Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
CNC(=O)c1ncc2cncn2c1Nc1ccc(I)cc1F
InChiKey
FTDJLZBVBJFFLS-UHFFFAOYSA-N
Route Signature
3fa48789f815aa9ddb5c7dee2e27fd6a2f332455684ad13f331a6b7c57ab86c9
Synthesis route with 7 steps
Route tree structure (JSON format)
{
"route": {
"id": "sa_f8751d8014dd03a1fbd5109b",
"signature": "3fa48789f815aa9ddb5c7dee2e27fd6a2f332455684ad13f331a6b7c57ab86c9",
"contentHash": "c2322785cdf6d24cb9efe094fa3882ecc084c5d5a7b624e747f821d4d7d6586f",
"length": 7,
"isConvergent": false
},
"target": {
"id": "sa_0c39a88f9a27eeda46cc37fc",
"benchmarkSetId": "61e696668b63e77d7c2a29c0821768e1c383de8313852d6e995224859494442e",
"targetId": "n5-01023",
"moleculeId": "sa_db7818b001613568d7b655fd",
"smiles": "CNC(=O)c1ncc2cncn2c1Nc1ccc(I)cc1F",
"routeLength": 7,
"isConvergent": false,
"metadata": null,
"molecule": {
"id": "sa_db7818b001613568d7b655fd",
"inchikey": "FTDJLZBVBJFFLS-UHFFFAOYSA-N",
"smiles": "CNC(=O)c1ncc2cncn2c1Nc1ccc(I)cc1F"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "13991",
"routeId": "sa_f8751d8014dd03a1fbd5109b",
"moleculeId": "sa_db7818b001613568d7b655fd",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_db7818b001613568d7b655fd",
"inchikey": "FTDJLZBVBJFFLS-UHFFFAOYSA-N",
"smiles": "CNC(=O)c1ncc2cncn2c1Nc1ccc(I)cc1F"
},
"smiles": "CNC(=O)c1ncc2cncn2c1Nc1ccc(I)cc1F",
"reactionStepId": "sa_607d6813bafc72e3bcd01ff3",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20120309765A1;0426;1308178\",\"rsmi\":\"CO[C:3](=[O:4])[c:5]1[c:6]([NH:7][c:8]2[c:9]([F:10])[cH:11][c:12]([I:13])[cH:14][cH:15]2)[n:16]2[cH:17][n:18][cH:19][c:20]2[cH:21][n:22]1.[CH3:1][NH2:2]>C1CCOC1.CCOC(C)=O.CO>[CH3:1][NH:2][C:3](=[O:4])[c:5]1[c:6]([NH:7][c:8]2[c:9]([F:10])[cH:11][c:12]([I:13])[cH:14][cH:15]2)[n:16]2[cH:17][n:18][cH:19][c:20]2[cH:21][n:22]1\"},\"mapped_reaction_smiles\":\"CO[C:3](=[O:4])[c:5]1[c:6]([NH:7][c:8]2[c:9]([F:10])[cH:11][c:12]([I:13])[cH:14][cH:15]2)[n:16]2[cH:17][n:18][cH:19][c:20]2[cH:21][n:22]1.[CH3:1][NH2:2]>C1CCOC1.CCOC(C)=O.CO>[CH3:1][NH:2][C:3](=[O:4])[c:5]1[c:6]([NH:7][c:8]2[c:9]([F:10])[cH:11][c:12]([I:13])[cH:14][cH:15]2)[n:16]2[cH:17][n:18][cH:19][c:20]2[cH:21][n:22]1\"}",
"reactionStep": {
"id": "sa_607d6813bafc72e3bcd01ff3",
"reactionHash": "acfc5f6416b26c4d4afc32c96617bed020e89e5093e1d0a2ff4db980a686faf5"
},
"children": [
{
"id": "13992",
"routeId": "sa_f8751d8014dd03a1fbd5109b",
"moleculeId": "sa_e00cdbb7fb9d3ecf114a19d3",
"parentId": "13991",
"isLeaf": true,
"molecule": {
"id": "sa_e00cdbb7fb9d3ecf114a19d3",
