Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
CC1(NC(=O)OC(C)(C)C)CCCN(c2c(N)cnc3c2CCC3)C1
InChiKey
DMUGDRKLZRAHGQ-UHFFFAOYSA-N
Route Signature
99d57757955f6aae594218a3cbffbc407ab99c12afb72451aa75e80e489bdfe8
Synthesis route with 6 steps
Route tree structure (JSON format)
{
"route": {
"id": "sa_f34708388fa334aadcbaac02",
"signature": "99d57757955f6aae594218a3cbffbc407ab99c12afb72451aa75e80e489bdfe8",
"contentHash": "32e07d87df5913845cbbd3818d0ab75fcd78e6a59afbf365aa32bbb51530e0c2",
"length": 6,
"isConvergent": false
},
"target": {
"id": "sa_98ebb1c745bb024440b9762e",
"benchmarkSetId": "f925e688d731a0ad4e3aa6a505df094f6d3ca64ce3facc312bc5f64731921b33",
"targetId": "n5-00164",
"moleculeId": "sa_f5017bce83df8879ca682cee",
"smiles": "CC1(NC(=O)OC(C)(C)C)CCCN(c2c(N)cnc3c2CCC3)C1",
"routeLength": 6,
"isConvergent": false,
"metadata": null,
"molecule": {
"id": "sa_f5017bce83df8879ca682cee",
"inchikey": "DMUGDRKLZRAHGQ-UHFFFAOYSA-N",
"smiles": "CC1(NC(=O)OC(C)(C)C)CCCN(c2c(N)cnc3c2CCC3)C1"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "3556",
"routeId": "sa_f34708388fa334aadcbaac02",
"moleculeId": "sa_f5017bce83df8879ca682cee",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_f5017bce83df8879ca682cee",
"inchikey": "DMUGDRKLZRAHGQ-UHFFFAOYSA-N",
"smiles": "CC1(NC(=O)OC(C)(C)C)CCCN(c2c(N)cnc3c2CCC3)C1"
},
"smiles": "CC1(NC(=O)OC(C)(C)C)CCCN(c2c(N)cnc3c2CCC3)C1",
"reactionStepId": "sa_4a14f46e82c4451174f640f5",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US09200004B2;1035;1702144\",\"rsmi\":\"O=[N+:24]([O-])[c:23]1[c:15]([N:14]2[CH2:13][CH2:12][CH2:11][C:2]([CH3:1])([NH:3][C:4](=[O:5])[O:6][C:7]([CH3:8])([CH3:9])[CH3:10])[CH2:25]2)[c:16]2[c:20]([n:21][cH:22]1)[CH2:19][CH2:18][CH2:17]2>CC(=O)O.CCOC(C)=O.[Fe]>[CH3:1][C:2]1([NH:3][C:4](=[O:5])[O:6][C:7]([CH3:8])([CH3:9])[CH3:10])[CH2:11][CH2:12][CH2:13][N:14]([c:15]2[c:16]3[c:20]([n:21][cH:22][c:23]2[NH2:24])[CH2:19][CH2:18][CH2:17]3)[CH2:25]1\"},\"mapped_reaction_smiles\":\"O=[N+:24]([O-])[c:23]1[c:15]([N:14]2[CH2:13][CH2:12][CH2:11][C:2]([CH3:1])([NH:3][C:4](=[O:5])[O:6][C:7]([CH3:8])([CH3:9])[CH3:10])[CH2:25]2)[c:16]2[c:20]([n:21][cH:22]1)[CH2:19][CH2:18][CH2:17]2>CC(=O)O.CCOC(C)=O.[Fe]>[CH3:1][C:2]1([NH:3][C:4](=[O:5])[O:6][C:7]([CH3:8])([CH3:9])[CH3:10])[CH2:11][CH2:12][CH2:13][N:14]([c:15]2[c:16]3[c:20]([n:21][cH:22][c:23]2[NH2:24])[CH2:19][CH2:18][CH2:17]3)[CH2:25]1\"}",
"reactionStep": {
"id": "sa_4a14f46e82c4451174f640f5",
"reactionHash": "bd9cf38a968a7a63617d8aac7454dc070be952f62f299597cc6545855cdccc4d"
