Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
CC1=NN(c2ccc3c(c2)CCO3)C(=O)C1=NNc1cc(F)cc(-c2cccc(C(=O)O)c2)c1O
InChiKey
YKEJWTUEVHGMMG-UHFFFAOYSA-N
Route Signature
3583d74bbdcc2218dfef7c3d806537e1dc45e0c218d31227694b132cdd2a89a5
Synthesis route with 6 steps
Route tree structure (JSON format)
{
"route": {
"id": "sa_e8bf492a4c972fa1eb79650a",
"signature": "3583d74bbdcc2218dfef7c3d806537e1dc45e0c218d31227694b132cdd2a89a5",
"contentHash": "13e48fff0d9ce8d723d20052464320012991f37e95473d36a50ca94f496ff1a8",
"length": 6,
"isConvergent": false
},
"target": {
"id": "sa_9e2a5ce067bc12c576ecc2d7",
"benchmarkSetId": "61e696668b63e77d7c2a29c0821768e1c383de8313852d6e995224859494442e",
"targetId": "n5-00320",
"moleculeId": "sa_fdbc72ff5fd9167d2d1b14e5",
"smiles": "CC1=NN(c2ccc3c(c2)CCO3)C(=O)C1=NNc1cc(F)cc(-c2cccc(C(=O)O)c2)c1O",
"routeLength": 6,
"isConvergent": false,
"metadata": null,
"molecule": {
"id": "sa_fdbc72ff5fd9167d2d1b14e5",
"inchikey": "YKEJWTUEVHGMMG-UHFFFAOYSA-N",
"smiles": "CC1=NN(c2ccc3c(c2)CCO3)C(=O)C1=NNc1cc(F)cc(-c2cccc(C(=O)O)c2)c1O"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "13035",
"routeId": "sa_e8bf492a4c972fa1eb79650a",
"moleculeId": "sa_fdbc72ff5fd9167d2d1b14e5",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_fdbc72ff5fd9167d2d1b14e5",
"inchikey": "YKEJWTUEVHGMMG-UHFFFAOYSA-N",
"smiles": "CC1=NN(c2ccc3c(c2)CCO3)C(=O)C1=NNc1cc(F)cc(-c2cccc(C(=O)O)c2)c1O"
},
"smiles": "CC1=NN(c2ccc3c(c2)CCO3)C(=O)C1=NNc1cc(F)cc(-c2cccc(C(=O)O)c2)c1O",
"reactionStepId": "sa_337fda6ceed74ea421af6ded",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20130123507A1;0220;1369554\",\"rsmi\":\"O=[N:17]O.[CH3:1][C:2]1=[N:3][N:4]([c:5]2[cH:6][c:7]3[c:8]([cH:9][cH:10]2)[O:11][CH2:12][CH2:13]3)[C:14](=[O:15])[CH2:16]1.[NH2:18][c:19]1[cH:20][c:21]([F:22])[cH:23][c:24](-[c:25]2[cH:26][c:27]([C:28](=[O:29])[OH:30])[cH:31][cH:32][cH:33]2)[c:34]1[OH:35]>Cl.Cl.O=C(O)O.[Na+].[Na+]>[CH3:1][C:2]1=[N:3][N:4]([c:5]2[cH:6][c:7]3[c:8]([cH:9][cH:10]2)[O:11][CH2:12][CH2:13]3)[C:14](=[O:15])[C:16]1=[N:17][NH:18][c:19]1[cH:20][c:21]([F:22])[cH:23][c:24](-[c:25]2[cH:26][c:27]([C:28](=[O:29])[OH:30])[cH:31][cH:32][cH:33]2)[c:34]1[OH:35]\"},\"mapped_reaction_smiles\":\"O=[N:17]O.[CH3:1][C:2]1=[N:3][N:4]([c:5]2[cH:6][c:7]3[c:8]([cH:9][cH:10]2)[O:11][CH2:12][CH2:13]3)[C:14](=[O:15])[CH2:16]1.[NH2:18][c:19]1[cH:20][c:21]([F:22])[cH:23][c:24](-[c:25]2[cH:26][c:27]([C:28](=[O:29])[OH:30])[cH:31][cH:32][cH:33]2)[c:34]1[OH:35]>Cl.Cl.O=C(O)O.[Na+].[Na+]>[CH3:1][C:2]1=[N:3][N:4]([c:5]2[cH:6][c:7]3[c:8]([cH:9][cH:10]2)[O:11][CH2:12][CH2:13]3)[C:14](=[O:15])[C:16]1=[N:17][NH:18][c:19]1[cH:20][c:21]([F:22])[cH:23][c:24](-[c:25]2[cH:26][c:27]([C:28](=[O:29])[OH:30])[cH:31][cH:32][cH:33]2)[c:34]1[OH:35]\"}",
"reactionStep": {
"id": "sa_337fda6ceed74ea421af6ded",
