Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
CN1C(=O)Cc2c1ccc(-c1cncc(C3CC3)c1)c2Cl
InChiKey
ACVUWDSDOZHREI-UHFFFAOYSA-N
Route Signature
6b8b497c8efbd1b8b3bb134c63e2d0fa381840445b45e4ec3f2334be5e3c61be
Synthesis route with 6 steps
Route tree structure (JSON format)
{
"route": {
"id": "sa_91bff29638b2dace69dd823d",
"signature": "6b8b497c8efbd1b8b3bb134c63e2d0fa381840445b45e4ec3f2334be5e3c61be",
"contentHash": "2096d30b55586d9b50acc9429fa5cd76ec4f3b24076236d58ac60b25f0fc0d16",
"length": 6,
"isConvergent": false
},
"target": {
"id": "sa_47f0a9c98e016c10bfdef778",
"benchmarkSetId": "61e696668b63e77d7c2a29c0821768e1c383de8313852d6e995224859494442e",
"targetId": "n5-00948",
"moleculeId": "sa_23b5a86a7b51ea00ea78a6cb",
"smiles": "CN1C(=O)Cc2c1ccc(-c1cncc(C3CC3)c1)c2Cl",
"routeLength": 6,
"isConvergent": false,
"metadata": null,
"molecule": {
"id": "sa_23b5a86a7b51ea00ea78a6cb",
"inchikey": "ACVUWDSDOZHREI-UHFFFAOYSA-N",
"smiles": "CN1C(=O)Cc2c1ccc(-c1cncc(C3CC3)c1)c2Cl"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "13940",
"routeId": "sa_91bff29638b2dace69dd823d",
"moleculeId": "sa_23b5a86a7b51ea00ea78a6cb",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_23b5a86a7b51ea00ea78a6cb",
"inchikey": "ACVUWDSDOZHREI-UHFFFAOYSA-N",
"smiles": "CN1C(=O)Cc2c1ccc(-c1cncc(C3CC3)c1)c2Cl"
},
"smiles": "CN1C(=O)Cc2c1ccc(-c1cncc(C3CC3)c1)c2Cl",
"reactionStepId": "sa_420b3abc0d27c7d28e6057ff",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20120071512A1;0361;1193958\",\"rsmi\":\"Br[c:12]1[cH:11][c:10](-[c:9]2[c:7]([Cl:8])[c:6]3[c:21]([cH:20][cH:19]2)[N:2]([CH3:1])[C:3](=[O:4])[CH2:5]3)[cH:18][n:17][cH:16]1.F[B-](F)(F)[CH:13]1[CH2:14][CH2:15]1>C1CCOC1.ClCCl.O=C(O)O.O=P(O)(O)O.[K+].[K+].[K+].[K+].[Na+]>[CH3:1][N:2]1[C:3](=[O:4])[CH2:5][c:6]2[c:7]([Cl:8])[c:9](-[c:10]3[cH:11][c:12]([CH:13]4[CH2:14][CH2:15]4)[cH:16][n:17][cH:18]3)[cH:19][cH:20][c:21]21\"},\"mapped_reaction_smiles\":\"Br[c:12]1[cH:11][c:10](-[c:9]2[c:7]([Cl:8])[c:6]3[c:21]([cH:20][cH:19]2)[N:2]([CH3:1])[C:3](=[O:4])[CH2:5]3)[cH:18][n:17][cH:16]1.F[B-](F)(F)[CH:13]1[CH2:14][CH2:15]1>C1CCOC1.ClCCl.O=C(O)O.O=P(O)(O)O.[K+].[K+].[K+].[K+].[Na+]>[CH3:1][N:2]1[C:3](=[O:4])[CH2:5][c:6]2[c:7]([Cl:8])[c:9](-[c:10]3[cH:11][c:12]([CH:13]4[CH2:14][CH2:15]4)[cH:16][n:17][cH:18]3)[cH:19][cH:20][c:21]21\"}",
"reactionStep": {
"id": "sa_420b3abc0d27c7d28e6057ff",
"reactionHash": "8b9b3bcc0703818807352e3e2f3ebe1df0e61357f083a186adb7f157986f33ba"
},
"children": [
{
"id": "13941",
"routeId": "sa_91bff29638b2dace69dd823d",
"moleculeId": "sa_c8ed062aabb01f2593e45226",
"parentId": "13940",
"isLeaf": true,
"molecule": {
