Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
Cn1nccc1Nc1nccc(-c2cc(F)n3c(C(CCO)Oc4ccccc4)nnc3c2)n1
InChiKey
RXFNOIKPHVDLEZ-UHFFFAOYSA-N
Route Signature
e87775f25d4abee2627e16ad07d5f83788e5a10d509d095b611d65f32a9d9aec
Synthesis route with 5 steps (convergent)
Route tree structure (JSON format)
{
"route": {
"id": "sa_988f6437f1d233e4b8752660",
"signature": "e87775f25d4abee2627e16ad07d5f83788e5a10d509d095b611d65f32a9d9aec",
"contentHash": "c7e558574cf5f71bb21d5d2fa58af43e302ea8ec77ef3f4b422c4d8ebe1f209c",
"length": 5,
"isConvergent": true
},
"target": {
"id": "sa_d01580ce5b24b49e5cb710b6",
"benchmarkSetId": "3895c2909c53593560c5ba610abc7e6df80513dfd8624165c560451735097d36",
"targetId": "n5-00472",
"moleculeId": "sa_ebe57d1aeabd34f52cc54b14",
"smiles": "Cn1nccc1Nc1nccc(-c2cc(F)n3c(C(CCO)Oc4ccccc4)nnc3c2)n1",
"routeLength": 5,
"isConvergent": true,
"metadata": null,
"molecule": {
"id": "sa_ebe57d1aeabd34f52cc54b14",
"inchikey": "RXFNOIKPHVDLEZ-UHFFFAOYSA-N",
"smiles": "Cn1nccc1Nc1nccc(-c2cc(F)n3c(C(CCO)Oc4ccccc4)nnc3c2)n1"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "9498",
"routeId": "sa_988f6437f1d233e4b8752660",
"moleculeId": "sa_ebe57d1aeabd34f52cc54b14",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_ebe57d1aeabd34f52cc54b14",
"inchikey": "RXFNOIKPHVDLEZ-UHFFFAOYSA-N",
"smiles": "Cn1nccc1Nc1nccc(-c2cc(F)n3c(C(CCO)Oc4ccccc4)nnc3c2)n1"
},
"smiles": "Cn1nccc1Nc1nccc(-c2cc(F)n3c(C(CCO)Oc4ccccc4)nnc3c2)n1",
"reactionStepId": "sa_01b88282f5f801bc22f74e30",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20150182537A1;0480;1714909\",\"rsmi\":\"CC(C)(C)[Si](C)(C)[O:22][CH2:21][CH2:20][CH:19]([c:18]1[n:17][n:16][c:15]2[cH:14][c:13](-[c:12]3[cH:11][cH:10][n:9][c:8]([NH:7][c:6]4[n:2]([CH3:1])[n:3][cH:4][cH:5]4)[n:34]3)[cH:33][c:31]([F:32])[n:30]21)[O:23][c:24]1[cH:25][cH:26][cH:27][cH:28][cH:29]1>CCOCC.ClCCl.FB(F)F>[CH3:1][n:2]1[n:3][cH:4][cH:5][c:6]1[NH:7][c:8]1[n:9][cH:10][cH:11][c:12](-[c:13]2[cH:14][c:15]3[n:16][n:17][c:18]([CH:19]([CH2:20][CH2:21][OH:22])[O:23][c:24]4[cH:25][cH:26][cH:27][cH:28][cH:29]4)[n:30]3[c:31]([F:32])[cH:33]2)[n:34]1\"},\"mapped_reaction_smiles\":\"CC(C)(C)[Si](C)(C)[O:22][CH2:21][CH2:20][CH:19]([c:18]1[n:17][n:16][c:15]2[cH:14][c:13](-[c:12]3[cH:11][cH:10][n:9][c:8]([NH:7][c:6]4[n:2]([CH3:1])[n:3][cH:4][cH:5]4)[n:34]3)[cH:33][c:31]([F:32])[n:30]21)[O:23][c:24]1[cH:25][cH:26][cH:27][cH:28][cH:29]1>CCOCC.ClCCl.FB(F)F>[CH3:1][n:2]1[n:3][cH:4][cH:5][c:6]1[NH:7][c:8]1[n:9][cH:10][cH:11][c:12](-[c:13]2[cH:14][c:15]3[n:16][n:17][c:18]([CH:19]([CH2:20][CH2:21][OH:22])[O:23][c:24]4[cH:25][cH:26][cH:27][cH:28][cH:29]4)[n:30]3[c:31]([F:32])[cH:33]2)[n:34]1\"}",
"reactionStep": {
"id": "sa_01b88282f5f801bc22f74e30",
"reactionHash": "3de8d70ec0c104528a09df02e0f034b8cde420f15b2f1a1974b00339257a108c"
},
"children": [
{
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"routeId": "sa_988f6437f1d233e4b8752660",
"moleculeId": "sa_1f502b5ed42e8deaae952c1e",