"reactionHash": "e39e009abc572951340e0185f70d23d9214ffe2e7f88dd01ada03282d36391d8"
},
"children": [
{
"id": "13036",
"routeId": "sa_e8bf492a4c972fa1eb79650a",
"moleculeId": "sa_81c0446884d57a7253ff6b54",
"parentId": "13035",
"isLeaf": true,
"molecule": {
"id": "sa_81c0446884d57a7253ff6b54",
"inchikey": "IOVCWXUNBOPUCH-UHFFFAOYSA-N",
"smiles": "[O-]N=[OH+]"
},
"smiles": "O=NO",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "13037",
"routeId": "sa_e8bf492a4c972fa1eb79650a",
"moleculeId": "sa_d1307309f79c5ac78fff1457",
"parentId": "13035",
"isLeaf": true,
"molecule": {
"id": "sa_d1307309f79c5ac78fff1457",
"inchikey": "KBOGEGUAFGNMNM-UHFFFAOYSA-N",
"smiles": "CC1=NN(c2ccc3c(c2)CCO3)C(=O)C1"
},
"smiles": "CC1=NN(c2ccc3c(c2)CCO3)C(=O)C1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "13038",
"routeId": "sa_e8bf492a4c972fa1eb79650a",
"moleculeId": "sa_c194ab449a804b106d964d75",
"parentId": "13035",
"isLeaf": false,
"molecule": {
"id": "sa_c194ab449a804b106d964d75",
"inchikey": "ZKFZFBOAGWUBQI-UHFFFAOYSA-N",
"smiles": "Nc1cc(F)cc(-c2cccc(C(=O)O)c2)c1O"
},
"smiles": "Nc1cc(F)cc(-c2cccc(C(=O)O)c2)c1O",
"reactionStepId": "sa_282598fa0b48b9a6e28ebab9",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20130123507A1;0105;1369517\",\"rsmi\":\"O=[N+:1]([O-])[c:2]1[cH:3][c:4]([F:5])[cH:6][c:7](-[c:8]2[cH:9][c:10]([C:11](=[O:12])[OH:13])[cH:14][cH:15][cH:16]2)[c:17]1[OH:18]>Br.CCO.O=CO.N.[Pd]>[NH2:1][c:2]1[cH:3][c:4]([F:5])[cH:6][c:7](-[c:8]2[cH:9][c:10]([C:11](=[O:12])[OH:13])[cH:14][cH:15][cH:16]2)[c:17]1[OH:18]\"},\"mapped_reaction_smiles\":\"O=[N+:1]([O-])[c:2]1[cH:3][c:4]([F:5])[cH:6][c:7](-[c:8]2[cH:9][c:10]([C:11](=[O:12])[OH:13])[cH:14][cH:15][cH:16]2)[c:17]1[OH:18]>Br.CCO.O=CO.N.[Pd]>[NH2:1][c:2]1[cH:3][c:4]([F:5])[cH:6][c:7](-[c:8]2[cH:9][c:10]([C:11](=[O:12])[OH:13])[cH:14][cH:15][cH:16]2)[c:17]1[OH:18]\"}",
"reactionStep": {
"id": "sa_282598fa0b48b9a6e28ebab9",
"reactionHash": "2319531873526d986cbbbff9f48a6d31947226895dfd7e9d3bec68b833c80673"
},
"children": [
{
"id": "13039",
"routeId": "sa_e8bf492a4c972fa1eb79650a",
"moleculeId": "sa_cbb3799a032036d6e7655797",
"parentId": "13038",
"isLeaf": false,
"molecule": {
"id": "sa_cbb3799a032036d6e7655797",
"inchikey": "RGUUEAHVNUOJSC-UHFFFAOYSA-N",
"smiles": "O=C(O)c1cccc(-c2cc(F)cc([N+](=O)[O-])c2O)c1"
},
"smiles": "O=C(O)c1cccc(-c2cc(F)cc([N+](=O)[O-])c2O)c1",
"reactionStepId": "sa_d1a577757c4faffbc14c77a9",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20130123507A1;0103;1369516\",\"rsmi\":\"C[O:11][c:10]1[c:9](-[c:8]2[cH:7][cH:6][cH:5][c:4]([C:2](=[O:1])[OH:3])[cH:20]2)[cH:19][c:17]([F:18])[cH:16][c:12]1[N+:13](=[O:14])[O-:15]>Br>[O:1]=[C:2]([OH:3])[c:4]1[cH:5][cH:6][cH:7][c:8](-[c:9]2[c:10]([OH:11])[c:12]([N+:13](=[O:14])[O-:15])[cH:16][c:17]([F:18])[cH:19]2)[cH:20]1\"},\"mapped_reaction_smiles\":\"C[O:11][c:10]1[c:9](-[c:8]2[cH:7][cH:6][cH:5][c:4]([C:2](=[O:1])[OH:3])[cH:20]2)[cH:19][c:17]([F:18])[cH:16][c:12]1[N+:13](=[O:14])[O-:15]>Br>[O:1]=[C:2]([OH:3])[c:4]1[cH:5][cH:6][cH:7][c:8](-[c:9]2[c:10]([OH:11])[c:12]([N+:13](=[O:14])[O-:15])[cH:16][c:17]([F:18])[cH:19]2)[cH:20]1\"}",
