Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
Cc1ccc(-c2cc(C(=O)O)cc(-n3cnnn3)c2)cc1
InChiKey
VKYJXDOIGACUMA-UHFFFAOYSA-N
Route Signature
56f841c72229aeaea0088aeac41f49147731f4c9762171ee3d4d8dd5c171b32e
Synthesis route with 6 steps
Route tree structure (JSON format)
{
"route": {
"id": "sa_4d16fa7a3a7cd459c98d5a84",
"signature": "56f841c72229aeaea0088aeac41f49147731f4c9762171ee3d4d8dd5c171b32e",
"contentHash": "b2793b460c91e82cf31f170d4353db4eb2657bc19ba59ef85e31784c26b2c486",
"length": 6,
"isConvergent": false
},
"target": {
"id": "sa_194e0426c1fe3cfb543f9966",
"benchmarkSetId": "61e696668b63e77d7c2a29c0821768e1c383de8313852d6e995224859494442e",
"targetId": "n5-00077",
"moleculeId": "sa_aae0851e13647ffa04256b9f",
"smiles": "Cc1ccc(-c2cc(C(=O)O)cc(-n3cnnn3)c2)cc1",
"routeLength": 6,
"isConvergent": false,
"metadata": null,
"molecule": {
"id": "sa_aae0851e13647ffa04256b9f",
"inchikey": "VKYJXDOIGACUMA-UHFFFAOYSA-N",
"smiles": "Cc1ccc(-c2cc(C(=O)O)cc(-n3cnnn3)c2)cc1"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "12327",
"routeId": "sa_4d16fa7a3a7cd459c98d5a84",
"moleculeId": "sa_aae0851e13647ffa04256b9f",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_aae0851e13647ffa04256b9f",
"inchikey": "VKYJXDOIGACUMA-UHFFFAOYSA-N",
"smiles": "Cc1ccc(-c2cc(C(=O)O)cc(-n3cnnn3)c2)cc1"
},
"smiles": "Cc1ccc(-c2cc(C(=O)O)cc(-n3cnnn3)c2)cc1",
"reactionStepId": "sa_2cacec02129537965811ec9f",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20150065506A1;0683;1660282\",\"rsmi\":\"C[O:11][C:9]([c:8]1[cH:7][c:6](-[c:5]2[cH:4][cH:3][c:2]([CH3:1])[cH:21][cH:20]2)[cH:19][c:13](-[n:14]2[cH:15][n:16][n:17][n:18]2)[cH:12]1)=[O:10]>C1CCOC1.O.O.[Li]O>[CH3:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[cH:7][c:8]([C:9](=[O:10])[OH:11])[cH:12][c:13](-[n:14]3[cH:15][n:16][n:17][n:18]3)[cH:19]2)[cH:20][cH:21]1\"},\"mapped_reaction_smiles\":\"C[O:11][C:9]([c:8]1[cH:7][c:6](-[c:5]2[cH:4][cH:3][c:2]([CH3:1])[cH:21][cH:20]2)[cH:19][c:13](-[n:14]2[cH:15][n:16][n:17][n:18]2)[cH:12]1)=[O:10]>C1CCOC1.O.O.[Li]O>[CH3:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[cH:7][c:8]([C:9](=[O:10])[OH:11])[cH:12][c:13](-[n:14]3[cH:15][n:16][n:17][n:18]3)[cH:19]2)[cH:20][cH:21]1\"}",
"reactionStep": {
"id": "sa_2cacec02129537965811ec9f",
"reactionHash": "6b59400755ea30399eda748741869aaecbf06c60d78feca45f05f8a126b9deb1"
},
"children": [
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"moleculeId": "sa_e651b2a535abc65a3d52cdc4",
"parentId": "12327",
"isLeaf": false,
"molecule": {
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"inchikey": "AJWCXASDUNFEJT-UHFFFAOYSA-N",
"smiles": "COC(=O)c1cc(-c2ccc(C)cc2)cc(-n2cnnn2)c1"
},
"smiles": "COC(=O)c1cc(-c2ccc(C)cc2)cc(-n2cnnn2)c1",
"reactionStepId": "sa_d9c6f31f0c0bbf710a104ab9",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20150065506A1;0682;1660281\",\"rsmi\":\"CCO[CH:9](OCC)OCC.[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]([NH2:8])[cH:13][c:14](-[c:15]2[cH:16][cH:17][c:18]([CH3:19])[cH:20][cH:21]2)[cH:22]1.[N-:10]=[N+:11]=[N-:12]>CC(=O)O.[Na+]>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7](-[n:8]2[cH:9][n:10][n:11][n:12]2)[cH:13][c:14](-[c:15]2[cH:16][cH:17][c:18]([CH3:19])[cH:20][cH:21]2)[cH:22]1\"},\"mapped_reaction_smiles\":\"CCO[CH:9](OCC)OCC.[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]([NH2:8])[cH:13][c:14](-[c:15]2[cH:16][cH:17][c:18]([CH3:19])[cH:20][cH:21]2)[cH:22]1.[N-:10]=[N+:11]=[N-:12]>CC(=O)O.[Na+]>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7](-[n:8]2[cH:9][n:10][n:11][n:12]2)[cH:13][c:14](-[c:15]2[cH:16][cH:17][c:18]([CH3:19])[cH:20][cH:21]2)[cH:22]1\"}",
