14][c:15]([CH2:16][C:17](=[O:18])[NH:19][CH:20]([c:21]3[cH:22][cH:23][cH:24][cH:25][cH:26]3)[c:27]3[c:28]([CH3:29])[cH:30][c:31]([Cl:32])[cH:33][cH:34]3)[cH:35]2)[o:36]1\"}",
"reactionStep": {
"id": "sa_96ade445cdc165782f150894",
"reactionHash": "2447b265aa7f1ee4ab212a17814a7a0cb3d17541044d369895b5fb9aec943e6d"
},
"children": [
{
"id": "1167",
"routeId": "sa_e3d22058420221efece96f28",
"moleculeId": "sa_ea56f9569cb55189efae3559",
"parentId": "1166",
"isLeaf": false,
"molecule": {
"id": "sa_ea56f9569cb55189efae3559",
"inchikey": "PZAFTWMDKXTZFT-UHFFFAOYSA-N",
"smiles": "Cc1cc(Cl)ccc1C(NC(=O)Cc1ccc(O)c(NC(=O)c2c(C)ccnc2C)c1)c1ccccc1"
},
"smiles": "Cc1cc(Cl)ccc1C(NC(=O)Cc1ccc(O)c(NC(=O)c2c(C)ccnc2C)c1)c1ccccc1",
"reactionStepId": "sa_f99c7f40f9fc39f5be41876b",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20140315881A1;0901;1601171\",\"rsmi\":\"O[C:9]([c:8]1[c:2]([CH3:1])[cH:3][cH:4][n:5][c:6]1[CH3:7])=[O:10].[NH2:11][c:12]1[c:13]([OH:14])[cH:15][cH:16][c:17]([CH2:18][C:19](=[O:20])[NH:21][CH:22]([c:23]2[cH:24][cH:25][cH:26][cH:27][cH:28]2)[c:29]2[c:30]([CH3:31])[cH:32][c:33]([Cl:34])[cH:35][cH:36]2)[cH:37]1>CCN(C(C)C)C(C)C.ClCCl.O.O=S(Cl)Cl>[CH3:1][c:2]1[cH:3][cH:4][n:5][c:6]([CH3:7])[c:8]1[C:9](=[O:10])[NH:11][c:12]1[c:13]([OH:14])[cH:15][cH:16][c:17]([CH2:18][C:19](=[O:20])[NH:21][CH:22]([c:23]2[cH:24][cH:25][cH:26][cH:27][cH:28]2)[c:29]2[c:30]([CH3:31])[cH:32][c:33]([Cl:34])[cH:35][cH:36]2)[cH:37]1\"},\"mapped_reaction_smiles\":\"O[C:9]([c:8]1[c:2]([CH3:1])[cH:3][cH:4][n:5][c:6]1[CH3:7])=[O:10].[NH2:11][c:12]1[c:13]([OH:14])[cH:15][cH:16][c:17]([CH2:18][C:19](=[O:20])[NH:21][CH:22]([c:23]2[cH:24][cH:25][cH:26][cH:27][cH:28]2)[c:29]2[c:30]([CH3:31])[cH:32][c:33]([Cl:34])[cH:35][cH:36]2)[cH:37]1>CCN(C(C)C)C(C)C.ClCCl.O.O=S(Cl)Cl>[CH3:1][c:2]1[cH:3][cH:4][n:5][c:6]([CH3:7])[c:8]1[C:9](=[O:10])[NH:11][c:12]1[c:13]([OH:14])[cH:15][cH:16][c:17]([CH2:18][C:19](=[O:20])[NH:21][CH:22]([c:23]2[cH:24][cH:25][cH:26][cH:27][cH:28]2)[c:29]2[c:30]([CH3:31])[cH:32][c:33]([Cl:34])[cH:35][cH:36]2)[cH:37]1\"}",
"reactionStep": {
"id": "sa_f99c7f40f9fc39f5be41876b",
"reactionHash": "8ef4912b9640b6062315864403393e0eb64b3230613a0968c5effac7a13bc76a"
},
"children": [
{
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"moleculeId": "sa_26dcdd52b72ac3a972da085c",
"parentId": "1167",
"isLeaf": false,
"molecule": {
"id": "sa_26dcdd52b72ac3a972da085c",
"inchikey": "LXKHCPDPTCGSCL-UHFFFAOYSA-N",
"smiles": "Cc1cc(Cl)ccc1C(NC(=O)Cc1ccc(O)c(N)c1)c1ccccc1"
},
"smiles": "Cc1cc(Cl)ccc1C(NC(=O)Cc1ccc(O)c(N)c1)c1ccccc1",
