Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
N#Cc1ccc(N2CCC[C@@H](Nc3ccnc(-c4cnc5ccc(C#N)cn45)n3)C2)c(F)c1
InChiKey
XERTVYFLPUZRLN-GOSISDBHSA-N
Route Signature
b85f95c23ff09bd94d952e14b11f8ec8a4b84edb56e9d3f910698c70d7daaf29
Synthesis route with 6 steps
Route tree structure (JSON format)
{
"route": {
"id": "sa_3d209bdb1c71cce2ab14815c",
"signature": "b85f95c23ff09bd94d952e14b11f8ec8a4b84edb56e9d3f910698c70d7daaf29",
"contentHash": "75d942b782546672909ee1895bbc145c01dd33cdf020f21b89de237d69a79147",
"length": 6,
"isConvergent": false
},
"target": {
"id": "sa_dd08fc0e1ccdc9b7454522df",
"benchmarkSetId": "f925e688d731a0ad4e3aa6a505df094f6d3ca64ce3facc312bc5f64731921b33",
"targetId": "n5-00903",
"moleculeId": "sa_1fe2e4cdf8e3a7bf3dbecdf0",
"smiles": "N#Cc1ccc(N2CCC[C@@H](Nc3ccnc(-c4cnc5ccc(C#N)cn45)n3)C2)c(F)c1",
"routeLength": 6,
"isConvergent": false,
"metadata": null,
"molecule": {
"id": "sa_1fe2e4cdf8e3a7bf3dbecdf0",
"inchikey": "XERTVYFLPUZRLN-GOSISDBHSA-N",
"smiles": "N#Cc1ccc(N2CCC[C@@H](Nc3ccnc(-c4cnc5ccc(C#N)cn45)n3)C2)c(F)c1"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 2
},
"rootNode": {
"id": "5108",
"routeId": "sa_3d209bdb1c71cce2ab14815c",
"moleculeId": "sa_1fe2e4cdf8e3a7bf3dbecdf0",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_1fe2e4cdf8e3a7bf3dbecdf0",
"inchikey": "XERTVYFLPUZRLN-GOSISDBHSA-N",
"smiles": "N#Cc1ccc(N2CCC[C@@H](Nc3ccnc(-c4cnc5ccc(C#N)cn45)n3)C2)c(F)c1"
},
"smiles": "N#Cc1ccc(N2CCC[C@@H](Nc3ccnc(-c4cnc5ccc(C#N)cn45)n3)C2)c(F)c1",
"reactionStepId": "sa_1340ee826cdda74fb50c86a5",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20130216498A1;1623;1408951\",\"rsmi\":\"F[c:7]1[c:5]([F:6])[cH:4][c:3]([C:2]#[N:1])[cH:33][cH:32]1.[NH:8]1[CH2:9][CH2:10][CH2:11][C@@H:12]([NH:13][c:14]2[n:15][c:16](-[c:17]3[cH:18][n:19][c:20]4[cH:21][cH:22][c:23]([C:24]#[N:25])[cH:26][n:27]34)[n:28][cH:29][cH:30]2)[CH2:31]1>CN(C)C=O.O=C(O)O.[K+].[K+]>[N:1]#[C:2][c:3]1[cH:4][c:5]([F:6])[c:7]([N:8]2[CH2:9][CH2:10][CH2:11][C@@H:12]([NH:13][c:14]3[n:15][c:16](-[c:17]4[cH:18][n:19][c:20]5[cH:21][cH:22][c:23]([C:24]#[N:25])[cH:26][n:27]45)[n:28][cH:29][cH:30]3)[CH2:31]2)[cH:32][cH:33]1\"},\"mapped_reaction_smiles\":\"F[c:7]1[c:5]([F:6])[cH:4][c:3]([C:2]#[N:1])[cH:33][cH:32]1.[NH:8]1[CH2:9][CH2:10][CH2:11][C@@H:12]([NH:13][c:14]2[n:15][c:16](-[c:17]3[cH:18][n:19][c:20]4[cH:21][cH:22][c:23]([C:24]#[N:25])[cH:26][n:27]34)[n:28][cH:29][cH:30]2)[CH2:31]1>CN(C)C=O.O=C(O)O.[K+].[K+]>[N:1]#[C:2][c:3]1[cH:4][c:5]([F:6])[c:7]([N:8]2[CH2:9][CH2:10][CH2:11][C@@H:12]([NH:13][c:14]3[n:15][c:16](-[c:17]4[cH:18][n:19][c:20]5[cH:21][cH:22][c:23]([C:24]#[N:25])[cH:26][n:27]45)[n:28][cH:29][cH:30]3)[CH2:31]2)[cH:32][cH:33]1\"}",
"reactionStep": {
"id": "sa_1340ee826cdda74fb50c86a5",
"reactionHash": "9692346a336b743af4c38ea702a6f21e21bbd775922dbd76d764abc0bf69028e"