"inchikey": "BAVYZALUXZFZLV-UHFFFAOYSA-N",
"smiles": "CN"
},
"smiles": "CN",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "13993",
"routeId": "sa_f8751d8014dd03a1fbd5109b",
"moleculeId": "sa_3282fb6afd4c744732a3df5a",
"parentId": "13991",
"isLeaf": false,
"molecule": {
"id": "sa_3282fb6afd4c744732a3df5a",
"inchikey": "UQJRKDDBQFEUTP-UHFFFAOYSA-N",
"smiles": "COC(=O)c1ncc2cncn2c1Nc1ccc(I)cc1F"
},
"smiles": "COC(=O)c1ncc2cncn2c1Nc1ccc(I)cc1F",
"reactionStepId": "sa_a606d0877fc6d05731626bdb",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20120309765A1;0363;1308150\",\"rsmi\":\"O=[CH:17][NH:18][CH2:19][c:20]1[n:16][c:6]([NH:7][c:8]2[c:9]([F:10])[cH:11][c:12]([I:13])[cH:14][cH:15]2)[c:5]([C:3]([O:2][CH3:1])=[O:4])[n:22][cH:21]1>Cc1ccccc1.O=P(Cl)(Cl)Cl>[CH3:1][O:2][C:3](=[O:4])[c:5]1[c:6]([NH:7][c:8]2[c:9]([F:10])[cH:11][c:12]([I:13])[cH:14][cH:15]2)[n:16]2[cH:17][n:18][cH:19][c:20]2[cH:21][n:22]1\"},\"mapped_reaction_smiles\":\"O=[CH:17][NH:18][CH2:19][c:20]1[n:16][c:6]([NH:7][c:8]2[c:9]([F:10])[cH:11][c:12]([I:13])[cH:14][cH:15]2)[c:5]([C:3]([O:2][CH3:1])=[O:4])[n:22][cH:21]1>Cc1ccccc1.O=P(Cl)(Cl)Cl>[CH3:1][O:2][C:3](=[O:4])[c:5]1[c:6]([NH:7][c:8]2[c:9]([F:10])[cH:11][c:12]([I:13])[cH:14][cH:15]2)[n:16]2[cH:17][n:18][cH:19][c:20]2[cH:21][n:22]1\"}",
"reactionStep": {
"id": "sa_a606d0877fc6d05731626bdb",
"reactionHash": "211f3da50b792cfe6a870072134764b204a02288fd6d18de2d81cbe6e83eebfc"
},
"children": [
{
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"moleculeId": "sa_7136eb2fad05548e24def0ff",
"parentId": "13993",
"isLeaf": false,
"molecule": {
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"inchikey": "WXFSXPSDMIMMMO-UHFFFAOYSA-N",
"smiles": "COC(=O)c1ncc(CNC=O)nc1Nc1ccc(I)cc1F"
},
"smiles": "COC(=O)c1ncc(CNC=O)nc1Nc1ccc(I)cc1F",
"reactionStepId": "sa_b98f71a9c98088522c351fa6",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20120309765A1;0362;1308149\",\"rsmi\":\"C[Si](C)(C)[c:20]1[cH:19][c:17]([F:18])[c:16]([NH:15][c:14]2[c:5]([C:3]([O:2][CH3:1])=[O:4])[n:6][cH:7][c:8]([CH2:9][NH:10][CH:11]=[O:12])[n:13]2)[cH:23][cH:22]1.Cl[I:21]>ClCCl>[CH3:1][O:2][C:3](=[O:4])[c:5]1[n:6][cH:7][c:8]([CH2:9][NH:10][CH:11]=[O:12])[n:13][c:14]1[NH:15][c:16]1[c:17]([F:18])[cH:19][c:20]([I:21])[cH:22][cH:23]1\"},\"mapped_reaction_smiles\":\"C[Si](C)(C)[c:20]1[cH:19][c:17]([F:18])[c:16]([NH:15][c:14]2[c:5]([C:3]([O:2][CH3:1])=[O:4])[n:6][cH:7][c:8]([CH2:9][NH:10][CH:11]=[O:12])[n:13]2)[cH:23][cH:22]1.Cl[I:21]>ClCCl>[CH3:1][O:2][C:3](=[O:4])[c:5]1[n:6][cH:7][c:8]([CH2:9][NH:10][CH:11]=[O:12])[n:13][c:14]1[NH:15][c:16]1[c:17]([F:18])[cH:19][c:20]([I:21])[cH:22][cH:23]1\"}",
