Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
COC(=O)c1ccc(CCCN2C(=O)CCC2CCC(Cc2cccc(F)c2)O[Si](C)(C)C(C)(C)C)cc1
InChiKey
DZBBOAWSQOJBOM-UHFFFAOYSA-N
Route Signature
7621f7fb0b69f9329279bca606c39a0fe71f0f68d8ed9b2b3af189540ee5ce7b
Synthesis route with 4 steps (convergent)
Route tree structure (JSON format)
{
"route": {
"id": "sa_fde3d71132b2690202bca6af",
"signature": "7621f7fb0b69f9329279bca606c39a0fe71f0f68d8ed9b2b3af189540ee5ce7b",
"contentHash": "d07c0fddf66caa0af36729c48414b0aeb210fecd4fd2b16859df780a197f6947",
"length": 4,
"isConvergent": true
},
"target": {
"id": "sa_2dcbdb1ff30d405a97f3f260",
"benchmarkSetId": "3895c2909c53593560c5ba610abc7e6df80513dfd8624165c560451735097d36",
"targetId": "n5-00385",
"moleculeId": "sa_927cf62f0439233485e346e5",
"smiles": "COC(=O)c1ccc(CCCN2C(=O)CCC2CCC(Cc2cccc(F)c2)O[Si](C)(C)C(C)(C)C)cc1",
"routeLength": 4,
"isConvergent": true,
"metadata": null,
"molecule": {
"id": "sa_927cf62f0439233485e346e5",
"inchikey": "DZBBOAWSQOJBOM-UHFFFAOYSA-N",
"smiles": "COC(=O)c1ccc(CCCN2C(=O)CCC2CCC(Cc2cccc(F)c2)O[Si](C)(C)C(C)(C)C)cc1"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "9453",
"routeId": "sa_fde3d71132b2690202bca6af",
"moleculeId": "sa_927cf62f0439233485e346e5",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_927cf62f0439233485e346e5",
"inchikey": "DZBBOAWSQOJBOM-UHFFFAOYSA-N",
"smiles": "COC(=O)c1ccc(CCCN2C(=O)CCC2CCC(Cc2cccc(F)c2)O[Si](C)(C)C(C)(C)C)cc1"
},
"smiles": "COC(=O)c1ccc(CCCN2C(=O)CCC2CCC(Cc2cccc(F)c2)O[Si](C)(C)C(C)(C)C)cc1",
"reactionStepId": "sa_19c3a6d4fced86f41c83a855",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20040259921A1;0265;214168\",\"rsmi\":\"Br[CH2:11][CH2:10][CH2:9][c:8]1[cH:7][cH:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[cH:38][cH:37]1.[NH:12]1[C:13](=[O:14])[CH2:15][CH2:16][CH:17]1[CH2:18][CH2:19][CH:20]([CH2:21][c:22]1[cH:23][c:24]([F:25])[cH:26][cH:27][cH:28]1)[O:29][Si:30]([CH3:31])([CH3:32])[C:33]([CH3:34])([CH3:35])[CH3:36]>CCOC(C)=O.CO.C[Si](C)(C)N[Si](C)(C)C.ClCCl.[Na+]>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([CH2:9][CH2:10][CH2:11][N:12]2[C:13](=[O:14])[CH2:15][CH2:16][CH:17]2[CH2:18][CH2:19][CH:20]([CH2:21][c:22]2[cH:23][c:24]([F:25])[cH:26][cH:27][cH:28]2)[O:29][Si:30]([CH3:31])([CH3:32])[C:33]([CH3:34])([CH3:35])[CH3:36])[cH:37][cH:38]1\"},\"mapped_reaction_smiles\":\"Br[CH2:11][CH2:10][CH2:9][c:8]1[cH:7][cH:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[cH:38][cH:37]1.[NH:12]1[C:13](=[O:14])[CH2:15][CH2:16][CH:17]1[CH2:18][CH2:19][CH:20]([CH2:21][c:22]1[cH:23][c:24]([F:25])[cH:26][cH:27][cH:28]1)[O:29][Si:30]([CH3:31])([CH3:32])[C:33]([CH3:34])([CH3:35])[CH3:36]>CCOC(C)=O.CO.C[Si](C)(C)N[Si](C)(C)C.ClCCl.[Na+]>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([CH2:9][CH2:10][CH2:11][N:12]2[C:13](=[O:14])[CH2:15][CH2:16][CH:17]2[CH2:18][CH2:19][CH:20]([CH2:21][c:22]2[cH:23][c:24]([F:25])[cH:26][cH:27][cH:28]2)[O:29][Si:30]([CH3:31])([CH3:32])[C:33]([CH3:34])([CH3:35])[CH3:36])[cH:37][cH:38]1\"}",