},
"children": [
{
"id": "5109",
"routeId": "sa_3d209bdb1c71cce2ab14815c",
"moleculeId": "sa_ae4fd31eac27e00787fb2fdf",
"parentId": "5108",
"isLeaf": true,
"molecule": {
"id": "sa_ae4fd31eac27e00787fb2fdf",
"inchikey": "BTBFCBQZFMQBNT-UHFFFAOYSA-N",
"smiles": "N#Cc1ccc(F)c(F)c1"
},
"smiles": "N#Cc1ccc(F)c(F)c1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "5110",
"routeId": "sa_3d209bdb1c71cce2ab14815c",
"moleculeId": "sa_c445b5bc22839ba31a7d843b",
"parentId": "5108",
"isLeaf": false,
"molecule": {
"id": "sa_c445b5bc22839ba31a7d843b",
"inchikey": "HUTKGUCAXSTUHX-CYBMUJFWSA-N",
"smiles": "N#Cc1ccc2ncc(-c3nccc(N[C@@H]4CCCNC4)n3)n2c1"
},
"smiles": "N#Cc1ccc2ncc(-c3nccc(N[C@@H]4CCCNC4)n3)n2c1",
"reactionStepId": "sa_f9a6a3a05e7dcadcdb2ffdc4",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20130216498A1;0837;1408830\",\"rsmi\":\"CC(C)(C)OC(=O)[N:17]1[CH2:16][CH2:15][CH2:14][C@@H:13]([NH:12][c:11]2[cH:10][cH:9][n:8][c:7](-[c:6]3[n:5]4[cH:4][c:3]([C:2]#[N:1])[cH:24][cH:23][c:22]4[n:21][cH:20]3)[n:19]2)[CH2:18]1>ClCCl.O.O=C(O)C(F)(F)F.O=C(O)O.[Na+]>[N:1]#[C:2][c:3]1[cH:4][n:5]2[c:6](-[c:7]3[n:8][cH:9][cH:10][c:11]([NH:12][C@@H:13]4[CH2:14][CH2:15][CH2:16][NH:17][CH2:18]4)[n:19]3)[cH:20][n:21][c:22]2[cH:23][cH:24]1\"},\"mapped_reaction_smiles\":\"CC(C)(C)OC(=O)[N:17]1[CH2:16][CH2:15][CH2:14][C@@H:13]([NH:12][c:11]2[cH:10][cH:9][n:8][c:7](-[c:6]3[n:5]4[cH:4][c:3]([C:2]#[N:1])[cH:24][cH:23][c:22]4[n:21][cH:20]3)[n:19]2)[CH2:18]1>ClCCl.O.O=C(O)C(F)(F)F.O=C(O)O.[Na+]>[N:1]#[C:2][c:3]1[cH:4][n:5]2[c:6](-[c:7]3[n:8][cH:9][cH:10][c:11]([NH:12][C@@H:13]4[CH2:14][CH2:15][CH2:16][NH:17][CH2:18]4)[n:19]3)[cH:20][n:21][c:22]2[cH:23][cH:24]1\"}",
"reactionStep": {
"id": "sa_f9a6a3a05e7dcadcdb2ffdc4",
"reactionHash": "524cd79fe031a55584ab06d38d720746d3b53ccc35b606b96167561a78efd6ec"
},
"children": [
{
"id": "5111",
"routeId": "sa_3d209bdb1c71cce2ab14815c",
"moleculeId": "sa_cab54cf25fa420ffe9984554",
"parentId": "5110",
"isLeaf": false,
"molecule": {
"id": "sa_cab54cf25fa420ffe9984554",
"inchikey": "SHJOPRLZCGLBAI-MRXNPFEDSA-N",
"smiles": "CC(C)(C)OC(=O)N1CCC[C@@H](Nc2ccnc(-c3cnc4ccc(C#N)cn34)n2)C1"
},
"smiles": "CC(C)(C)OC(=O)N1CCC[C@@H](Nc2ccnc(-c3cnc4ccc(C#N)cn34)n2)C1",
"reactionStepId": "sa_a0bb7dc7cdec393b1766a956",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20130216498A1;0834;1408829\",\"rsmi\":\"O[c:14]1[n:15][c:16](-[c:17]2[cH:18][n:19][c:20]3[cH:21][cH:22][c:23]([C:24]#[N:25])[cH:26][n:27]23)[n:28][cH:29][cH:30]1.[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][CH2:11][C@@H:12]([NH2:13])[CH2:31]1>C1CCC2=NCCCN2CC1.CCOC(C)=O.CN(C)C=O.CN(C)[P+](On1nnc2ccccc21)(N(C)C)N(C)C.F[PH](F)(F)(F)(F)F.O>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][CH2:11][C@@H:12]([NH:13][c:14]2[n:15][c:16](-[c:17]3[cH:18][n:19][c:20]4[cH:21][cH:22][c:23]([C:24]#[N:25])[cH:26][n:27]34)[n:28][cH:29][cH:30]2)[CH2:31]1\"},\"mapped_reaction_smiles\":\"O[c:14]1[n:15][c:16](-[c:17]2[cH:18][n:19][c:20]3[cH:21][cH:22][c:23]([C:24]#[N:25])[cH:26][n:27]23)[n:28][cH:29][cH:30]1.