},
"children": [
{
"id": "3557",
"routeId": "sa_f34708388fa334aadcbaac02",
"moleculeId": "sa_59c170bf6bac5481000ba59d",
"parentId": "3556",
"isLeaf": false,
"molecule": {
"id": "sa_59c170bf6bac5481000ba59d",
"inchikey": "NMICTUQZCIOHGF-UHFFFAOYSA-N",
"smiles": "CC1(NC(=O)OC(C)(C)C)CCCN(c2c([N+](=O)[O-])cnc3c2CCC3)C1"
},
"smiles": "CC1(NC(=O)OC(C)(C)C)CCCN(c2c([N+](=O)[O-])cnc3c2CCC3)C1",
"reactionStepId": "sa_d4656da7f78639a8401c299b",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US09200004B2;1033;1702143\",\"rsmi\":\"Cl[c:15]1[c:16]2[c:20]([n:21][cH:22][c:23]1[N+:24](=[O:25])[O-:26])[CH2:19][CH2:18][CH2:17]2.[CH3:1][C:2]1([NH:3][C:4](=[O:5])[O:6][C:7]([CH3:8])([CH3:9])[CH3:10])[CH2:11][CH2:12][CH2:13][NH:14][CH2:27]1>CC(C)O.CCN(CC)CC>[CH3:1][C:2]1([NH:3][C:4](=[O:5])[O:6][C:7]([CH3:8])([CH3:9])[CH3:10])[CH2:11][CH2:12][CH2:13][N:14]([c:15]2[c:16]3[c:20]([n:21][cH:22][c:23]2[N+:24](=[O:25])[O-:26])[CH2:19][CH2:18][CH2:17]3)[CH2:27]1\"},\"mapped_reaction_smiles\":\"Cl[c:15]1[c:16]2[c:20]([n:21][cH:22][c:23]1[N+:24](=[O:25])[O-:26])[CH2:19][CH2:18][CH2:17]2.[CH3:1][C:2]1([NH:3][C:4](=[O:5])[O:6][C:7]([CH3:8])([CH3:9])[CH3:10])[CH2:11][CH2:12][CH2:13][NH:14][CH2:27]1>CC(C)O.CCN(CC)CC>[CH3:1][C:2]1([NH:3][C:4](=[O:5])[O:6][C:7]([CH3:8])([CH3:9])[CH3:10])[CH2:11][CH2:12][CH2:13][N:14]([c:15]2[c:16]3[c:20]([n:21][cH:22][c:23]2[N+:24](=[O:25])[O-:26])[CH2:19][CH2:18][CH2:17]3)[CH2:27]1\"}",
"reactionStep": {
"id": "sa_d4656da7f78639a8401c299b",
"reactionHash": "59f1e4690f970697b34f87eb6b7afc194167beeb3bdd816b7cfe469c4c4cd209"
},
"children": [
{
"id": "3558",
"routeId": "sa_f34708388fa334aadcbaac02",
"moleculeId": "sa_3fdfd74769596fe20455614e",
"parentId": "3557",
"isLeaf": false,
"molecule": {
"id": "sa_3fdfd74769596fe20455614e",
"inchikey": "HBDOSWBGMPHGBZ-UHFFFAOYSA-N",
"smiles": "O=[N+]([O-])c1cnc2c(c1Cl)CCC2"
},
"smiles": "O=[N+]([O-])c1cnc2c(c1Cl)CCC2",
"reactionStepId": "sa_c6fb0e43ffc3b990d697b06c",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US09200004B2;0693;1702038\",\"rsmi\":\"O=P(Cl)(Cl)[Cl:13].O[c:12]1[c:4]([N+:2](=[O:1])[O-:3])[cH:5][n:6][c:7]2[c:11]1[CH2:10][CH2:9][CH2:8]2>>[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][n:6][c:7]2[c:11]([c:12]1[Cl:13])[CH2:10][CH2:9][CH2:8]2\"},\"mapped_reaction_smiles\":\"O=P(Cl)(Cl)[Cl:13].O[c:12]1[c:4]([N+:2](=[O:1])[O-:3])[cH:5][n:6][c:7]2[c:11]1[CH2:10][CH2:9][CH2:8]2>>[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][n:6][c:7]2[c:11]([c:12]1[Cl:13])[CH2:10][CH2:9][CH2:8]2\"}",