"id": "sa_c8ed062aabb01f2593e45226",
"inchikey": "LNRKQGKIYKWOEH-UHFFFAOYSA-N",
"smiles": "F[B-](F)(F)C1CC1"
},
"smiles": "F[B-](F)(F)C1CC1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "13942",
"routeId": "sa_91bff29638b2dace69dd823d",
"moleculeId": "sa_500a3e61151754bbd4fc8662",
"parentId": "13940",
"isLeaf": false,
"molecule": {
"id": "sa_500a3e61151754bbd4fc8662",
"inchikey": "QDKHDYXNDZNCKC-UHFFFAOYSA-N",
"smiles": "CN1C(=O)Cc2c1ccc(-c1cncc(Br)c1)c2Cl"
},
"smiles": "CN1C(=O)Cc2c1ccc(-c1cncc(Br)c1)c2Cl",
"reactionStepId": "sa_5491103419e5fb2bc7e67924",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20120071512A1;0351;1193955\",\"rsmi\":\"Br[c:10]1[cH:11][c:12]([Br:13])[cH:14][n:15][cH:16]1.CC1(C)OB([c:9]2[c:7]([Cl:8])[c:6]3[c:19]([cH:18][cH:17]2)[N:2]([CH3:1])[C:3](=[O:4])[CH2:5]3)OC1(C)C>COCCOC.ClCCl.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][N:2]1[C:3](=[O:4])[CH2:5][c:6]2[c:7]([Cl:8])[c:9](-[c:10]3[cH:11][c:12]([Br:13])[cH:14][n:15][cH:16]3)[cH:17][cH:18][c:19]21\"},\"mapped_reaction_smiles\":\"Br[c:10]1[cH:11][c:12]([Br:13])[cH:14][n:15][cH:16]1.CC1(C)OB([c:9]2[c:7]([Cl:8])[c:6]3[c:19]([cH:18][cH:17]2)[N:2]([CH3:1])[C:3](=[O:4])[CH2:5]3)OC1(C)C>COCCOC.ClCCl.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][N:2]1[C:3](=[O:4])[CH2:5][c:6]2[c:7]([Cl:8])[c:9](-[c:10]3[cH:11][c:12]([Br:13])[cH:14][n:15][cH:16]3)[cH:17][cH:18][c:19]21\"}",
"reactionStep": {
"id": "sa_5491103419e5fb2bc7e67924",
"reactionHash": "6e7fc125ec83e2d2d6d2cf87a96af8e4703ca8b2c572ca35084ff33dd452cb0b"
},
"children": [
{
"id": "13943",
"routeId": "sa_91bff29638b2dace69dd823d",
"moleculeId": "sa_a347d464941f81a862b19bb0",
"parentId": "13942",
"isLeaf": true,
"molecule": {
"id": "sa_a347d464941f81a862b19bb0",
"inchikey": "SOSPMXMEOFGPIM-UHFFFAOYSA-N",
"smiles": "Brc1cncc(Br)c1"
},
"smiles": "Brc1cncc(Br)c1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "13944",
"routeId": "sa_91bff29638b2dace69dd823d",
"moleculeId": "sa_e1dfe1ae619d122bc1e027a6",
"parentId": "13942",
"isLeaf": false,
"molecule": {
"id": "sa_e1dfe1ae619d122bc1e027a6",
"inchikey": "ZECMXNFTQFWKMY-UHFFFAOYSA-N",
"smiles": "CN1C(=O)Cc2c1ccc(B1OC(C)(C)C(C)(C)O1)c2Cl"
},
"smiles": "CN1C(=O)Cc2c1ccc(B1OC(C)(C)C(C)(C)O1)c2Cl",
