Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
CCNC(=O)[C@@H](NC(=O)c1ccc([N+](=O)[O-])cc1O)[C@@H](C)O
InChiKey
VALIHLZYUNVCJI-HQJQHLMTSA-N
Route Signature
a124baf084c3bccb7556afffac189f4e3a52211d1717d8dd1217925df518e7a0
Synthesis route with 7 steps
Route tree structure (JSON format)
{
"route": {
"id": "sa_4872c6b88a5be24d4b78a8e2",
"signature": "a124baf084c3bccb7556afffac189f4e3a52211d1717d8dd1217925df518e7a0",
"contentHash": "9e4aa982402cb398b6fb15333ad7b973473601b9c93ac58d0b3f054cd4fafbd8",
"length": 7,
"isConvergent": false
},
"target": {
"id": "sa_19d5d6aafdc7a7410fcded86",
"benchmarkSetId": "61e696668b63e77d7c2a29c0821768e1c383de8313852d6e995224859494442e",
"targetId": "n5-00283",
"moleculeId": "sa_c35fdb7928869b4f5cae5674",
"smiles": "CCNC(=O)[C@@H](NC(=O)c1ccc([N+](=O)[O-])cc1O)[C@@H](C)O",
"routeLength": 7,
"isConvergent": false,
"metadata": null,
"molecule": {
"id": "sa_c35fdb7928869b4f5cae5674",
"inchikey": "VALIHLZYUNVCJI-HQJQHLMTSA-N",
"smiles": "CCNC(=O)[C@@H](NC(=O)c1ccc([N+](=O)[O-])cc1O)[C@@H](C)O"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "12976",
"routeId": "sa_4872c6b88a5be24d4b78a8e2",
"moleculeId": "sa_c35fdb7928869b4f5cae5674",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_c35fdb7928869b4f5cae5674",
"inchikey": "VALIHLZYUNVCJI-HQJQHLMTSA-N",
"smiles": "CCNC(=O)[C@@H](NC(=O)c1ccc([N+](=O)[O-])cc1O)[C@@H](C)O"
},
"smiles": "CCNC(=O)[C@@H](NC(=O)c1ccc([N+](=O)[O-])cc1O)[C@@H](C)O",
"reactionStepId": "sa_df5950d7fe16ef64e418596a",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20160002269A1;0219;1815127\",\"rsmi\":\"c1ccc(C[O:12][c:11]2[c:10]([C:8]([NH:7][C@H:6]([C:4]([NH:3][CH2:2][CH3:1])=[O:5])[C@@H:20]([CH3:21])[OH:22])=[O:9])[cH:19][cH:18][c:14]([N+:15](=[O:16])[O-:17])[cH:13]2)cc1>CCCCCC.CO.ClC(Cl)Cl.ClC(Cl)Cl.ClCCl>[CH3:1][CH2:2][NH:3][C:4](=[O:5])[C@@H:6]([NH:7][C:8](=[O:9])[c:10]1[c:11]([OH:12])[cH:13][c:14]([N+:15](=[O:16])[O-:17])[cH:18][cH:19]1)[C@@H:20]([CH3:21])[OH:22]\"},\"mapped_reaction_smiles\":\"c1ccc(C[O:12][c:11]2[c:10]([C:8]([NH:7][C@H:6]([C:4]([NH:3][CH2:2][CH3:1])=[O:5])[C@@H:20]([CH3:21])[OH:22])=[O:9])[cH:19][cH:18][c:14]([N+:15](=[O:16])[O-:17])[cH:13]2)cc1>CCCCCC.CO.ClC(Cl)Cl.ClC(Cl)Cl.ClCCl>[CH3:1][CH2:2][NH:3][C:4](=[O:5])[C@@H:6]([NH:7][C:8](=[O:9])[c:10]1[c:11]([OH:12])[cH:13][c:14]([N+:15](=[O:16])[O-:17])[cH:18][cH:19]1)[C@@H:20]([CH3:21])[OH:22]\"}",
"reactionStep": {
"id": "sa_df5950d7fe16ef64e418596a",
"reactionHash": "157b11463241acafe762e58e8282c2d2aac1befa96edd39dd0f5898023b18076"
},
"children": [
{
"id": "12977",
"routeId": "sa_4872c6b88a5be24d4b78a8e2",
