Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
Cc1noc(-c2ccc(Cl)cc2-c2nc3cc(-c4cnc(N)nc4)ccc3n2C(C)(C)C)n1
InChiKey
UQTJLOMVGOJXNN-UHFFFAOYSA-N
Route Signature
1c98d57f1384de7ed8a006046783ca609e5971553c4798cc9dd2568b58cf8f23
Synthesis route with 4 steps (convergent)
Route tree structure (JSON format)
{
"route": {
"id": "sa_f5d3ce978fc14bcc2689f036",
"signature": "1c98d57f1384de7ed8a006046783ca609e5971553c4798cc9dd2568b58cf8f23",
"contentHash": "b8d764a10c556d419fae3e100358f07decf104f0d7a67fecc7933c70b45e48a0",
"length": 4,
"isConvergent": true
},
"target": {
"id": "sa_b0952ba480ed524c50dea0cf",
"benchmarkSetId": "3895c2909c53593560c5ba610abc7e6df80513dfd8624165c560451735097d36",
"targetId": "n5-01288",
"moleculeId": "sa_fbbf7e0acea6de24b74e6aa4",
"smiles": "Cc1noc(-c2ccc(Cl)cc2-c2nc3cc(-c4cnc(N)nc4)ccc3n2C(C)(C)C)n1",
"routeLength": 4,
"isConvergent": true,
"metadata": null,
"molecule": {
"id": "sa_fbbf7e0acea6de24b74e6aa4",
"inchikey": "UQTJLOMVGOJXNN-UHFFFAOYSA-N",
"smiles": "Cc1noc(-c2ccc(Cl)cc2-c2nc3cc(-c4cnc(N)nc4)ccc3n2C(C)(C)C)n1"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "10055",
"routeId": "sa_f5d3ce978fc14bcc2689f036",
"moleculeId": "sa_fbbf7e0acea6de24b74e6aa4",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_fbbf7e0acea6de24b74e6aa4",
"inchikey": "UQTJLOMVGOJXNN-UHFFFAOYSA-N",
"smiles": "Cc1noc(-c2ccc(Cl)cc2-c2nc3cc(-c4cnc(N)nc4)ccc3n2C(C)(C)C)n1"
},
"smiles": "Cc1noc(-c2ccc(Cl)cc2-c2nc3cc(-c4cnc(N)nc4)ccc3n2C(C)(C)C)n1",
"reactionStepId": "sa_ec38aee3ef22415bbd5a6f46",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US08420655B2;0369;1309994\",\"rsmi\":\"O=[CH:8][c:7]1[c:6](-[c:5]2[o:4][n:3][c:2]([CH3:1])[n:33]2)[cH:32][cH:31][c:29]([Cl:30])[cH:28]1.[NH2:9][c:10]1[c:11]([NH:23][C:24]([CH3:25])([CH3:26])[CH3:27])[cH:12][cH:13][c:14](-[c:15]2[cH:16][n:17][c:18]([NH2:19])[n:20][cH:21]2)[cH:22]1>CN(C)C=O.O.O=S(O)OO.[K+]>[CH3:1][c:2]1[n:3][o:4][c:5](-[c:6]2[c:7](-[c:8]3[n:9][c:10]4[c:11]([cH:12][cH:13][c:14](-[c:15]5[cH:16][n:17][c:18]([NH2:19])[n:20][cH:21]5)[cH:22]4)[n:23]3[C:24]([CH3:25])([CH3:26])[CH3:27])[cH:28][c:29]([Cl:30])[cH:31][cH:32]2)[n:33]1\"},\"mapped_reaction_smiles\":\"O=[CH:8][c:7]1[c:6](-[c:5]2[o:4][n:3][c:2]([CH3:1])[n:33]2)[cH:32][cH:31][c:29]([Cl:30])[cH:28]1.[NH2:9][c:10]1[c:11]([NH:23][C:24]([CH3:25])([CH3:26])[CH3:27])[cH:12][cH:13][c:14](-[c:15]2[cH:16][n:17][c:18]([NH2:19])[n:20][cH:21]2)[cH:22]1>CN(C)C=O.O.O=S(O)OO.[K+]>[CH3:1][c:2]1[n:3][o:4][c:5](-[c:6]2[c:7](-[c:8]3[n:9][c:10]4[c:11]([cH:12][cH:13][c:14](-[c:15]5[cH:16][n:17][c:18]([NH2:19])[n:20][cH:21]5)[cH:22]4)[n:23]3[C:24]([CH3:25])([CH3:26])[CH3:27])[cH:28][c:29]([Cl:30])[cH:31][cH:32]2)[n:33]1\"}",
