Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
O=C(NCCCN1CCN(c2cccc([N+](=O)[O-])n2)CC1)C1CCCCC1
InChiKey
GMRRDDNJPXASIO-UHFFFAOYSA-N
Route Signature
1fa2020d8ce1d4f5a96c9737b6bdbb32486359ab1e3d7b045d77d04d127b72b7
Synthesis route with 5 steps
Route tree structure (JSON format)
{
"route": {
"id": "sa_5762e49b1812855b1c9f457f",
"signature": "1fa2020d8ce1d4f5a96c9737b6bdbb32486359ab1e3d7b045d77d04d127b72b7",
"contentHash": "d0a42db5d5d14b2a87d7c15959638123ec4df592f2d4ab46ed17c3d42433a4fc",
"length": 5,
"isConvergent": false
},
"target": {
"id": "sa_dfd91fddfc9bdc9486e7e6ba",
"benchmarkSetId": "f925e688d731a0ad4e3aa6a505df094f6d3ca64ce3facc312bc5f64731921b33",
"targetId": "n5-01689",
"moleculeId": "sa_73c2b4c0c159b6685e46e620",
"smiles": "O=C(NCCCN1CCN(c2cccc([N+](=O)[O-])n2)CC1)C1CCCCC1",
"routeLength": 5,
"isConvergent": false,
"metadata": null,
"molecule": {
"id": "sa_73c2b4c0c159b6685e46e620",
"inchikey": "GMRRDDNJPXASIO-UHFFFAOYSA-N",
"smiles": "O=C(NCCCN1CCN(c2cccc([N+](=O)[O-])n2)CC1)C1CCCCC1"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "5934",
"routeId": "sa_5762e49b1812855b1c9f457f",
"moleculeId": "sa_73c2b4c0c159b6685e46e620",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_73c2b4c0c159b6685e46e620",
"inchikey": "GMRRDDNJPXASIO-UHFFFAOYSA-N",
"smiles": "O=C(NCCCN1CCN(c2cccc([N+](=O)[O-])n2)CC1)C1CCCCC1"
},
"smiles": "O=C(NCCCN1CCN(c2cccc([N+](=O)[O-])n2)CC1)C1CCCCC1",
"reactionStepId": "sa_7b6672d9ec4a2679e58e2c14",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20130064770A1;0469;1343989\",\"rsmi\":\"Cl[c:11]1[n:12][c:13]([N+:14](=[O:15])[O-:16])[cH:17][cH:18][cH:19]1.[O:1]=[C:2]([NH:3][CH2:4][CH2:5][CH2:6][N:7]1[CH2:8][CH2:9][NH:10][CH2:20][CH2:21]1)[CH:22]1[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27]1>CC#N.CCN(C(C)C)C(C)C.CCOC(C)=O.CO>[O:1]=[C:2]([NH:3][CH2:4][CH2:5][CH2:6][N:7]1[CH2:8][CH2:9][N:10]([c:11]2[n:12][c:13]([N+:14](=[O:15])[O-:16])[cH:17][cH:18][cH:19]2)[CH2:20][CH2:21]1)[CH:22]1[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27]1\"},\"mapped_reaction_smiles\":\"Cl[c:11]1[n:12][c:13]([N+:14](=[O:15])[O-:16])[cH:17][cH:18][cH:19]1.[O:1]=[C:2]([NH:3][CH2:4][CH2:5][CH2:6][N:7]1[CH2:8][CH2:9][NH:10][CH2:20][CH2:21]1)[CH:22]1[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27]1>CC#N.CCN(C(C)C)C(C)C.CCOC(C)=O.CO>[O:1]=[C:2]([NH:3][CH2:4][CH2:5][CH2:6][N:7]1[CH2:8][CH2:9][N:10]([c:11]2[n:12][c:13]([N+:14](=[O:15])[O-:16])[cH:17][cH:18][cH:19]2)[CH2:20][CH2:21]1)[CH:22]1[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27]1\"}",
