Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
COC(=O)c1cc(Cc2ccc(-n3cccn3)cc2)c(C2CC2)cc1OS(=O)(=O)C(F)(F)F
InChiKey
DNEPGUYVTNAEKF-UHFFFAOYSA-N
Route Signature
ad77d1dcdd9be0cd0578c5bef8d0a8b3111f63b70212a1c2945769778cead0fd
Synthesis route with 6 steps
Route tree structure (JSON format)
{
"route": {
"id": "sa_e0ee8e87a2e544acea147924",
"signature": "ad77d1dcdd9be0cd0578c5bef8d0a8b3111f63b70212a1c2945769778cead0fd",
"contentHash": "61efc6c00fa44c6768048433dfc00498491d9298ff4b2c93d0b6c25e19e2a448",
"length": 6,
"isConvergent": false
},
"target": {
"id": "sa_1ac3dc76b03b6f0e11ce6113",
"benchmarkSetId": "f925e688d731a0ad4e3aa6a505df094f6d3ca64ce3facc312bc5f64731921b33",
"targetId": "n5-01278",
"moleculeId": "sa_9f570c098a8843d3a14ed75d",
"smiles": "COC(=O)c1cc(Cc2ccc(-n3cccn3)cc2)c(C2CC2)cc1OS(=O)(=O)C(F)(F)F",
"routeLength": 6,
"isConvergent": false,
"metadata": null,
"molecule": {
"id": "sa_9f570c098a8843d3a14ed75d",
"inchikey": "DNEPGUYVTNAEKF-UHFFFAOYSA-N",
"smiles": "COC(=O)c1cc(Cc2ccc(-n3cccn3)cc2)c(C2CC2)cc1OS(=O)(=O)C(F)(F)F"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 2
},
"rootNode": {
"id": "5392",
"routeId": "sa_e0ee8e87a2e544acea147924",
"moleculeId": "sa_9f570c098a8843d3a14ed75d",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_9f570c098a8843d3a14ed75d",
"inchikey": "DNEPGUYVTNAEKF-UHFFFAOYSA-N",
"smiles": "COC(=O)c1cc(Cc2ccc(-n3cccn3)cc2)c(C2CC2)cc1OS(=O)(=O)C(F)(F)F"
},
"smiles": "COC(=O)c1cc(Cc2ccc(-n3cccn3)cc2)c(C2CC2)cc1OS(=O)(=O)C(F)(F)F",
"reactionStepId": "sa_b3eaa4a9baa8bab614a3b059",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20160152603A1;0773;1884991\",\"rsmi\":\"O=S(=O)(N(c1ccccc1)[S:8](=[O:9])(=[O:10])[C:11]([F:12])([F:13])[F:14])C(F)(F)F.[CH3:1][O:2][C:3](=[O:4])[c:5]1[c:6]([OH:7])[cH:15][c:16]([CH:17]2[CH2:18][CH2:19]2)[c:20]([CH2:21][c:22]2[cH:23][cH:24][c:25](-[n:26]3[cH:27][cH:28][cH:29][n:30]3)[cH:31][cH:32]2)[cH:33]1>CN(C)C=O.Cl.[HH].[Na+]>[CH3:1][O:2][C:3](=[O:4])[c:5]1[c:6]([O:7][S:8](=[O:9])(=[O:10])[C:11]([F:12])([F:13])[F:14])[cH:15][c:16]([CH:17]2[CH2:18][CH2:19]2)[c:20]([CH2:21][c:22]2[cH:23][cH:24][c:25](-[n:26]3[cH:27][cH:28][cH:29][n:30]3)[cH:31][cH:32]2)[cH:33]1\"},\"mapped_reaction_smiles\":\"O=S(=O)(N(c1ccccc1)[S:8](=[O:9])(=[O:10])[C:11]([F:12])([F:13])[F:14])C(F)(F)F.[CH3:1][O:2][C:3](=[O:4])[c:5]1[c:6]([OH:7])[cH:15][c:16]([CH:17]2[CH2:18][CH2:19]2)[c:20]([CH2:21][c:22]2[cH:23][cH:24][c:25](-[n:26]3[cH:27][cH:28][cH:29][n:30]3)[cH:31][cH:32]2)[cH:33]1>CN(C)C=O.Cl.[HH].[Na+]>[CH3:1][O:2][C:3](=[O:4])[c:5]1[c:6]([O:7][S:8](=[O:9])(=[O:10])[C:11]([F:12])([F:13])[F:14])[cH:15][c:16]([CH:17]2[CH2:18][CH2:19]2)[c:20]([CH2:21][c:22]2[cH:23][cH:24][c:25](-[n:26]3[cH:27][cH:28][cH:29][n:30]3)[cH:31][cH:32]2)[cH:33]1\"}",
"reactionStep": {
"id": "sa_b3eaa4a9baa8bab614a3b059",
"reactionHash": "0095667de0bc26ed3f51b46ce851fa7234e37639874fba033298dca6e7f79f3a"
},
"children": [
{
"id": "5393",
"routeId": "sa_e0ee8e87a2e544acea147924",
"moleculeId": "sa_24bc5b50442cd9e5fcf68f54",
"parentId": "5392",
