Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
CCCN(CCCn1c2ccc(C(C)=O)cc2c2c3c(ccc21)C(=O)CC3)S(=O)(=O)c1ccccc1[N+](=O)[O-]
InChiKey
JLLVJSZXPQXCQI-UHFFFAOYSA-N
Route Signature
3f30f0a4aca8d39dc7ce5761b4dafe86267ddaf23a5c61b3a951debcf689b506
Synthesis route with 5 steps (convergent)
Route tree structure (JSON format)
{
"route": {
"id": "sa_98a1b92ae2f11a29fbd6ba01",
"signature": "3f30f0a4aca8d39dc7ce5761b4dafe86267ddaf23a5c61b3a951debcf689b506",
"contentHash": "ea5611afc45f03731c41d4b85da347c4f839a02546881300eab8f1e073b28244",
"length": 5,
"isConvergent": true
},
"target": {
"id": "sa_05980ee642278f15e07d9ef3",
"benchmarkSetId": "7390a9c2522b1c81605e80a42a8de7c7ad9a5797d028633b54904bc78f091bb8",
"targetId": "n5-00230",
"moleculeId": "sa_528e4c7d6aef93e4a31e9a54",
"smiles": "CCCN(CCCn1c2ccc(C(C)=O)cc2c2c3c(ccc21)C(=O)CC3)S(=O)(=O)c1ccccc1[N+](=O)[O-]",
"routeLength": 5,
"isConvergent": true,
"metadata": null,
"molecule": {
"id": "sa_528e4c7d6aef93e4a31e9a54",
"inchikey": "JLLVJSZXPQXCQI-UHFFFAOYSA-N",
"smiles": "CCCN(CCCn1c2ccc(C(C)=O)cc2c2c3c(ccc21)C(=O)CC3)S(=O)(=O)c1ccccc1[N+](=O)[O-]"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 2
},
"rootNode": {
"id": "471",
"routeId": "sa_98a1b92ae2f11a29fbd6ba01",
"moleculeId": "sa_528e4c7d6aef93e4a31e9a54",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_528e4c7d6aef93e4a31e9a54",
"inchikey": "JLLVJSZXPQXCQI-UHFFFAOYSA-N",
"smiles": "CCCN(CCCn1c2ccc(C(C)=O)cc2c2c3c(ccc21)C(=O)CC3)S(=O)(=O)c1ccccc1[N+](=O)[O-]"
},
"smiles": "CCCN(CCCn1c2ccc(C(C)=O)cc2c2c3c(ccc21)C(=O)CC3)S(=O)(=O)c1ccccc1[N+](=O)[O-]",
"reactionStepId": "sa_3d10a249d2add3848c5bcd46",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20150342927A1;0288;1792978\",\"rsmi\":\"Cl[C:13]([CH3:14])=[O:15].[CH3:1][CH2:2][CH2:3][N:4]([CH2:5][CH2:6][CH2:7][n:8]1[c:9]2[c:10]([cH:11][cH:12][cH:16][cH:17]2)[c:18]2[c:19]1[cH:20][cH:21][c:22]1[c:23]2[CH2:24][CH2:25][C:26]1=[O:27])[S:28](=[O:29])(=[O:30])[c:31]1[c:32]([N+:33](=[O:34])[O-:35])[cH:36][cH:37][cH:38][cH:39]1>O.O=[N+]([O-])c1ccccc1.[Al+3].Cl.Cl.Cl>[CH3:1][CH2:2][CH2:3][N:4]([CH2:5][CH2:6][CH2:7][n:8]1[c:9]2[c:10]([cH:11][c:12]([C:13]([CH3:14])=[O:15])[cH:16][cH:17]2)[c:18]2[c:19]1[cH:20][cH:21][c:22]1[c:23]2[CH2:24][CH2:25][C:26]1=[O:27])[S:28](=[O:29])(=[O:30])[c:31]1[c:32]([N+:33](=[O:34])[O-:35])[cH:36][cH:37][cH:38][cH:39]1\"},\"mapped_reaction_smiles\":\"Cl[C:13]([CH3:14])=[O:15].