"reactionStep": {
"id": "sa_d1a577757c4faffbc14c77a9",
"reactionHash": "a79ed9061452ff61a2effa4f143639bcf1efe9ef7fa00257fdf24195f03e3da3"
},
"children": [
{
"id": "13040",
"routeId": "sa_e8bf492a4c972fa1eb79650a",
"moleculeId": "sa_fb68f18005ff95561a90d355",
"parentId": "13039",
"isLeaf": false,
"molecule": {
"id": "sa_fb68f18005ff95561a90d355",
"inchikey": "HNZIVMYTHZWCDU-UHFFFAOYSA-N",
"smiles": "COc1c(-c2cccc(C(=O)O)c2)cc(F)cc1[N+](=O)[O-]"
},
"smiles": "COc1c(-c2cccc(C(=O)O)c2)cc(F)cc1[N+](=O)[O-]",
"reactionStepId": "sa_8b7f2bbc39188955f3fe7b49",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20130123507A1;0100;1369515\",\"rsmi\":\"Br[c:4]1[c:3]([O:2][CH3:1])[c:18]([N+:19](=[O:20])[O-:21])[cH:17][c:15]([F:16])[cH:14]1.OB(O)[c:5]1[cH:6][c:7]([C:8](=[O:9])[OH:10])[cH:11][cH:12][cH:13]1>C1COCCO1.O=C(O)O.[Na+].[Na+].c1ccc([PH](c2ccccc2)(c2ccccc2)[Pd]([PH](c2ccccc2)(c2ccccc2)c2ccccc2)([PH](c2ccccc2)(c2ccccc2)c2ccccc2)[PH](c2ccccc2)(c2ccccc2)c2ccccc2)cc1>[CH3:1][O:2][c:3]1[c:4](-[c:5]2[cH:6][c:7]([C:8](=[O:9])[OH:10])[cH:11][cH:12][cH:13]2)[cH:14][c:15]([F:16])[cH:17][c:18]1[N+:19](=[O:20])[O-:21]\"},\"mapped_reaction_smiles\":\"Br[c:4]1[c:3]([O:2][CH3:1])[c:18]([N+:19](=[O:20])[O-:21])[cH:17][c:15]([F:16])[cH:14]1.OB(O)[c:5]1[cH:6][c:7]([C:8](=[O:9])[OH:10])[cH:11][cH:12][cH:13]1>C1COCCO1.O=C(O)O.[Na+].[Na+].c1ccc([PH](c2ccccc2)(c2ccccc2)[Pd]([PH](c2ccccc2)(c2ccccc2)c2ccccc2)([PH](c2ccccc2)(c2ccccc2)c2ccccc2)[PH](c2ccccc2)(c2ccccc2)c2ccccc2)cc1>[CH3:1][O:2][c:3]1[c:4](-[c:5]2[cH:6][c:7]([C:8](=[O:9])[OH:10])[cH:11][cH:12][cH:13]2)[cH:14][c:15]([F:16])[cH:17][c:18]1[N+:19](=[O:20])[O-:21]\"}",
"reactionStep": {
"id": "sa_8b7f2bbc39188955f3fe7b49",
"reactionHash": "3e93815925664b25e91d3581ae112cec0e1ca82eebfc650042ccafff71e5b47a"
},
"children": [
{
"id": "13041",
"routeId": "sa_e8bf492a4c972fa1eb79650a",
"moleculeId": "sa_7e0aa76b02eb6881f1616f1d",
"parentId": "13040",
"isLeaf": true,
"molecule": {
"id": "sa_7e0aa76b02eb6881f1616f1d",
"inchikey": "DBVFWZMQJQMJCB-UHFFFAOYSA-N",
"smiles": "O=C(O)c1cccc(B(O)O)c1"
},
"smiles": "O=C(O)c1cccc(B(O)O)c1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "13042",
"routeId": "sa_e8bf492a4c972fa1eb79650a",
"moleculeId": "sa_af547ff9d0e14242147d5a5c",
"parentId": "13040",
"isLeaf": false,
"molecule": {
"id": "sa_af547ff9d0e14242147d5a5c",
"inchikey": "RMUJVOPHLHFICQ-UHFFFAOYSA-N",
"smiles": "COc1c(Br)cc(F)cc1[N+](=O)[O-]"
},
"smiles": "COc1c(Br)cc(F)cc1[N+](=O)[O-]",