"reactionStep": {
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"reactionHash": "6679578b5efbe67f6bf78d72a4248098ab22d6e7275f386a251c5d6f60c94fd3"
},
"children": [
{
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"moleculeId": "sa_c4b46e3aee83f4d1c94bf664",
"parentId": "13994",
"isLeaf": false,
"molecule": {
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"inchikey": "GMUJDKLBERKTRU-UHFFFAOYSA-N",
"smiles": "COC(=O)c1ncc(CNC=O)nc1Nc1ccc([Si](C)(C)C)cc1F"
},
"smiles": "COC(=O)c1ncc(CNC=O)nc1Nc1ccc([Si](C)(C)C)cc1F",
"reactionStepId": "sa_88a40090b2fd2da88254ad53",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20120309765A1;0360;1308148\",\"rsmi\":\"O[CH:11]=[O:12].[CH3:1][O:2][C:3](=[O:4])[c:5]1[n:6][cH:7][c:8]([CH2:9][NH2:10])[n:13][c:14]1[NH:15][c:16]1[c:17]([F:18])[cH:19][c:20]([Si:21]([CH3:22])([CH3:23])[CH3:24])[cH:25][cH:26]1>CC(=O)OC(C)=O>[CH3:1][O:2][C:3](=[O:4])[c:5]1[n:6][cH:7][c:8]([CH2:9][NH:10][CH:11]=[O:12])[n:13][c:14]1[NH:15][c:16]1[c:17]([F:18])[cH:19][c:20]([Si:21]([CH3:22])([CH3:23])[CH3:24])[cH:25][cH:26]1\"},\"mapped_reaction_smiles\":\"O[CH:11]=[O:12].[CH3:1][O:2][C:3](=[O:4])[c:5]1[n:6][cH:7][c:8]([CH2:9][NH2:10])[n:13][c:14]1[NH:15][c:16]1[c:17]([F:18])[cH:19][c:20]([Si:21]([CH3:22])([CH3:23])[CH3:24])[cH:25][cH:26]1>CC(=O)OC(C)=O>[CH3:1][O:2][C:3](=[O:4])[c:5]1[n:6][cH:7][c:8]([CH2:9][NH:10][CH:11]=[O:12])[n:13][c:14]1[NH:15][c:16]1[c:17]([F:18])[cH:19][c:20]([Si:21]([CH3:22])([CH3:23])[CH3:24])[cH:25][cH:26]1\"}",
"reactionStep": {
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"reactionHash": "0af2c6e5b1b872a3018c451b7184b57068c6554c5b79d9ee36847301a9729940"
},
"children": [
{
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"routeId": "sa_f8751d8014dd03a1fbd5109b",
"moleculeId": "sa_3bff5ea8042027b95a7e61c6",
"parentId": "13995",
"isLeaf": true,
"molecule": {
"id": "sa_3bff5ea8042027b95a7e61c6",
"inchikey": "BDAGIHXWWSANSR-UHFFFAOYSA-N",
"smiles": "O=CO"
},
"smiles": "O=CO",
"reactionStepId": null,
"template": null,
"metadata": null,
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},
{
"id": "13997",
"routeId": "sa_f8751d8014dd03a1fbd5109b",
"moleculeId": "sa_971c71e6d2e386b97889d475",
"parentId": "13995",
"isLeaf": false,
"molecule": {
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"inchikey": "LXOOVIVWVPDJAV-UHFFFAOYSA-N",
"smiles": "COC(=O)c1ncc(CN)nc1Nc1ccc([Si](C)(C)C)cc1F"
},
