Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
CC(=O)Nc1ccc2c(c1)NCC(CN(C)C)C2
InChiKey
HVKAAOLCWCPNDL-UHFFFAOYSA-N
Route Signature
da4b5d68603036680a4261c7fccb2c5cb16f64754a370f180c49d5d02ccb4b87
Synthesis route with 6 steps
Route tree structure (JSON format)
{
"route": {
"id": "sa_3fefd995be97b4ebd0e483a4",
"signature": "da4b5d68603036680a4261c7fccb2c5cb16f64754a370f180c49d5d02ccb4b87",
"contentHash": "e45e349bfe9fd9f3f4fae12355bd2c1143f16d4795c87294332f80b2f91c3d46",
"length": 6,
"isConvergent": false
},
"target": {
"id": "sa_d3e36e06c373c31a533b1c1c",
"benchmarkSetId": "61e696668b63e77d7c2a29c0821768e1c383de8313852d6e995224859494442e",
"targetId": "n5-00788",
"moleculeId": "sa_c9116362417052b802c85a1f",
"smiles": "CC(=O)Nc1ccc2c(c1)NCC(CN(C)C)C2",
"routeLength": 6,
"isConvergent": false,
"metadata": null,
"molecule": {
"id": "sa_c9116362417052b802c85a1f",
"inchikey": "HVKAAOLCWCPNDL-UHFFFAOYSA-N",
"smiles": "CC(=O)Nc1ccc2c(c1)NCC(CN(C)C)C2"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "13780",
"routeId": "sa_3fefd995be97b4ebd0e483a4",
"moleculeId": "sa_c9116362417052b802c85a1f",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_c9116362417052b802c85a1f",
"inchikey": "HVKAAOLCWCPNDL-UHFFFAOYSA-N",
"smiles": "CC(=O)Nc1ccc2c(c1)NCC(CN(C)C)C2"
},
"smiles": "CC(=O)Nc1ccc2c(c1)NCC(CN(C)C)C2",
"reactionStepId": "sa_8d894c0cd05b8ab8487dfc4e",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US06329389B1;;538595\",\"rsmi\":\"CC(=O)O[C:2]([CH3:1])=[O:3].[NH2:4][c:5]1[cH:6][cH:7][c:8]2[c:17]([cH:18]1)[NH:16][CH2:15][CH:10]([CH2:11][N:12]([CH3:13])[CH3:14])[CH2:9]2>C1CCOC1.c1ccncc1>[CH3:1][C:2](=[O:3])[NH:4][c:5]1[cH:6][cH:7][c:8]2[c:17]([cH:18]1)[NH:16][CH2:15][CH:10]([CH2:11][N:12]([CH3:13])[CH3:14])[CH2:9]2\"},\"mapped_reaction_smiles\":\"CC(=O)O[C:2]([CH3:1])=[O:3].[NH2:4][c:5]1[cH:6][cH:7][c:8]2[c:17]([cH:18]1)[NH:16][CH2:15][CH:10]([CH2:11][N:12]([CH3:13])[CH3:14])[CH2:9]2>C1CCOC1.c1ccncc1>[CH3:1][C:2](=[O:3])[NH:4][c:5]1[cH:6][cH:7][c:8]2[c:17]([cH:18]1)[NH:16][CH2:15][CH:10]([CH2:11][N:12]([CH3:13])[CH3:14])[CH2:9]2\"}",
"reactionStep": {
"id": "sa_8d894c0cd05b8ab8487dfc4e",
"reactionHash": "1f50caf2081ecf512046e71c96c10f183afaa008b8080e50aed969d025016554"
},
"children": [
{
"id": "13781",
"routeId": "sa_3fefd995be97b4ebd0e483a4",
"moleculeId": "sa_c00b59e43a75050dedc99ff4",
"parentId": "13780",
"isLeaf": false,
"molecule": {
"id": "sa_c00b59e43a75050dedc99ff4",
"inchikey": "BUISKCKFUQJWEO-UHFFFAOYSA-N",
"smiles": "CN(C)CC1CNc2cc(N)ccc2C1"
},
"smiles": "CN(C)CC1CNc2cc(N)ccc2C1",