"reactionStep": {
"id": "sa_d9c6f31f0c0bbf710a104ab9",
"reactionHash": "e0e58445942089285aa3196682b2b67a9bb97565c12f58e0cd096d94b88d383a"
},
"children": [
{
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"moleculeId": "sa_dc98236d967ab0cdbd0fcd04",
"parentId": "12328",
"isLeaf": true,
"molecule": {
"id": "sa_dc98236d967ab0cdbd0fcd04",
"inchikey": "GKASDNZWUGIAMG-UHFFFAOYSA-N",
"smiles": "CCOC(OCC)OCC"
},
"smiles": "CCOC(OCC)OCC",
"reactionStepId": null,
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"metadata": null,
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"children": []
},
{
"id": "12330",
"routeId": "sa_4d16fa7a3a7cd459c98d5a84",
"moleculeId": "sa_e5e3d46ddd45cb413eb6332d",
"parentId": "12328",
"isLeaf": false,
"molecule": {
"id": "sa_e5e3d46ddd45cb413eb6332d",
"inchikey": "IQQPUQIPEUETMX-UHFFFAOYSA-N",
"smiles": "COC(=O)c1cc(N)cc(-c2ccc(C)cc2)c1"
},
"smiles": "COC(=O)c1cc(N)cc(-c2ccc(C)cc2)c1",
"reactionStepId": "sa_a6cadfa7419287a08c6855f7",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20150065506A1;0681;1660280\",\"rsmi\":\"O=[N+:8]([O-])[c:7]1[cH:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[cH:18][c:10](-[c:11]2[cH:12][cH:13][c:14]([CH3:15])[cH:16][cH:17]2)[cH:9]1>CO.Cl[Sn]Cl>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]([NH2:8])[cH:9][c:10](-[c:11]2[cH:12][cH:13][c:14]([CH3:15])[cH:16][cH:17]2)[cH:18]1\"},\"mapped_reaction_smiles\":\"O=[N+:8]([O-])[c:7]1[cH:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[cH:18][c:10](-[c:11]2[cH:12][cH:13][c:14]([CH3:15])[cH:16][cH:17]2)[cH:9]1>CO.Cl[Sn]Cl>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]([NH2:8])[cH:9][c:10](-[c:11]2[cH:12][cH:13][c:14]([CH3:15])[cH:16][cH:17]2)[cH:18]1\"}",
"reactionStep": {
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"reactionHash": "d895d35a9dcc339b060baf0e11c47a8d9c219b04a118cafe7c88503b1d4e9d36"
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"children": [
{
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"moleculeId": "sa_4ab2a111a5a335f00bad5260",
"parentId": "12330",
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"molecule": {
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"inchikey": "YWUWJWNTRLJCSZ-UHFFFAOYSA-N",
"smiles": "COC(=O)c1cc(-c2ccc(C)cc2)cc([N+](=O)[O-])c1"
},
"smiles": "COC(=O)c1cc(-c2ccc(C)cc2)cc([N+](=O)[O-])c1",
"reactionStepId": "sa_a0e55a1ae8b364f8086f428c",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20150065506A1;0680;1660279\",\"rsmi\":\"O[C:3](=[O:4])[c:5]1[cH:6][c:7]([N+:8](=[O:9])[O-:10])[cH:11][c:12](-[c:13]2[cH:14][cH:15][c:16]([CH3:17])[cH:18][cH:19]2)[cH:20]1.[CH3:1][OH:2]>O=S(Cl)Cl>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]([N+:8](=[O:9])[O-:10])[cH:11][c:12](-[c:13]2[cH:14][cH:15][c:16]([CH3:17])[cH:18][cH:19]2)[cH:20]1\"},\"mapped_reaction_smiles\":\"O[C:3](=[O:4])[c:5]1[cH:6][c:7]([N+:8](=[O:9])[O-:10])[cH:11][c:12](-[c:13]2[cH:14][cH:15][c:16]([CH3:17])[cH:18][cH:19]2)[cH:20]1.[CH3:1][OH:2]>O=S(Cl)Cl>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]([N+:8](=[O:9])[O-:10])[cH:11][c:12](-[c:13]2[cH:14][cH:15][c:16]([CH3:17])[cH:18][cH:19]2)[cH:20]1\"}",
"reactionStep": {
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"reactionHash": "f97d97d12cccec6bdb8d383586e60bb50fb3e62a10e2344540df4f7399cbc4a6"
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"children": [
{
"id": "12332",
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"moleculeId": "sa_9b4c3079f5690e44bb71c559",
"parentId": "12331",
"isLeaf": false,
"molecule": {
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"inchikey": "FXYMLBWUVKFDCI-UHFFFAOYSA-N",