[CH3:1][CH2:2][CH2:3][N:4]([CH2:5][CH2:6][CH2:7][n:8]1[c:9]2[c:10]([cH:11][cH:12][cH:16][cH:17]2)[c:18]2[c:19]1[cH:20][cH:21][c:22]1[c:23]2[CH2:24][CH2:25][C:26]1=[O:27])[S:28](=[O:29])(=[O:30])[c:31]1[c:32]([N+:33](=[O:34])[O-:35])[cH:36][cH:37][cH:38][cH:39]1>O.O=[N+]([O-])c1ccccc1.[Al+3].Cl.Cl.Cl>[CH3:1][CH2:2][CH2:3][N:4]([CH2:5][CH2:6][CH2:7][n:8]1[c:9]2[c:10]([cH:11][c:12]([C:13]([CH3:14])=[O:15])[cH:16][cH:17]2)[c:18]2[c:19]1[cH:20][cH:21][c:22]1[c:23]2[CH2:24][CH2:25][C:26]1=[O:27])[S:28](=[O:29])(=[O:30])[c:31]1[c:32]([N+:33](=[O:34])[O-:35])[cH:36][cH:37][cH:38][cH:39]1\"}",
"reactionStep": {
"id": "sa_3d10a249d2add3848c5bcd46",
"reactionHash": "5ed6d6c61f4763061d07ccd11313f29214322c233214d57cc2a59a347e3b7c97"
},
"children": [
{
"id": "472",
"routeId": "sa_98a1b92ae2f11a29fbd6ba01",
"moleculeId": "sa_14f371796a307bbc5e9ae2ff",
"parentId": "471",
"isLeaf": false,
"molecule": {
"id": "sa_14f371796a307bbc5e9ae2ff",
"inchikey": "HLQJAGOUFYTDGC-UHFFFAOYSA-N",
"smiles": "CCCN(CCCn1c2ccccc2c2c3c(ccc21)C(=O)CC3)S(=O)(=O)c1ccccc1[N+](=O)[O-]"
},
"smiles": "CCCN(CCCn1c2ccccc2c2c3c(ccc21)C(=O)CC3)S(=O)(=O)c1ccccc1[N+](=O)[O-]",
"reactionStepId": "sa_a82e41d245f5df43aa428987",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20150342927A1;0287;1792977\",\"rsmi\":\"Br[CH2:7][CH2:6][CH2:5][N:4]([CH2:3][CH2:2][CH3:1])[S:25](=[O:26])(=[O:27])[c:28]1[c:29]([N+:30](=[O:31])[O-:32])[cH:33][cH:34][cH:35][cH:36]1.[nH:8]1[c:9]2[c:10]([cH:11][cH:12][cH:13][cH:14]2)[c:15]2[c:16]1[cH:17][cH:18][c:19]1[c:20]2[CH2:21][CH2:22][C:23]1=[O:24]>CCCCCC.CCOC(C)=O.ClCCl.[HH].[Na+]>[CH3:1][CH2:2][CH2:3][N:4]([CH2:5][CH2:6][CH2:7][n:8]1[c:9]2[c:10]([cH:11][cH:12][cH:13][cH:14]2)[c:15]2[c:16]1[cH:17][cH:18][c:19]1[c:20]2[CH2:21][CH2:22][C:23]1=[O:24])[S:25](=[O:26])(=[O:27])[c:28]1[c:29]([N+:30](=[O:31])[O-:32])[cH:33][cH:34][cH:35][cH:36]1\"},\"mapped_reaction_smiles\":\"Br[CH2:7][CH2:6][CH2:5][N:4]([CH2:3][CH2:2][CH3:1])[S:25](=[O:26])(=[O:27])[c:28]1[c:29]([N+:30](=[O:31])[O-:32])[cH:33][cH:34][cH:35][cH:36]1.[nH:8]1[c:9]2[c:10]([cH:11][cH:12][cH:13][cH:14]2)[c:15]2[c:16]1[cH:17][cH:18][c:19]1[c:20]2[CH2:21][CH2:22][C:23]1=[O:24]>CCCCCC.CCOC(C)=O.ClCCl.[HH].[Na+]>[CH3:1][CH2:2][CH2:3][N:4]([CH2:5][CH2:6][CH2:7][n:8]1[c:9]2[c:10]([cH:11][cH:12][cH:13][cH:14]2)[c:15]2[c:16]1[cH:17][cH:18][c:19]1[c:20]2[CH2:21][CH2:22][C:23]1=[O:24])[S:25](=[O:26])(=[O:27])[c:28]1[c:29]([N+:30](=[O:31])[O-:32])[cH:33][cH:34][cH:35][cH:36]1\"}",
"reactionStep": {
"id": "sa_a82e41d245f5df43aa428987",