"parentId": "9498",
"isLeaf": false,
"molecule": {
"id": "sa_1f502b5ed42e8deaae952c1e",
"inchikey": "UIUPDZHITZXYEU-UHFFFAOYSA-N",
"smiles": "Cn1nccc1Nc1nccc(-c2cc(F)n3c(C(CCO[Si](C)(C)C(C)(C)C)Oc4ccccc4)nnc3c2)n1"
},
"smiles": "Cn1nccc1Nc1nccc(-c2cc(F)n3c(C(CCO[Si](C)(C)C(C)(C)C)Oc4ccccc4)nnc3c2)n1",
"reactionStepId": "sa_fdad319cd8a8eb0ac389c27c",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20150182537A1;0479;1714908\",\"rsmi\":\"O=[C:18]([NH:17][NH:16][c:15]1[cH:14][c:13](-[c:12]2[cH:11][cH:10][n:9][c:8]([NH:7][c:6]3[n:2]([CH3:1])[n:3][cH:4][cH:5]3)[n:41]2)[cH:40][c:38]([F:39])[n:37]1)[CH:19]([CH2:20][CH2:21][O:22][Si:23]([CH3:24])([CH3:25])[C:26]([CH3:27])([CH3:28])[CH3:29])[O:30][c:31]1[cH:32][cH:33][cH:34][cH:35][cH:36]1>BrBr.CC#N.CCN(C(C)C)C(C)C.O.c1ccc(P(c2ccccc2)c2ccccc2)cc1>[CH3:1][n:2]1[n:3][cH:4][cH:5][c:6]1[NH:7][c:8]1[n:9][cH:10][cH:11][c:12](-[c:13]2[cH:14][c:15]3[n:16][n:17][c:18]([CH:19]([CH2:20][CH2:21][O:22][Si:23]([CH3:24])([CH3:25])[C:26]([CH3:27])([CH3:28])[CH3:29])[O:30][c:31]4[cH:32][cH:33][cH:34][cH:35][cH:36]4)[n:37]3[c:38]([F:39])[cH:40]2)[n:41]1\"},\"mapped_reaction_smiles\":\"O=[C:18]([NH:17][NH:16][c:15]1[cH:14][c:13](-[c:12]2[cH:11][cH:10][n:9][c:8]([NH:7][c:6]3[n:2]([CH3:1])[n:3][cH:4][cH:5]3)[n:41]2)[cH:40][c:38]([F:39])[n:37]1)[CH:19]([CH2:20][CH2:21][O:22][Si:23]([CH3:24])([CH3:25])[C:26]([CH3:27])([CH3:28])[CH3:29])[O:30][c:31]1[cH:32][cH:33][cH:34][cH:35][cH:36]1>BrBr.CC#N.CCN(C(C)C)C(C)C.O.c1ccc(P(c2ccccc2)c2ccccc2)cc1>[CH3:1][n:2]1[n:3][cH:4][cH:5][c:6]1[NH:7][c:8]1[n:9][cH:10][cH:11][c:12](-[c:13]2[cH:14][c:15]3[n:16][n:17][c:18]([CH:19]([CH2:20][CH2:21][O:22][Si:23]([CH3:24])([CH3:25])[C:26]([CH3:27])([CH3:28])[CH3:29])[O:30][c:31]4[cH:32][cH:33][cH:34][cH:35][cH:36]4)[n:37]3[c:38]([F:39])[cH:40]2)[n:41]1\"}",
"reactionStep": {
"id": "sa_fdad319cd8a8eb0ac389c27c",
"reactionHash": "55d3224d5683d8b89d0bd9870073948ea72f7ca76de1edad7e9740e764d33ad0"
},
"children": [
{
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"routeId": "sa_988f6437f1d233e4b8752660",
"moleculeId": "sa_7275b8f093f44e59912e2f76",
"parentId": "9499",
"isLeaf": false,
"molecule": {
"id": "sa_7275b8f093f44e59912e2f76",
"inchikey": "WIZHLTIEQKXKET-UHFFFAOYSA-N",
"smiles": "Cn1nccc1Nc1nccc(-c2cc(F)nc(NNC(=O)C(CCO[Si](C)(C)C(C)(C)C)Oc3ccccc3)c2)n1"
},
"smiles": "Cn1nccc1Nc1nccc(-c2cc(F)nc(NNC(=O)C(CCO[Si](C)(C)C(C)(C)C)Oc3ccccc3)c2)n1",
"reactionStepId": "sa_095d713938e30aa90504ffbf",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20150182537A1;0478;1714907\",\"rsmi\":\"O[C:18](=[O:19])[CH:20]([CH2:21][CH2:22][O:23][Si:24]([CH3:25])([CH3:26])[C:27]([CH3:28])([CH3:29])[CH3:30])[O:31][c:32]1[cH:33][cH:34][cH:35][cH:36][cH:37]1.