Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
COc1cc(N2CCN(C)CC2)c([N+](=O)[O-])cc1Nc1nccc(-c2cn(C)c3ccccc23)n1
InChiKey
HACMLTQTHAZCLX-UHFFFAOYSA-N
Route Signature
fcfdef4634ac1a16cd5cd06275b2a4c4405cee56d4f8a7ece6d215d1e4a19a33
Synthesis route with 4 steps (convergent)
Route tree structure (JSON format)
{
"route": {
"id": "sa_ddcdbc739e0bcd0efb22c18a",
"signature": "fcfdef4634ac1a16cd5cd06275b2a4c4405cee56d4f8a7ece6d215d1e4a19a33",
"contentHash": "b3f47d085622603653795cc5a5971dbd1faea73031e04789c17b4ef335d203c4",
"length": 4,
"isConvergent": true
},
"target": {
"id": "sa_2eb4bd6188c2e3f034aac4e7",
"benchmarkSetId": "3895c2909c53593560c5ba610abc7e6df80513dfd8624165c560451735097d36",
"targetId": "n5-00576",
"moleculeId": "sa_58f5e443aba73615c9befed9",
"smiles": "COc1cc(N2CCN(C)CC2)c([N+](=O)[O-])cc1Nc1nccc(-c2cn(C)c3ccccc23)n1",
"routeLength": 4,
"isConvergent": true,
"metadata": null,
"molecule": {
"id": "sa_58f5e443aba73615c9befed9",
"inchikey": "HACMLTQTHAZCLX-UHFFFAOYSA-N",
"smiles": "COc1cc(N2CCN(C)CC2)c([N+](=O)[O-])cc1Nc1nccc(-c2cn(C)c3ccccc23)n1"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "926",
"routeId": "sa_ddcdbc739e0bcd0efb22c18a",
"moleculeId": "sa_58f5e443aba73615c9befed9",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_58f5e443aba73615c9befed9",
"inchikey": "HACMLTQTHAZCLX-UHFFFAOYSA-N",
"smiles": "COc1cc(N2CCN(C)CC2)c([N+](=O)[O-])cc1Nc1nccc(-c2cn(C)c3ccccc23)n1"
},
"smiles": "COc1cc(N2CCN(C)CC2)c([N+](=O)[O-])cc1Nc1nccc(-c2cn(C)c3ccccc23)n1",
"reactionStepId": "sa_2d2b1c9209b516a9734a1f62",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20130053409A1;0640;1339667\",\"rsmi\":\"F[c:27]1[c:23]([N+:24](=[O:25])[O-:26])[cH:22][c:4]([NH:5][c:6]2[n:7][cH:8][cH:9][c:10](-[c:11]3[cH:12][n:13]([CH3:14])[c:15]4[cH:16][cH:17][cH:18][cH:19][c:20]34)[n:21]2)[c:3]([O:2][CH3:1])[cH:35]1.[NH:28]1[CH2:29][CH2:30][N:31]([CH3:32])[CH2:33][CH2:34]1>CC(=O)N(C)C.CCN(C(C)C)C(C)C.CO.COc1cc(F)c([N+](=O)[O-])cc1Nc1ncc(Cl)c(-c2cn(C)c3ccccc23)n1>[CH3:1][O:2][c:3]1[c:4]([NH:5][c:6]2[n:7][cH:8][cH:9][c:10](-[c:11]3[cH:12][n:13]([CH3:14])[c:15]4[cH:16][cH:17][cH:18][cH:19][c:20]34)[n:21]2)[cH:22][c:23]([N+:24](=[O:25])[O-:26])[c:27]([N:28]2[CH2:29][CH2:30][N:31]([CH3:32])[CH2:33][CH2:34]2)[cH:35]1\"},\"mapped_reaction_smiles\":\"F[c:27]1[c:23]([N+:24](=[O:25])[O-:26])[cH:22][c:4]([NH:5][c:6]2[n:7][cH:8][cH:9][c:10](-[c:11]3[cH:12][n:13]([CH3:14])[c:15]4[cH:16][cH:17][cH:18][cH:19][c:20]34)[n:21]2)[c:3]([O:2][CH3:1])[cH:35]1.