Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
Nc1ncc(C(=O)NCC(O)CO)c2scc(COc3ccc(Br)cc3)c12
InChiKey
NRGXTVPPRHONIC-UHFFFAOYSA-N
Route Signature
8a582b718b41da3096ec1a16722f4bf3fbaed00edc71600388f1b879c57d42ae
Synthesis route with 5 steps
Route tree structure (JSON format)
{
"route": {
"id": "sa_eb15f11df961924f68bc7b45",
"signature": "8a582b718b41da3096ec1a16722f4bf3fbaed00edc71600388f1b879c57d42ae",
"contentHash": "05da8d890150ea9d9f0f85d21e9b40ad6da0877160ced144ef6cbe055bfb225d",
"length": 5,
"isConvergent": false
},
"target": {
"id": "sa_ac0302cd6557258fea4e32a3",
"benchmarkSetId": "61e696668b63e77d7c2a29c0821768e1c383de8313852d6e995224859494442e",
"targetId": "n5-00582",
"moleculeId": "sa_3a5e6520f934cc35aaaa8f9d",
"smiles": "Nc1ncc(C(=O)NCC(O)CO)c2scc(COc3ccc(Br)cc3)c12",
"routeLength": 5,
"isConvergent": false,
"metadata": null,
"molecule": {
"id": "sa_3a5e6520f934cc35aaaa8f9d",
"inchikey": "NRGXTVPPRHONIC-UHFFFAOYSA-N",
"smiles": "Nc1ncc(C(=O)NCC(O)CO)c2scc(COc3ccc(Br)cc3)c12"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "13530",
"routeId": "sa_eb15f11df961924f68bc7b45",
"moleculeId": "sa_3a5e6520f934cc35aaaa8f9d",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_3a5e6520f934cc35aaaa8f9d",
"inchikey": "NRGXTVPPRHONIC-UHFFFAOYSA-N",
"smiles": "Nc1ncc(C(=O)NCC(O)CO)c2scc(COc3ccc(Br)cc3)c12"
},
"smiles": "Nc1ncc(C(=O)NCC(O)CO)c2scc(COc3ccc(Br)cc3)c12",
"reactionStepId": "sa_1d079a8d5a9d1613a3f5fc69",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20110071147A1;0258;1029759\",\"rsmi\":\"CCO[C:6]([c:5]1[cH:4][n:3][c:2]([NH2:1])[c:15]2[c:14]1[s:27][cH:26][c:16]2[CH2:17][O:18][c:19]1[cH:20][cH:21][c:22]([Br:23])[cH:24][cH:25]1)=[O:7].[NH2:8][CH2:9][CH:10]([OH:11])[CH2:12][OH:13]>CCOC(C)=O.CO>[NH2:1][c:2]1[n:3][cH:4][c:5]([C:6](=[O:7])[NH:8][CH2:9][CH:10]([OH:11])[CH2:12][OH:13])[c:14]2[c:15]1[c:16]([CH2:17][O:18][c:19]1[cH:20][cH:21][c:22]([Br:23])[cH:24][cH:25]1)[cH:26][s:27]2\"},\"mapped_reaction_smiles\":\"CCO[C:6]([c:5]1[cH:4][n:3][c:2]([NH2:1])[c:15]2[c:14]1[s:27][cH:26][c:16]2[CH2:17][O:18][c:19]1[cH:20][cH:21][c:22]([Br:23])[cH:24][cH:25]1)=[O:7].[NH2:8][CH2:9][CH:10]([OH:11])[CH2:12][OH:13]>CCOC(C)=O.CO>[NH2:1][c:2]1[n:3][cH:4][c:5]([C:6](=[O:7])[NH:8][CH2:9][CH:10]([OH:11])[CH2:12][OH:13])[c:14]2[c:15]1[c:16]([CH2:17][O:18][c:19]1[cH:20][cH:21][c:22]([Br:23])[cH:24][cH:25]1)[cH:26][s:27]2\"}",
"reactionStep": {
"id": "sa_1d079a8d5a9d1613a3f5fc69",
"reactionHash": "9d166dfa7a68bc0a2e57fb8fed2faa02d7cf1bd66f961f59c442691d08f179a2"
},
"children": [
{
"id": "13531",
"routeId": "sa_eb15f11df961924f68bc7b45",
"moleculeId": "sa_44037bd93869a4ce9110378e",
"parentId": "13530",
"isLeaf": false,
"molecule": {
"id": "sa_44037bd93869a4ce9110378e",
"inchikey": "AGSBUGHXQWLWRV-UHFFFAOYSA-N",
"smiles": "CCOC(=O)c1cnc(N)c2c(COc3ccc(Br)cc3)csc12"
},
"smiles": "CCOC(=O)c1cnc(N)c2c(COc3ccc(Br)cc3)csc12",
