Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
CN(c1cc2c(cn1)ncn2C)c1ccc(C2CN(S(C)(=O)=O)C2)cc1F
InChiKey
HSOIZPCFDNLXLS-UHFFFAOYSA-N
Route Signature
085617da5b5074bc26ef3859ec30b66a3a6db966bc0171be38b2d61bfc0626e2
Synthesis route with 5 steps
Route tree structure (JSON format)
{
"route": {
"id": "sa_a9d5dca89b5436122b2030c3",
"signature": "085617da5b5074bc26ef3859ec30b66a3a6db966bc0171be38b2d61bfc0626e2",
"contentHash": "9ba7ecfbd4b6bc18268440432acb475cfe2e0d25f16fe71f6cf848cbd8235ab7",
"length": 5,
"isConvergent": false
},
"target": {
"id": "sa_ee632b40926dc3e877774889",
"benchmarkSetId": "61e696668b63e77d7c2a29c0821768e1c383de8313852d6e995224859494442e",
"targetId": "n5-02039",
"moleculeId": "sa_b8c6c5335f41b9460908642f",
"smiles": "CN(c1cc2c(cn1)ncn2C)c1ccc(C2CN(S(C)(=O)=O)C2)cc1F",
"routeLength": 5,
"isConvergent": false,
"metadata": null,
"molecule": {
"id": "sa_b8c6c5335f41b9460908642f",
"inchikey": "HSOIZPCFDNLXLS-UHFFFAOYSA-N",
"smiles": "CN(c1cc2c(cn1)ncn2C)c1ccc(C2CN(S(C)(=O)=O)C2)cc1F"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "14629",
"routeId": "sa_a9d5dca89b5436122b2030c3",
"moleculeId": "sa_b8c6c5335f41b9460908642f",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_b8c6c5335f41b9460908642f",
"inchikey": "HSOIZPCFDNLXLS-UHFFFAOYSA-N",
"smiles": "CN(c1cc2c(cn1)ncn2C)c1ccc(C2CN(S(C)(=O)=O)C2)cc1F"
},
"smiles": "CN(c1cc2c(cn1)ncn2C)c1ccc(C2CN(S(C)(=O)=O)C2)cc1F",
"reactionStepId": "sa_4dbb3a24c490597d8abdfe5c",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20130217664A1;1783;1411815\",\"rsmi\":\"Cl[S:19]([CH3:20])(=[O:21])=[O:22].[CH3:1][n:2]1[cH:3][n:4][c:5]2[c:6]1[cH:7][c:8]([N:9]([CH3:10])[c:11]1[c:12]([F:13])[cH:14][c:15]([CH:16]3[CH2:17][NH:18][CH2:23]3)[cH:24][cH:25]1)[n:26][cH:27]2>CCN(CC)CC.ClCCl>[CH3:1][n:2]1[cH:3][n:4][c:5]2[c:6]1[cH:7][c:8]([N:9]([CH3:10])[c:11]1[c:12]([F:13])[cH:14][c:15]([CH:16]3[CH2:17][N:18]([S:19]([CH3:20])(=[O:21])=[O:22])[CH2:23]3)[cH:24][cH:25]1)[n:26][cH:27]2\"},\"mapped_reaction_smiles\":\"Cl[S:19]([CH3:20])(=[O:21])=[O:22].[CH3:1][n:2]1[cH:3][n:4][c:5]2[c:6]1[cH:7][c:8]([N:9]([CH3:10])[c:11]1[c:12]([F:13])[cH:14][c:15]([CH:16]3[CH2:17][NH:18][CH2:23]3)[cH:24][cH:25]1)[n:26][cH:27]2>CCN(CC)CC.ClCCl>[CH3:1][n:2]1[cH:3][n:4][c:5]2[c:6]1[cH:7][c:8]([N:9]([CH3:10])[c:11]1[c:12]([F:13])[cH:14][c:15]([CH:16]3[CH2:17][N:18]([S:19]([CH3:20])(=[O:21])=[O:22])[CH2:23]3)[cH:24][cH:25]1)[n:26][cH:27]2\"}",
"reactionStep": {
"id": "sa_4dbb3a24c490597d8abdfe5c",
"reactionHash": "d3c5865fda8cce435de6fd36f6edf02897b4c38353a34efadfa1eef9bf946777"
},
"children": [
{
"id": "14630",