"reactionStep": {
"id": "sa_7b6672d9ec4a2679e58e2c14",
"reactionHash": "9c5b01a9cf7f2f73189f80179264bca3a896a3ead6c30fe9819c7cfcc22741ef"
},
"children": [
{
"id": "5935",
"routeId": "sa_5762e49b1812855b1c9f457f",
"moleculeId": "sa_50616aee214859fd2315047f",
"parentId": "5934",
"isLeaf": false,
"molecule": {
"id": "sa_50616aee214859fd2315047f",
"inchikey": "LGORDWCAJCNNCK-UHFFFAOYSA-N",
"smiles": "O=C(NCCCN1CCNCC1)C1CCCCC1"
},
"smiles": "O=C(NCCCN1CCNCC1)C1CCCCC1",
"reactionStepId": "sa_94dd5ac41e7f25a2084b1d3b",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20130064770A1;0465;1343988\",\"rsmi\":\"c1ccc(C[N:10]2[CH2:9][CH2:8][N:7]([CH2:6][CH2:5][CH2:4][NH:3][C:2](=[O:1])[CH:13]3[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18]3)[CH2:12][CH2:11]2)cc1>CC(=O)O.Cl.O=C(O)O.[K+].[K+].[Pd]>[O:1]=[C:2]([NH:3][CH2:4][CH2:5][CH2:6][N:7]1[CH2:8][CH2:9][NH:10][CH2:11][CH2:12]1)[CH:13]1[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18]1\"},\"mapped_reaction_smiles\":\"c1ccc(C[N:10]2[CH2:9][CH2:8][N:7]([CH2:6][CH2:5][CH2:4][NH:3][C:2](=[O:1])[CH:13]3[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18]3)[CH2:12][CH2:11]2)cc1>CC(=O)O.Cl.O=C(O)O.[K+].[K+].[Pd]>[O:1]=[C:2]([NH:3][CH2:4][CH2:5][CH2:6][N:7]1[CH2:8][CH2:9][NH:10][CH2:11][CH2:12]1)[CH:13]1[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18]1\"}",
"reactionStep": {
"id": "sa_94dd5ac41e7f25a2084b1d3b",
"reactionHash": "df9c69bd45c642448035e197376bab8c98526104e27ea39811b1e7f5f8356deb"
},
"children": [
{
"id": "5936",
"routeId": "sa_5762e49b1812855b1c9f457f",
"moleculeId": "sa_600f68ec4c9a127c0a386e20",
"parentId": "5935",
"isLeaf": false,
"molecule": {
"id": "sa_600f68ec4c9a127c0a386e20",
"inchikey": "UHFAZEJZGWRYOI-UHFFFAOYSA-N",
"smiles": "O=C(NCCCN1CCN(Cc2ccccc2)CC1)C1CCCCC1"
},
"smiles": "O=C(NCCCN1CCN(Cc2ccccc2)CC1)C1CCCCC1",
"reactionStepId": "sa_770e3ea0ddb46ddf26802ee8",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20130064770A1;0461;1343987\",\"rsmi\":\"Cl[C:2](=[O:1])[CH:20]1[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25]1.[NH2:3][CH2:4][CH2:5][CH2:6][N:7]1[CH2:8][CH2:9][N:10]([CH2:11][c:12]2[cH:13][cH:14][cH:15][cH:16][cH:17]2)[CH2:18][CH2:19]1>CCN(CC)CC.CO.ClCCl.ClCCl.O=C1c2ccccc2C(=O)C1(O)O>[O:1]=[C:2]([NH:3][CH2:4][CH2:5][CH2:6][N:7]1[CH2:8][CH2:9][N:10]([CH2:11][c:12]2[cH:13][cH:14][cH:15][cH:16][cH:17]2)[CH2:18][CH2:19]1)[CH:20]1[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25]1\"},\"mapped_reaction_smiles\":\"Cl[C:2](=[O:1])[CH:20]1[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25]1.