"reactionStep": {
"id": "sa_19c3a6d4fced86f41c83a855",
"reactionHash": "92cf1732ba3a447d760f78a6bd4285ec71586c4f426c89b73c7c0ef98d705237"
},
"children": [
{
"id": "9454",
"routeId": "sa_fde3d71132b2690202bca6af",
"moleculeId": "sa_8e4c2e221c973dc539184648",
"parentId": "9453",
"isLeaf": false,
"molecule": {
"id": "sa_8e4c2e221c973dc539184648",
"inchikey": "NNKQTVQXEWLWJP-UHFFFAOYSA-N",
"smiles": "CC(C)(C)[Si](C)(C)OC(CCC1CCC(=O)N1)Cc1cccc(F)c1"
},
"smiles": "CC(C)(C)[Si](C)(C)OC(CCC1CCC(=O)N1)Cc1cccc(F)c1",
"reactionStepId": "sa_af659b1b285546fb7520b9a5",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20040259921A1;0264;214167\",\"rsmi\":\"Cl[Si:5]([C:2]([CH3:1])([CH3:3])[CH3:4])([CH3:6])[CH3:7].[OH:8][CH:9]([CH2:10][CH2:11][CH:12]1[CH2:13][CH2:14][C:15](=[O:16])[NH:17]1)[CH2:18][c:19]1[cH:20][c:21]([F:22])[cH:23][cH:24][cH:25]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[Si:5]([CH3:6])([CH3:7])[O:8][CH:9]([CH2:10][CH2:11][CH:12]1[CH2:13][CH2:14][C:15](=[O:16])[NH:17]1)[CH2:18][c:19]1[cH:20][c:21]([F:22])[cH:23][cH:24][cH:25]1\"},\"mapped_reaction_smiles\":\"Cl[Si:5]([C:2]([CH3:1])([CH3:3])[CH3:4])([CH3:6])[CH3:7].[OH:8][CH:9]([CH2:10][CH2:11][CH:12]1[CH2:13][CH2:14][C:15](=[O:16])[NH:17]1)[CH2:18][c:19]1[cH:20][c:21]([F:22])[cH:23][cH:24][cH:25]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[Si:5]([CH3:6])([CH3:7])[O:8][CH:9]([CH2:10][CH2:11][CH:12]1[CH2:13][CH2:14][C:15](=[O:16])[NH:17]1)[CH2:18][c:19]1[cH:20][c:21]([F:22])[cH:23][cH:24][cH:25]1\"}",
"reactionStep": {
"id": "sa_af659b1b285546fb7520b9a5",
"reactionHash": "e31d4defe734358831cad83cf5463e8bec445af269679b08b032385127da0a05"
},
"children": [
{
"id": "9455",
"routeId": "sa_fde3d71132b2690202bca6af",
"moleculeId": "sa_1785e67b778eb91f7e04c15a",
"parentId": "9454",
"isLeaf": true,
"molecule": {
"id": "sa_1785e67b778eb91f7e04c15a",
"inchikey": "BCNZYOJHNLTNEZ-UHFFFAOYSA-N",
"smiles": "CC(C)(C)[Si](C)(C)Cl"
},
"smiles": "CC(C)(C)[Si](C)(C)Cl",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "9456",
"routeId": "sa_fde3d71132b2690202bca6af",
"moleculeId": "sa_05b0cc32e7763dc5e72c9e25",
"parentId": "9454",
"isLeaf": false,
"molecule": {
"id": "sa_05b0cc32e7763dc5e72c9e25",
"inchikey": "YTRBMRZOSVXYNE-UHFFFAOYSA-N",
"smiles": "O=C1CCC(CCC(O)Cc2cccc(F)c2)N1"
},
"smiles": "O=C1CCC(CCC(O)Cc2cccc(F)c2)N1",
"reactionStepId": "sa_5085bb95ba077dec79b6e36b",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20040259921A1;0263;214166\",\"rsmi\":\"[O:1]=[C:2]1[CH2:3][CH2:4][CH:5]([CH2:6][CH2:7][C:8](=[O:9])[CH2:10][c:11]2[cH:12][c:13]([F:14])[cH:15][cH:16][cH:17]2)[NH:18]1>B.[Na+]>[O:1]=[C:2]1[CH2:3][CH2:4][CH:5]([CH2:6][CH2:7][CH:8]([OH:9])[CH2:10][c:11]2[cH:12][c:13]([F:14])[cH:15][cH:16][cH:17]2)[NH:18]1\"},\"mapped_reaction_smiles\":\"[O:1]=[C:2]1[CH2:3][CH2:4][CH:5]([CH2:6][CH2:7][C:8](=[O:9])[CH2:10][c:11]2[cH:12][c:13]([F:14])[cH:15][cH:16][cH:17]2)[NH:18]1>B.[Na+]>[O:1]=[C:2]1[CH2:3][CH2:4][CH:5]([CH2:6][CH2:7][CH:8]([OH:9])[CH2:10][c:11]2[cH:12][c:13]([F:14])[cH:15][cH:16][cH:17]2)[NH:18]1\"}",