"reactionStep": {
"id": "sa_ec38aee3ef22415bbd5a6f46",
"reactionHash": "cbb2ca292a5578e756536f79fa1f79dd0d39ba3c02c22f4b43f326913f74c2b8"
},
"children": [
{
"id": "10056",
"routeId": "sa_f5d3ce978fc14bcc2689f036",
"moleculeId": "sa_686845e53f4fae550fc8ccbe",
"parentId": "10055",
"isLeaf": false,
"molecule": {
"id": "sa_686845e53f4fae550fc8ccbe",
"inchikey": "PHAHMWYTOITBRR-UHFFFAOYSA-N",
"smiles": "Cc1noc(-c2ccc(Cl)cc2C=O)n1"
},
"smiles": "Cc1noc(-c2ccc(Cl)cc2C=O)n1",
"reactionStepId": "sa_59c00482383d20dea72f98c6",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US08420655B2;0368;1309993\",\"rsmi\":\"[CH3:1][c:2]1[n:3][o:4][c:5](-[c:6]2[c:7]([CH2:8][OH:9])[cH:10][c:11]([Cl:12])[cH:13][cH:14]2)[n:15]1>ClCCl.O=[Mn]=O>[CH3:1][c:2]1[n:3][o:4][c:5](-[c:6]2[c:7]([CH:8]=[O:9])[cH:10][c:11]([Cl:12])[cH:13][cH:14]2)[n:15]1\"},\"mapped_reaction_smiles\":\"[CH3:1][c:2]1[n:3][o:4][c:5](-[c:6]2[c:7]([CH2:8][OH:9])[cH:10][c:11]([Cl:12])[cH:13][cH:14]2)[n:15]1>ClCCl.O=[Mn]=O>[CH3:1][c:2]1[n:3][o:4][c:5](-[c:6]2[c:7]([CH:8]=[O:9])[cH:10][c:11]([Cl:12])[cH:13][cH:14]2)[n:15]1\"}",
"reactionStep": {
"id": "sa_59c00482383d20dea72f98c6",
"reactionHash": "971b8df3ed581bb662a4f161b8f8a76802f9028323bc17f67d9875556c42ad41"
},
"children": [
{
"id": "10057",
"routeId": "sa_f5d3ce978fc14bcc2689f036",
"moleculeId": "sa_c5af42c4966d79489d6b0d8c",
"parentId": "10056",
"isLeaf": false,
"molecule": {
"id": "sa_c5af42c4966d79489d6b0d8c",
"inchikey": "GOZGMWVQASQXSZ-UHFFFAOYSA-N",
"smiles": "Cc1noc(-c2ccc(Cl)cc2CO)n1"
},
"smiles": "Cc1noc(-c2ccc(Cl)cc2CO)n1",
"reactionStepId": "sa_6eac0093c0040e83ef42792b",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US08420655B2;0367;1309992\",\"rsmi\":\"CO[C:8]([c:7]1[c:6](-[c:5]2[o:4][n:3][c:2]([CH3:1])[n:15]2)[cH:14][cH:13][c:11]([Cl:12])[cH:10]1)=[O:9]>C1CCOC1.B.[Li+]>[CH3:1][c:2]1[n:3][o:4][c:5](-[c:6]2[c:7]([CH2:8][OH:9])[cH:10][c:11]([Cl:12])[cH:13][cH:14]2)[n:15]1\"},\"mapped_reaction_smiles\":\"CO[C:8]([c:7]1[c:6](-[c:5]2[o:4][n:3][c:2]([CH3:1])[n:15]2)[cH:14][cH:13][c:11]([Cl:12])[cH:10]1)=[O:9]>C1CCOC1.B.[Li+]>[CH3:1][c:2]1[n:3][o:4][c:5](-[c:6]2[c:7]([CH2:8][OH:9])[cH:10][c:11]([Cl:12])[cH:13][cH:14]2)[n:15]1\"}",
"reactionStep": {
"id": "sa_6eac0093c0040e83ef42792b",
"reactionHash": "80f2411e47429c13ecde728e161658008b275201ab137cae279dd58f17592ed0"
},
"children": [
{
"id": "10058",
"routeId": "sa_f5d3ce978fc14bcc2689f036",
"moleculeId": "sa_94865b62b427124dbbd02a4d",
"parentId": "10057",
"isLeaf": true,
"molecule": {
"id": "sa_94865b62b427124dbbd02a4d",
"inchikey": "LABQFPHLUUMCBT-UHFFFAOYSA-N",
"smiles": "COC(=O)c1cc(Cl)ccc1-c1nc(C)no1"
},
