Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
CC(C)Cc1nc(C(=O)N2CCOC3(CCN(Cc4cccc(CCO)c4F)CC3)C2)cs1
InChiKey
SHUHYHLIVDKYGF-UHFFFAOYSA-N
Route Signature
276d687bf3f3493eb18a313cb2a7726eb37d91316a6e0ffb502409af2a9034d8
Synthesis route with 4 steps (convergent)
Route tree structure (JSON format)
{
"route": {
"id": "sa_35732ea56c184adc78399b8b",
"signature": "276d687bf3f3493eb18a313cb2a7726eb37d91316a6e0ffb502409af2a9034d8",
"contentHash": "681747135b55210dfecc95352b591494ac00c58fd3dba5ffc535d456a998bfd1",
"length": 4,
"isConvergent": true
},
"target": {
"id": "sa_a30b2508761f39446bb423e2",
"benchmarkSetId": "3895c2909c53593560c5ba610abc7e6df80513dfd8624165c560451735097d36",
"targetId": "n5-01601",
"moleculeId": "sa_5da1acf5c70c1e02f97e993d",
"smiles": "CC(C)Cc1nc(C(=O)N2CCOC3(CCN(Cc4cccc(CCO)c4F)CC3)C2)cs1",
"routeLength": 4,
"isConvergent": true,
"metadata": null,
"molecule": {
"id": "sa_5da1acf5c70c1e02f97e993d",
"inchikey": "SHUHYHLIVDKYGF-UHFFFAOYSA-N",
"smiles": "CC(C)Cc1nc(C(=O)N2CCOC3(CCN(Cc4cccc(CCO)c4F)CC3)C2)cs1"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "10330",
"routeId": "sa_35732ea56c184adc78399b8b",
"moleculeId": "sa_5da1acf5c70c1e02f97e993d",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_5da1acf5c70c1e02f97e993d",
"inchikey": "SHUHYHLIVDKYGF-UHFFFAOYSA-N",
"smiles": "CC(C)Cc1nc(C(=O)N2CCOC3(CCN(Cc4cccc(CCO)c4F)CC3)C2)cs1"
},
"smiles": "CC(C)Cc1nc(C(=O)N2CCOC3(CCN(Cc4cccc(CCO)c4F)CC3)C2)cs1",
"reactionStepId": "sa_ea51837a669625691c2917ef",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20090298807A1;1478;800801\",\"rsmi\":\"O[C:8]([c:7]1[n:6][c:5]([CH2:4][CH:2]([CH3:1])[CH3:3])[s:33][cH:32]1)=[O:9].[NH:10]1[CH2:11][CH2:12][O:13][C:14]2([CH2:15][CH2:16][N:17]([CH2:18][c:19]3[c:20]([F:21])[c:22]([CH2:23][CH2:24][OH:25])[cH:26][cH:27][cH:28]3)[CH2:29][CH2:30]2)[CH2:31]1>CCN(CC)CC.CN(C)C(On1nnc2cccnc21)=[N+](C)C.CN(C)C=O.F[PH](F)(F)(F)(F)F>[CH3:1][CH:2]([CH3:3])[CH2:4][c:5]1[n:6][c:7]([C:8](=[O:9])[N:10]2[CH2:11][CH2:12][O:13][C:14]3([CH2:15][CH2:16][N:17]([CH2:18][c:19]4[c:20]([F:21])[c:22]([CH2:23][CH2:24][OH:25])[cH:26][cH:27][cH:28]4)[CH2:29][CH2:30]3)[CH2:31]2)[cH:32][s:33]1\"},\"mapped_reaction_smiles\":\"O[C:8]([c:7]1[n:6][c:5]([CH2:4][CH:2]([CH3:1])[CH3:3])[s:33][cH:32]1)=[O:9].[NH:10]1[CH2:11][CH2:12][O:13][C:14]2([CH2:15][CH2:16][N:17]([CH2:18][c:19]3[c:20]([F:21])[c:22]([CH2:23][CH2:24][OH:25])[cH:26][cH:27][cH:28]3)[CH2:29][CH2:30]2)[CH2:31]1>CCN(CC)CC.CN(C)C(On1nnc2cccnc21)=[N+](C)C.CN(C)C=O.F[PH](F)(F)(F)(F)F>[CH3:1][CH:2]([CH3:3])[CH2:4][c:5]1[n:6][c:7]([C:8](=[O:9])[N:10]2[CH2:11][CH2:12][O:13][C:14]3([CH2:15][CH2:16][N:17]([CH2:18][c:19]4[c:20]([F:21])[c:22]([CH2:23][CH2:24][OH:25])[cH:26][cH:27][cH:28]4)[CH2:29][CH2:30]3)[CH2:31]2)[cH:32][s:33]1\"}",