"reactionHash": "2d03cd2aeebafd09303384e725a72857bc3d0c8b75f3e44c6a02d9ce63fa7407"
},
"children": [
{
"id": "473",
"routeId": "sa_98a1b92ae2f11a29fbd6ba01",
"moleculeId": "sa_d6107e803414ec8ad4081799",
"parentId": "472",
"isLeaf": false,
"molecule": {
"id": "sa_d6107e803414ec8ad4081799",
"inchikey": "XUJGRQNBLBKYOD-UHFFFAOYSA-N",
"smiles": "CCCN(CCCBr)S(=O)(=O)c1ccccc1[N+](=O)[O-]"
},
"smiles": "CCCN(CCCBr)S(=O)(=O)c1ccccc1[N+](=O)[O-]",
"reactionStepId": "sa_becd3ca349a99d16ca93df3a",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20150342927A1;0286;1792976\",\"rsmi\":\"Br[CH2:5][CH2:6][CH2:7][Br:8].[CH3:1][CH2:2][CH2:3][NH:4][S:9](=[O:10])(=[O:11])[c:12]1[c:13]([N+:14](=[O:15])[O-:16])[cH:17][cH:18][cH:19][cH:20]1>CN(C)C=O.ClCCl.[HH].[Na+]>[CH3:1][CH2:2][CH2:3][N:4]([CH2:5][CH2:6][CH2:7][Br:8])[S:9](=[O:10])(=[O:11])[c:12]1[c:13]([N+:14](=[O:15])[O-:16])[cH:17][cH:18][cH:19][cH:20]1\"},\"mapped_reaction_smiles\":\"Br[CH2:5][CH2:6][CH2:7][Br:8].[CH3:1][CH2:2][CH2:3][NH:4][S:9](=[O:10])(=[O:11])[c:12]1[c:13]([N+:14](=[O:15])[O-:16])[cH:17][cH:18][cH:19][cH:20]1>CN(C)C=O.ClCCl.[HH].[Na+]>[CH3:1][CH2:2][CH2:3][N:4]([CH2:5][CH2:6][CH2:7][Br:8])[S:9](=[O:10])(=[O:11])[c:12]1[c:13]([N+:14](=[O:15])[O-:16])[cH:17][cH:18][cH:19][cH:20]1\"}",
"reactionStep": {
"id": "sa_becd3ca349a99d16ca93df3a",
"reactionHash": "e27da1ca995c05127b76da47663913f07d2d975ae4e185c9933fad8525a2166a"
},
"children": [
{
"id": "474",
"routeId": "sa_98a1b92ae2f11a29fbd6ba01",
"moleculeId": "sa_5e9eb06782c9c3bab5925790",
"parentId": "473",
"isLeaf": true,
"molecule": {
"id": "sa_5e9eb06782c9c3bab5925790",
"inchikey": "ACOSRAUGLQAPTG-UHFFFAOYSA-N",
"smiles": "CCCNS(=O)(=O)c1ccccc1[N+](=O)[O-]"
},
"smiles": "CCCNS(=O)(=O)c1ccccc1[N+](=O)[O-]",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "475",
"routeId": "sa_98a1b92ae2f11a29fbd6ba01",
"moleculeId": "sa_e7a0e2a8bae1aa2177d1b502",
"parentId": "473",
"isLeaf": true,
"molecule": {
"id": "sa_e7a0e2a8bae1aa2177d1b502",
"inchikey": "VEFLKXRACNJHOV-UHFFFAOYSA-N",
"smiles": "BrCCCBr"
},
"smiles": "BrCCCBr",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
},
{
"id": "476",
"routeId": "sa_98a1b92ae2f11a29fbd6ba01",
"moleculeId": "sa_1003e2deb8672b8fee66614b",
"parentId": "472",
"isLeaf": false,
"molecule": {
"id": "sa_1003e2deb8672b8fee66614b",
"inchikey": "ZTXUVVLEYYDPSR-UHFFFAOYSA-N",
"smiles": "O=C1CCc2c1ccc1[nH]c3ccccc3c21"
},
"smiles": "O=C1CCc2c1ccc1[nH]c3ccccc3c21",