"reactionStepId": "sa_d5bf2be751ccb4464a288fa8",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20120071512A1;0347;1193953\",\"rsmi\":\"Br[c:9]1[c:7]([Cl:8])[c:6]2[c:21]([cH:20][cH:19]1)[N:2]([CH3:1])[C:3](=[O:4])[CH2:5]2.CC1(C)OB([B:10]2[O:11][C:12]([CH3:13])([CH3:14])[C:15]([CH3:16])([CH3:17])[O:18]2)OC1(C)C>CC(=O)O.CS(C)=O.ClCCl.Cl[Pd]Cl.[Fe+2].[K+]>[CH3:1][N:2]1[C:3](=[O:4])[CH2:5][c:6]2[c:7]([Cl:8])[c:9]([B:10]3[O:11][C:12]([CH3:13])([CH3:14])[C:15]([CH3:16])([CH3:17])[O:18]3)[cH:19][cH:20][c:21]21\"},\"mapped_reaction_smiles\":\"Br[c:9]1[c:7]([Cl:8])[c:6]2[c:21]([cH:20][cH:19]1)[N:2]([CH3:1])[C:3](=[O:4])[CH2:5]2.CC1(C)OB([B:10]2[O:11][C:12]([CH3:13])([CH3:14])[C:15]([CH3:16])([CH3:17])[O:18]2)OC1(C)C>CC(=O)O.CS(C)=O.ClCCl.Cl[Pd]Cl.[Fe+2].[K+]>[CH3:1][N:2]1[C:3](=[O:4])[CH2:5][c:6]2[c:7]([Cl:8])[c:9]([B:10]3[O:11][C:12]([CH3:13])([CH3:14])[C:15]([CH3:16])([CH3:17])[O:18]3)[cH:19][cH:20][c:21]21\"}",
"reactionStep": {
"id": "sa_d5bf2be751ccb4464a288fa8",
"reactionHash": "3d13d67ec81d571762c39c36761b1fea488884f3103464a5c8d41b5facc0e99d"
},
"children": [
{
"id": "13945",
"routeId": "sa_91bff29638b2dace69dd823d",
"moleculeId": "sa_e6c301388ac142801d4af5a2",
"parentId": "13944",
"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,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "13946",
"routeId": "sa_91bff29638b2dace69dd823d",
"moleculeId": "sa_64bb17e02ef5dccbc8da31da",
"parentId": "13944",
"isLeaf": false,
"molecule": {
"id": "sa_64bb17e02ef5dccbc8da31da",
"inchikey": "WKMACJQHHVRNIY-UHFFFAOYSA-N",
"smiles": "CN1C(=O)Cc2c1ccc(Br)c2Cl"
},
"smiles": "CN1C(=O)Cc2c1ccc(Br)c2Cl",
"reactionStepId": "sa_f0388d2c8328ac95b103a1cf",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20120071512A1;0343;1193951\",\"rsmi\":\"Br[Br:10].[CH3:1][N:2]1[C:3](=[O:4])[CH2:5][c:6]2[c:7]([Cl:8])[cH:9][cH:11][cH:12][c:13]21>ClCCl.O.O=C(O)O.O=S(O)(O)=S.Br.[K+].[Na+].[Na+].[Na+]>[CH3:1][N:2]1[C:3](=[O:4])[CH2:5][c:6]2[c:7]([Cl:8])[c:9]([Br:10])[cH:11][cH:12][c:13]21\"},\"mapped_reaction_smiles\":\"Br[Br:10].[CH3:1][N:2]1[C:3](=[O:4])[CH2:5][c:6]2[c:7]([Cl:8])[cH:9][cH:11][cH:12][c:13]21>ClCCl.O.O=C(O)O.O=S(O)(O)=S.Br.[K+].[Na+].[Na+].[Na+]>[CH3:1][N:2]1[C:3](=[O:4])[CH2:5][c:6]2[c:7]([Cl:8])[c:9]([Br:10])[cH:11][cH:12][c:13]21\"}",
"reactionStep": {
"id": "sa_f0388d2c8328ac95b103a1cf",
"reactionHash": "ed09c0b3247c5b8d021aa71ae4f2b98e62a9a1eab21bef2f2132cce79c400882"
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"children": [
{
"id": "13947",
"routeId": "sa_91bff29638b2dace69dd823d",
"moleculeId": "sa_24211e89e565c162ea935f73",
"parentId": "13946",
"isLeaf": true,
"molecule": {
"id": "sa_24211e89e565c162ea935f73",
"inchikey": "GDTBXPJZTBHREO-UHFFFAOYSA-N",
"smiles": "BrBr"
},
"smiles": "BrBr",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "13948",
"routeId": "sa_91bff29638b2dace69dd823d",
"moleculeId": "sa_fd7cdcf5fd917e5173f81a25",
"parentId": "13946",
"isLeaf": false,
"molecule": {
"id": "sa_fd7cdcf5fd917e5173f81a25",
