Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
CCC(Nc1ncnc2[nH]cnc12)c1nc2cccc(C)n2c(=O)c1-c1cncc(F)c1
InChiKey
SBXYNLLYXZFXHQ-UHFFFAOYSA-N
Route Signature
219e456ab4c2dcb31feb00c4ee7050407d67f1876ccdd8a57c6ae7a35492d914
Synthesis route with 7 steps
Route tree structure (JSON format)
{
"route": {
"id": "sa_b853b7173d0d5397b58fab32",
"signature": "219e456ab4c2dcb31feb00c4ee7050407d67f1876ccdd8a57c6ae7a35492d914",
"contentHash": "b12c05f3d6bd6f3e60c9e660234506d6281a526e43b537c35adcaba72ad9d4cb",
"length": 7,
"isConvergent": false
},
"target": {
"id": "sa_7fb988440c2ed973feb66210",
"benchmarkSetId": "61e696668b63e77d7c2a29c0821768e1c383de8313852d6e995224859494442e",
"targetId": "n5-00194",
"moleculeId": "sa_a66c6175aa493de828e2a1d6",
"smiles": "CCC(Nc1ncnc2[nH]cnc12)c1nc2cccc(C)n2c(=O)c1-c1cncc(F)c1",
"routeLength": 7,
"isConvergent": false,
"metadata": null,
"molecule": {
"id": "sa_a66c6175aa493de828e2a1d6",
"inchikey": "SBXYNLLYXZFXHQ-UHFFFAOYSA-N",
"smiles": "CCC(Nc1ncnc2[nH]cnc12)c1nc2cccc(C)n2c(=O)c1-c1cncc(F)c1"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "12715",
"routeId": "sa_b853b7173d0d5397b58fab32",
"moleculeId": "sa_a66c6175aa493de828e2a1d6",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_a66c6175aa493de828e2a1d6",
"inchikey": "SBXYNLLYXZFXHQ-UHFFFAOYSA-N",
"smiles": "CCC(Nc1ncnc2[nH]cnc12)c1nc2cccc(C)n2c(=O)c1-c1cncc(F)c1"
},
"smiles": "CCC(Nc1ncnc2[nH]cnc12)c1nc2cccc(C)n2c(=O)c1-c1cncc(F)c1",
"reactionStepId": "sa_c0e11a9a45772e5e61b3a9c9",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US09434746B2;0332;1802491\",\"rsmi\":\"I[c:15]1[c:14]([CH:3]([CH2:2][CH3:1])[NH:4][c:5]2[c:6]3[n:7][cH:8][nH:9][c:10]3[n:11][cH:12][n:13]2)[n:32][c:31]2[n:25]([c:23]1=[O:24])[c:26]([CH3:27])[cH:28][cH:29][cH:30]2.OB(O)[c:16]1[cH:17][c:18]([F:19])[cH:20][n:21][cH:22]1>C1COCCO1.CCOC(C)=O.O.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][CH2:2][CH:3]([NH:4][c:5]1[c:6]2[n:7][cH:8][nH:9][c:10]2[n:11][cH:12][n:13]1)[c:14]1[c:15](-[c:16]2[cH:17][c:18]([F:19])[cH:20][n:21][cH:22]2)[c:23](=[O:24])[n:25]2[c:26]([CH3:27])[cH:28][cH:29][cH:30][c:31]2[n:32]1\"},\"mapped_reaction_smiles\":\"I[c:15]1[c:14]([CH:3]([CH2:2][CH3:1])[NH:4][c:5]2[c:6]3[n:7][cH:8][nH:9][c:10]3[n:11][cH:12][n:13]2)[n:32][c:31]2[n:25]([c:23]1=[O:24])[c:26]([CH3:27])[cH:28][cH:29][cH:30]2.OB(O)[c:16]1[cH:17][c:18]([F:19])[cH:20][n:21][cH:22]1>C1COCCO1.CCOC(C)=O.O.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][CH2:2][CH:3]([NH:4][c:5]1[c:6]2[n:7][cH:8][nH:9][c:10]2[n:11][cH:12][n:13]1)[c:14]1[c:15](-[c:16]2[cH:17][c:18]([F:19])[cH:20][n:21][cH:22]2)[c:23](=[O:24])[n:25]2[c:26]([CH3:27])[cH:28][cH:29][cH:30][c:31]2[n:32]1\"}",
"reactionStep": {
"id": "sa_c0e11a9a45772e5e61b3a9c9",
"reactionHash": "1da35e1a35d4c2852827d7c62ae2a84edf99c3422e0fce9b29311080005625f3"
},
"children": [
{
"id": "12716",
"routeId": "sa_b853b7173d0d5397b58fab32",
"moleculeId": "sa_db2d4f8aa7019244e731ce60",
"parentId": "12715",
"isLeaf": true,