"moleculeId": "sa_7ba2cda03ca4f07659a6a6c8",
"parentId": "12976",
"isLeaf": false,
"molecule": {
"id": "sa_7ba2cda03ca4f07659a6a6c8",
"inchikey": "JXXNLAVROLQWAX-ACJLOTCBSA-N",
"smiles": "CCNC(=O)[C@@H](NC(=O)c1ccc([N+](=O)[O-])cc1OCc1ccccc1)[C@@H](C)O"
},
"smiles": "CCNC(=O)[C@@H](NC(=O)c1ccc([N+](=O)[O-])cc1OCc1ccccc1)[C@@H](C)O",
"reactionStepId": "sa_88be694cc4123c7a9be4b8de",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20160002269A1;0218;1815126\",\"rsmi\":\"O[C:4](=[O:5])[C@@H:6]([NH:7][C:8](=[O:9])[c:10]1[c:11]([O:12][CH2:13][c:14]2[cH:15][cH:16][cH:17][cH:18][cH:19]2)[cH:20][c:21]([N+:22](=[O:23])[O-:24])[cH:25][cH:26]1)[C@@H:27]([CH3:28])[OH:29].[CH3:1][CH2:2][NH2:3]>C(=NC1CCCCC1)=NC1CCCCC1.C1CCOC1.CO.O.O=C1CCC(=O)N1O>[CH3:1][CH2:2][NH:3][C:4](=[O:5])[C@@H:6]([NH:7][C:8](=[O:9])[c:10]1[c:11]([O:12][CH2:13][c:14]2[cH:15][cH:16][cH:17][cH:18][cH:19]2)[cH:20][c:21]([N+:22](=[O:23])[O-:24])[cH:25][cH:26]1)[C@@H:27]([CH3:28])[OH:29]\"},\"mapped_reaction_smiles\":\"O[C:4](=[O:5])[C@@H:6]([NH:7][C:8](=[O:9])[c:10]1[c:11]([O:12][CH2:13][c:14]2[cH:15][cH:16][cH:17][cH:18][cH:19]2)[cH:20][c:21]([N+:22](=[O:23])[O-:24])[cH:25][cH:26]1)[C@@H:27]([CH3:28])[OH:29].[CH3:1][CH2:2][NH2:3]>C(=NC1CCCCC1)=NC1CCCCC1.C1CCOC1.CO.O.O=C1CCC(=O)N1O>[CH3:1][CH2:2][NH:3][C:4](=[O:5])[C@@H:6]([NH:7][C:8](=[O:9])[c:10]1[c:11]([O:12][CH2:13][c:14]2[cH:15][cH:16][cH:17][cH:18][cH:19]2)[cH:20][c:21]([N+:22](=[O:23])[O-:24])[cH:25][cH:26]1)[C@@H:27]([CH3:28])[OH:29]\"}",
"reactionStep": {
"id": "sa_88be694cc4123c7a9be4b8de",
"reactionHash": "fe08f33de5c212f6476be08b970c9e5ccf32c9d3244ab4b253072777d4143eab"
},
"children": [
{
"id": "12978",
"routeId": "sa_4872c6b88a5be24d4b78a8e2",
"moleculeId": "sa_da0aff84bc3e3ac55fe05431",
"parentId": "12977",
"isLeaf": false,
"molecule": {
"id": "sa_da0aff84bc3e3ac55fe05431",
"inchikey": "HWOHXZCRANRXGS-BZNIZROVSA-N",
"smiles": "C[C@@H](O)[C@H](NC(=O)c1ccc([N+](=O)[O-])cc1OCc1ccccc1)C(=O)O"
},
"smiles": "C[C@@H](O)[C@H](NC(=O)c1ccc([N+](=O)[O-])cc1OCc1ccccc1)C(=O)O",
"reactionStepId": "sa_881deee40eba45ded693561b",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20160002269A1;0217;1815125\",\"rsmi\":\"C[O:27][C:25]([C@H:4]([C@@H:2]([CH3:1])[OH:3])[NH:5][C:6](=[O:7])[c:8]1[c:9]([O:10][CH2:11][c:12]2[cH:13][cH:14][cH:15][cH:16][cH:17]2)[cH:18][c:19]([N+:20](=[O:21])[O-:22])[cH:23][cH:24]1)=[O:26]>CO.ClC(Cl)Cl.