"smiles": "COC(=O)c1cc(Cl)ccc1-c1nc(C)no1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
}
]
},
{
"id": "10059",
"routeId": "sa_f5d3ce978fc14bcc2689f036",
"moleculeId": "sa_df232e146a0c3cd9ff99a638",
"parentId": "10055",
"isLeaf": false,
"molecule": {
"id": "sa_df232e146a0c3cd9ff99a638",
"inchikey": "WKYHUCHEQMVMIW-UHFFFAOYSA-N",
"smiles": "CC(C)(C)Nc1ccc(-c2cnc(N)nc2)cc1N"
},
"smiles": "CC(C)(C)Nc1ccc(-c2cnc(N)nc2)cc1N",
"reactionStepId": "sa_45bf89e67c538929f1539959",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US08420655B2;0212;1309941\",\"rsmi\":\"O=[N+:19]([O-])[c:18]1[c:6]([NH:5][C:2]([CH3:1])([CH3:3])[CH3:4])[cH:7][cH:8][c:9](-[c:10]2[cH:11][n:12][c:13]([NH2:14])[n:15][cH:16]2)[cH:17]1>CCO.O=CO.N.[Zn]>[CH3:1][C:2]([CH3:3])([CH3:4])[NH:5][c:6]1[cH:7][cH:8][c:9](-[c:10]2[cH:11][n:12][c:13]([NH2:14])[n:15][cH:16]2)[cH:17][c:18]1[NH2:19]\"},\"mapped_reaction_smiles\":\"O=[N+:19]([O-])[c:18]1[c:6]([NH:5][C:2]([CH3:1])([CH3:3])[CH3:4])[cH:7][cH:8][c:9](-[c:10]2[cH:11][n:12][c:13]([NH2:14])[n:15][cH:16]2)[cH:17]1>CCO.O=CO.N.[Zn]>[CH3:1][C:2]([CH3:3])([CH3:4])[NH:5][c:6]1[cH:7][cH:8][c:9](-[c:10]2[cH:11][n:12][c:13]([NH2:14])[n:15][cH:16]2)[cH:17][c:18]1[NH2:19]\"}",
"reactionStep": {
"id": "sa_45bf89e67c538929f1539959",
"reactionHash": "7ae47d95cecc6f2bda521a9978fded0589f8820d8a67977944317e792095bf20"
},
"children": [
{
"id": "10060",
"routeId": "sa_f5d3ce978fc14bcc2689f036",
"moleculeId": "sa_12a014841563977aa19fb2f7",
"parentId": "10059",
"isLeaf": false,
"molecule": {
"id": "sa_12a014841563977aa19fb2f7",
"inchikey": "OIMMMVKHGNTUFZ-UHFFFAOYSA-N",
"smiles": "CC(C)(C)Nc1ccc(-c2cnc(N)nc2)cc1[N+](=O)[O-]"
},
"smiles": "CC(C)(C)Nc1ccc(-c2cnc(N)nc2)cc1[N+](=O)[O-]",
"reactionStepId": "sa_a1a85051f6d53e9296ffa35f",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US08420655B2;0211;1309940\",\"rsmi\":\"Br[c:12]1[cH:11][c:7]([N+:8](=[O:9])[O-:10])[c:6]([NH:5][C:2]([CH3:1])([CH3:3])[CH3:4])[cH:21][cH:20]1.CC1(C)OB([c:13]2[cH:14][n:15][c:16]([NH2:17])[n:18][cH:19]2)OC1(C)C>CN(C)C=O.O.O=C(O)O.[K+].[K+].c1ccc([PH](c2ccccc2)(c2ccccc2)[Pd]([PH](c2ccccc2)(c2ccccc2)c2ccccc2)([PH](c2ccccc2)(c2ccccc2)c2ccccc2)[PH](c2ccccc2)(c2ccccc2)c2ccccc2)cc1>[CH3:1][C:2]([CH3:3])([CH3:4])[NH:5][c:6]1[c:7]([N+:8](=[O:9])[O-:10])[cH:11][c:12](-[c:13]2[cH:14][n:15][c:16]([NH2:17])[n:18][cH:19]2)[cH:20][cH:21]1\"},\"mapped_reaction_smiles\":\"Br[c:12]1[cH:11][c:7]([N+:8](=[O:9])[O-:10])[c:6]([NH:5][C:2]([CH3:1])([CH3:3])[CH3:4])[cH:21][cH:20]1.CC1(C)OB([c:13]2[cH:14][n:15][c:16]([NH2:17])[n:18][cH:19]2)OC1(C)C>CN(C)C=O.O.O=C(O)O.[K+].[K+].c1ccc([PH](c2ccccc2)(c2ccccc2)[Pd]([PH](c2ccccc2)(c2ccccc2)c2ccccc2)([PH](c2ccccc2)(c2ccccc2)c2ccccc2)[PH](c2ccccc2)(c2ccccc2)c2ccccc2)cc1>[CH3:1][C:2]([CH3:3])([CH3:4])[NH:5][c:6]1[c:7]([N+:8](=[O:9])[O-:10])[cH:11][c:12](-[c:13]2[cH:14][n:15][c:16]([NH2:17])[n:18][cH:19]2)[cH:20][cH:21]1\"}",