"reactionStepId": "sa_75ad99a64c44f34079989acf",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20140315881A1;0900;1601170\",\"rsmi\":\"O=[N+:12]([O-])[c:11]1[cH:10][c:9]([CH2:8][C:6]([NH:5][CH:4]([c:3]2[c:2]([CH3:1])[cH:27][c:25]([Cl:26])[cH:24][cH:23]2)[c:17]2[cH:18][cH:19][cH:20][cH:21][cH:22]2)=[O:7])[cH:16][cH:15][c:13]1[OH:14]>CCO.Cl.N.[Zn]>[CH3:1][c:2]1[c:3]([CH:4]([NH:5][C:6](=[O:7])[CH2:8][c:9]2[cH:10][c:11]([NH2:12])[c:13]([OH:14])[cH:15][cH:16]2)[c:17]2[cH:18][cH:19][cH:20][cH:21][cH:22]2)[cH:23][cH:24][c:25]([Cl:26])[cH:27]1\"},\"mapped_reaction_smiles\":\"O=[N+:12]([O-])[c:11]1[cH:10][c:9]([CH2:8][C:6]([NH:5][CH:4]([c:3]2[c:2]([CH3:1])[cH:27][c:25]([Cl:26])[cH:24][cH:23]2)[c:17]2[cH:18][cH:19][cH:20][cH:21][cH:22]2)=[O:7])[cH:16][cH:15][c:13]1[OH:14]>CCO.Cl.N.[Zn]>[CH3:1][c:2]1[c:3]([CH:4]([NH:5][C:6](=[O:7])[CH2:8][c:9]2[cH:10][c:11]([NH2:12])[c:13]([OH:14])[cH:15][cH:16]2)[c:17]2[cH:18][cH:19][cH:20][cH:21][cH:22]2)[cH:23][cH:24][c:25]([Cl:26])[cH:27]1\"}",
"reactionStep": {
"id": "sa_75ad99a64c44f34079989acf",
"reactionHash": "5bb4bdf75c91a3a2ef5c7180fd7a11c72e0a00a7dcaf1276e0414cc8e08758db"
},
"children": [
{
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"routeId": "sa_e3d22058420221efece96f28",
"moleculeId": "sa_6e6e72781e71f6f25cdef6b0",
"parentId": "1168",
"isLeaf": false,
"molecule": {
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"inchikey": "NFKIJVFAHHABMP-UHFFFAOYSA-N",
"smiles": "Cc1cc(Cl)ccc1C(NC(=O)Cc1ccc(O)c([N+](=O)[O-])c1)c1ccccc1"
},
"smiles": "Cc1cc(Cl)ccc1C(NC(=O)Cc1ccc(O)c([N+](=O)[O-])c1)c1ccccc1",
"reactionStepId": "sa_d1cc8b82ed86fe40a43db29e",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20140315881A1;0899;1601169\",\"rsmi\":\"O[C:6](=[O:7])[CH2:8][c:9]1[cH:10][c:11]([N+:12](=[O:13])[O-:14])[c:15]([OH:16])[cH:17][cH:18]1.[CH3:1][c:2]1[c:3]([CH:4]([NH2:5])[c:19]2[cH:20][cH:21][cH:22][cH:23][cH:24]2)[cH:25][cH:26][c:27]([Cl:28])[cH:29]1>>[CH3:1][c:2]1[c:3]([CH:4]([NH:5][C:6](=[O:7])[CH2:8][c:9]2[cH:10][c:11]([N+:12](=[O:13])[O-:14])[c:15]([OH:16])[cH:17][cH:18]2)[c:19]2[cH:20][cH:21][cH:22][cH:23][cH:24]2)[cH:25][cH:26][c:27]([Cl:28])[cH:29]1\"},\"mapped_reaction_smiles\":\"O[C:6](=[O:7])[CH2:8][c:9]1[cH:10][c:11]([N+:12](=[O:13])[O-:14])[c:15]([OH:16])[cH:17][cH:18]1.[CH3:1][c:2]1[c:3]([CH:4]([NH2:5])[c:19]2[cH:20][cH:21][cH:22][cH:23][cH:24]2)[cH:25][cH:26][c:27]([Cl:28])[cH:29]1>>[CH3:1][c:2]1[c:3]([CH:4]([NH:5][C:6](=[O:7])[CH2:8][c:9]2[cH:10][c:11]([N+:12](=[O:13])[O-:14])[c:15]([OH:16])[cH:17][cH:18]2)[c:19]2[cH:20][cH:21][cH:22][cH:23][cH:24]2)[cH:25][cH:26][c:27]([Cl:28])[cH:29]1\"}",
"reactionStep": {
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"reactionHash": "a366437b67920cbdcdb9aaa3b8ff442bdba706b71f51145e62eaf640bc10cd55"
},
"children": [
{
"id": "1170",
"routeId": "sa_e3d22058420221efece96f28",
"moleculeId": "sa_a8f74915b37b4de4e0c7a9fa",
"parentId": "1169",
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"molecule": {
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"inchikey": "NOYJJOPHQRWBCO-UHFFFAOYSA-N",