"molecule": {
"id": "sa_db2d4f8aa7019244e731ce60",
"inchikey": "FVEDGBRHTGXPOK-UHFFFAOYSA-N",
"smiles": "OB(O)c1cncc(F)c1"
},
"smiles": "OB(O)c1cncc(F)c1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "12717",
"routeId": "sa_b853b7173d0d5397b58fab32",
"moleculeId": "sa_0129af30b683433f789d830e",
"parentId": "12715",
"isLeaf": false,
"molecule": {
"id": "sa_0129af30b683433f789d830e",
"inchikey": "KPSBBXPRUWIDAF-UHFFFAOYSA-N",
"smiles": "CCC(Nc1ncnc2[nH]cnc12)c1nc2cccc(C)n2c(=O)c1I"
},
"smiles": "CCC(Nc1ncnc2[nH]cnc12)c1nc2cccc(C)n2c(=O)c1I",
"reactionStepId": "sa_18d0ba71e55a5212051d8f57",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US09434746B2;0331;1802490\",\"rsmi\":\"Br[c:5]1[c:6]2[n:7][cH:8][nH:9][c:10]2[n:11][cH:12][n:13]1.[CH3:1][CH2:2][CH:3]([NH2:4])[c:14]1[c:15]([I:16])[c:17](=[O:18])[n:19]2[c:20]([CH3:21])[cH:22][cH:23][cH:24][c:25]2[n:26]1>CCN(C(C)C)C(C)C.CCO>[CH3:1][CH2:2][CH:3]([NH:4][c:5]1[c:6]2[n:7][cH:8][nH:9][c:10]2[n:11][cH:12][n:13]1)[c:14]1[c:15]([I:16])[c:17](=[O:18])[n:19]2[c:20]([CH3:21])[cH:22][cH:23][cH:24][c:25]2[n:26]1\"},\"mapped_reaction_smiles\":\"Br[c:5]1[c:6]2[n:7][cH:8][nH:9][c:10]2[n:11][cH:12][n:13]1.[CH3:1][CH2:2][CH:3]([NH2:4])[c:14]1[c:15]([I:16])[c:17](=[O:18])[n:19]2[c:20]([CH3:21])[cH:22][cH:23][cH:24][c:25]2[n:26]1>CCN(C(C)C)C(C)C.CCO>[CH3:1][CH2:2][CH:3]([NH:4][c:5]1[c:6]2[n:7][cH:8][nH:9][c:10]2[n:11][cH:12][n:13]1)[c:14]1[c:15]([I:16])[c:17](=[O:18])[n:19]2[c:20]([CH3:21])[cH:22][cH:23][cH:24][c:25]2[n:26]1\"}",
"reactionStep": {
"id": "sa_18d0ba71e55a5212051d8f57",
"reactionHash": "5d43815fcf9eab79115515ea663a3ec90d88a7258e5196ec90d9d9b1a8966123"
},
"children": [
{
"id": "12718",
"routeId": "sa_b853b7173d0d5397b58fab32",
"moleculeId": "sa_a0ddf6857dd37eb0d19943cc",
"parentId": "12717",
"isLeaf": true,
"molecule": {
"id": "sa_a0ddf6857dd37eb0d19943cc",
"inchikey": "CTGFGRDVWBZYNB-UHFFFAOYSA-N",
"smiles": "Brc1ncnc2nc[nH]c12"
},
"smiles": "Brc1ncnc2[nH]cnc12",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "12719",
"routeId": "sa_b853b7173d0d5397b58fab32",
"moleculeId": "sa_2f28e56ffbee1abe393908db",
"parentId": "12717",
"isLeaf": false,
"molecule": {
"id": "sa_2f28e56ffbee1abe393908db",
"inchikey": "GLUPLKGHUYWXNJ-UHFFFAOYSA-N",
"smiles": "CCC(N)c1nc2cccc(C)n2c(=O)c1I"
},
"smiles": "CCC(N)c1nc2cccc(C)n2c(=O)c1I",
"reactionStepId": "sa_85bede1c73a785922c666e10",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US09434746B2;0330;1802489\",\"rsmi\":\"[N-]=[N+]=[N:4][CH:3]([CH2:2][CH3:1])[c:5]1[c:6]([I:7])[c:8](=[O:9])[n:10]2[c:11]([CH3:12])[cH:13][cH:14][cH:15][c:16]2[n:17]1>C1CCOC1.CCOC(C)=O.CP(C)C.O>[CH3:1][CH2:2][CH:3]([NH2:4])[c:5]1[c:6]([I:7])[c:8](=[O:9])[n:10]2[c:11]([CH3:12])[cH:13][cH:14][cH:15][c:16]2[n:17]1\"},\"mapped_reaction_smiles\":\"[N-]=[N+]=[N:4][CH:3]([CH2:2][CH3:1])[c:5]1[c:6]([I:7])[c:8](=[O:9])[n:10]2[c:11]([CH3:12])[cH:13][cH:14][cH:15][c:16]2[n:17]1>C1CCOC1.CCOC(C)=O.CP(C)C.O>[CH3:1][CH2:2][CH:3]([NH2:4])[c:5]1[c:6]([I:7])[c:8](=[O:9])[n:10]2[c:11]([CH3:12])[cH:13][cH:14][cH:15][c:16]2[n:17]1\"}",