[NH2:3][CH2:4][CH2:5][CH2:6][N:7]1[CH2:8][CH2:9][N:10]([CH2:11][c:12]2[cH:13][cH:14][cH:15][cH:16][cH:17]2)[CH2:18][CH2:19]1>CCN(CC)CC.CO.ClCCl.ClCCl.O=C1c2ccccc2C(=O)C1(O)O>[O:1]=[C:2]([NH:3][CH2:4][CH2:5][CH2:6][N:7]1[CH2:8][CH2:9][N:10]([CH2:11][c:12]2[cH:13][cH:14][cH:15][cH:16][cH:17]2)[CH2:18][CH2:19]1)[CH:20]1[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25]1\"}",
"reactionStep": {
"id": "sa_770e3ea0ddb46ddf26802ee8",
"reactionHash": "d4d18513e4631217698c0c08830f96564ce5b5167c3f3e0a1086598741760e2b"
},
"children": [
{
"id": "5937",
"routeId": "sa_5762e49b1812855b1c9f457f",
"moleculeId": "sa_95297493d3a0369a4136e9fc",
"parentId": "5936",
"isLeaf": false,
"molecule": {
"id": "sa_95297493d3a0369a4136e9fc",
"inchikey": "DQZBCJSBHYEUAY-UHFFFAOYSA-N",
"smiles": "NCCCN1CCN(Cc2ccccc2)CC1"
},
"smiles": "NCCCN1CCN(Cc2ccccc2)CC1",
"reactionStepId": "sa_82393704cad2630983479acf",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20130064770A1;0457;1343986\",\"rsmi\":\"O=C1c2ccccc2C(=O)[N:1]1[CH2:2][CH2:3][CH2:4][N:5]1[CH2:6][CH2:7][N:8]([CH2:9][c:10]2[cH:11][cH:12][cH:13][cH:14][cH:15]2)[CH2:16][CH2:17]1>CCO.NN.O>[NH2:1][CH2:2][CH2:3][CH2:4][N:5]1[CH2:6][CH2:7][N:8]([CH2:9][c:10]2[cH:11][cH:12][cH:13][cH:14][cH:15]2)[CH2:16][CH2:17]1\"},\"mapped_reaction_smiles\":\"O=C1c2ccccc2C(=O)[N:1]1[CH2:2][CH2:3][CH2:4][N:5]1[CH2:6][CH2:7][N:8]([CH2:9][c:10]2[cH:11][cH:12][cH:13][cH:14][cH:15]2)[CH2:16][CH2:17]1>CCO.NN.O>[NH2:1][CH2:2][CH2:3][CH2:4][N:5]1[CH2:6][CH2:7][N:8]([CH2:9][c:10]2[cH:11][cH:12][cH:13][cH:14][cH:15]2)[CH2:16][CH2:17]1\"}",
"reactionStep": {
"id": "sa_82393704cad2630983479acf",
"reactionHash": "c4be830866a602d297ac216d944eb4042d9be0e5665f1701780bf25ed6763bbc"
},
"children": [
{
"id": "5938",
"routeId": "sa_5762e49b1812855b1c9f457f",
"moleculeId": "sa_c8b8df008862de74c5dc301f",
"parentId": "5937",
"isLeaf": false,
"molecule": {
"id": "sa_c8b8df008862de74c5dc301f",
"inchikey": "PYNDAXKJBVMGSA-UHFFFAOYSA-N",
"smiles": "O=C1c2ccccc2C(=O)N1CCCN1CCN(Cc2ccccc2)CC1"
},
"smiles": "O=C1c2ccccc2C(=O)N1CCCN1CCN(Cc2ccccc2)CC1",