"isLeaf": true,
"molecule": {
"id": "sa_24bc5b50442cd9e5fcf68f54",
"inchikey": "DIOHEXPTUTVCNX-UHFFFAOYSA-N",
"smiles": "O=S(=O)(N(c1ccccc1)S(=O)(=O)C(F)(F)F)C(F)(F)F"
},
"smiles": "O=S(=O)(N(c1ccccc1)S(=O)(=O)C(F)(F)F)C(F)(F)F",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "5394",
"routeId": "sa_e0ee8e87a2e544acea147924",
"moleculeId": "sa_9e4936e25b73c91951f6ff34",
"parentId": "5392",
"isLeaf": false,
"molecule": {
"id": "sa_9e4936e25b73c91951f6ff34",
"inchikey": "YUAQWBYDWYVQRC-UHFFFAOYSA-N",
"smiles": "COC(=O)c1cc(Cc2ccc(-n3cccn3)cc2)c(C2CC2)cc1O"
},
"smiles": "COC(=O)c1cc(Cc2ccc(-n3cccn3)cc2)c(C2CC2)cc1O",
"reactionStepId": "sa_7facb611490f8a91de8c958e",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20160152603A1;0771;1884990\",\"rsmi\":\"Br[CH2:14][c:15]1[cH:16][cH:17][c:18](-[n:19]2[cH:20][cH:21][cH:22][n:23]2)[cH:24][cH:25]1.CC1(C)OB([c:13]2[c:9]([CH:10]3[CH2:11][CH2:12]3)[cH:8][c:6]([OH:7])[c:5]([C:3]([O:2][CH3:1])=[O:4])[cH:26]2)OC1(C)C>CCOC(C)=O.COCCOC.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][O:2][C:3](=[O:4])[c:5]1[c:6]([OH:7])[cH:8][c:9]([CH:10]2[CH2:11][CH2:12]2)[c:13]([CH2:14][c:15]2[cH:16][cH:17][c:18](-[n:19]3[cH:20][cH:21][cH:22][n:23]3)[cH:24][cH:25]2)[cH:26]1\"},\"mapped_reaction_smiles\":\"Br[CH2:14][c:15]1[cH:16][cH:17][c:18](-[n:19]2[cH:20][cH:21][cH:22][n:23]2)[cH:24][cH:25]1.CC1(C)OB([c:13]2[c:9]([CH:10]3[CH2:11][CH2:12]3)[cH:8][c:6]([OH:7])[c:5]([C:3]([O:2][CH3:1])=[O:4])[cH:26]2)OC1(C)C>CCOC(C)=O.COCCOC.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][O:2][C:3](=[O:4])[c:5]1[c:6]([OH:7])[cH:8][c:9]([CH:10]2[CH2:11][CH2:12]2)[c:13]([CH2:14][c:15]2[cH:16][cH:17][c:18](-[n:19]3[cH:20][cH:21][cH:22][n:23]3)[cH:24][cH:25]2)[cH:26]1\"}",
"reactionStep": {
"id": "sa_7facb611490f8a91de8c958e",
"reactionHash": "4c63ae85c9cad682f8d8ce6f745fd33951cbf536c6c12f9755a642feac6d8205"
},
"children": [
{
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"routeId": "sa_e0ee8e87a2e544acea147924",
"moleculeId": "sa_08c27027ed328dd3651cb64c",
"parentId": "5394",
"isLeaf": false,
"molecule": {
"id": "sa_08c27027ed328dd3651cb64c",
"inchikey": "CRUYFSKILGXIJZ-UHFFFAOYSA-N",
"smiles": "COC(=O)c1cc(B2OC(C)(C)C(C)(C)O2)c(C2CC2)cc1O"
},
"smiles": "COC(=O)c1cc(B2OC(C)(C)C(C)(C)O2)c(C2CC2)cc1O",
"reactionStepId": "sa_a0c85edb65d7f1659ba6e8eb",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20160152603A1;0769;1884989\",\"rsmi\":\"Br[c:13]1[c:9]([CH:10]2[CH2:11][CH2:12]2)[cH:8][c:6]([OH:7])[c:5]([C:3]([O:2][CH3:1])=[O:4])[cH:23]1.CC1(C)OB([B:14]2[O:15][C:16]([CH3:17])([CH3:18])[C:19]([CH3:20])([CH3:21])[O:22]2)OC1(C)C>CC(=O)O.CCOC(C)=O.Cc1ccccc1.Cl[Pd](Cl)([PH](c1ccccc1)(c1ccccc1)c1ccccc1)[PH](c1ccccc1)(c1ccccc1)c1ccccc1.O.[K+]>[CH3:1][O:2][C:3](=[O:4])[c:5]1[c:6]([OH:7])[cH:8][c:9]([CH:10]2[CH2:11][CH2:12]2)[c:13]([B:14]2[O:15][C:16]([CH3:17])([CH3:18])[C:19]([CH3:20])([CH3:21])[O:22]2)[cH:23]1\"},\"mapped_reaction_smiles\":\"Br[c:13]1[c:9]([CH:10]2[CH2:11][CH2:12]2)[cH:8][c:6]([OH:7])[c:5]([C:3]([O:2][CH3:1])=[O:4])[cH:23]1.CC1(C)OB([B:14]2[O:15][C:16]([CH3:17])([CH3:18])[C:19]([CH3:20])([CH3:21])[O:22]2)OC1(C)C>CC(=O)O.CCOC(C)=O.Cc1ccccc1.Cl[Pd](Cl)([PH](c1ccccc1)(c1ccccc1)c1ccccc1)[PH](c1ccccc1)(c1ccccc1)c1ccccc1.O.[K+]>[CH3:1][O:2][C:3](=[O:4])[c:5]1[c:6]([OH:7])[cH:8][c:9]([CH:10]2[CH2:11][CH2:12]2)[c:13]([B:14]2[O:15][C:16]([CH3:17])([CH3:18])[C:19]([CH3:20])([CH3:21])[O:22]2)[cH:23]1\"}",