"smiles": "COC(=O)c1ncc(CN)nc1Nc1ccc([Si](C)(C)C)cc1F",
"reactionStepId": "sa_9da869d338f22227bc37d81c",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20120309765A1;0358;1308147\",\"rsmi\":\"[CH3:1][O:2][C:3](=[O:4])[c:5]1[n:6][cH:7][c:8]([C:9]#[N:10])[n:11][c:12]1[NH:13][c:14]1[c:15]([F:16])[cH:17][c:18]([Si:19]([CH3:20])([CH3:21])[CH3:22])[cH:23][cH:24]1>CC(=O)O.[Pd]>[CH3:1][O:2][C:3](=[O:4])[c:5]1[n:6][cH:7][c:8]([CH2:9][NH2:10])[n:11][c:12]1[NH:13][c:14]1[c:15]([F:16])[cH:17][c:18]([Si:19]([CH3:20])([CH3:21])[CH3:22])[cH:23][cH:24]1\"},\"mapped_reaction_smiles\":\"[CH3:1][O:2][C:3](=[O:4])[c:5]1[n:6][cH:7][c:8]([C:9]#[N:10])[n:11][c:12]1[NH:13][c:14]1[c:15]([F:16])[cH:17][c:18]([Si:19]([CH3:20])([CH3:21])[CH3:22])[cH:23][cH:24]1>CC(=O)O.[Pd]>[CH3:1][O:2][C:3](=[O:4])[c:5]1[n:6][cH:7][c:8]([CH2:9][NH2:10])[n:11][c:12]1[NH:13][c:14]1[c:15]([F:16])[cH:17][c:18]([Si:19]([CH3:20])([CH3:21])[CH3:22])[cH:23][cH:24]1\"}",
"reactionStep": {
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"reactionHash": "3456f5831fa78419b60e4d9a836eb099fe390e2ac28c3399809913fb55e7d225"
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"children": [
{
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"routeId": "sa_f8751d8014dd03a1fbd5109b",
"moleculeId": "sa_41bab69967d05f2f6244cfa5",
"parentId": "13997",
"isLeaf": false,
"molecule": {
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"inchikey": "RPCQFNOAESRBOV-UHFFFAOYSA-N",
"smiles": "COC(=O)c1ncc(C#N)nc1Nc1ccc([Si](C)(C)C)cc1F"
},
"smiles": "COC(=O)c1ncc(C#N)nc1Nc1ccc([Si](C)(C)C)cc1F",
"reactionStepId": "sa_f39a22115e951ec28a3208c5",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20120309765A1;0356;1308146\",\"rsmi\":\"Cl[c:8]1[cH:7][n:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[c:12]([NH:13][c:14]2[c:15]([F:16])[cH:17][c:18]([Si:19]([CH3:20])([CH3:21])[CH3:22])[cH:23][cH:24]2)[n:11]1.[CH:9]#[N:10]>CCOC(C)=O.CN(C)C=O.CO.C#N.[Zn+2].c1ccc([PH](c2ccccc2)(c2ccccc2)[Pd]([PH](c2ccccc2)(c2ccccc2)c2ccccc2)([PH](c2ccccc2)(c2ccccc2)c2ccccc2)[PH](c2ccccc2)(c2ccccc2)c2ccccc2)cc1>[CH3:1][O:2][C:3](=[O:4])[c:5]1[n:6][cH:7][c:8]([C:9]#[N:10])[n:11][c:12]1[NH:13][c:14]1[c:15]([F:16])[cH:17][c:18]([Si:19]([CH3:20])([CH3:21])[CH3:22])[cH:23][cH:24]1\"},\"mapped_reaction_smiles\":\"Cl[c:8]1[cH:7][n:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[c:12]([NH:13][c:14]2[c:15]([F:16])[cH:17][c:18]([Si:19]([CH3:20])([CH3:21])[CH3:22])[cH:23][cH:24]2)[n:11]1.[CH:9]#[N:10]>CCOC(C)=O.CN(C)C=O.CO.C#N.[Zn+2].c1ccc([PH](c2ccccc2)(c2ccccc2)[Pd]([PH](c2ccccc2)(c2ccccc2)c2ccccc2)([PH](c2ccccc2)(c2ccccc2)c2ccccc2)[PH](c2ccccc2)(c2ccccc2)c2ccccc2)cc1>[CH3:1][O:2][C:3](=[O:4])[c:5]1[n:6][cH:7][c:8]([C:9]#[N:10])[n:11][c:12]1[NH:13][c:14]1[c:15]([F:16])[cH:17][c:18]([Si:19]([CH3:20])([CH3:21])[CH3:22])[cH:23][cH:24]1\"}",