"reactionStepId": "sa_23f17acc913b877926a440c4",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20130064770A1;0453;1343985\",\"rsmi\":\"Br[CH2:14][CH2:13][CH2:12][N:11]1[C:2](=[O:1])[c:3]2[cH:4][cH:5][cH:6][cH:7][c:8]2[C:9]1=[O:10].[NH:15]1[CH2:16][CH2:17][N:18]([CH2:19][c:20]2[cH:21][cH:22][cH:23][cH:24][cH:25]2)[CH2:26][CH2:27]1>CC#N.CCN(C(C)C)C(C)C>[O:1]=[C:2]1[c:3]2[cH:4][cH:5][cH:6][cH:7][c:8]2[C:9](=[O:10])[N:11]1[CH2:12][CH2:13][CH2:14][N:15]1[CH2:16][CH2:17][N:18]([CH2:19][c:20]2[cH:21][cH:22][cH:23][cH:24][cH:25]2)[CH2:26][CH2:27]1\"},\"mapped_reaction_smiles\":\"Br[CH2:14][CH2:13][CH2:12][N:11]1[C:2](=[O:1])[c:3]2[cH:4][cH:5][cH:6][cH:7][c:8]2[C:9]1=[O:10].[NH:15]1[CH2:16][CH2:17][N:18]([CH2:19][c:20]2[cH:21][cH:22][cH:23][cH:24][cH:25]2)[CH2:26][CH2:27]1>CC#N.CCN(C(C)C)C(C)C>[O:1]=[C:2]1[c:3]2[cH:4][cH:5][cH:6][cH:7][c:8]2[C:9](=[O:10])[N:11]1[CH2:12][CH2:13][CH2:14][N:15]1[CH2:16][CH2:17][N:18]([CH2:19][c:20]2[cH:21][cH:22][cH:23][cH:24][cH:25]2)[CH2:26][CH2:27]1\"}",
"reactionStep": {
"id": "sa_23f17acc913b877926a440c4",
"reactionHash": "32d3cfbfd407773b78f25947f278182ffcd76bcd24374b99948841ce3672ad0a"
},
"children": [
{
"id": "5939",
"routeId": "sa_5762e49b1812855b1c9f457f",
"moleculeId": "sa_09e36465fb6a137e9dd00b2f",
"parentId": "5938",
"isLeaf": true,
"molecule": {
"id": "sa_09e36465fb6a137e9dd00b2f",
"inchikey": "IQXXEPZFOOTTBA-UHFFFAOYSA-N",
"smiles": "c1ccc(CN2CCNCC2)cc1"
},
"smiles": "c1ccc(CN2CCNCC2)cc1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "5940",
"routeId": "sa_5762e49b1812855b1c9f457f",
"moleculeId": "sa_a290cad240d2c7ba66fb90d3",
"parentId": "5938",
"isLeaf": true,
"molecule": {
"id": "sa_a290cad240d2c7ba66fb90d3",
"inchikey": "VKJCJJYNVIYVQR-UHFFFAOYSA-N",
"smiles": "O=C1c2ccccc2C(=O)N1CCCBr"
},
"smiles": "O=C1c2ccccc2C(=O)N1CCCBr",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
}
]
},
{
"id": "5941",
"routeId": "sa_5762e49b1812855b1c9f457f",
"moleculeId": "sa_dde4c3d56711d60b94e66931",
"parentId": "5936",
"isLeaf": true,
"molecule": {
"id": "sa_dde4c3d56711d60b94e66931",
"inchikey": "RVOJTCZRIKWHDX-UHFFFAOYSA-N",
"smiles": "O=C(Cl)C1CCCCC1"
},
"smiles": "O=C(Cl)C1CCCCC1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
}
]
},
{
"id": "5942",
"routeId": "sa_5762e49b1812855b1c9f457f",
"moleculeId": "sa_fdbc5df99a5e51922c80efa6",
"parentId": "5934",
"isLeaf": true,
"molecule": {
"id": "sa_fdbc5df99a5e51922c80efa6",
"inchikey": "YRSNXUYQRUULNJ-UHFFFAOYSA-N",
"smiles": "O=[N+]([O-])c1cccc(Cl)n1"
},
"smiles": "O=[N+]([O-])c1cccc(Cl)n1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
}
}