"routeId": "sa_a9d5dca89b5436122b2030c3",
"moleculeId": "sa_3e7708b780f63d873bea6538",
"parentId": "14629",
"isLeaf": false,
"molecule": {
"id": "sa_3e7708b780f63d873bea6538",
"inchikey": "DLMLXEMHURISBN-UHFFFAOYSA-N",
"smiles": "CN(c1cc2c(cn1)ncn2C)c1ccc(C2CNC2)cc1F"
},
"smiles": "CN(c1cc2c(cn1)ncn2C)c1ccc(C2CNC2)cc1F",
"reactionStepId": "sa_ec98a5e2e25c16217ce56139",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20130217664A1;1782;1411814\",\"rsmi\":\"CC(C)(C)OC(=O)[N:18]1[CH2:17][CH:16]([c:15]2[cH:14][c:12]([F:13])[c:11]([N:9]([c:8]3[cH:7][c:6]4[n:2]([CH3:1])[cH:3][n:4][c:5]4[cH:23][n:22]3)[CH3:10])[cH:21][cH:20]2)[CH2:19]1>ClCCl.O=C(O)C(F)(F)F>[CH3:1][n:2]1[cH:3][n:4][c:5]2[c:6]1[cH:7][c:8]([N:9]([CH3:10])[c:11]1[c:12]([F:13])[cH:14][c:15]([CH:16]3[CH2:17][NH:18][CH2:19]3)[cH:20][cH:21]1)[n:22][cH:23]2\"},\"mapped_reaction_smiles\":\"CC(C)(C)OC(=O)[N:18]1[CH2:17][CH:16]([c:15]2[cH:14][c:12]([F:13])[c:11]([N:9]([c:8]3[cH:7][c:6]4[n:2]([CH3:1])[cH:3][n:4][c:5]4[cH:23][n:22]3)[CH3:10])[cH:21][cH:20]2)[CH2:19]1>ClCCl.O=C(O)C(F)(F)F>[CH3:1][n:2]1[cH:3][n:4][c:5]2[c:6]1[cH:7][c:8]([N:9]([CH3:10])[c:11]1[c:12]([F:13])[cH:14][c:15]([CH:16]3[CH2:17][NH:18][CH2:19]3)[cH:20][cH:21]1)[n:22][cH:23]2\"}",
"reactionStep": {
"id": "sa_ec98a5e2e25c16217ce56139",
"reactionHash": "db5468a8a0aaad510c3a62061b2a3c7baace8f88e75ed07c1377775859599fe1"
},
"children": [
{
"id": "14631",
"routeId": "sa_a9d5dca89b5436122b2030c3",
"moleculeId": "sa_6603734d4c6c6e258f74b848",
"parentId": "14630",
"isLeaf": false,
"molecule": {
"id": "sa_6603734d4c6c6e258f74b848",
"inchikey": "BWEBLTWNHMLYDQ-UHFFFAOYSA-N",
"smiles": "CN(c1cc2c(cn1)ncn2C)c1ccc(C2CN(C(=O)OC(C)(C)C)C2)cc1F"
},
"smiles": "CN(c1cc2c(cn1)ncn2C)c1ccc(C2CN(C(=O)OC(C)(C)C)C2)cc1F",
"reactionStepId": "sa_224f928dce2d8fec0b6b4ce1",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20130217664A1;1781;1411813\",\"rsmi\":\"I[CH3:10].[CH3:1][n:2]1[cH:3][n:4][c:5]2[c:6]1[cH:7][c:8]([NH:9][c:11]1[c:12]([F:13])[cH:14][c:15]([CH:16]3[CH2:17][N:18]([C:19](=[O:20])[O:21][C:22]([CH3:23])([CH3:24])[CH3:25])[CH2:26]3)[cH:27][cH:28]1)[n:29][cH:30]2>C1CCOC1.CN(C)C=O.C[Si](C)(C)N[Si](C)(C)C.[Na+]>[CH3:1][n:2]1[cH:3][n:4][c:5]2[c:6]1[cH:7][c:8]([N:9]([CH3:10])[c:11]1[c:12]([F:13])[cH:14][c:15]([CH:16]3[CH2:17][N:18]([C:19](=[O:20])[O:21][C:22]([CH3:23])([CH3:24])[CH3:25])[CH2:26]3)[cH:27][cH:28]1)[n:29][cH:30]2\"},\"mapped_reaction_smiles\":\"I[CH3:10].[CH3:1][n:2]1[cH:3][n:4][c:5]2[c:6]1[cH:7][c:8]([NH:9][c:11]1[c:12]([F:13])[cH:14][c:15]([CH:16]3[CH2:17][N:18]([C:19](=[O:20])[O:21][C:22]([CH3:23])([CH3:24])[CH3:25])[CH2:26]3)[cH:27][cH:28]1)[n:29][cH:30]2>C1CCOC1.CN(C)C=O.C[Si](C)(C)N[Si](C)(C)C.[Na+]>[CH3:1][n:2]1[cH:3][n:4][c:5]2[c:6]1[cH:7][c:8]([N:9]([CH3:10])[c:11]1[c:12]([F:13])[cH:14][c:15]([CH:16]3[CH2:17][N:18]([C:19](=[O:20])[O:21][C:22]([CH3:23])([CH3:24])[CH3:25])[CH2:26]3)[cH:27][cH:28]1)[n:29][cH:30]2\"}",