"reactionStep": {
"id": "sa_ea51837a669625691c2917ef",
"reactionHash": "59b075c4f08fad2c5bf9d2f913aa958aa7d086f0f755b6928e1a1321c3955dc2"
},
"children": [
{
"id": "10331",
"routeId": "sa_35732ea56c184adc78399b8b",
"moleculeId": "sa_b3a8ef9212d9e36497d9136e",
"parentId": "10330",
"isLeaf": false,
"molecule": {
"id": "sa_b3a8ef9212d9e36497d9136e",
"inchikey": "GELCNJDITWBJJG-UHFFFAOYSA-N",
"smiles": "CC(C)Cc1nc(C(=O)O)cs1"
},
"smiles": "CC(C)Cc1nc(C(=O)O)cs1",
"reactionStepId": "sa_142111c46b676228702780d3",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20090298807A1;1475;800800\",\"rsmi\":\"CC[O:10][C:8]([c:7]1[n:6][c:5]([CH2:4][CH:2]([CH3:1])[CH3:3])[s:12][cH:11]1)=[O:9]>C1CCOC1.Cl.O.O.[Li+].O>[CH3:1][CH:2]([CH3:3])[CH2:4][c:5]1[n:6][c:7]([C:8](=[O:9])[OH:10])[cH:11][s:12]1\"},\"mapped_reaction_smiles\":\"CC[O:10][C:8]([c:7]1[n:6][c:5]([CH2:4][CH:2]([CH3:1])[CH3:3])[s:12][cH:11]1)=[O:9]>C1CCOC1.Cl.O.O.[Li+].O>[CH3:1][CH:2]([CH3:3])[CH2:4][c:5]1[n:6][c:7]([C:8](=[O:9])[OH:10])[cH:11][s:12]1\"}",
"reactionStep": {
"id": "sa_142111c46b676228702780d3",
"reactionHash": "e6e77a8fdaffd3bc0377a8797b0c34d038edea982fbb590f8e67a8fe2b42e03c"
},
"children": [
{
"id": "10332",
"routeId": "sa_35732ea56c184adc78399b8b",
"moleculeId": "sa_6f97e0c4a77279ca56ed4341",
"parentId": "10331",
"isLeaf": false,
"molecule": {
"id": "sa_6f97e0c4a77279ca56ed4341",
"inchikey": "DIJHMSPHFZFWJS-UHFFFAOYSA-N",
"smiles": "CCOC(=O)c1csc(CC(C)C)n1"
},
"smiles": "CCOC(=O)c1csc(CC(C)C)n1",
"reactionStepId": "sa_76e2d3e1e9203283b459bfba",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20090298807A1;1472;800799\",\"rsmi\":\"O=[C:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[CH2:7]Br.[S:8]=[C:9]([CH2:10][CH:11]([CH3:12])[CH3:13])[NH2:14]>CCO>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][s:8][c:9]([CH2:10][CH:11]([CH3:12])[CH3:13])[n:14]1\"},\"mapped_reaction_smiles\":\"O=[C:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[CH2:7]Br.[S:8]=[C:9]([CH2:10][CH:11]([CH3:12])[CH3:13])[NH2:14]>CCO>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][s:8][c:9]([CH2:10][CH:11]([CH3:12])[CH3:13])[n:14]1\"}",
"reactionStep": {
"id": "sa_76e2d3e1e9203283b459bfba",
"reactionHash": "9d1d388ee0b5b6c61b7f474d8b437bc0ae81c37ca27d9f152e5fac18303b7f73"
},
"children": [
{
"id": "10333",
"routeId": "sa_35732ea56c184adc78399b8b",
"moleculeId": "sa_05ab7cab69d265ceef65f5b0",
"parentId": "10332",
"isLeaf": true,
"molecule": {
"id": "sa_05ab7cab69d265ceef65f5b0",
"inchikey": "NFWCTMFZCLAVSD-UHFFFAOYSA-N",
"smiles": "CC(C)CC(N)=S"
},
"smiles": "CC(C)CC(N)=S",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "10334",
"routeId": "sa_35732ea56c184adc78399b8b",