"smiles": "Cc1cc(Cl)ccc1C(N)c1ccccc1"
},
"smiles": "Cc1cc(Cl)ccc1C(N)c1ccccc1",
"reactionStepId": "sa_ab43430218227b7bfff79145",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20140315881A1;0831;1601131\",\"rsmi\":\"Br[Mg][c:6]1[cH:7][cH:8][cH:9][cH:10][cH:11]1.[CH3:1][c:2]1[c:3]([C:4]#[N:5])[cH:12][cH:13][c:14]([Cl:15])[cH:16]1>>[CH3:1][c:2]1[c:3]([CH:4]([NH2:5])[c:6]2[cH:7][cH:8][cH:9][cH:10][cH:11]2)[cH:12][cH:13][c:14]([Cl:15])[cH:16]1\"},\"mapped_reaction_smiles\":\"Br[Mg][c:6]1[cH:7][cH:8][cH:9][cH:10][cH:11]1.[CH3:1][c:2]1[c:3]([C:4]#[N:5])[cH:12][cH:13][c:14]([Cl:15])[cH:16]1>>[CH3:1][c:2]1[c:3]([CH:4]([NH2:5])[c:6]2[cH:7][cH:8][cH:9][cH:10][cH:11]2)[cH:12][cH:13][c:14]([Cl:15])[cH:16]1\"}",
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"children": [
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"molecule": {
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"smiles": "[Br][Mg][c]1ccccc1"
},
"smiles": "[Br][Mg][c]1ccccc1",
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},
{
"id": "1172",
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"molecule": {
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"inchikey": "ZZAJFWXXFZTTLH-UHFFFAOYSA-N",
"smiles": "Cc1cc(Cl)ccc1C#N"
},
"smiles": "Cc1cc(Cl)ccc1C#N",
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{
"id": "1173",
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"molecule": {
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"inchikey": "QBHBHOSRLDPIHG-UHFFFAOYSA-N",
"smiles": "O=C(O)Cc1ccc(O)c([N+](=O)[O-])c1"
},
"smiles": "O=C(O)Cc1ccc(O)c([N+](=O)[O-])c1",
"reactionStepId": "sa_d19248f9609fa52279dd6121",
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"metadata": "{\"annotations\":{\"ID\":\"US20140315881A1;0699;1601083\",\"rsmi\":\"O[N+:8](=[O:9])[O-:10].[O:1]=[C:2]([OH:3])[CH2:4][c:5]1[cH:6][cH:7][c:11]([OH:12])[cH:13][cH:14]1>CC(=O)O>[O:1]=[C:2]([OH:3])[CH2:4][c:5]1[cH:6][c:7]([N+:8](=[O:9])[O-:10])[c:11]([OH:12])[cH:13][cH:14]1\"},\"mapped_reaction_smiles\":\"O[N+:8](=[O:9])[O-:10].[O:1]=[C:2]([OH:3])[CH2:4][c:5]1[cH:6][cH:7][c:11]([OH:12])[cH:13][cH:14]1>CC(=O)O>[O:1]=[C:2]([OH:3])[CH2:4][c:5]1[cH:6][c:7]([N+:8](=[O:9])[O-:10])[c:11]([OH:12])[cH:13][cH:14]1\"}",
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{
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"smiles": "O=C(O)Cc1ccc(O)cc1"
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"smiles": "O=C(O)Cc1ccc(O)cc1",
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},
{
"id": "1176",
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"molecule": {
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"smiles": "Cc1ccnc(C)c1C(=O)O"
},
"smiles": "Cc1ccnc(C)c1C(=O)O",
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}
]
}
]
}
}