"reactionStep": {
"id": "sa_a1a85051f6d53e9296ffa35f",
"reactionHash": "e336cd35a1063bb45fcd9de28f177592d4121ed448c19d4cee19a86c1667b616"
},
"children": [
{
"id": "10061",
"routeId": "sa_f5d3ce978fc14bcc2689f036",
"moleculeId": "sa_b99d18964d781d1b814e72b2",
"parentId": "10060",
"isLeaf": true,
"molecule": {
"id": "sa_b99d18964d781d1b814e72b2",
"inchikey": "BPQVMIDUTRJYSC-UHFFFAOYSA-N",
"smiles": "CC1(C)OB(c2cnc(=N)[nH]c2)OC1(C)C"
},
"smiles": "CC1(C)OB(c2cnc(N)nc2)OC1(C)C",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "10062",
"routeId": "sa_f5d3ce978fc14bcc2689f036",
"moleculeId": "sa_a16e963707adb8c45f3e51ca",
"parentId": "10060",
"isLeaf": false,
"molecule": {
"id": "sa_a16e963707adb8c45f3e51ca",
"inchikey": "SUIOMWQYRMBEHM-UHFFFAOYSA-N",
"smiles": "CC(C)(C)Nc1ccc(Br)cc1[N+](=O)[O-]"
},
"smiles": "CC(C)(C)Nc1ccc(Br)cc1[N+](=O)[O-]",
"reactionStepId": "sa_cf01ae23ad1eb9b96dc39e3f",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US08420655B2;0210;1309939\",\"rsmi\":\"F[c:6]1[c:7]([N+:8](=[O:9])[O-:10])[cH:11][c:12]([Br:13])[cH:14][cH:15]1.[CH3:1][C:2]([CH3:3])([CH3:4])[NH2:5]>C1CCOC1>[CH3:1][C:2]([CH3:3])([CH3:4])[NH:5][c:6]1[c:7]([N+:8](=[O:9])[O-:10])[cH:11][c:12]([Br:13])[cH:14][cH:15]1\"},\"mapped_reaction_smiles\":\"F[c:6]1[c:7]([N+:8](=[O:9])[O-:10])[cH:11][c:12]([Br:13])[cH:14][cH:15]1.[CH3:1][C:2]([CH3:3])([CH3:4])[NH2:5]>C1CCOC1>[CH3:1][C:2]([CH3:3])([CH3:4])[NH:5][c:6]1[c:7]([N+:8](=[O:9])[O-:10])[cH:11][c:12]([Br:13])[cH:14][cH:15]1\"}",
"reactionStep": {
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"reactionHash": "149078fb80ab7a4377a48a2f3b1cc73c35614a3445becf7458a499b463fa7761"
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"children": [
{
"id": "10063",
"routeId": "sa_f5d3ce978fc14bcc2689f036",
"moleculeId": "sa_f3f9dcb2cec4fdf93d84cde3",
"parentId": "10062",
"isLeaf": true,
"molecule": {
"id": "sa_f3f9dcb2cec4fdf93d84cde3",
"inchikey": "UQEANKGXXSENNF-UHFFFAOYSA-N",
"smiles": "O=[N+]([O-])c1cc(Br)ccc1F"
},
"smiles": "O=[N+]([O-])c1cc(Br)ccc1F",
"reactionStepId": null,
"template": null,
"metadata": null,
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},
{
"id": "10064",
"routeId": "sa_f5d3ce978fc14bcc2689f036",
"moleculeId": "sa_8413f5aed68586ea647bdeb5",
"parentId": "10062",
"isLeaf": true,
"molecule": {
"id": "sa_8413f5aed68586ea647bdeb5",
"inchikey": "YBRBMKDOPFTVDT-UHFFFAOYSA-N",
"smiles": "CC(C)(C)N"
},
"smiles": "CC(C)(C)N",
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"children": []
}
]
}
]
}
]
}
]
}
}