"moleculeId": "sa_89a2572697761e44833945b6",
"parentId": "10332",
"isLeaf": true,
"molecule": {
"id": "sa_89a2572697761e44833945b6",
"inchikey": "VICYTAYPKBLQFB-UHFFFAOYSA-N",
"smiles": "CCOC(=O)C(=O)CBr"
},
"smiles": "CCOC(=O)C(=O)CBr",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
}
]
},
{
"id": "10335",
"routeId": "sa_35732ea56c184adc78399b8b",
"moleculeId": "sa_15c4d7cd8b92c01aa97ad94d",
"parentId": "10330",
"isLeaf": false,
"molecule": {
"id": "sa_15c4d7cd8b92c01aa97ad94d",
"inchikey": "KMRREWVYTIZCKV-UHFFFAOYSA-N",
"smiles": "OCCc1cccc(CN2CCC3(CC2)CNCCO3)c1F"
},
"smiles": "OCCc1cccc(CN2CCC3(CC2)CNCCO3)c1F",
"reactionStepId": "sa_2de5c2b8ba04dd4d65d6ec16",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20090298807A1;1404;800790\",\"rsmi\":\"O=C(C(F)(F)F)[N:16]1[CH2:15][C:12]2([CH2:11][CH2:10][N:9]([CH2:8][c:7]3[c:5]([F:6])[c:4]([CH2:3][CH2:2][OH:1])[cH:22][cH:21][cH:20]3)[CH2:14][CH2:13]2)[O:19][CH2:18][CH2:17]1>CO.N>[OH:1][CH2:2][CH2:3][c:4]1[c:5]([F:6])[c:7]([CH2:8][N:9]2[CH2:10][CH2:11][C:12]3([CH2:13][CH2:14]2)[CH2:15][NH:16][CH2:17][CH2:18][O:19]3)[cH:20][cH:21][cH:22]1\"},\"mapped_reaction_smiles\":\"O=C(C(F)(F)F)[N:16]1[CH2:15][C:12]2([CH2:11][CH2:10][N:9]([CH2:8][c:7]3[c:5]([F:6])[c:4]([CH2:3][CH2:2][OH:1])[cH:22][cH:21][cH:20]3)[CH2:14][CH2:13]2)[O:19][CH2:18][CH2:17]1>CO.N>[OH:1][CH2:2][CH2:3][c:4]1[c:5]([F:6])[c:7]([CH2:8][N:9]2[CH2:10][CH2:11][C:12]3([CH2:13][CH2:14]2)[CH2:15][NH:16][CH2:17][CH2:18][O:19]3)[cH:20][cH:21][cH:22]1\"}",
"reactionStep": {
"id": "sa_2de5c2b8ba04dd4d65d6ec16",
"reactionHash": "f0129dc78797e611637972ce8208f4664d5305238d2c81c49c76aef1df3a93e3"
},
"children": [
{
"id": "10336",
"routeId": "sa_35732ea56c184adc78399b8b",
"moleculeId": "sa_b964de9846f87252d71ee18c",
"parentId": "10335",
"isLeaf": false,
"molecule": {
"id": "sa_b964de9846f87252d71ee18c",
"inchikey": "LVCWZJGPMGZUCF-UHFFFAOYSA-N",
"smiles": "O=C(N1CCOC2(CCN(Cc3cccc(CCO)c3F)CC2)C1)C(F)(F)F"
},
"smiles": "O=C(N1CCOC2(CCN(Cc3cccc(CCO)c3F)CC2)C1)C(F)(F)F",
"reactionStepId": "sa_72c8bafe3507d2bd4026cab2",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20090298807A1;1402;800789\",\"rsmi\":\"O=[CH:11][c:12]1[c:13]([F:14])[c:15]([CH2:16][CH2:17][OH:18])[cH:19][cH:20][cH:21]1.[O:1]=[C:2]([N:3]1[CH2:4][CH2:5][O:6][C:7]2([CH2:8][CH2:9][NH:10][CH2:22][CH2:23]2)[CH2:24]1)[C:25]([F:26])([F:27])[F:28]>CC(=O)O.CC(=O)OB(OC(C)=O)OC(C)=O.CN1CCCC1=O.O.O=C(O)C(F)(F)F.O=C(O)O.[Na+].[Na+]>[O:1]=[C:2]([N:3]1[CH2:4][CH2:5][O:6][C:7]2([CH2:8][CH2:9][N:10]([CH2:11][c:12]3[c:13]([F:14])[c:15]([CH2:16][CH2:17][OH:18])[cH:19][cH:20][cH:21]3)[CH2:22][CH2:23]2)[CH2:24]1)[C:25]([F:26])([F:27])[F:28]\"},\"mapped_reaction_smiles\":\"O=[CH:11][c:12]1[c:13]([F:14])[c:15]([CH2:16][CH2:17][OH:18])[cH:19][cH:20][cH:21]1.