"reactionStep": {
"id": "sa_a0c85edb65d7f1659ba6e8eb",
"reactionHash": "fb5e1157f106ed8e0add6dd972592061a9999edcc27b73b281d35f306947ef91"
},
"children": [
{
"id": "5396",
"routeId": "sa_e0ee8e87a2e544acea147924",
"moleculeId": "sa_b73db6aa21fcae00d40947a4",
"parentId": "5395",
"isLeaf": false,
"molecule": {
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"inchikey": "ICESCLJJZHGZGD-UHFFFAOYSA-N",
"smiles": "COC(=O)c1cc(Br)c(C2CC2)cc1O"
},
"smiles": "COC(=O)c1cc(Br)c(C2CC2)cc1O",
"reactionStepId": "sa_bdb64c87407043a91c77224a",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20160152603A1;0767;1884988\",\"rsmi\":\"Br[Br:14].[CH3:1][O:2][C:3](=[O:4])[c:5]1[c:6]([OH:7])[cH:8][c:9]([CH:10]2[CH2:11][CH2:12]2)[cH:13][cH:15]1>CC(=O)O.O>[CH3:1][O:2][C:3](=[O:4])[c:5]1[c:6]([OH:7])[cH:8][c:9]([CH:10]2[CH2:11][CH2:12]2)[c:13]([Br:14])[cH:15]1\"},\"mapped_reaction_smiles\":\"Br[Br:14].[CH3:1][O:2][C:3](=[O:4])[c:5]1[c:6]([OH:7])[cH:8][c:9]([CH:10]2[CH2:11][CH2:12]2)[cH:13][cH:15]1>CC(=O)O.O>[CH3:1][O:2][C:3](=[O:4])[c:5]1[c:6]([OH:7])[cH:8][c:9]([CH:10]2[CH2:11][CH2:12]2)[c:13]([Br:14])[cH:15]1\"}",
"reactionStep": {
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"reactionHash": "ed384fb23f5b81eee4d65c377e802d90050b6cb5cf69a82d37b8e3c2da84a1b5"
},
"children": [
{
"id": "5397",
"routeId": "sa_e0ee8e87a2e544acea147924",
"moleculeId": "sa_3695b42611c0d89f64fa6f30",
"parentId": "5396",
"isLeaf": false,
"molecule": {
"id": "sa_3695b42611c0d89f64fa6f30",
"inchikey": "ALURDONIZLSXIY-UHFFFAOYSA-N",
"smiles": "COC(=O)c1ccc(C2CC2)cc1O"
},
"smiles": "COC(=O)c1ccc(C2CC2)cc1O",
"reactionStepId": "sa_2d1cd7a194f3abdf30a8dcb6",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20160152603A1;0765;1884987\",\"rsmi\":\"Br[c:9]1[cH:8][c:6]([OH:7])[c:5]([C:3]([O:2][CH3:1])=[O:4])[cH:14][cH:13]1.OB(O)[CH:10]1[CH2:11][CH2:12]1>CCOC(C)=O.COc1cccc(OC)c1-c1ccccc1P(C1CCCCC1)C1CCCCC1.Cc1ccccc1.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.[Na+].[Na+].[Pd].[Pd]>[CH3:1][O:2][C:3](=[O:4])[c:5]1[c:6]([OH:7])[cH:8][c:9]([CH:10]2[CH2:11][CH2:12]2)[cH:13][cH:14]1\"},\"mapped_reaction_smiles\":\"Br[c:9]1[cH:8][c:6]([OH:7])[c:5]([C:3]([O:2][CH3:1])=[O:4])[cH:14][cH:13]1.OB(O)[CH:10]1[CH2:11][CH2:12]1>CCOC(C)=O.COc1cccc(OC)c1-c1ccccc1P(C1CCCCC1)C1CCCCC1.Cc1ccccc1.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.[Na+].[Na+].[Pd].[Pd]>[CH3:1][O:2][C:3](=[O:4])[c:5]1[c:6]([OH:7])[cH:8][c:9]([CH:10]2[CH2:11][CH2:12]2)[cH:13][cH:14]1\"}",
"reactionStep": {
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"reactionHash": "f33db058df24349ab98439fc70689e1825a9f2ee9ef80bc5afb4b1f0d5709d29"