"reactionStepId": "sa_e46ca93b01948e28024aa606",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US06329389B1;;538594\",\"rsmi\":\"O=[C:4]([N:2]([CH3:1])[CH3:3])[CH:5]1[C:6](=O)[NH:7][c:8]2[cH:9][c:10]([NH2:11])[cH:12][cH:13][c:14]2[CH2:15]1>C1CCOC1.O>[CH3:1][N:2]([CH3:3])[CH2:4][CH:5]1[CH2:6][NH:7][c:8]2[cH:9][c:10]([NH2:11])[cH:12][cH:13][c:14]2[CH2:15]1\"},\"mapped_reaction_smiles\":\"O=[C:4]([N:2]([CH3:1])[CH3:3])[CH:5]1[C:6](=O)[NH:7][c:8]2[cH:9][c:10]([NH2:11])[cH:12][cH:13][c:14]2[CH2:15]1>C1CCOC1.O>[CH3:1][N:2]([CH3:3])[CH2:4][CH:5]1[CH2:6][NH:7][c:8]2[cH:9][c:10]([NH2:11])[cH:12][cH:13][c:14]2[CH2:15]1\"}",
"reactionStep": {
"id": "sa_e46ca93b01948e28024aa606",
"reactionHash": "9ff26f2bf2480ca4c6040d031349a80ba0b993b796f70ad0ea782341d5507351"
},
"children": [
{
"id": "13782",
"routeId": "sa_3fefd995be97b4ebd0e483a4",
"moleculeId": "sa_a73bc122ce2bca3b916f4da1",
"parentId": "13781",
"isLeaf": false,
"molecule": {
"id": "sa_a73bc122ce2bca3b916f4da1",
"inchikey": "MSLMPBHHABUCKS-UHFFFAOYSA-N",
"smiles": "CN(C)C(=O)C1Cc2ccc(N)cc2NC1=O"
},
"smiles": "CN(C)C(=O)C1Cc2ccc(N)cc2NC1=O",
"reactionStepId": "sa_a19c9725d75ca2c09dc0342b",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US06329389B1;;538593\",\"rsmi\":\"O=C(OCc1ccccc1)[NH:12][c:11]1[cH:10][cH:9][c:8]2[c:14]([cH:13]1)[NH:15][C:16](=[O:17])[CH:6]([C:4]([N:2]([CH3:1])[CH3:3])=[O:5])[CH2:7]2>C.C1CCOC1.CO.[H][H].[Pd]>[CH3:1][N:2]([CH3:3])[C:4](=[O:5])[CH:6]1[CH2:7][c:8]2[cH:9][cH:10][c:11]([NH2:12])[cH:13][c:14]2[NH:15][C:16]1=[O:17]\"},\"mapped_reaction_smiles\":\"O=C(OCc1ccccc1)[NH:12][c:11]1[cH:10][cH:9][c:8]2[c:14]([cH:13]1)[NH:15][C:16](=[O:17])[CH:6]([C:4]([N:2]([CH3:1])[CH3:3])=[O:5])[CH2:7]2>C.C1CCOC1.CO.[H][H].[Pd]>[CH3:1][N:2]([CH3:3])[C:4](=[O:5])[CH:6]1[CH2:7][c:8]2[cH:9][cH:10][c:11]([NH2:12])[cH:13][c:14]2[NH:15][C:16]1=[O:17]\"}",
"reactionStep": {
"id": "sa_a19c9725d75ca2c09dc0342b",
"reactionHash": "780e974e93c9686f798fb95d7e408882479bcbe13a49b851abd80625155cbea7"
},
"children": [
{
"id": "13783",
"routeId": "sa_3fefd995be97b4ebd0e483a4",
"moleculeId": "sa_22b471a03ad68111c666b9e1",
"parentId": "13782",
"isLeaf": false,
"molecule": {
"id": "sa_22b471a03ad68111c666b9e1",
"inchikey": "WXRVLISTPHCQGX-UHFFFAOYSA-N",
"smiles": "CN(C)C(=O)C1Cc2ccc(NC(=O)OCc3ccccc3)cc2NC1=O"
},
"smiles": "CN(C)C(=O)C1Cc2ccc(NC(=O)OCc3ccccc3)cc2NC1=O",
"reactionStepId": "sa_eb02bd083a88a58a89be774e",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US06329389B1;;538592\",\"rsmi\":\"O[C:4](=[O:5])[CH:6]1[CH2:7][c:8]2[cH:9][cH:10][c:11]([NH:12][C:13](=[O:14])[O:15][CH2:16][c:17]3[cH:18][cH:19][cH:20][cH:21][cH:22]3)[cH:23][c:24]2[NH:25][C:26]1=[O:27].