"reactionStepId": "sa_96fb8e373883f38d751e4b6f",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20150342927A1;0324;1792997\",\"rsmi\":\"O=[N+:17]([O-])[c:12]1[c:11](-[c:10]2[c:5]3[c:6]([cH:7][cH:8][cH:9]2)[C:2](=[O:1])[CH2:3][CH2:4]3)[cH:16][cH:15][cH:14][cH:13]1>CCOP(OCC)OCC>[O:1]=[C:2]1[CH2:3][CH2:4][c:5]2[c:6]1[cH:7][cH:8][c:9]1[c:10]2[c:11]2[c:12]([cH:13][cH:14][cH:15][cH:16]2)[nH:17]1\"},\"mapped_reaction_smiles\":\"O=[N+:17]([O-])[c:12]1[c:11](-[c:10]2[c:5]3[c:6]([cH:7][cH:8][cH:9]2)[C:2](=[O:1])[CH2:3][CH2:4]3)[cH:16][cH:15][cH:14][cH:13]1>CCOP(OCC)OCC>[O:1]=[C:2]1[CH2:3][CH2:4][c:5]2[c:6]1[cH:7][cH:8][c:9]1[c:10]2[c:11]2[c:12]([cH:13][cH:14][cH:15][cH:16]2)[nH:17]1\"}",
"reactionStep": {
"id": "sa_96fb8e373883f38d751e4b6f",
"reactionHash": "f91e02522c9510c5916204422570067aca6e5f89b9263102bdd0b35378194fca"
},
"children": [
{
"id": "477",
"routeId": "sa_98a1b92ae2f11a29fbd6ba01",
"moleculeId": "sa_f3a7dc01267b1254f1cb7908",
"parentId": "476",
"isLeaf": false,
"molecule": {
"id": "sa_f3a7dc01267b1254f1cb7908",
"inchikey": "BKEBFIFUFBLHSV-UHFFFAOYSA-N",
"smiles": "O=C1CCc2c1cccc2-c1ccccc1[N+](=O)[O-]"
},
"smiles": "O=C1CCc2c1cccc2-c1ccccc1[N+](=O)[O-]",
"reactionStepId": "sa_14b05d38eb675fb992389792",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20150342927A1;0323;1792996\",\"rsmi\":\"CC1(C)OB([c:6]2[c:5]3[c:19]([cH:18][cH:17][cH:16]2)[C:2](=[O:1])[CH2:3][CH2:4]3)OC1(C)C.Cl[c:7]1[c:8]([N+:9](=[O:10])[O-:11])[cH:12][cH:13][cH:14][cH:15]1>CCOC(C)=O.Cc1ccccc1.O.O=C(O)O.[Na+].[Na+].c1ccc([PH](c2ccccc2)(c2ccccc2)[Pd]([PH](c2ccccc2)(c2ccccc2)c2ccccc2)([PH](c2ccccc2)(c2ccccc2)c2ccccc2)[PH](c2ccccc2)(c2ccccc2)c2ccccc2)cc1>[O:1]=[C:2]1[CH2:3][CH2:4][c:5]2[c:6](-[c:7]3[c:8]([N+:9](=[O:10])[O-:11])[cH:12][cH:13][cH:14][cH:15]3)[cH:16][cH:17][cH:18][c:19]21\"},\"mapped_reaction_smiles\":\"CC1(C)OB([c:6]2[c:5]3[c:19]([cH:18][cH:17][cH:16]2)[C:2](=[O:1])[CH2:3][CH2:4]3)OC1(C)C.Cl[c:7]1[c:8]([N+:9](=[O:10])[O-:11])[cH:12][cH:13][cH:14][cH:15]1>CCOC(C)=O.Cc1ccccc1.O.O=C(O)O.[Na+].[Na+].c1ccc([PH](c2ccccc2)(c2ccccc2)[Pd]([PH](c2ccccc2)(c2ccccc2)c2ccccc2)([PH](c2ccccc2)(c2ccccc2)c2ccccc2)[PH](c2ccccc2)(c2ccccc2)c2ccccc2)cc1>[O:1]=[C:2]1[CH2:3][CH2:4][c:5]2[c:6](-[c:7]3[c:8]([N+:9](=[O:10])[O-:11])[cH:12][cH:13][cH:14][cH:15]3)[cH:16][cH:17][cH:18][c:19]21\"}",
"reactionStep": {
"id": "sa_14b05d38eb675fb992389792",
"reactionHash": "dc7ae04c6148ece8951b151c1037d8f19b93d178efbeff0710457ce6d49c95e1"
},
"children": [
{
"id": "478",
"routeId": "sa_98a1b92ae2f11a29fbd6ba01",
"moleculeId": "sa_33c0dc44a7624695ae3a690b",