[Na+].O>[CH3:1][C@@H:2]([OH:3])[C@H:4]([NH:5][C:6](=[O:7])[c:8]1[c:9]([O:10][CH2:11][c:12]2[cH:13][cH:14][cH:15][cH:16][cH:17]2)[cH:18][c:19]([N+:20](=[O:21])[O-:22])[cH:23][cH:24]1)[C:25](=[O:26])[OH:27]\"},\"mapped_reaction_smiles\":\"C[O:27][C:25]([C@H:4]([C@@H:2]([CH3:1])[OH:3])[NH:5][C:6](=[O:7])[c:8]1[c:9]([O:10][CH2:11][c:12]2[cH:13][cH:14][cH:15][cH:16][cH:17]2)[cH:18][c:19]([N+:20](=[O:21])[O-:22])[cH:23][cH:24]1)=[O:26]>CO.ClC(Cl)Cl.[Na+].O>[CH3:1][C@@H:2]([OH:3])[C@H:4]([NH:5][C:6](=[O:7])[c:8]1[c:9]([O:10][CH2:11][c:12]2[cH:13][cH:14][cH:15][cH:16][cH:17]2)[cH:18][c:19]([N+:20](=[O:21])[O-:22])[cH:23][cH:24]1)[C:25](=[O:26])[OH:27]\"}",
"reactionStep": {
"id": "sa_881deee40eba45ded693561b",
"reactionHash": "9f46f3ad2cdcd9e97417978821e237f462444e8bb175f3138a6c556325757bf6"
},
"children": [
{
"id": "12979",
"routeId": "sa_4872c6b88a5be24d4b78a8e2",
"moleculeId": "sa_4dd635fa16374c303aaeade9",
"parentId": "12978",
"isLeaf": false,
"molecule": {
"id": "sa_4dd635fa16374c303aaeade9",
"inchikey": "FVSPTIWRRSLZJY-PXAZEXFGSA-N",
"smiles": "COC(=O)[C@@H](NC(=O)c1ccc([N+](=O)[O-])cc1OCc1ccccc1)[C@@H](C)O"
},
"smiles": "COC(=O)[C@@H](NC(=O)c1ccc([N+](=O)[O-])cc1OCc1ccccc1)[C@@H](C)O",
"reactionStepId": "sa_6a5677694cee0916589a2442",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20160002269A1;0216;1815124\",\"rsmi\":\"O=[C:7]([OH:8])[c:9]1[c:10]([O:11][CH2:12][c:13]2[cH:14][cH:15][cH:16][cH:17][cH:18]2)[cH:19][c:20]([N+:21](=[O:22])[O-:23])[cH:24][cH:25]1.[CH3:1][O:2][C:3](=[O:4])[C@@H:5]([NH2:6])[C@@H:26]([CH3:27])[OH:28]>C(=NC1CCCCC1)=NC1CCCCC1.CCN(CC)CC.CCOC(C)=O.Cl.ClCCl.On1nnc2ccccc21>[CH3:1][O:2][C:3](=[O:4])[C@@H:5]([NH:6][C:7](=[O:8])[c:9]1[c:10]([O:11][CH2:12][c:13]2[cH:14][cH:15][cH:16][cH:17][cH:18]2)[cH:19][c:20]([N+:21](=[O:22])[O-:23])[cH:24][cH:25]1)[C@@H:26]([CH3:27])[OH:28]\"},\"mapped_reaction_smiles\":\"O=[C:7]([OH:8])[c:9]1[c:10]([O:11][CH2:12][c:13]2[cH:14][cH:15][cH:16][cH:17][cH:18]2)[cH:19][c:20]([N+:21](=[O:22])[O-:23])[cH:24][cH:25]1.[CH3:1][O:2][C:3](=[O:4])[C@@H:5]([NH2:6])[C@@H:26]([CH3:27])[OH:28]>C(=NC1CCCCC1)=NC1CCCCC1.CCN(CC)CC.CCOC(C)=O.Cl.ClCCl.On1nnc2ccccc21>[CH3:1][O:2][C:3](=[O:4])[C@@H:5]([NH:6][C:7](=[O:8])[c:9]1[c:10]([O:11][CH2:12][c:13]2[cH:14][cH:15][cH:16][cH:17][cH:18]2)[cH:19][c:20]([N+:21](=[O:22])[O-:23])[cH:24][cH:25]1)[C@@H:26]([CH3:27])[OH:28]\"}",
"reactionStep": {
"id": "sa_6a5677694cee0916589a2442",
"reactionHash": "461bcc26ff71e48268b9ab3cf5a688f20f6598f75cf966e1c9fe38d914ae6077"
},
"children": [
{
"id": "12980",
"routeId": "sa_4872c6b88a5be24d4b78a8e2",
"moleculeId": "sa_18ff59d53fb21d81254b2f96",
"parentId": "12979",
"isLeaf": false,
"molecule": {
"id": "sa_18ff59d53fb21d81254b2f96",
"inchikey": "LXYSQNGVLVKMDZ-UHFFFAOYSA-N",
"smiles": "O=C(O)c1ccc([N+](=O)[O-])cc1OCc1ccccc1"