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"children": [
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"molecule": {
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"inchikey": "JEMVEVUWSJXZMX-UHFFFAOYSA-N",
"smiles": "COC(=O)c1ccc(Br)cc1O"
},
"smiles": "COC(=O)c1ccc(Br)cc1O",
"reactionStepId": "sa_b7e1b7c95583fc72a16d51e8",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20160152603A1;0763;1884986\",\"rsmi\":\"O[C:3](=[O:4])[c:5]1[c:6]([OH:7])[cH:8][c:9]([Br:10])[cH:11][cH:12]1.[CH3:1][OH:2]>O=S(Cl)Cl>[CH3:1][O:2][C:3](=[O:4])[c:5]1[c:6]([OH:7])[cH:8][c:9]([Br:10])[cH:11][cH:12]1\"},\"mapped_reaction_smiles\":\"O[C:3](=[O:4])[c:5]1[c:6]([OH:7])[cH:8][c:9]([Br:10])[cH:11][cH:12]1.[CH3:1][OH:2]>O=S(Cl)Cl>[CH3:1][O:2][C:3](=[O:4])[c:5]1[c:6]([OH:7])[cH:8][c:9]([Br:10])[cH:11][cH:12]1\"}",
"reactionStep": {
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"children": [
{
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"parentId": "5398",
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"molecule": {
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"inchikey": "FYAKLZKQJDBBKW-UHFFFAOYSA-N",
"smiles": "O=C(O)c1ccc(Br)cc1O"
},
"smiles": "O=C(O)c1ccc(Br)cc1O",
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{
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"molecule": {
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"inchikey": "OKKJLVBELUTLKV-UHFFFAOYSA-N",
"smiles": "CO"
},
"smiles": "CO",
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}
]
},
{
"id": "5401",
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"molecule": {
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"smiles": "OB(O)C1CC1"
},
"smiles": "OB(O)C1CC1",
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}
]
},
{
"id": "5402",
"routeId": "sa_e0ee8e87a2e544acea147924",
"moleculeId": "sa_24211e89e565c162ea935f73",
"parentId": "5396",
"isLeaf": true,
"molecule": {
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"inchikey": "GDTBXPJZTBHREO-UHFFFAOYSA-N",
"smiles": "BrBr"
},
"smiles": "BrBr",
"reactionStepId": null,
"template": null,
"metadata": null,
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"children": []
}
]
},
{
"id": "5403",
"routeId": "sa_e0ee8e87a2e544acea147924",
"moleculeId": "sa_e6c301388ac142801d4af5a2",
"parentId": "5395",
"isLeaf": true,
"molecule": {
"id": "sa_e6c301388ac142801d4af5a2",
"inchikey": "IPWKHHSGDUIRAH-UHFFFAOYSA-N",
"smiles": "CC1(C)OB(B2OC(C)(C)C(C)(C)O2)OC1(C)C"
},
"smiles": "CC1(C)OB(B2OC(C)(C)C(C)(C)O2)OC1(C)C",
"reactionStepId": null,
"template": null,
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}
]
},
{
"id": "5404",
"routeId": "sa_e0ee8e87a2e544acea147924",
"moleculeId": "sa_31396b71cc52456ff60b0e3c",
"parentId": "5394",
"isLeaf": true,
"molecule": {
"id": "sa_31396b71cc52456ff60b0e3c",
"inchikey": "PHNRBSHOFSWNII-UHFFFAOYSA-N",
"smiles": "BrCc1ccc(-n2cccn2)cc1"
},
"smiles": "BrCc1ccc(-n2cccn2)cc1",
"reactionStepId": null,
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}
]
}
]
}
}