"reactionStep": {
"id": "sa_5085bb95ba077dec79b6e36b",
"reactionHash": "f1648091c2532be1b5f7fa665733806b56a9f39d54b8cadd23add2082cf4b51f"
},
"children": [
{
"id": "9457",
"routeId": "sa_fde3d71132b2690202bca6af",
"moleculeId": "sa_820a02f8249b2cde4f29b072",
"parentId": "9456",
"isLeaf": true,
"molecule": {
"id": "sa_820a02f8249b2cde4f29b072",
"inchikey": "GNDPTVGVYYVVOT-UHFFFAOYSA-N",
"smiles": "O=C(CCC1CCC(=O)N1)Cc1cccc(F)c1"
},
"smiles": "O=C(CCC1CCC(=O)N1)Cc1cccc(F)c1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
}
]
},
{
"id": "9458",
"routeId": "sa_fde3d71132b2690202bca6af",
"moleculeId": "sa_d5fff9fd23aac3ecbcb680fb",
"parentId": "9453",
"isLeaf": false,
"molecule": {
"id": "sa_d5fff9fd23aac3ecbcb680fb",
"inchikey": "VMHPVAWXMHRICK-UHFFFAOYSA-N",
"smiles": "COC(=O)c1ccc(CCCBr)cc1"
},
"smiles": "COC(=O)c1ccc(CCCBr)cc1",
"reactionStepId": "sa_8adb3336227798bcf1ff0a07",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20040259921A1;0406;214185\",\"rsmi\":\"C=CC[Br:12].O[CH2:11][CH2:10][CH2:9][c:8]1[cH:7][cH:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[cH:14][cH:13]1>CC#N.O=C(O)O.O=C(n1ccnc1)n1ccnc1.[Na+]>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([CH2:9][CH2:10][CH2:11][Br:12])[cH:13][cH:14]1\"},\"mapped_reaction_smiles\":\"C=CC[Br:12].O[CH2:11][CH2:10][CH2:9][c:8]1[cH:7][cH:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[cH:14][cH:13]1>CC#N.O=C(O)O.O=C(n1ccnc1)n1ccnc1.[Na+]>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([CH2:9][CH2:10][CH2:11][Br:12])[cH:13][cH:14]1\"}",
"reactionStep": {
"id": "sa_8adb3336227798bcf1ff0a07",
"reactionHash": "7e1835012d61dc3513b134ee2374e08c859235298ee7c4efa365c5b2d9826ea8"
},
"children": [
{
"id": "9459",
"routeId": "sa_fde3d71132b2690202bca6af",
"moleculeId": "sa_130eb52884b6b81b4827a1ab",
"parentId": "9458",
"isLeaf": false,
"molecule": {
"id": "sa_130eb52884b6b81b4827a1ab",
"inchikey": "ARNGRGQYXABYAT-UHFFFAOYSA-N",
"smiles": "COC(=O)c1ccc(CCCO)cc1"
},
"smiles": "COC(=O)c1ccc(CCCO)cc1",
"reactionStepId": "sa_17a3e6df5b032254fe1ad2a1",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20040259921A1;0405;214184\",\"rsmi\":\"[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([C:9]#[C:10][CH2:11][OH:12])[cH:13][cH:14]1>CCOC(C)=O.CO.[Pd]>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([CH2:9][CH2:10][CH2:11][OH:12])[cH:13][cH:14]1\"},\"mapped_reaction_smiles\":\"[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([C:9]#[C:10][CH2:11][OH:12])[cH:13][cH:14]1>CCOC(C)=O.CO.[Pd]>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([CH2:9][CH2:10][CH2:11][OH:12])[cH:13][cH:14]1\"}",