},
"smiles": "O=C(O)c1ccc([N+](=O)[O-])cc1OCc1ccccc1",
"reactionStepId": "sa_70eaea1dbfbb6011803bdbbb",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20160002269A1;0215;1815123\",\"rsmi\":\"C[O:3][C:2](=[O:1])[c:4]1[c:5]([O:6][CH2:7][c:8]2[cH:9][cH:10][cH:11][cH:12][cH:13]2)[cH:14][c:15]([N+:16](=[O:17])[O-:18])[cH:19][cH:20]1>C1CCOC1.CO.Cl.[Na+].O>[O:1]=[C:2]([OH:3])[c:4]1[c:5]([O:6][CH2:7][c:8]2[cH:9][cH:10][cH:11][cH:12][cH:13]2)[cH:14][c:15]([N+:16](=[O:17])[O-:18])[cH:19][cH:20]1\"},\"mapped_reaction_smiles\":\"C[O:3][C:2](=[O:1])[c:4]1[c:5]([O:6][CH2:7][c:8]2[cH:9][cH:10][cH:11][cH:12][cH:13]2)[cH:14][c:15]([N+:16](=[O:17])[O-:18])[cH:19][cH:20]1>C1CCOC1.CO.Cl.[Na+].O>[O:1]=[C:2]([OH:3])[c:4]1[c:5]([O:6][CH2:7][c:8]2[cH:9][cH:10][cH:11][cH:12][cH:13]2)[cH:14][c:15]([N+:16](=[O:17])[O-:18])[cH:19][cH:20]1\"}",
"reactionStep": {
"id": "sa_70eaea1dbfbb6011803bdbbb",
"reactionHash": "d2693f2d6795ca55e7c6ff676deb09ab352f83b736a7785253989bcb130a828e"
},
"children": [
{
"id": "12981",
"routeId": "sa_4872c6b88a5be24d4b78a8e2",
"moleculeId": "sa_cfb83c6cc26ae07dfe5b57fc",
"parentId": "12980",
"isLeaf": false,
"molecule": {
"id": "sa_cfb83c6cc26ae07dfe5b57fc",
"inchikey": "FQWRZUSFAOJHST-UHFFFAOYSA-N",
"smiles": "COC(=O)c1ccc([N+](=O)[O-])cc1OCc1ccccc1"
},
"smiles": "COC(=O)c1ccc([N+](=O)[O-])cc1OCc1ccccc1",
"reactionStepId": "sa_622d98b2f46913a52723f5ef",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20160002269A1;0214;1815122\",\"rsmi\":\"Br[CH2:8][c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1.[CH3:1][O:2][C:3](=[O:4])[c:5]1[c:6]([OH:7])[cH:15][c:16]([N+:17](=[O:18])[O-:19])[cH:20][cH:21]1>CC(C)=O.O=C(O)O.[K+].[K+]>[CH3:1][O:2][C:3](=[O:4])[c:5]1[c:6]([O:7][CH2:8][c:9]2[cH:10][cH:11][cH:12][cH:13][cH:14]2)[cH:15][c:16]([N+:17](=[O:18])[O-:19])[cH:20][cH:21]1\"},\"mapped_reaction_smiles\":\"Br[CH2:8][c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1.[CH3:1][O:2][C:3](=[O:4])[c:5]1[c:6]([OH:7])[cH:15][c:16]([N+:17](=[O:18])[O-:19])[cH:20][cH:21]1>CC(C)=O.O=C(O)O.[K+].[K+]>[CH3:1][O:2][C:3](=[O:4])[c:5]1[c:6]([O:7][CH2:8][c:9]2[cH:10][cH:11][cH:12][cH:13][cH:14]2)[cH:15][c:16]([N+:17](=[O:18])[O-:19])[cH:20][cH:21]1\"}",
"reactionStep": {
"id": "sa_622d98b2f46913a52723f5ef",
"reactionHash": "4bfcf67d541bbec409801e8cb757bdc898f29832f2e322facf292493c99f7289"
},
"children": [
{
"id": "12982",
"routeId": "sa_4872c6b88a5be24d4b78a8e2",
"moleculeId": "sa_4ff2e4de9d80150de333c065",
"parentId": "12981",
"isLeaf": true,
"molecule": {
"id": "sa_4ff2e4de9d80150de333c065",
"inchikey": "AGEZXYOZHKGVCM-UHFFFAOYSA-N",