"reactionStep": {
"id": "sa_224f928dce2d8fec0b6b4ce1",
"reactionHash": "253a8c9c606c890c996f880448ecc0b28ca1a02f97ca81d36c0eb5491c3235fd"
},
"children": [
{
"id": "14632",
"routeId": "sa_a9d5dca89b5436122b2030c3",
"moleculeId": "sa_82fdccf7d1cc329c9db73f21",
"parentId": "14631",
"isLeaf": true,
"molecule": {
"id": "sa_82fdccf7d1cc329c9db73f21",
"inchikey": "INQOMBQAUSQDDS-UHFFFAOYSA-N",
"smiles": "CI"
},
"smiles": "CI",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "14633",
"routeId": "sa_a9d5dca89b5436122b2030c3",
"moleculeId": "sa_25d608303e1267307c171468",
"parentId": "14631",
"isLeaf": false,
"molecule": {
"id": "sa_25d608303e1267307c171468",
"inchikey": "YHRACQRKSBASHP-UHFFFAOYSA-N",
"smiles": "Cn1cnc2cnc(Nc3ccc(C4CN(C(=O)OC(C)(C)C)C4)cc3F)cc21"
},
"smiles": "Cn1cnc2cnc(Nc3ccc(C4CN(C(=O)OC(C)(C)C)C4)cc3F)cc21",
"reactionStepId": "sa_695275419c1fa308103cabd3",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20130217664A1;1780;1411812\",\"rsmi\":\"Cl[c:8]1[cH:7][c:6]2[n:2]([CH3:1])[cH:3][n:4][c:5]2[cH:29][n:28]1.[NH2:9][c:10]1[c:11]([F:12])[cH:13][c:14]([CH:15]2[CH2:16][N:17]([C:18](=[O:19])[O:20][C:21]([CH3:22])([CH3:23])[CH3:24])[CH2:25]2)[cH:26][cH:27]1>C1COCCO1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(O)O.[Cs+].[Cs+].[Pd].[Pd].c1ccc(P(c2ccccc2)c2ccc3ccccc3c2-c2c(P(c3ccccc3)c3ccccc3)ccc3ccccc23)cc1>[CH3:1][n:2]1[cH:3][n:4][c:5]2[c:6]1[cH:7][c:8]([NH:9][c:10]1[c:11]([F:12])[cH:13][c:14]([CH:15]3[CH2:16][N:17]([C:18](=[O:19])[O:20][C:21]([CH3:22])([CH3:23])[CH3:24])[CH2:25]3)[cH:26][cH:27]1)[n:28][cH:29]2\"},\"mapped_reaction_smiles\":\"Cl[c:8]1[cH:7][c:6]2[n:2]([CH3:1])[cH:3][n:4][c:5]2[cH:29][n:28]1.[NH2:9][c:10]1[c:11]([F:12])[cH:13][c:14]([CH:15]2[CH2:16][N:17]([C:18](=[O:19])[O:20][C:21]([CH3:22])([CH3:23])[CH3:24])[CH2:25]2)[cH:26][cH:27]1>C1COCCO1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(O)O.[Cs+].[Cs+].[Pd].[Pd].c1ccc(P(c2ccccc2)c2ccc3ccccc3c2-c2c(P(c3ccccc3)c3ccccc3)ccc3ccccc23)cc1>[CH3:1][n:2]1[cH:3][n:4][c:5]2[c:6]1[cH:7][c:8]([NH:9][c:10]1[c:11]([F:12])[cH:13][c:14]([CH:15]3[CH2:16][N:17]([C:18](=[O:19])[O:20][C:21]([CH3:22])([CH3:23])[CH3:24])[CH2:25]3)[cH:26][cH:27]1)[n:28][cH:29]2\"}",
"reactionStep": {
"id": "sa_695275419c1fa308103cabd3",
"reactionHash": "d28db71fbaa23b12242faa882c27d23f1b2c25c00e69d1fb41850d1a2b25fd7f"