"reactionStepId": "sa_ba63045d26385012c67b52c1",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20130123507A1;0097;1369514\",\"rsmi\":\"I[CH3:1].[OH:2][c:3]1[c:4]([Br:5])[cH:6][c:7]([F:8])[cH:9][c:10]1[N+:11](=[O:12])[O-:13]>CC(C)=O.O=C(O)O.[K+].[K+]>[CH3:1][O:2][c:3]1[c:4]([Br:5])[cH:6][c:7]([F:8])[cH:9][c:10]1[N+:11](=[O:12])[O-:13]\"},\"mapped_reaction_smiles\":\"I[CH3:1].[OH:2][c:3]1[c:4]([Br:5])[cH:6][c:7]([F:8])[cH:9][c:10]1[N+:11](=[O:12])[O-:13]>CC(C)=O.O=C(O)O.[K+].[K+]>[CH3:1][O:2][c:3]1[c:4]([Br:5])[cH:6][c:7]([F:8])[cH:9][c:10]1[N+:11](=[O:12])[O-:13]\"}",
"reactionStep": {
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"children": [
{
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"moleculeId": "sa_6066b396c91a678df3556d33",
"parentId": "13042",
"isLeaf": false,
"molecule": {
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"inchikey": "DFHGOCSWFGXYSQ-UHFFFAOYSA-N",
"smiles": "O=[N+]([O-])c1cc(F)cc(Br)c1O"
},
"smiles": "O=[N+]([O-])c1cc(F)cc(Br)c1O",
"reactionStepId": "sa_ddfff42a25471c7de0bc6e8f",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20130123507A1;0096;1369513\",\"rsmi\":\"O[N+:2](=[O:1])[O-:3].[cH:4]1[cH:5][c:6]([F:7])[cH:8][c:9]([Br:10])[c:11]1[OH:12]>O.O=S(=O)(O)O.[Na+]>[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][c:6]([F:7])[cH:8][c:9]([Br:10])[c:11]1[OH:12]\"},\"mapped_reaction_smiles\":\"O[N+:2](=[O:1])[O-:3].[cH:4]1[cH:5][c:6]([F:7])[cH:8][c:9]([Br:10])[c:11]1[OH:12]>O.O=S(=O)(O)O.[Na+]>[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][c:6]([F:7])[cH:8][c:9]([Br:10])[c:11]1[OH:12]\"}",
"reactionStep": {
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"reactionHash": "5ffc861d4dcfbdcb8d47b49a6210fee9e20c4eea6a320e77a7138e3d271e7950"
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"children": [
{
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"moleculeId": "sa_edac0a7fd043198784a28dd9",
"parentId": "13043",
"isLeaf": true,
"molecule": {
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"inchikey": "GRYLNZFGIOXLOG-UHFFFAOYSA-N",
"smiles": "O=[N+]([O-])O"
},
"smiles": "O=[N+]([O-])O",
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},
{
"id": "13045",
"routeId": "sa_e8bf492a4c972fa1eb79650a",
"moleculeId": "sa_9608e7c2c9c83724cbf0eb56",
"parentId": "13043",
"isLeaf": true,
"molecule": {
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"inchikey": "MEYRABVEYCFHHB-UHFFFAOYSA-N",
"smiles": "Oc1ccc(F)cc1Br"
},
"smiles": "Oc1ccc(F)cc1Br",
"reactionStepId": null,
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}
]
},
{
"id": "13046",
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"moleculeId": "sa_82fdccf7d1cc329c9db73f21",
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"molecule": {
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"inchikey": "INQOMBQAUSQDDS-UHFFFAOYSA-N",
"smiles": "CI"
},
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}
]
}
]
}
]
}
]
}
]
}
}