[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][CH2:11][C@@H:12]([NH2:13])[CH2:31]1>C1CCC2=NCCCN2CC1.CCOC(C)=O.CN(C)C=O.CN(C)[P+](On1nnc2ccccc21)(N(C)C)N(C)C.F[PH](F)(F)(F)(F)F.O>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][CH2:11][C@@H:12]([NH:13][c:14]2[n:15][c:16](-[c:17]3[cH:18][n:19][c:20]4[cH:21][cH:22][c:23]([C:24]#[N:25])[cH:26][n:27]34)[n:28][cH:29][cH:30]2)[CH2:31]1\"}",
"reactionStep": {
"id": "sa_a0bb7dc7cdec393b1766a956",
"reactionHash": "210c6d8609edc97fd8c09c76b3e81c3c11f0f652623b033277dc30ab901c9bf7"
},
"children": [
{
"id": "5112",
"routeId": "sa_3d209bdb1c71cce2ab14815c",
"moleculeId": "sa_08e7e777703c4906eed98980",
"parentId": "5111",
"isLeaf": true,
"molecule": {
"id": "sa_08e7e777703c4906eed98980",
"inchikey": "AKQXKEBCONUWCL-MRVPVSSYSA-N",
"smiles": "CC(C)(C)OC(=O)N1CCC[C@@H](N)C1"
},
"smiles": "CC(C)(C)OC(=O)N1CCC[C@@H](N)C1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "5113",
"routeId": "sa_3d209bdb1c71cce2ab14815c",
"moleculeId": "sa_f405a3c399af90b6ce373215",
"parentId": "5111",
"isLeaf": false,
"molecule": {
"id": "sa_f405a3c399af90b6ce373215",
"inchikey": "AUCPABFFIVCXNH-UHFFFAOYSA-N",
"smiles": "N#Cc1ccc2ncc(-c3nccc(O)n3)n2c1"
},
"smiles": "N#Cc1ccc2ncc(-c3nccc(O)n3)n2c1",
"reactionStepId": "sa_63f3a04d3119b514010856a5",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20130216498A1;0830;1408828\",\"rsmi\":\"C[O:12][c:11]1[cH:10][cH:9][n:8][c:7](-[c:6]2[n:5]3[cH:4][c:3]([C:2]#[N:1])[cH:18][cH:17][c:16]3[n:15][cH:14]2)[n:13]1>CC#N.C[Si](C)(C)Cl.I.[Na+]>[N:1]#[C:2][c:3]1[cH:4][n:5]2[c:6](-[c:7]3[n:8][cH:9][cH:10][c:11]([OH:12])[n:13]3)[cH:14][n:15][c:16]2[cH:17][cH:18]1\"},\"mapped_reaction_smiles\":\"C[O:12][c:11]1[cH:10][cH:9][n:8][c:7](-[c:6]2[n:5]3[cH:4][c:3]([C:2]#[N:1])[cH:18][cH:17][c:16]3[n:15][cH:14]2)[n:13]1>CC#N.C[Si](C)(C)Cl.I.[Na+]>[N:1]#[C:2][c:3]1[cH:4][n:5]2[c:6](-[c:7]3[n:8][cH:9][cH:10][c:11]([OH:12])[n:13]3)[cH:14][n:15][c:16]2[cH:17][cH:18]1\"}",
"reactionStep": {
"id": "sa_63f3a04d3119b514010856a5",
"reactionHash": "bccb13d3bdc76465bd73701bade394418469b0d60d02ab62182958e396ad88b5"
},
"children": [
{
"id": "5114",
"routeId": "sa_3d209bdb1c71cce2ab14815c",
"moleculeId": "sa_7d09747fc553a9454775a740",
"parentId": "5113",
"isLeaf": false,
"molecule": {
"id": "sa_7d09747fc553a9454775a740",
"inchikey": "ZAZAMAPUFXLVSG-UHFFFAOYSA-N",
"smiles": "COc1ccnc(-c2cnc3ccc(C#N)cn23)n1"
},
"smiles": "COc1ccnc(-c2cnc3ccc(C#N)cn23)n1",