[CH3:1][NH:2][CH3:3]>C1CCOC1.CC#N.CCN(CC)CC.CCN=C=NCCCN(C)C.Cl.O.On1nnc2ccccc21>[CH3:1][N:2]([CH3:3])[C:4](=[O:5])[CH:6]1[CH2:7][c:8]2[cH:9][cH:10][c:11]([NH:12][C:13](=[O:14])[O:15][CH2:16][c:17]3[cH:18][cH:19][cH:20][cH:21][cH:22]3)[cH:23][c:24]2[NH:25][C:26]1=[O:27]\"},\"mapped_reaction_smiles\":\"O[C:4](=[O:5])[CH:6]1[CH2:7][c:8]2[cH:9][cH:10][c:11]([NH:12][C:13](=[O:14])[O:15][CH2:16][c:17]3[cH:18][cH:19][cH:20][cH:21][cH:22]3)[cH:23][c:24]2[NH:25][C:26]1=[O:27].[CH3:1][NH:2][CH3:3]>C1CCOC1.CC#N.CCN(CC)CC.CCN=C=NCCCN(C)C.Cl.O.On1nnc2ccccc21>[CH3:1][N:2]([CH3:3])[C:4](=[O:5])[CH:6]1[CH2:7][c:8]2[cH:9][cH:10][c:11]([NH:12][C:13](=[O:14])[O:15][CH2:16][c:17]3[cH:18][cH:19][cH:20][cH:21][cH:22]3)[cH:23][c:24]2[NH:25][C:26]1=[O:27]\"}",
"reactionStep": {
"id": "sa_eb02bd083a88a58a89be774e",
"reactionHash": "fd16177b4af09805eb5135e0a42a8da9f71efb81375ec21531e666f178fbac4f"
},
"children": [
{
"id": "13784",
"routeId": "sa_3fefd995be97b4ebd0e483a4",
"moleculeId": "sa_119580f8cfbb083070612d7a",
"parentId": "13783",
"isLeaf": false,
"molecule": {
"id": "sa_119580f8cfbb083070612d7a",
"inchikey": "RDGGWCKOAZOCBU-UHFFFAOYSA-N",
"smiles": "O=C(Nc1ccc2c(c1)NC(=O)C(C(=O)O)C2)OCc1ccccc1"
},
"smiles": "O=C(Nc1ccc2c(c1)NC(=O)C(C(=O)O)C2)OCc1ccccc1",
"reactionStepId": "sa_59b0d06238d2727da70f99c1",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US06329389B1;;538591\",\"rsmi\":\"CC[O:12][C:10]([CH:9]1[CH2:8][c:7]2[cH:6][cH:5][c:4]([NH:3][C:2](=[O:1])[O:18][CH2:19][c:20]3[cH:21][cH:22][cH:23][cH:24][cH:25]3)[cH:17][c:16]2[NH:15][C:13]1=[O:14])=[O:11]>C1CCOC1.CO.Cl.Cl.[Na+].[Na+].O>[O:1]=[C:2]([NH:3][c:4]1[cH:5][cH:6][c:7]2[c:16]([cH:17]1)[NH:15][C:13](=[O:14])[CH:9]([C:10](=[O:11])[OH:12])[CH2:8]2)[O:18][CH2:19][c:20]1[cH:21][cH:22][cH:23][cH:24][cH:25]1\"},\"mapped_reaction_smiles\":\"CC[O:12][C:10]([CH:9]1[CH2:8][c:7]2[cH:6][cH:5][c:4]([NH:3][C:2](=[O:1])[O:18][CH2:19][c:20]3[cH:21][cH:22][cH:23][cH:24][cH:25]3)[cH:17][c:16]2[NH:15][C:13]1=[O:14])=[O:11]>C1CCOC1.CO.Cl.Cl.[Na+].[Na+].O>[O:1]=[C:2]([NH:3][c:4]1[cH:5][cH:6][c:7]2[c:16]([cH:17]1)[NH:15][C:13](=[O:14])[CH:9]([C:10](=[O:11])[OH:12])[CH2:8]2)[O:18][CH2:19][c:20]1[cH:21][cH:22][cH:23][cH:24][cH:25]1\"}",
"reactionStep": {
"id": "sa_59b0d06238d2727da70f99c1",
"reactionHash": "d79eedad90b305677f5e62ffb007162c927e5babe35edb846f905708160b5ca2"
},
"children": [
{
"id": "13785",
"routeId": "sa_3fefd995be97b4ebd0e483a4",
"moleculeId": "sa_ba1bb5dc56d68835b8521619",
"parentId": "13784",
"isLeaf": false,
"molecule": {
"id": "sa_ba1bb5dc56d68835b8521619",
"inchikey": "ILZQRYCKQMVUOE-UHFFFAOYSA-N",
"smiles": "CCOC(=O)C1Cc2ccc(NC(=O)OCc3ccccc3)cc2NC1=O"
},
"smiles": "CCOC(=O)C1Cc2ccc(NC(=O)OCc3ccccc3)cc2NC1=O",