[CH3:1][n:2]1[n:3][cH:4][cH:5][c:6]1[NH:7][c:8]1[n:9][cH:10][cH:11][c:12](-[c:13]2[cH:14][c:15]([NH:16][NH2:17])[n:38][c:39]([F:40])[cH:41]2)[n:42]1>CCN(C(C)C)C(C)C.CN(C)C(On1nnc2cccnc21)=[N+](C)C.CN(C)C=O.F[PH](F)(F)(F)(F)F.O>[CH3:1][n:2]1[n:3][cH:4][cH:5][c:6]1[NH:7][c:8]1[n:9][cH:10][cH:11][c:12](-[c:13]2[cH:14][c:15]([NH:16][NH:17][C:18](=[O:19])[CH:20]([CH2:21][CH2:22][O:23][Si:24]([CH3:25])([CH3:26])[C:27]([CH3:28])([CH3:29])[CH3:30])[O:31][c:32]3[cH:33][cH:34][cH:35][cH:36][cH:37]3)[n:38][c:39]([F:40])[cH:41]2)[n:42]1\"},\"mapped_reaction_smiles\":\"O[C:18](=[O:19])[CH:20]([CH2:21][CH2:22][O:23][Si:24]([CH3:25])([CH3:26])[C:27]([CH3:28])([CH3:29])[CH3:30])[O:31][c:32]1[cH:33][cH:34][cH:35][cH:36][cH:37]1.[CH3:1][n:2]1[n:3][cH:4][cH:5][c:6]1[NH:7][c:8]1[n:9][cH:10][cH:11][c:12](-[c:13]2[cH:14][c:15]([NH:16][NH2:17])[n:38][c:39]([F:40])[cH:41]2)[n:42]1>CCN(C(C)C)C(C)C.CN(C)C(On1nnc2cccnc21)=[N+](C)C.CN(C)C=O.F[PH](F)(F)(F)(F)F.O>[CH3:1][n:2]1[n:3][cH:4][cH:5][c:6]1[NH:7][c:8]1[n:9][cH:10][cH:11][c:12](-[c:13]2[cH:14][c:15]([NH:16][NH:17][C:18](=[O:19])[CH:20]([CH2:21][CH2:22][O:23][Si:24]([CH3:25])([CH3:26])[C:27]([CH3:28])([CH3:29])[CH3:30])[O:31][c:32]3[cH:33][cH:34][cH:35][cH:36][cH:37]3)[n:38][c:39]([F:40])[cH:41]2)[n:42]1\"}",
"reactionStep": {
"id": "sa_095d713938e30aa90504ffbf",
"reactionHash": "566762a12683e941a2962c91317aa14f832b72ff8395c194bdcc4db68fdf9d4b"
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"children": [
{
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"moleculeId": "sa_e3eeadca881fd7a0304287f7",
"parentId": "9500",
"isLeaf": false,
"molecule": {
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"inchikey": "WBDXIKMPPCKTDA-UHFFFAOYSA-N",
"smiles": "Cn1nccc1Nc1nccc(-c2cc(F)nc(NN)c2)n1"
},
"smiles": "Cn1nccc1Nc1nccc(-c2cc(F)nc(NN)c2)n1",
"reactionStepId": "sa_25b74516055a4c53ffee45fd",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20150182537A1;0212;1714863\",\"rsmi\":\"F[c:18]1[n:17][c:15]([F:16])[cH:14][c:13](-[c:12]2[cH:11][cH:10][n:9][c:8]([NH:7][c:6]3[n:2]([CH3:1])[n:3][cH:4][cH:5]3)[n:22]2)[cH:21]1.[NH2:19][NH2:20]>CCO>[CH3:1][n:2]1[n:3][cH:4][cH:5][c:6]1[NH:7][c:8]1[n:9][cH:10][cH:11][c:12](-[c:13]2[cH:14][c:15]([F:16])[n:17][c:18]([NH:19][NH2:20])[cH:21]2)[n:22]1\"},\"mapped_reaction_smiles\":\"F[c:18]1[n:17][c:15]([F:16])[cH:14][c:13](-[c:12]2[cH:11][cH:10][n:9][c:8]([NH:7][c:6]3[n:2]([CH3:1])[n:3][cH:4][cH:5]3)[n:22]2)[cH:21]1.[NH2:19][NH2:20]>CCO>[CH3:1][n:2]1[n:3][cH:4][cH:5][c:6]1[NH:7][c:8]1[n:9][cH:10][cH:11][c:12](-[c:13]2[cH:14][c:15]([F:16])[n:17][c:18]([NH:19][NH2:20])[cH:21]2)[n:22]1\"}",
"reactionStep": {
"id": "sa_25b74516055a4c53ffee45fd",
"reactionHash": "bf3cf9040b8f76aa7b1ceacd7d97ad926878080d865d66327b2749b003d81d44"
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"children": [
{
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"moleculeId": "sa_8d03dbea6e72885a550c7f8d",
"parentId": "9501",
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"molecule": {
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"inchikey": "JGAYZUXNCMUWER-UHFFFAOYSA-N",
"smiles": "Cn1nccc1Nc1nccc(-c2cc(F)nc(F)c2)n1"
},
"smiles": "Cn1nccc1Nc1nccc(-c2cc(F)nc(F)c2)n1",