"reactionStepId": "sa_ac705959f6f93c80375e113f",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20110071147A1;0201;1029737\",\"rsmi\":\"Cl[c:9]1[n:8][cH:7][c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[c:12]2[c:11]1[c:15]([CH2:16][O:17][c:18]1[cH:19][cH:20][c:21]([Br:22])[cH:23][cH:24]1)[cH:14][s:13]2.[NH3:10]>C1COCCO1>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][n:8][c:9]([NH2:10])[c:11]2[c:12]1[s:13][cH:14][c:15]2[CH2:16][O:17][c:18]1[cH:19][cH:20][c:21]([Br:22])[cH:23][cH:24]1\"},\"mapped_reaction_smiles\":\"Cl[c:9]1[n:8][cH:7][c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[c:12]2[c:11]1[c:15]([CH2:16][O:17][c:18]1[cH:19][cH:20][c:21]([Br:22])[cH:23][cH:24]1)[cH:14][s:13]2.[NH3:10]>C1COCCO1>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][n:8][c:9]([NH2:10])[c:11]2[c:12]1[s:13][cH:14][c:15]2[CH2:16][O:17][c:18]1[cH:19][cH:20][c:21]([Br:22])[cH:23][cH:24]1\"}",
"reactionStep": {
"id": "sa_ac705959f6f93c80375e113f",
"reactionHash": "f34b7090e4238b8578761ee06d17980f955ee1f5916b567d0acecbbbd9444a9f"
},
"children": [
{
"id": "13532",
"routeId": "sa_eb15f11df961924f68bc7b45",
"moleculeId": "sa_0ff6ad76618ab2e4306a4126",
"parentId": "13531",
"isLeaf": false,
"molecule": {
"id": "sa_0ff6ad76618ab2e4306a4126",
"inchikey": "HWIIISIMJCDAIJ-UHFFFAOYSA-N",
"smiles": "CCOC(=O)c1cnc(Cl)c2c(COc3ccc(Br)cc3)csc12"
},
"smiles": "CCOC(=O)c1cnc(Cl)c2c(COc3ccc(Br)cc3)csc12",
"reactionStepId": "sa_7be25195a2dc0fa0eea096c5",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20110071147A1;0198;1029736\",\"rsmi\":\"Br[CH2:16][c:15]1[c:11]2[c:9]([Cl:10])[n:8][cH:7][c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[c:12]2[s:13][cH:14]1.[OH:17][c:18]1[cH:19][cH:20][c:21]([Br:22])[cH:23][cH:24]1>C1CCOC1.CN(C)C=O.O=C(O)O.[K+].[K+]>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][n:8][c:9]([Cl:10])[c:11]2[c:12]1[s:13][cH:14][c:15]2[CH2:16][O:17][c:18]1[cH:19][cH:20][c:21]([Br:22])[cH:23][cH:24]1\"},\"mapped_reaction_smiles\":\"Br[CH2:16][c:15]1[c:11]2[c:9]([Cl:10])[n:8][cH:7][c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[c:12]2[s:13][cH:14]1.[OH:17][c:18]1[cH:19][cH:20][c:21]([Br:22])[cH:23][cH:24]1>C1CCOC1.CN(C)C=O.O=C(O)O.[K+].[K+]>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][n:8][c:9]([Cl:10])[c:11]2[c:12]1[s:13][cH:14][c:15]2[CH2:16][O:17][c:18]1[cH:19][cH:20][c:21]([Br:22])[cH:23][cH:24]1\"}",
"reactionStep": {
"id": "sa_7be25195a2dc0fa0eea096c5",
"reactionHash": "e6c9a23662ee95004daa4036a177bdba3e4d57ffdf70657ef0a9fcbcd9bc8ce9"
},
"children": [
{
"id": "13533",
"routeId": "sa_eb15f11df961924f68bc7b45",
"moleculeId": "sa_a39df90fd8de03f4af45b4e1",
"parentId": "13532",
"isLeaf": true,
"molecule": {
"id": "sa_a39df90fd8de03f4af45b4e1",
"inchikey": "GZFGOTFRPZRKDS-UHFFFAOYSA-N",
"smiles": "Oc1ccc(Br)cc1"
},
"smiles": "Oc1ccc(Br)cc1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "13534",
"routeId": "sa_eb15f11df961924f68bc7b45",
"moleculeId": "sa_40337abd21ee1ea9418f20df",
"parentId": "13532",
"isLeaf": false,
"molecule": {
"id": "sa_40337abd21ee1ea9418f20df",
"inchikey": "LXLXFZVZXDUUSO-UHFFFAOYSA-N",
"smiles": "CCOC(=O)c1cnc(Cl)c2c(CBr)csc12"
},
"smiles": "CCOC(=O)c1cnc(Cl)c2c(CBr)csc12",
"reactionStepId": "sa_19efb994dc8f50565fa2cac1",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20110071147A1;0185;1029732\",\"rsmi\":\"O=C1CCC(=O)N1[Br:17].[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][n:8][c:9]([Cl:10])[c:11]2[c:12]1[s:13][cH:14][c:15]2[CH3:16]>CC(C)(C#N)N=NC(C)(C)C#N.ClC(Cl)(Cl)Cl>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][n:8][c:9]([Cl:10])[c:11]2[c:12]1[s:13][cH:14][c:15]2[CH2:16][Br:17]\"},\"mapped_reaction_smiles\":\"O=C1CCC(=O)N1[Br:17].[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][n:8][c:9]([Cl:10])[c:11]2[c:12]1[s:13][cH:14][c:15]2[CH3:16]>CC(C)(C#N)N=NC(C)(C)C#N.ClC(Cl)(Cl)Cl>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][n:8][c:9]([Cl:10])[c:11]2[c:12]1[s:13][cH:14][c:15]2[CH2:16][Br:17]\"}",