"reactionStepId": "sa_b2f7ba221151aed1997cddf2",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20130216498A1;0827;1408827\",\"rsmi\":\"Cl[c:5]1[n:4][c:3]([O:2][CH3:1])[cH:19][cH:18][n:17]1.[cH:6]1[cH:7][n:8][c:9]2[cH:10][cH:11][c:12]([C:13]#[N:14])[cH:15][n:16]12>C1COCCO1.CC(=O)O.CC(=O)O.CCO.O=C(O)O.[K+].[K+].[Pd+2].c1ccc(P(c2ccccc2)c2ccccc2)cc1>[CH3:1][O:2][c:3]1[n:4][c:5](-[c:6]2[cH:7][n:8][c:9]3[cH:10][cH:11][c:12]([C:13]#[N:14])[cH:15][n:16]23)[n:17][cH:18][cH:19]1\"},\"mapped_reaction_smiles\":\"Cl[c:5]1[n:4][c:3]([O:2][CH3:1])[cH:19][cH:18][n:17]1.[cH:6]1[cH:7][n:8][c:9]2[cH:10][cH:11][c:12]([C:13]#[N:14])[cH:15][n:16]12>C1COCCO1.CC(=O)O.CC(=O)O.CCO.O=C(O)O.[K+].[K+].[Pd+2].c1ccc(P(c2ccccc2)c2ccccc2)cc1>[CH3:1][O:2][c:3]1[n:4][c:5](-[c:6]2[cH:7][n:8][c:9]3[cH:10][cH:11][c:12]([C:13]#[N:14])[cH:15][n:16]23)[n:17][cH:18][cH:19]1\"}",
"reactionStep": {
"id": "sa_b2f7ba221151aed1997cddf2",
"reactionHash": "e498a602d9a0f7c0687d1800d7d027c4a588f877adeccec7aa8151cb81c64547"
},
"children": [
{
"id": "5115",
"routeId": "sa_3d209bdb1c71cce2ab14815c",
"moleculeId": "sa_4119c27c31791f67ffc85250",
"parentId": "5114",
"isLeaf": true,
"molecule": {
"id": "sa_4119c27c31791f67ffc85250",
"inchikey": "BDXYNMVQMBCTDB-UHFFFAOYSA-N",
"smiles": "COc1ccnc(Cl)n1"
},
"smiles": "COc1ccnc(Cl)n1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "5116",
"routeId": "sa_3d209bdb1c71cce2ab14815c",
"moleculeId": "sa_42245e39538831ad4e872fac",
"parentId": "5114",
"isLeaf": false,
"molecule": {
"id": "sa_42245e39538831ad4e872fac",
"inchikey": "LRJOKNYELSECDZ-UHFFFAOYSA-N",
"smiles": "N#Cc1ccc2nccn2c1"
},
"smiles": "N#Cc1ccc2nccn2c1",
"reactionStepId": "sa_96706f0cd165bcd05f69d67f",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20130216498A1;0815;1408826\",\"rsmi\":\"O=[CH:7][CH2:6]Cl.[N:1]#[C:2][c:3]1[cH:4][n:5][c:9]([NH2:8])[cH:10][cH:11]1>CC#N>[N:1]#[C:2][c:3]1[cH:4][n:5]2[cH:6][cH:7][n:8][c:9]2[cH:10][cH:11]1\"},\"mapped_reaction_smiles\":\"O=[CH:7][CH2:6]Cl.[N:1]#[C:2][c:3]1[cH:4][n:5][c:9]([NH2:8])[cH:10][cH:11]1>CC#N>[N:1]#[C:2][c:3]1[cH:4][n:5]2[cH:6][cH:7][n:8][c:9]2[cH:10][cH:11]1\"}",
"reactionStep": {
"id": "sa_96706f0cd165bcd05f69d67f",
"reactionHash": "edf176074418a00e749e0cf95ca266c5040f89d4ef8f2d39bd1cf08d04a218e8"
},
"children": [
{
"id": "5117",
"routeId": "sa_3d209bdb1c71cce2ab14815c",
"moleculeId": "sa_2ff4d6814d4db149eb8104d3",
"parentId": "5116",
"isLeaf": true,
"molecule": {
"id": "sa_2ff4d6814d4db149eb8104d3",
"inchikey": "KDVBYUUGYXUXNL-UHFFFAOYSA-N",
"smiles": "N#Cc1ccc(=N)[nH]c1"
},
"smiles": "N#Cc1ccc(N)nc1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "5118",
"routeId": "sa_3d209bdb1c71cce2ab14815c",
"moleculeId": "sa_382388fd75f2f5ac3e02185a",
"parentId": "5116",
"isLeaf": true,
"molecule": {
"id": "sa_382388fd75f2f5ac3e02185a",
"inchikey": "QSKPIOLLBIHNAC-UHFFFAOYSA-N",
"smiles": "O=CCCl"
},
"smiles": "O=CCCl",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
}
]
}
]
}
]
}
]
}
]
}
}