[O:1]=[C:2]([N:3]1[CH2:4][CH2:5][O:6][C:7]2([CH2:8][CH2:9][NH:10][CH2:22][CH2:23]2)[CH2:24]1)[C:25]([F:26])([F:27])[F:28]>CC(=O)O.CC(=O)OB(OC(C)=O)OC(C)=O.CN1CCCC1=O.O.O=C(O)C(F)(F)F.O=C(O)O.[Na+].[Na+]>[O:1]=[C:2]([N:3]1[CH2:4][CH2:5][O:6][C:7]2([CH2:8][CH2:9][N:10]([CH2:11][c:12]3[c:13]([F:14])[c:15]([CH2:16][CH2:17][OH:18])[cH:19][cH:20][cH:21]3)[CH2:22][CH2:23]2)[CH2:24]1)[C:25]([F:26])([F:27])[F:28]\"}",
"reactionStep": {
"id": "sa_72c8bafe3507d2bd4026cab2",
"reactionHash": "1fe18b748ebcdae7fa9bb92a9521a802c3f228786fbfd7d4c29750e2e3e0e2d5"
},
"children": [
{
"id": "10337",
"routeId": "sa_35732ea56c184adc78399b8b",
"moleculeId": "sa_59fe87ee05eb4375b016a413",
"parentId": "10336",
"isLeaf": true,
"molecule": {
"id": "sa_59fe87ee05eb4375b016a413",
"inchikey": "HRGDRFGTDVYRGQ-UHFFFAOYSA-N",
"smiles": "O=C(N1CCOC2(CCNCC2)C1)C(F)(F)F"
},
"smiles": "O=C(N1CCOC2(CCNCC2)C1)C(F)(F)F",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "10338",
"routeId": "sa_35732ea56c184adc78399b8b",
"moleculeId": "sa_38bfdff8ef7c72fe60f806c8",
"parentId": "10336",
"isLeaf": false,
"molecule": {
"id": "sa_38bfdff8ef7c72fe60f806c8",
"inchikey": "KHZGIGWOFXVFTL-UHFFFAOYSA-N",
"smiles": "O=Cc1cccc(CCO)c1F"
},
"smiles": "O=Cc1cccc(CCO)c1F",
"reactionStepId": "sa_3c12cffea7e8087f61de0b1b",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20090298807A1;1117;800736\",\"rsmi\":\"CN(C)[CH:2]=[O:1].[cH:3]1[c:4]([F:5])[c:6]([CH2:7][CH2:8][OH:9])[cH:10][cH:11][cH:12]1>C1CCOC1.CC1(C)CCCC(C)(C)N1.[Li]CCCC>[O:1]=[CH:2][c:3]1[c:4]([F:5])[c:6]([CH2:7][CH2:8][OH:9])[cH:10][cH:11][cH:12]1\"},\"mapped_reaction_smiles\":\"CN(C)[CH:2]=[O:1].[cH:3]1[c:4]([F:5])[c:6]([CH2:7][CH2:8][OH:9])[cH:10][cH:11][cH:12]1>C1CCOC1.CC1(C)CCCC(C)(C)N1.[Li]CCCC>[O:1]=[CH:2][c:3]1[c:4]([F:5])[c:6]([CH2:7][CH2:8][OH:9])[cH:10][cH:11][cH:12]1\"}",
"reactionStep": {
"id": "sa_3c12cffea7e8087f61de0b1b",
"reactionHash": "153b708c69b73253d469cea5453f43e4538c7b7a0fb082aad2a68d07c2ab324a"
},
"children": [
{
"id": "10339",
"routeId": "sa_35732ea56c184adc78399b8b",
"moleculeId": "sa_24ba2503fd54fa3ccc0816ec",
"parentId": "10338",
"isLeaf": true,
"molecule": {
"id": "sa_24ba2503fd54fa3ccc0816ec",
"inchikey": "HNIGZVZDWCTFPR-UHFFFAOYSA-N",
"smiles": "OCCc1ccccc1F"
},
"smiles": "OCCc1ccccc1F",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "10340",
"routeId": "sa_35732ea56c184adc78399b8b",
"moleculeId": "sa_e0b5e93d36242e79e81ef68c",
"parentId": "10338",
"isLeaf": true,
"molecule": {
"id": "sa_e0b5e93d36242e79e81ef68c",
"inchikey": "ZMXDDKWLCZADIW-UHFFFAOYSA-N",
"smiles": "CN(C)C=O"
},
"smiles": "CN(C)C=O",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
}
]
}
]
}
]
}
}