[NH:28]1[CH2:29][CH2:30][N:31]([CH3:32])[CH2:33][CH2:34]1>CC(=O)N(C)C.CCN(C(C)C)C(C)C.CO.COc1cc(F)c([N+](=O)[O-])cc1Nc1ncc(Cl)c(-c2cn(C)c3ccccc23)n1>[CH3:1][O:2][c:3]1[c:4]([NH:5][c:6]2[n:7][cH:8][cH:9][c:10](-[c:11]3[cH:12][n:13]([CH3:14])[c:15]4[cH:16][cH:17][cH:18][cH:19][c:20]34)[n:21]2)[cH:22][c:23]([N+:24](=[O:25])[O-:26])[c:27]([N:28]2[CH2:29][CH2:30][N:31]([CH3:32])[CH2:33][CH2:34]2)[cH:35]1\"}",
"reactionStep": {
"id": "sa_2d2b1c9209b516a9734a1f62",
"reactionHash": "99cf9047cf77cdead91dbe12be9b2115036f71e61a53d1ce2fd92dd9b50b3732"
},
"children": [
{
"id": "927",
"routeId": "sa_ddcdbc739e0bcd0efb22c18a",
"moleculeId": "sa_513cbf1b8d13aff0b62eb838",
"parentId": "926",
"isLeaf": true,
"molecule": {
"id": "sa_513cbf1b8d13aff0b62eb838",
"inchikey": "PVOAHINGSUIXLS-UHFFFAOYSA-N",
"smiles": "CN1CCNCC1"
},
"smiles": "CN1CCNCC1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "928",
"routeId": "sa_ddcdbc739e0bcd0efb22c18a",
"moleculeId": "sa_11f601b43476c61a85fbaecd",
"parentId": "926",
"isLeaf": false,
"molecule": {
"id": "sa_11f601b43476c61a85fbaecd",
"inchikey": "SZTYQQYYIMVETL-UHFFFAOYSA-N",
"smiles": "COc1cc(F)c([N+](=O)[O-])cc1Nc1nccc(-c2cn(C)c3ccccc23)n1"
},
"smiles": "COc1cc(F)c([N+](=O)[O-])cc1Nc1nccc(-c2cn(C)c3ccccc23)n1",
"reactionStepId": "sa_cc592a324f038dd07d2308f9",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20130053409A1;0659;1339684\",\"rsmi\":\"Cl[c:6]1[n:7][cH:8][cH:9][c:10](-[c:11]2[cH:12][n:13]([CH3:14])[c:15]3[cH:16][cH:17][cH:18][cH:19][c:20]23)[n:21]1.[CH3:1][O:2][c:3]1[c:4]([NH2:5])[cH:22][c:23]([N+:24](=[O:25])[O-:26])[c:27]([F:28])[cH:29]1>CCCC(C)O.Cc1ccc(S(=O)(=O)O)cc1.O>[CH3:1][O:2][c:3]1[c:4]([NH:5][c:6]2[n:7][cH:8][cH:9][c:10](-[c:11]3[cH:12][n:13]([CH3:14])[c:15]4[cH:16][cH:17][cH:18][cH:19][c:20]34)[n:21]2)[cH:22][c:23]([N+:24](=[O:25])[O-:26])[c:27]([F:28])[cH:29]1\"},\"mapped_reaction_smiles\":\"Cl[c:6]1[n:7][cH:8][cH:9][c:10](-[c:11]2[cH:12][n:13]([CH3:14])[c:15]3[cH:16][cH:17][cH:18][cH:19][c:20]23)[n:21]1.[CH3:1][O:2][c:3]1[c:4]([NH2:5])[cH:22][c:23]([N+:24](=[O:25])[O-:26])[c:27]([F:28])[cH:29]1>CCCC(C)O.Cc1ccc(S(=O)(=O)O)cc1.O>[CH3:1][O:2][c:3]1[c:4]([NH:5][c:6]2[n:7][cH:8][cH:9][c:10](-[c:11]3[cH:12][n:13]([CH3:14])[c:15]4[cH:16][cH:17][cH:18][cH:19][c:20]34)[n:21]2)[cH:22][c:23]([N+:24](=[O:25])[O-:26])[c:27]([F:28])[cH:29]1\"}",
"reactionStep": {
"id": "sa_cc592a324f038dd07d2308f9",