"reactionStepId": "sa_fa0e45defad56382307e1094",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US06329389B1;;538590\",\"rsmi\":\"Cl[C:13](=[O:14])[O:15][CH2:16][c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1.[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]1[CH2:7][c:8]2[cH:9][cH:10][c:11]([NH2:12])[cH:23][c:24]2[NH:25][C:26]1=[O:27]>C1CCOC1.O.O=C(O)O.[Na+].[Na+]>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]1[CH2:7][c:8]2[cH:9][cH:10][c:11]([NH:12][C:13](=[O:14])[O:15][CH2:16][c:17]3[cH:18][cH:19][cH:20][cH:21][cH:22]3)[cH:23][c:24]2[NH:25][C:26]1=[O:27]\"},\"mapped_reaction_smiles\":\"Cl[C:13](=[O:14])[O:15][CH2:16][c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1.[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]1[CH2:7][c:8]2[cH:9][cH:10][c:11]([NH2:12])[cH:23][c:24]2[NH:25][C:26]1=[O:27]>C1CCOC1.O.O=C(O)O.[Na+].[Na+]>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]1[CH2:7][c:8]2[cH:9][cH:10][c:11]([NH:12][C:13](=[O:14])[O:15][CH2:16][c:17]3[cH:18][cH:19][cH:20][cH:21][cH:22]3)[cH:23][c:24]2[NH:25][C:26]1=[O:27]\"}",
"reactionStep": {
"id": "sa_fa0e45defad56382307e1094",
"reactionHash": "1ee1994be03e715f9bba79efe4db2de5904699f86a305688664f5ebd0cf63709"
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"children": [
{
"id": "13786",
"routeId": "sa_3fefd995be97b4ebd0e483a4",
"moleculeId": "sa_06629d8564abb4533c2256c8",
"parentId": "13785",
"isLeaf": true,
"molecule": {
"id": "sa_06629d8564abb4533c2256c8",
"inchikey": "DWLCHCZQBNUGOL-UHFFFAOYSA-N",
"smiles": "CCOC(=O)C1Cc2ccc(N)cc2NC1=O"
},
"smiles": "CCOC(=O)C1Cc2ccc(N)cc2NC1=O",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "13787",
"routeId": "sa_3fefd995be97b4ebd0e483a4",
"moleculeId": "sa_1514403cfb4a58c3c6f69a71",
"parentId": "13785",
"isLeaf": true,
"molecule": {
"id": "sa_1514403cfb4a58c3c6f69a71",
"inchikey": "HSDAJNMJOMSNEV-UHFFFAOYSA-N",
"smiles": "O=C(Cl)OCc1ccccc1"
},
"smiles": "O=C(Cl)OCc1ccccc1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
}
]
},
{
"id": "13788",
"routeId": "sa_3fefd995be97b4ebd0e483a4",
"moleculeId": "sa_e2676e5c7c9d7a020ed1780e",
"parentId": "13783",
"isLeaf": true,
"molecule": {
"id": "sa_e2676e5c7c9d7a020ed1780e",
"inchikey": "ROSDSFDQCJNGOL-UHFFFAOYSA-N",
"smiles": "CNC"
},
"smiles": "CNC",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
}
]
}
]
},
{
"id": "13789",
"routeId": "sa_3fefd995be97b4ebd0e483a4",
"moleculeId": "sa_a7893fcf81826693d9b4bed4",
"parentId": "13780",
"isLeaf": true,
"molecule": {
"id": "sa_a7893fcf81826693d9b4bed4",
"inchikey": "WFDIJRYMOXRFFG-UHFFFAOYSA-N",
"smiles": "CC(=O)OC(C)=O"
},
"smiles": "CC(=O)OC(C)=O",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
}
}