},
"children": [
{
"id": "14634",
"routeId": "sa_a9d5dca89b5436122b2030c3",
"moleculeId": "sa_016ed454dc807f0c24e7ad42",
"parentId": "14633",
"isLeaf": true,
"molecule": {
"id": "sa_016ed454dc807f0c24e7ad42",
"inchikey": "JCYRHFDFONVARJ-UHFFFAOYSA-N",
"smiles": "CC(C)(C)OC(=O)N1CC(c2ccc(N)c(F)c2)C1"
},
"smiles": "CC(C)(C)OC(=O)N1CC(c2ccc(N)c(F)c2)C1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "14635",
"routeId": "sa_a9d5dca89b5436122b2030c3",
"moleculeId": "sa_61829a782b492a843f636595",
"parentId": "14633",
"isLeaf": false,
"molecule": {
"id": "sa_61829a782b492a843f636595",
"inchikey": "RUVZGKRCLXIBFX-UHFFFAOYSA-N",
"smiles": "Cn1cnc2cnc(Cl)cc21"
},
"smiles": "Cn1cnc2cnc(Cl)cc21",
"reactionStepId": "sa_4d97a6900c3ebfb49120b826",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20130217664A1;1243;1411687\",\"rsmi\":\"CO[CH:3](OC)OC.[CH3:1][NH:2][c:5]1[c:6]([NH2:4])[cH:7][c:8]([Cl:9])[n:10][cH:11]1>O.O=CO>[CH3:1][n:2]1[cH:3][n:4][c:5]2[c:6]1[cH:7][c:8]([Cl:9])[n:10][cH:11]2\"},\"mapped_reaction_smiles\":\"CO[CH:3](OC)OC.[CH3:1][NH:2][c:5]1[c:6]([NH2:4])[cH:7][c:8]([Cl:9])[n:10][cH:11]1>O.O=CO>[CH3:1][n:2]1[cH:3][n:4][c:5]2[c:6]1[cH:7][c:8]([Cl:9])[n:10][cH:11]2\"}",
"reactionStep": {
"id": "sa_4d97a6900c3ebfb49120b826",
"reactionHash": "92ecfa91ec6e41d5bff38b0c2591e3d2f1c7ea45b0945446be18487bccf8b46b"
},
"children": [
{
"id": "14636",
"routeId": "sa_a9d5dca89b5436122b2030c3",
"moleculeId": "sa_2608384363270bf1e8ad72a0",
"parentId": "14635",
"isLeaf": true,
"molecule": {
"id": "sa_2608384363270bf1e8ad72a0",
"inchikey": "NWADLCQEXCASKF-UHFFFAOYSA-N",
"smiles": "CNc1cnc(Cl)cc1N"
},
"smiles": "CNc1cnc(Cl)cc1N",
"reactionStepId": null,
"template": null,
"metadata": null,
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"children": []
},
{
"id": "14637",
"routeId": "sa_a9d5dca89b5436122b2030c3",
"moleculeId": "sa_c9fbce0da7a922c8ea07398a",
"parentId": "14635",
"isLeaf": true,
"molecule": {
"id": "sa_c9fbce0da7a922c8ea07398a",
"inchikey": "PYOKUURKVVELLB-UHFFFAOYSA-N",
"smiles": "COC(OC)OC"
},
"smiles": "COC(OC)OC",
"reactionStepId": null,
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"children": []
}
]
}
]
}
]
}
]
},
{
"id": "14638",
"routeId": "sa_a9d5dca89b5436122b2030c3",
"moleculeId": "sa_d2a31ea58046b00856f61ca5",
"parentId": "14629",
"isLeaf": true,
"molecule": {
"id": "sa_d2a31ea58046b00856f61ca5",
"inchikey": "QARBMVPHQWIHKH-UHFFFAOYSA-N",
"smiles": "CS(=O)(=O)Cl"
},
"smiles": "CS(=O)(=O)Cl",
"reactionStepId": null,
"template": null,
"metadata": null,
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"children": []
}
]
}
}