"reactionHash": "ca9bffb7938a128a6eee048810db1788cb06efa157c999ea5619550407584618"
},
"children": [
{
"id": "929",
"routeId": "sa_ddcdbc739e0bcd0efb22c18a",
"moleculeId": "sa_338d09ba3b3f38cf56fa0347",
"parentId": "928",
"isLeaf": false,
"molecule": {
"id": "sa_338d09ba3b3f38cf56fa0347",
"inchikey": "FYSIGSQCZXQTIH-UHFFFAOYSA-N",
"smiles": "COc1cc(F)c([N+](=O)[O-])cc1N"
},
"smiles": "COc1cc(F)c([N+](=O)[O-])cc1N",
"reactionStepId": "sa_2accc798f21241202b09b4e4",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20130053409A1;0547;1339593\",\"rsmi\":\"[CH3:1][O:2][c:3]1[c:4]([NH2:5])[cH:6][cH:7][c:11]([F:12])[cH:13]1.O[N+:8](=[O:9])[O-:10]>O=S(=O)(O)O.[K+].N.O>[CH3:1][O:2][c:3]1[c:4]([NH2:5])[cH:6][c:7]([N+:8](=[O:9])[O-:10])[c:11]([F:12])[cH:13]1\"},\"mapped_reaction_smiles\":\"[CH3:1][O:2][c:3]1[c:4]([NH2:5])[cH:6][cH:7][c:11]([F:12])[cH:13]1.O[N+:8](=[O:9])[O-:10]>O=S(=O)(O)O.[K+].N.O>[CH3:1][O:2][c:3]1[c:4]([NH2:5])[cH:6][c:7]([N+:8](=[O:9])[O-:10])[c:11]([F:12])[cH:13]1\"}",
"reactionStep": {
"id": "sa_2accc798f21241202b09b4e4",
"reactionHash": "d63225ce1b0ea700495ac24ab8bc7862746afec5fdc3619a62f09ed862ae3454"
},
"children": [
{
"id": "930",
"routeId": "sa_ddcdbc739e0bcd0efb22c18a",
"moleculeId": "sa_3f31caf7cabc1fa99669f894",
"parentId": "929",
"isLeaf": true,
"molecule": {
"id": "sa_3f31caf7cabc1fa99669f894",
"inchikey": "BNRRMRUVYDETQC-UHFFFAOYSA-N",
"smiles": "COc1cc(F)ccc1N"
},
"smiles": "COc1cc(F)ccc1N",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "931",
"routeId": "sa_ddcdbc739e0bcd0efb22c18a",
"moleculeId": "sa_edac0a7fd043198784a28dd9",
"parentId": "929",
"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": "932",
"routeId": "sa_ddcdbc739e0bcd0efb22c18a",
"moleculeId": "sa_41bbe78c6b7a0769aaf0b265",
"parentId": "928",
"isLeaf": false,
"molecule": {
"id": "sa_41bbe78c6b7a0769aaf0b265",
"inchikey": "IIBWXYHPBMUNJP-UHFFFAOYSA-N",
"smiles": "Cn1cc(-c2ccnc(Cl)n2)c2ccccc21"
},
"smiles": "Cn1cc(-c2ccnc(Cl)n2)c2ccccc21",
"reactionStepId": "sa_77cc492a743ec5277e9178fe",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20130053409A1;0660;1339685\",\"rsmi\":\"I[CH3:1].[nH:2]1[cH:3][c:4](-[c:5]2[n:6][c:7]([Cl:8])[n:9][cH:10][cH:11]2)[c:12]2[cH:13][cH:14][cH:15][cH:16][c:17]12>C1CCOC1.[HH].[Na+]>[CH3:1][n:2]1[cH:3][c:4](-[c:5]2[n:6][c:7]([Cl:8])[n:9][cH:10][cH:11]2)[c:12]2[cH:13][cH:14][cH:15][cH:16][c:17]12\"},\"mapped_reaction_smiles\":\"I[CH3:1].[nH:2]1[cH:3][c:4](-[c:5]2[n:6][c:7]([Cl:8])[n:9][cH:10][cH:11]2)[c:12]2[cH:13][cH:14][cH:15][cH:16][c:17]12>C1CCOC1.[HH].[Na+]>[CH3:1][n:2]1[cH:3][c:4](-[c:5]2[n:6][c:7]([Cl:8])[n:9][cH:10][cH:11]2)[c:12]2[cH:13][cH:14][cH:15][cH:16][c:17]12\"}",