"reactionStep": {
"id": "sa_c6fb0e43ffc3b990d697b06c",
"reactionHash": "ff1b31c44f4ebd3b36d3fbf98525521fc84cf96b4f28e58828816550c1f3ed14"
},
"children": [
{
"id": "3559",
"routeId": "sa_f34708388fa334aadcbaac02",
"moleculeId": "sa_999b47b1f785592f44f82e4c",
"parentId": "3558",
"isLeaf": false,
"molecule": {
"id": "sa_999b47b1f785592f44f82e4c",
"inchikey": "BUHVJKIYTUTIMG-UHFFFAOYSA-N",
"smiles": "O=[N+]([O-])c1cnc2c(c1O)CCC2"
},
"smiles": "O=[N+]([O-])c1cnc2c(c1O)CCC2",
"reactionStepId": "sa_382510c1099c73718b712167",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US09200004B2;0691;1702037\",\"rsmi\":\"C[O:13][c:12]1[c:4]([N+:2](=[O:1])[O-:3])[cH:5][n:6][c:7]2[c:11]1[CH2:10][CH2:9][CH2:8]2>Br.CC(=O)O>[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][n:6][c:7]2[c:11]([c:12]1[OH:13])[CH2:10][CH2:9][CH2:8]2\"},\"mapped_reaction_smiles\":\"C[O:13][c:12]1[c:4]([N+:2](=[O:1])[O-:3])[cH:5][n:6][c:7]2[c:11]1[CH2:10][CH2:9][CH2:8]2>Br.CC(=O)O>[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][n:6][c:7]2[c:11]([c:12]1[OH:13])[CH2:10][CH2:9][CH2:8]2\"}",
"reactionStep": {
"id": "sa_382510c1099c73718b712167",
"reactionHash": "9b84038b9fe063395537c33d351f0b133f35ffbe3ba5a038cda5f8edbd22839a"
},
"children": [
{
"id": "3560",
"routeId": "sa_f34708388fa334aadcbaac02",
"moleculeId": "sa_d24c99fbd8d3cc14c6b1862c",
"parentId": "3559",
"isLeaf": false,
"molecule": {
"id": "sa_d24c99fbd8d3cc14c6b1862c",
"inchikey": "UQWXOOVNSDNNHT-UHFFFAOYSA-N",
"smiles": "COc1c([N+](=O)[O-])cnc2c1CCC2"
},
"smiles": "COc1c([N+](=O)[O-])cnc2c1CCC2",
"reactionStepId": "sa_bcf2077af53035eb95664330",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US09200004B2;0689;1702036\",\"rsmi\":\"O=[N+:12]([OH:13])[O-:14].[CH3:1][O:2][c:3]1[c:4]2[c:8]([n:9][cH:10][cH:11]1)[CH2:7][CH2:6][CH2:5]2>O=S(=O)(O)O.[K+].[Na+].O>[CH3:1][O:2][c:3]1[c:4]2[c:8]([n:9][cH:10][c:11]1[N+:12](=[O:13])[O-:14])[CH2:7][CH2:6][CH2:5]2\"},\"mapped_reaction_smiles\":\"O=[N+:12]([OH:13])[O-:14].[CH3:1][O:2][c:3]1[c:4]2[c:8]([n:9][cH:10][cH:11]1)[CH2:7][CH2:6][CH2:5]2>O=S(=O)(O)O.[K+].[Na+].O>[CH3:1][O:2][c:3]1[c:4]2[c:8]([n:9][cH:10][c:11]1[N+:12](=[O:13])[O-:14])[CH2:7][CH2:6][CH2:5]2\"}",
"reactionStep": {
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"reactionHash": "979ecdf686b99d1d2bdf0384a2f58d396a3f6fd0e1c6c76909636637ac48c0db"
},
"children": [
{
"id": "3561",
"routeId": "sa_f34708388fa334aadcbaac02",
"moleculeId": "sa_edac0a7fd043198784a28dd9",
"parentId": "3560",
"isLeaf": true,
"molecule": {
"id": "sa_edac0a7fd043198784a28dd9",