"reactionStep": {
"id": "sa_19efb994dc8f50565fa2cac1",
"reactionHash": "49720a21e67e4e192fc1724e93b6f3285ab1086f6db41b5168d0e91489f9c165"
},
"children": [
{
"id": "13535",
"routeId": "sa_eb15f11df961924f68bc7b45",
"moleculeId": "sa_a36f2ce3c2bf4075080caed3",
"parentId": "13534",
"isLeaf": false,
"molecule": {
"id": "sa_a36f2ce3c2bf4075080caed3",
"inchikey": "OGGMPOZTPMKXCG-UHFFFAOYSA-N",
"smiles": "CCOC(=O)c1cnc(Cl)c2c(C)csc12"
},
"smiles": "CCOC(=O)c1cnc(Cl)c2c(C)csc12",
"reactionStepId": "sa_febc8535d593e7b550212b00",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20110071147A1;0182;1029731\",\"rsmi\":\"O=P(Cl)(Cl)[Cl:10].O=[c:9]1[nH:8][cH:7][c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[c:12]2[c:11]1[c:15]([CH3:16])[cH:14][s:13]2>CCN(C(C)C)C(C)C.CN(C)C=O>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][n:8][c:9]([Cl:10])[c:11]2[c:12]1[s:13][cH:14][c:15]2[CH3:16]\"},\"mapped_reaction_smiles\":\"O=P(Cl)(Cl)[Cl:10].O=[c:9]1[nH:8][cH:7][c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[c:12]2[c:11]1[c:15]([CH3:16])[cH:14][s:13]2>CCN(C(C)C)C(C)C.CN(C)C=O>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][n:8][c:9]([Cl:10])[c:11]2[c:12]1[s:13][cH:14][c:15]2[CH3:16]\"}",
"reactionStep": {
"id": "sa_febc8535d593e7b550212b00",
"reactionHash": "5638863c1de4465bd275a4538fd1ccf5d55da0afe5d7981b8f84d67354009b49"
},
"children": [
{
"id": "13536",
"routeId": "sa_eb15f11df961924f68bc7b45",
"moleculeId": "sa_312a7cd3d48a055e9bc98180",
"parentId": "13535",
"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": "13537",
"routeId": "sa_eb15f11df961924f68bc7b45",
"moleculeId": "sa_1091600c05248bce0cb31cff",
"parentId": "13535",
"isLeaf": true,
"molecule": {
"id": "sa_1091600c05248bce0cb31cff",
"inchikey": "ZQIKCKYDCDCDJE-UHFFFAOYSA-N",
"smiles": "CCOC(=O)c1c[nH]c(=O)c2c(C)csc12"
},
"smiles": "CCOC(=O)c1c[nH]c(=O)c2c(C)csc12",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
},
{
"id": "13538",
"routeId": "sa_eb15f11df961924f68bc7b45",
"moleculeId": "sa_ccdcf23ac83e7a68bfa4f2e5",
"parentId": "13534",
"isLeaf": true,
"molecule": {
"id": "sa_ccdcf23ac83e7a68bfa4f2e5",
"inchikey": "PCLIMKBDDGJMGD-UHFFFAOYSA-N",
"smiles": "O=C1CCC(=O)N1Br"
},
"smiles": "O=C1CCC(=O)N1Br",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
}
]
},
{
"id": "13539",
"routeId": "sa_eb15f11df961924f68bc7b45",
"moleculeId": "sa_c9679fdd876f32f86b77fb69",
"parentId": "13531",
"isLeaf": true,
"molecule": {
"id": "sa_c9679fdd876f32f86b77fb69",
"inchikey": "QGZKDVFQNNGYKY-UHFFFAOYSA-N",
"smiles": "N"
},
"smiles": "N",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
},
{
"id": "13540",
"routeId": "sa_eb15f11df961924f68bc7b45",
"moleculeId": "sa_0ada4edb01d3ecccaf41cd18",
"parentId": "13530",
"isLeaf": true,
"molecule": {
"id": "sa_0ada4edb01d3ecccaf41cd18",
"inchikey": "KQIGMPWTAHJUMN-UHFFFAOYSA-N",
"smiles": "NCC(O)CO"
},
"smiles": "NCC(O)CO",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
}
}