"parentId": "477",
"isLeaf": true,
"molecule": {
"id": "sa_33c0dc44a7624695ae3a690b",
"inchikey": "BFCFYVKQTRLZHA-UHFFFAOYSA-N",
"smiles": "O=[N+]([O-])c1ccccc1Cl"
},
"smiles": "O=[N+]([O-])c1ccccc1Cl",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "479",
"routeId": "sa_98a1b92ae2f11a29fbd6ba01",
"moleculeId": "sa_6ee9006436546200a85d32fd",
"parentId": "477",
"isLeaf": false,
"molecule": {
"id": "sa_6ee9006436546200a85d32fd",
"inchikey": "FBRLQBIQUOHVBS-UHFFFAOYSA-N",
"smiles": "CC1(C)OB(c2cccc3c2CCC3=O)OC1(C)C"
},
"smiles": "CC1(C)OB(c2cccc3c2CCC3=O)OC1(C)C",
"reactionStepId": "sa_59321d476c0705ce5a4a3c74",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20150342927A1;0267;1792967\",\"rsmi\":\"Br[c:6]1[c:7]2[c:12]([cH:13][cH:14][cH:15]1)[C:10](=[O:11])[CH2:9][CH2:8]2.CC1(C)OB([B:5]2[O:4][C:2]([CH3:1])([CH3:3])[C:17]([CH3:18])([CH3:19])[O:16]2)OC1(C)C>C1COCCO1.CC(=O)O.Cl[Pd]Cl.[Fe+2].[K+]>[CH3:1][C:2]1([CH3:3])[O:4][B:5]([c:6]2[c:7]3[c:12]([cH:13][cH:14][cH:15]2)[C:10](=[O:11])[CH2:9][CH2:8]3)[O:16][C:17]1([CH3:18])[CH3:19]\"},\"mapped_reaction_smiles\":\"Br[c:6]1[c:7]2[c:12]([cH:13][cH:14][cH:15]1)[C:10](=[O:11])[CH2:9][CH2:8]2.CC1(C)OB([B:5]2[O:4][C:2]([CH3:1])([CH3:3])[C:17]([CH3:18])([CH3:19])[O:16]2)OC1(C)C>C1COCCO1.CC(=O)O.Cl[Pd]Cl.[Fe+2].[K+]>[CH3:1][C:2]1([CH3:3])[O:4][B:5]([c:6]2[c:7]3[c:12]([cH:13][cH:14][cH:15]2)[C:10](=[O:11])[CH2:9][CH2:8]3)[O:16][C:17]1([CH3:18])[CH3:19]\"}",
"reactionStep": {
"id": "sa_59321d476c0705ce5a4a3c74",
"reactionHash": "34d49154f71e212561ac6070e1bf57de74e8db0bd8213a334d55f7b10fe4f428"
},
"children": [
{
"id": "480",
"routeId": "sa_98a1b92ae2f11a29fbd6ba01",
"moleculeId": "sa_e6c301388ac142801d4af5a2",
"parentId": "479",
"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": "481",
"routeId": "sa_98a1b92ae2f11a29fbd6ba01",
"moleculeId": "sa_144e23fa8b81fa3f3b4e8af2",
"parentId": "479",
"isLeaf": true,
"molecule": {
"id": "sa_144e23fa8b81fa3f3b4e8af2",
"inchikey": "UVVYFYLSZIMKMC-UHFFFAOYSA-N",
"smiles": "O=C1CCc2c(Br)cccc21"
},
"smiles": "O=C1CCc2c(Br)cccc21",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
}
]
}
]
}
]
},
{
"id": "482",
"routeId": "sa_98a1b92ae2f11a29fbd6ba01",
"moleculeId": "sa_7992c61d309177eaaf95fc6b",
"parentId": "471",
"isLeaf": true,
"molecule": {
"id": "sa_7992c61d309177eaaf95fc6b",
"inchikey": "WETWJCDKMRHUPV-UHFFFAOYSA-N",
"smiles": "CC(=O)Cl"
},
"smiles": "CC(=O)Cl",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
}
}