"smiles": "BrCc1ccccc1"
},
"smiles": "BrCc1ccccc1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "12983",
"routeId": "sa_4872c6b88a5be24d4b78a8e2",
"moleculeId": "sa_9ffc408f4d7d1bda5559f178",
"parentId": "12981",
"isLeaf": false,
"molecule": {
"id": "sa_9ffc408f4d7d1bda5559f178",
"inchikey": "DODUOCYKSQVFSW-UHFFFAOYSA-N",
"smiles": "COC(=O)c1ccc([N+](=O)[O-])cc1O"
},
"smiles": "COC(=O)c1ccc([N+](=O)[O-])cc1O",
"reactionStepId": "sa_407cac4a081ca20a7390185d",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20160002269A1;0213;1815121\",\"rsmi\":\"O[C:3](=[O:4])[c:5]1[c:6]([OH:7])[cH:8][c:9]([N+:10](=[O:11])[O-:12])[cH:13][cH:14]1.[CH3:1][OH:2]>O>[CH3:1][O:2][C:3](=[O:4])[c:5]1[c:6]([OH:7])[cH:8][c:9]([N+:10](=[O:11])[O-:12])[cH:13][cH:14]1\"},\"mapped_reaction_smiles\":\"O[C:3](=[O:4])[c:5]1[c:6]([OH:7])[cH:8][c:9]([N+:10](=[O:11])[O-:12])[cH:13][cH:14]1.[CH3:1][OH:2]>O>[CH3:1][O:2][C:3](=[O:4])[c:5]1[c:6]([OH:7])[cH:8][c:9]([N+:10](=[O:11])[O-:12])[cH:13][cH:14]1\"}",
"reactionStep": {
"id": "sa_407cac4a081ca20a7390185d",
"reactionHash": "5807a7036cea0c419ef5d50cae3f24c6e1fb95caad449cab8254cbbc12c6b96b"
},
"children": [
{
"id": "12984",
"routeId": "sa_4872c6b88a5be24d4b78a8e2",
"moleculeId": "sa_061a3efbe4d30c2cc87d48e7",
"parentId": "12983",
"isLeaf": true,
"molecule": {
"id": "sa_061a3efbe4d30c2cc87d48e7",
"inchikey": "OKKJLVBELUTLKV-UHFFFAOYSA-N",
"smiles": "CO"
},
"smiles": "CO",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "12985",
"routeId": "sa_4872c6b88a5be24d4b78a8e2",
"moleculeId": "sa_90412a5b310ade0c6a883b10",
"parentId": "12983",
"isLeaf": true,
"molecule": {
"id": "sa_90412a5b310ade0c6a883b10",
"inchikey": "UKWUOTZGXIZAJC-UHFFFAOYSA-N",
"smiles": "O=C(O)c1ccc([N+](=O)[O-])cc1O"
},
"smiles": "O=C(O)c1ccc([N+](=O)[O-])cc1O",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
}
]
}
]
},
{
"id": "12986",
"routeId": "sa_4872c6b88a5be24d4b78a8e2",
"moleculeId": "sa_17e8d54e63d645e09874575d",
"parentId": "12979",
"isLeaf": true,
"molecule": {
"id": "sa_17e8d54e63d645e09874575d",
"inchikey": "TVHCXXXXQNWQLP-DMTCNVIQSA-N",
"smiles": "COC(=O)[C@@H](N)[C@@H](C)O"
},
"smiles": "COC(=O)[C@@H](N)[C@@H](C)O",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
}
]
},
{
"id": "12987",
"routeId": "sa_4872c6b88a5be24d4b78a8e2",
"moleculeId": "sa_89fd0a98f6b54999b99c6e8f",
"parentId": "12977",
"isLeaf": true,
"molecule": {
"id": "sa_89fd0a98f6b54999b99c6e8f",
"inchikey": "QUSNBJAOOMFDIB-UHFFFAOYSA-N",
"smiles": "CCN"
},
"smiles": "CCN",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
}
]
}
}