"inchikey": "YBOFOUDWAVEWHL-UHFFFAOYSA-N",
"smiles": "CN1C(=O)Cc2c(Cl)cccc21"
},
"smiles": "CN1C(=O)Cc2c(Cl)cccc21",
"reactionStepId": "sa_67cecdffd4a1b53f2dbd06ad",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20120071512A1;0341;1193950\",\"rsmi\":\"O=[C:5]1[C:3](=[O:4])[N:2]([CH3:1])[c:12]2[c:6]1[c:7]([Cl:8])[cH:9][cH:10][cH:11]2>ClCCl.NN.O.O>[CH3:1][N:2]1[C:3](=[O:4])[CH2:5][c:6]2[c:7]([Cl:8])[cH:9][cH:10][cH:11][c:12]21\"},\"mapped_reaction_smiles\":\"O=[C:5]1[C:3](=[O:4])[N:2]([CH3:1])[c:12]2[c:6]1[c:7]([Cl:8])[cH:9][cH:10][cH:11]2>ClCCl.NN.O.O>[CH3:1][N:2]1[C:3](=[O:4])[CH2:5][c:6]2[c:7]([Cl:8])[cH:9][cH:10][cH:11][c:12]21\"}",
"reactionStep": {
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"children": [
{
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"molecule": {
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"inchikey": "UUJAPGNVDLZZLH-UHFFFAOYSA-N",
"smiles": "CN1C(=O)C(=O)c2c(Cl)cccc21"
},
"smiles": "CN1C(=O)C(=O)c2c(Cl)cccc21",
"reactionStepId": "sa_6d4abdd674eb51375637260b",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20120071512A1;0341;1193949\",\"rsmi\":\"I[CH3:1].[NH:2]1[C:3](=[O:4])[C:5](=[O:6])[c:7]2[c:8]([Cl:9])[cH:10][cH:11][cH:12][c:13]21>CC#N.O=C(O)O.[K+].[K+]>[CH3:1][N:2]1[C:3](=[O:4])[C:5](=[O:6])[c:7]2[c:8]([Cl:9])[cH:10][cH:11][cH:12][c:13]21\"},\"mapped_reaction_smiles\":\"I[CH3:1].[NH:2]1[C:3](=[O:4])[C:5](=[O:6])[c:7]2[c:8]([Cl:9])[cH:10][cH:11][cH:12][c:13]21>CC#N.O=C(O)O.[K+].[K+]>[CH3:1][N:2]1[C:3](=[O:4])[C:5](=[O:6])[c:7]2[c:8]([Cl:9])[cH:10][cH:11][cH:12][c:13]21\"}",
"reactionStep": {
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"reactionHash": "b29b1ee64b256ee3e205d177e82aa1177e0486d3417ba3790c304821fd9d4a8d"
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"children": [
{
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"routeId": "sa_91bff29638b2dace69dd823d",
"moleculeId": "sa_62faef539bb63693e59d1001",
"parentId": "13949",
"isLeaf": true,
"molecule": {
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"inchikey": "HSYFISNDMZKGRS-UHFFFAOYSA-N",
"smiles": "O=C1Nc2cccc(Cl)c2C1=O"
},
"smiles": "O=C1Nc2cccc(Cl)c2C1=O",
"reactionStepId": null,
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"metadata": null,
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},
{
"id": "13951",
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"molecule": {
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"inchikey": "INQOMBQAUSQDDS-UHFFFAOYSA-N",
"smiles": "CI"
},
"smiles": "CI",
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}
]
}
]
}
]
}
]
}
]
}
]
}
}