"reactionStep": {
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"children": [
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"molecule": {
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"smiles": "C#N"
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},
{
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"molecule": {
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},
"smiles": "COC(=O)c1ncc(Cl)nc1Nc1ccc([Si](C)(C)C)cc1F",
"reactionStepId": "sa_0a7d4f197882108e20ee8caf",
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"metadata": "{\"annotations\":{\"ID\":\"US20120309765A1;0354;1308145\",\"rsmi\":\"O[CH3:1].[OH:2][C:3](=[O:4])[c:5]1[n:6][cH:7][c:8]([Cl:9])[n:10][c:11]1[NH:12][c:13]1[c:14]([F:15])[cH:16][c:17]([Si:18]([CH3:19])([CH3:20])[CH3:21])[cH:22][cH:23]1>CCOC(C)=O.C[Si](C)(C)C=[N+]=[N-].Cc1ccccc1>[CH3:1][O:2][C:3](=[O:4])[c:5]1[n:6][cH:7][c:8]([Cl:9])[n:10][c:11]1[NH:12][c:13]1[c:14]([F:15])[cH:16][c:17]([Si:18]([CH3:19])([CH3:20])[CH3:21])[cH:22][cH:23]1\"},\"mapped_reaction_smiles\":\"O[CH3:1].[OH:2][C:3](=[O:4])[c:5]1[n:6][cH:7][c:8]([Cl:9])[n:10][c:11]1[NH:12][c:13]1[c:14]([F:15])[cH:16][c:17]([Si:18]([CH3:19])([CH3:20])[CH3:21])[cH:22][cH:23]1>CCOC(C)=O.C[Si](C)(C)C=[N+]=[N-].Cc1ccccc1>[CH3:1][O:2][C:3](=[O:4])[c:5]1[n:6][cH:7][c:8]([Cl:9])[n:10][c:11]1[NH:12][c:13]1[c:14]([F:15])[cH:16][c:17]([Si:18]([CH3:19])([CH3:20])[CH3:21])[cH:22][cH:23]1\"}",
"reactionStep": {
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"children": [
{
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"moleculeId": "sa_061a3efbe4d30c2cc87d48e7",
"parentId": "14000",
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"molecule": {
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"inchikey": "OKKJLVBELUTLKV-UHFFFAOYSA-N",
"smiles": "CO"
},
"smiles": "CO",
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},
{
"id": "14002",
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"parentId": "14000",
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"molecule": {
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"inchikey": "XZOQFAFFKKNARU-UHFFFAOYSA-N",
"smiles": "C[Si](C)(C)c1ccc(Nc2nc(Cl)cnc2C(=O)O)c(F)c1"
},
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