"smiles": "Cc1ccc(-c2cc(C(=O)O)cc([N+](=O)[O-])c2)cc1"
},
"smiles": "Cc1ccc(-c2cc(C(=O)O)cc([N+](=O)[O-])c2)cc1",
"reactionStepId": "sa_068466247ec3bbc2ccf6e392",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20150065506A1;0679;1660278\",\"rsmi\":\"I[c:6]1[cH:7][c:8]([C:9](=[O:10])[OH:11])[cH:12][c:13]([N+:14](=[O:15])[O-:16])[cH:17]1.OB(O)[c:5]1[cH:4][cH:3][c:2]([CH3:1])[cH:19][cH:18]1>CCO.Cc1ccccc1.O.O=C(O)O.[Cs+].[Cs+].[Na+].O.c1ccc([PH](c2ccccc2)(c2ccccc2)[Pd]([PH](c2ccccc2)(c2ccccc2)c2ccccc2)([PH](c2ccccc2)(c2ccccc2)c2ccccc2)[PH](c2ccccc2)(c2ccccc2)c2ccccc2)cc1>[CH3:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[cH:7][c:8]([C:9](=[O:10])[OH:11])[cH:12][c:13]([N+:14](=[O:15])[O-:16])[cH:17]2)[cH:18][cH:19]1\"},\"mapped_reaction_smiles\":\"I[c:6]1[cH:7][c:8]([C:9](=[O:10])[OH:11])[cH:12][c:13]([N+:14](=[O:15])[O-:16])[cH:17]1.OB(O)[c:5]1[cH:4][cH:3][c:2]([CH3:1])[cH:19][cH:18]1>CCO.Cc1ccccc1.O.O=C(O)O.[Cs+].[Cs+].[Na+].O.c1ccc([PH](c2ccccc2)(c2ccccc2)[Pd]([PH](c2ccccc2)(c2ccccc2)c2ccccc2)([PH](c2ccccc2)(c2ccccc2)c2ccccc2)[PH](c2ccccc2)(c2ccccc2)c2ccccc2)cc1>[CH3:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[cH:7][c:8]([C:9](=[O:10])[OH:11])[cH:12][c:13]([N+:14](=[O:15])[O-:16])[cH:17]2)[cH:18][cH:19]1\"}",
"reactionStep": {
"id": "sa_068466247ec3bbc2ccf6e392",
"reactionHash": "42628f5720324315e433ce59f31c0a2894c2f3f3da8d050779dd727656ac5be6"
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"children": [
{
"id": "12333",
"routeId": "sa_4d16fa7a3a7cd459c98d5a84",
"moleculeId": "sa_313822deb7655b1fc32f680d",
"parentId": "12332",
"isLeaf": true,
"molecule": {
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"inchikey": "BIWQNIMLAISTBV-UHFFFAOYSA-N",
"smiles": "Cc1ccc(B(O)O)cc1"
},
"smiles": "Cc1ccc(B(O)O)cc1",
"reactionStepId": null,
"template": null,
"metadata": null,
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},
{
"id": "12334",
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"molecule": {
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"inchikey": "GFGURBBHVJTXDU-UHFFFAOYSA-N",
"smiles": "O=C(O)c1cc(I)cc([N+](=O)[O-])c1"
},
"smiles": "O=C(O)c1cc(I)cc([N+](=O)[O-])c1",
"reactionStepId": "sa_4dcbb1b84245052516825a22",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20150065506A1;0678;1660277\",\"rsmi\":\"I[I:7].[O:1]=[C:2]([OH:3])[c:4]1[cH:5][cH:6][cH:8][c:9]([N+:10](=[O:11])[O-:12])[cH:13]1>O=S(=O)(O)O>[O:1]=[C:2]([OH:3])[c:4]1[cH:5][c:6]([I:7])[cH:8][c:9]([N+:10](=[O:11])[O-:12])[cH:13]1\"},\"mapped_reaction_smiles\":\"I[I:7].[O:1]=[C:2]([OH:3])[c:4]1[cH:5][cH:6][cH:8][c:9]([N+:10](=[O:11])[O-:12])[cH:13]1>O=S(=O)(O)O>[O:1]=[C:2]([OH:3])[c:4]1[cH:5][c:6]([I:7])[cH:8][c:9]([N+:10](=[O:11])[O-:12])[cH:13]1\"}",
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"molecule": {
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"inchikey": "AFPHTEQTJZKQAQ-UHFFFAOYSA-N",
"smiles": "O=C(O)c1cccc([N+](=O)[O-])c1"
},
"smiles": "O=C(O)c1cccc([N+](=O)[O-])c1",
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{
"id": "12336",
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"molecule": {
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"inchikey": "PNDPGZBMCMUPRI-UHFFFAOYSA-N",
"smiles": "II"
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{
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"molecule": {
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"smiles": "CO"
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{
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"smiles": "[N]N=[N-]"
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]
}
}