"inchikey": "GRYLNZFGIOXLOG-UHFFFAOYSA-N",
"smiles": "O=[N+]([O-])O"
},
"smiles": "O=[N+]([O-])O",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "3562",
"routeId": "sa_f34708388fa334aadcbaac02",
"moleculeId": "sa_50e9c2990dff33a02fc65558",
"parentId": "3560",
"isLeaf": false,
"molecule": {
"id": "sa_50e9c2990dff33a02fc65558",
"inchikey": "VTFDRLJZDKJRPA-UHFFFAOYSA-N",
"smiles": "COc1ccnc2c1CCC2"
},
"smiles": "COc1ccnc2c1CCC2",
"reactionStepId": "sa_86946af8e9a5bd38c32b690f",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US09200004B2;0687;1702035\",\"rsmi\":\"Cl[c:3]1[c:4]2[c:8]([n:9][cH:10][cH:11]1)[CH2:7][CH2:6][CH2:5]2.[CH3:1][OH:2]>CCOC(C)=O.CO.Cl.[Na+]>[CH3:1][O:2][c:3]1[c:4]2[c:8]([n:9][cH:10][cH:11]1)[CH2:7][CH2:6][CH2:5]2\"},\"mapped_reaction_smiles\":\"Cl[c:3]1[c:4]2[c:8]([n:9][cH:10][cH:11]1)[CH2:7][CH2:6][CH2:5]2.[CH3:1][OH:2]>CCOC(C)=O.CO.Cl.[Na+]>[CH3:1][O:2][c:3]1[c:4]2[c:8]([n:9][cH:10][cH:11]1)[CH2:7][CH2:6][CH2:5]2\"}",
"reactionStep": {
"id": "sa_86946af8e9a5bd38c32b690f",
"reactionHash": "ed457670cf1a4f66d9ee62cdba4c29c4b64ce52ccc1b17b94592957f0c7340f2"
},
"children": [
{
"id": "3563",
"routeId": "sa_f34708388fa334aadcbaac02",
"moleculeId": "sa_0a4dadab8bca0619b56206fd",
"parentId": "3562",
"isLeaf": true,
"molecule": {
"id": "sa_0a4dadab8bca0619b56206fd",
"inchikey": "IGDLNAWHTASKKG-UHFFFAOYSA-N",
"smiles": "Clc1ccnc2c1CCC2"
},
"smiles": "Clc1ccnc2c1CCC2",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "3564",
"routeId": "sa_f34708388fa334aadcbaac02",
"moleculeId": "sa_061a3efbe4d30c2cc87d48e7",
"parentId": "3562",
"isLeaf": true,
"molecule": {
"id": "sa_061a3efbe4d30c2cc87d48e7",
"inchikey": "OKKJLVBELUTLKV-UHFFFAOYSA-N",
"smiles": "CO"
},
"smiles": "CO",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
}
]
}
]
},
{
"id": "3565",
"routeId": "sa_f34708388fa334aadcbaac02",
"moleculeId": "sa_312a7cd3d48a055e9bc98180",
"parentId": "3558",
"isLeaf": true,
"molecule": {
"id": "sa_312a7cd3d48a055e9bc98180",
"inchikey": "XHXFXVLFKHQFAL-UHFFFAOYSA-N",
"smiles": "O=P(Cl)(Cl)Cl"
},
"smiles": "O=P(Cl)(Cl)Cl",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
},
{
"id": "3566",
"routeId": "sa_f34708388fa334aadcbaac02",
"moleculeId": "sa_d9ae13c8863f8bbca13a4a5f",
"parentId": "3557",
"isLeaf": true,
"molecule": {
"id": "sa_d9ae13c8863f8bbca13a4a5f",
"inchikey": "IKLFTJQKKCELGD-UHFFFAOYSA-N",
"smiles": "CC1(N=C(O)OC(C)(C)C)CCCNC1"
},
"smiles": "CC1(NC(=O)OC(C)(C)C)CCCNC1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
}
]
}
}