"reactionStep": {
"id": "sa_77cc492a743ec5277e9178fe",
"reactionHash": "87cbaf62b4bc7406fa70bf6f8d76a141fcbd4b1fd4c3038fb5bdcd75fbaa9754"
},
"children": [
{
"id": "933",
"routeId": "sa_ddcdbc739e0bcd0efb22c18a",
"moleculeId": "sa_82fdccf7d1cc329c9db73f21",
"parentId": "932",
"isLeaf": true,
"molecule": {
"id": "sa_82fdccf7d1cc329c9db73f21",
"inchikey": "INQOMBQAUSQDDS-UHFFFAOYSA-N",
"smiles": "CI"
},
"smiles": "CI",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "934",
"routeId": "sa_ddcdbc739e0bcd0efb22c18a",
"moleculeId": "sa_faac9715a1687b3e01a82eaf",
"parentId": "932",
"isLeaf": false,
"molecule": {
"id": "sa_faac9715a1687b3e01a82eaf",
"inchikey": "YJGKIMCJZOZIOQ-UHFFFAOYSA-N",
"smiles": "Clc1nccc(-c2c[nH]c3ccccc23)n1"
},
"smiles": "Clc1nccc(-c2c[nH]c3ccccc23)n1",
"reactionStepId": "sa_13f6efe8884a0e8eed520b9c",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20130053409A1;0662;1339686\",\"rsmi\":\"Cl[c:6]1[cH:5][cH:4][n:3][c:2]([Cl:1])[n:16]1.[cH:7]1[cH:8][nH:9][c:10]2[cH:11][cH:12][cH:13][cH:14][c:15]12>C[Mg+].ClCCCl.Br>[Cl:1][c:2]1[n:3][cH:4][cH:5][c:6](-[c:7]2[cH:8][nH:9][c:10]3[cH:11][cH:12][cH:13][cH:14][c:15]23)[n:16]1\"},\"mapped_reaction_smiles\":\"Cl[c:6]1[cH:5][cH:4][n:3][c:2]([Cl:1])[n:16]1.[cH:7]1[cH:8][nH:9][c:10]2[cH:11][cH:12][cH:13][cH:14][c:15]12>C[Mg+].ClCCCl.Br>[Cl:1][c:2]1[n:3][cH:4][cH:5][c:6](-[c:7]2[cH:8][nH:9][c:10]3[cH:11][cH:12][cH:13][cH:14][c:15]23)[n:16]1\"}",
"reactionStep": {
"id": "sa_13f6efe8884a0e8eed520b9c",
"reactionHash": "13a655d53c6fd392e9ab457201f524a14bb573cf810f6df36bb814c0de0d12c6"
},
"children": [
{
"id": "935",
"routeId": "sa_ddcdbc739e0bcd0efb22c18a",
"moleculeId": "sa_aeda22e5315bd455d285f564",
"parentId": "934",
"isLeaf": true,
"molecule": {
"id": "sa_aeda22e5315bd455d285f564",
"inchikey": "BTTNYQZNBZNDOR-UHFFFAOYSA-N",
"smiles": "Clc1ccnc(Cl)n1"
},
"smiles": "Clc1ccnc(Cl)n1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "936",
"routeId": "sa_ddcdbc739e0bcd0efb22c18a",
"moleculeId": "sa_ec9495137cd7174c24138b0d",
"parentId": "934",
"isLeaf": true,
"molecule": {
"id": "sa_ec9495137cd7174c24138b0d",
"inchikey": "SIKJAQJRHWYJAI-UHFFFAOYSA-N",
"smiles": "c1ccc2[nH]ccc2c1"
},
"smiles": "c1ccc2[nH]ccc2c1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
}
]
}
]
}
]
}
}