"reactionStep": {
"id": "sa_85bede1c73a785922c666e10",
"reactionHash": "ea31afe4296ae39cc9752c2a7ceda842eb31d82b3763383cf33bda0f4e403d32"
},
"children": [
{
"id": "12720",
"routeId": "sa_b853b7173d0d5397b58fab32",
"moleculeId": "sa_365f15ddcfa115ce4e1070df",
"parentId": "12719",
"isLeaf": false,
"molecule": {
"id": "sa_365f15ddcfa115ce4e1070df",
"inchikey": "BEOIIGYLPUDFMK-UHFFFAOYSA-N",
"smiles": "CCC(N=[N+]=[N-])c1nc2cccc(C)n2c(=O)c1I"
},
"smiles": "CCC(N=[N+]=[N-])c1nc2cccc(C)n2c(=O)c1I",
"reactionStepId": "sa_a218ff8c1494ac5a5e238604",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US09434746B2;0325;1802485\",\"rsmi\":\"Br[CH:3]([CH2:2][CH3:1])[c:7]1[c:8]([I:9])[c:10](=[O:11])[n:12]2[c:13]([CH3:14])[cH:15][cH:16][cH:17][c:18]2[n:19]1.[N-:4]=[N+:5]=[N-:6]>CCOC(C)=O.CN(C)C=O.[Na+]>[CH3:1][CH2:2][CH:3]([N:4]=[N+:5]=[N-:6])[c:7]1[c:8]([I:9])[c:10](=[O:11])[n:12]2[c:13]([CH3:14])[cH:15][cH:16][cH:17][c:18]2[n:19]1\"},\"mapped_reaction_smiles\":\"Br[CH:3]([CH2:2][CH3:1])[c:7]1[c:8]([I:9])[c:10](=[O:11])[n:12]2[c:13]([CH3:14])[cH:15][cH:16][cH:17][c:18]2[n:19]1.[N-:4]=[N+:5]=[N-:6]>CCOC(C)=O.CN(C)C=O.[Na+]>[CH3:1][CH2:2][CH:3]([N:4]=[N+:5]=[N-:6])[c:7]1[c:8]([I:9])[c:10](=[O:11])[n:12]2[c:13]([CH3:14])[cH:15][cH:16][cH:17][c:18]2[n:19]1\"}",
"reactionStep": {
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"children": [
{
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"parentId": "12720",
"isLeaf": true,
"molecule": {
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"inchikey": "IVRMZWNICZWHMI-UHFFFAOYSA-N",
"smiles": "[N]N=[N-]"
},
"smiles": "[N-]=[N+]=[N-]",
"reactionStepId": null,
"template": null,
"metadata": null,
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"children": []
},
{
"id": "12722",
"routeId": "sa_b853b7173d0d5397b58fab32",
"moleculeId": "sa_0b3e502b5d5a4cd2fb88fffd",
"parentId": "12720",
"isLeaf": false,
"molecule": {
"id": "sa_0b3e502b5d5a4cd2fb88fffd",
"inchikey": "VZNYUZWLMYRMIB-UHFFFAOYSA-N",
"smiles": "CCC(Br)c1nc2cccc(C)n2c(=O)c1I"
},
"smiles": "CCC(Br)c1nc2cccc(C)n2c(=O)c1I",
"reactionStepId": "sa_1b8d482f8f567c24276e6537",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US09434746B2;0324;1802484\",\"rsmi\":\"O=C1CCC(=O)N1[I:7].[CH3:1][CH2:2][CH:3]([Br:4])[c:5]1[cH:6][c:8](=[O:9])[n:10]2[c:11]([CH3:12])[cH:13][cH:14][cH:15][c:16]2[n:17]1>CC#N>[CH3:1][CH2:2][CH:3]([Br:4])[c:5]1[c:6]([I:7])[c:8](=[O:9])[n:10]2[c:11]([CH3:12])[cH:13][cH:14][cH:15][c:16]2[n:17]1\"},\"mapped_reaction_smiles\":\"O=C1CCC(=O)N1[I:7].[CH3:1][CH2:2][CH:3]([Br:4])[c:5]1[cH:6][c:8](=[O:9])[n:10]2[c:11]([CH3:12])[cH:13][cH:14][cH:15][c:16]2[n:17]1>CC#N>[CH3:1][CH2:2][CH:3]([Br:4])[c:5]1[c:6]([I:7])[c:8](=[O:9])[n:10]2[c:11]([CH3:12])[cH:13][cH:14][cH:15][c:16]2[n:17]1\"}",
"reactionStep": {
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"children": [
{
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"moleculeId": "sa_e0a6dc663dcf837255678d0a",