"reactionStepId": "sa_9953673f8ba2692b26ca4bfd",
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"metadata": "{\"annotations\":{\"ID\":\"US20150182537A1;0211;1714862\",\"rsmi\":\"Cl[c:8]1[n:9][cH:10][cH:11][c:12](-[c:13]2[cH:14][c:15]([F:16])[n:17][c:18]([F:19])[cH:20]2)[n:21]1.[CH3:1][n:2]1[n:3][cH:4][cH:5][c:6]1[NH2:7]>C1COCCO1.CC1(C)c2cccc(P(c3ccccc3)c3ccccc3)c2Oc2c(P(c3ccccc3)c3ccccc3)cccc21.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]>[CH3:1][n:2]1[n:3][cH:4][cH:5][c:6]1[NH:7][c:8]1[n:9][cH:10][cH:11][c:12](-[c:13]2[cH:14][c:15]([F:16])[n:17][c:18]([F:19])[cH:20]2)[n:21]1\"},\"mapped_reaction_smiles\":\"Cl[c:8]1[n:9][cH:10][cH:11][c:12](-[c:13]2[cH:14][c:15]([F:16])[n:17][c:18]([F:19])[cH:20]2)[n:21]1.[CH3:1][n:2]1[n:3][cH:4][cH:5][c:6]1[NH2:7]>C1COCCO1.CC1(C)c2cccc(P(c3ccccc3)c3ccccc3)c2Oc2c(P(c3ccccc3)c3ccccc3)cccc21.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]>[CH3:1][n:2]1[n:3][cH:4][cH:5][c:6]1[NH:7][c:8]1[n:9][cH:10][cH:11][c:12](-[c:13]2[cH:14][c:15]([F:16])[n:17][c:18]([F:19])[cH:20]2)[n:21]1\"}",
"reactionStep": {
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"molecule": {
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"smiles": "Cn1nccc1N"
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{
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},
"smiles": "Fc1cc(-c2ccnc(Cl)n2)cc(F)n1",
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}
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{
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"smiles": "NN"
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}
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},
{
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"smiles": "CC(C)(C)[Si](C)(C)OCCC(Oc1ccccc1)C(=O)O"
},
"smiles": "CC(C)(C)[Si](C)(C)OCCC(Oc1ccccc1)C(=O)O",
"reactionStepId": "sa_757a88f96b8c1bfda6f791bb",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20150182537A1;0477;1714906\",\"rsmi\":\"Cl[Si:5]([C:2]([CH3:1])([CH3:3])[CH3:4])([CH3:6])[CH3:7].[OH:8][CH2:9][CH2:10][CH:11]([O:12][c:13]1[cH:14][cH:15][cH:16][cH:17][cH:18]1)[C:19](=[O:20])[OH:21]>CN(C)C=O.O.c1c[nH]cn1>[CH3:1][C:2]([CH3:3])([CH3:4])[Si:5]([CH3:6])([CH3:7])[O:8][CH2:9][CH2:10][CH:11]([O:12][c:13]1[cH:14][cH:15][cH:16][cH:17][cH:18]1)[C:19](=[O:20])[OH:21]\"},\"mapped_reaction_smiles\":\"Cl[Si:5]([C:2]([CH3:1])([CH3:3])[CH3:4])([CH3:6])[CH3:7].[OH:8][CH2:9][CH2:10][CH:11]([O:12][c:13]1[cH:14][cH:15][cH:16][cH:17][cH:18]1)[C:19](=[O:20])[OH:21]>CN(C)C=O.O.c1c[nH]cn1>[CH3:1][C:2]([CH3:3])([CH3:4])[Si:5]([CH3:6])([CH3:7])[O:8][CH2:9][CH2:10][CH:11]([O:12][c:13]1[cH:14][cH:15][cH:16][cH:17][cH:18]1)[C:19](=[O:20])[OH:21]\"}",
"reactionStep": {
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},
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},
{
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},
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}
]
}
]
}
]
}
]
}
}