"reactionStep": {
"id": "sa_17a3e6df5b032254fe1ad2a1",
"reactionHash": "44a6ea13864ffc3ec8a9cc6c939fa4750fc8ee4482e2f6acdca17c7bf8b2383d"
},
"children": [
{
"id": "9460",
"routeId": "sa_fde3d71132b2690202bca6af",
"moleculeId": "sa_d4989309cd34a2719c4413fe",
"parentId": "9459",
"isLeaf": false,
"molecule": {
"id": "sa_d4989309cd34a2719c4413fe",
"inchikey": "QFLBWNWKBXCHKS-UHFFFAOYSA-N",
"smiles": "COC(=O)c1ccc(C#CCO)cc1"
},
"smiles": "COC(=O)c1ccc(C#CCO)cc1",
"reactionStepId": "sa_9f3143966006b743ab93185c",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20040259921A1;0404;214183\",\"rsmi\":\"I[c:8]1[cH:7][cH:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[cH:14][cH:13]1.[CH:9]#[C:10][CH2:11][OH:12]>CC#N.CCN(CC)CC.Cl[Pd](Cl)([PH](c1ccccc1)(c1ccccc1)c1ccccc1)[PH](c1ccccc1)(c1ccccc1)c1ccccc1.O.[Cu]I>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([C:9]#[C:10][CH2:11][OH:12])[cH:13][cH:14]1\"},\"mapped_reaction_smiles\":\"I[c:8]1[cH:7][cH:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[cH:14][cH:13]1.[CH:9]#[C:10][CH2:11][OH:12]>CC#N.CCN(CC)CC.Cl[Pd](Cl)([PH](c1ccccc1)(c1ccccc1)c1ccccc1)[PH](c1ccccc1)(c1ccccc1)c1ccccc1.O.[Cu]I>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([C:9]#[C:10][CH2:11][OH:12])[cH:13][cH:14]1\"}",
"reactionStep": {
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"reactionHash": "4f1fb88ff94e77dc4ff5d140750b54df225c17b2d6892c28abf8c21bcf01eeed"
},
"children": [
{
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"routeId": "sa_fde3d71132b2690202bca6af",
"moleculeId": "sa_5056183819cd0395d4c17581",
"parentId": "9460",
"isLeaf": true,
"molecule": {
"id": "sa_5056183819cd0395d4c17581",
"inchikey": "DYUWQWMXZHDZOR-UHFFFAOYSA-N",
"smiles": "COC(=O)c1ccc(I)cc1"
},
"smiles": "COC(=O)c1ccc(I)cc1",
"reactionStepId": null,
"template": null,
"metadata": null,
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},
{
"id": "9462",
"routeId": "sa_fde3d71132b2690202bca6af",
"moleculeId": "sa_c58a4b616256a73ac49fb169",
"parentId": "9460",
"isLeaf": true,
"molecule": {
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"inchikey": "TVDSBUOJIPERQY-UHFFFAOYSA-N",
"smiles": "C#CCO"
},
"smiles": "C#CCO",
"reactionStepId": null,
"template": null,
"metadata": null,
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"children": []
}
]
}
]
},
{
"id": "9463",
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"moleculeId": "sa_4f7394b6924d2d72cdf188f6",
"parentId": "9458",
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"molecule": {
"id": "sa_4f7394b6924d2d72cdf188f6",
"inchikey": "BHELZAPQIKSEDF-UHFFFAOYSA-N",
"smiles": "C=CCBr"
},
"smiles": "C=CCBr",
"reactionStepId": null,
"template": null,
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"children": []
}
]
}
]
}
}