"parentId": "12722",
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"molecule": {
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"inchikey": "LQZMLBORDGWNPD-UHFFFAOYSA-N",
"smiles": "O=C1CCC(=O)N1I"
},
"smiles": "O=C1CCC(=O)N1I",
"reactionStepId": null,
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{
"id": "12724",
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"molecule": {
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"inchikey": "NSAFVZWDKWAWLV-UHFFFAOYSA-N",
"smiles": "CCC(Br)c1cc(=O)n2c(C)cccc2n1"
},
"smiles": "CCC(Br)c1cc(=O)n2c(C)cccc2n1",
"reactionStepId": "sa_2b9c8c3a4a43add3afa22856",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US09434746B2;0323;1802483\",\"rsmi\":\"CO[C:7]([CH2:6][C:5](=O)[CH:3]([CH2:2][CH3:1])[Br:4])=[O:8].[n:9]1[c:10]([CH3:11])[cH:12][cH:13][cH:14][c:15]1[NH2:16]>[Na+].O>[CH3:1][CH2:2][CH:3]([Br:4])[c:5]1[cH:6][c:7](=[O:8])[n:9]2[c:10]([CH3:11])[cH:12][cH:13][cH:14][c:15]2[n:16]1\"},\"mapped_reaction_smiles\":\"CO[C:7]([CH2:6][C:5](=O)[CH:3]([CH2:2][CH3:1])[Br:4])=[O:8].[n:9]1[c:10]([CH3:11])[cH:12][cH:13][cH:14][c:15]1[NH2:16]>[Na+].O>[CH3:1][CH2:2][CH:3]([Br:4])[c:5]1[cH:6][c:7](=[O:8])[n:9]2[c:10]([CH3:11])[cH:12][cH:13][cH:14][c:15]2[n:16]1\"}",
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"children": [
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"smiles": "CCC(Br)C(=O)CC(=O)OC"
},
"smiles": "CCC(Br)C(=O)CC(=O)OC",
"reactionStepId": "sa_f41e7869ce6d5d66580c662e",
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"metadata": "{\"annotations\":{\"ID\":\"US09434746B2;0322;1802482\",\"rsmi\":\"Br[Br:4].[CH3:1][CH2:2][CH2:3][C:5](=[O:6])[CH2:7][C:8](=[O:9])[O:10][CH3:11]>ClC(Cl)Cl>[CH3:1][CH2:2][CH:3]([Br:4])[C:5](=[O:6])[CH2:7][C:8](=[O:9])[O:10][CH3:11]\"},\"mapped_reaction_smiles\":\"Br[Br:4].[CH3:1][CH2:2][CH2:3][C:5](=[O:6])[CH2:7][C:8](=[O:9])[O:10][CH3:11]>ClC(Cl)Cl>[CH3:1][CH2:2][CH:3]([Br:4])[C:5](=[O:6])[CH2:7][C:8](=[O:9])[O:10][CH3:11]\"}",
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"children": [
{
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"molecule": {
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"inchikey": "GDTBXPJZTBHREO-UHFFFAOYSA-N",
"smiles": "BrBr"
},
"smiles": "BrBr",
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},
{
"id": "12727",
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"molecule": {
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"smiles": "CCCC(=O)CC(=O)OC"
},
"smiles": "CCCC(=O)CC(=O)OC",
"reactionStepId": null,
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}
]
},
{
"id": "12728",
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"parentId": "12724",
"isLeaf": true,
"molecule": {
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"inchikey": "QUXLCYFNVNNRBE-UHFFFAOYSA-N",
"smiles": "Cc1cccc(N)n1"
},
"smiles": "Cc1cccc(N)n1",
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}
]
}
]
}
]
}
]
}
]
}
]
}
}