Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
CC(c1ccc(-c2ccc3cccnc3c2)cc1)N1CCC2(CC1)CN(C1CC1)C(=O)CO2
InChiKey
BQDYVCDTTGKUHT-UHFFFAOYSA-N
Route Signature
e42ec2b3b565ea3036a0b4ec3dddb8b930ad382a959020aee703a5de816e2a1b
Synthesis route with 3 steps (convergent)
Route tree structure (JSON format)
{
"route": {
"id": "sa_5d9f2757c669bebbb7c9de9a",
"signature": "e42ec2b3b565ea3036a0b4ec3dddb8b930ad382a959020aee703a5de816e2a1b",
"contentHash": "30496a79cb554149195f7a0f81954cee3c26cca958569a9d113119da83244a22",
"length": 3,
"isConvergent": true
},
"target": {
"id": "sa_548ca1694e2ed9b39fcd5390",
"benchmarkSetId": "3895c2909c53593560c5ba610abc7e6df80513dfd8624165c560451735097d36",
"targetId": "n5-00982",
"moleculeId": "sa_6def855ce4949250946ddd4d",
"smiles": "CC(c1ccc(-c2ccc3cccnc3c2)cc1)N1CCC2(CC1)CN(C1CC1)C(=O)CO2",
"routeLength": 3,
"isConvergent": true,
"metadata": null,
"molecule": {
"id": "sa_6def855ce4949250946ddd4d",
"inchikey": "BQDYVCDTTGKUHT-UHFFFAOYSA-N",
"smiles": "CC(c1ccc(-c2ccc3cccnc3c2)cc1)N1CCC2(CC1)CN(C1CC1)C(=O)CO2"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "9854",
"routeId": "sa_5d9f2757c669bebbb7c9de9a",
"moleculeId": "sa_6def855ce4949250946ddd4d",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_6def855ce4949250946ddd4d",
"inchikey": "BQDYVCDTTGKUHT-UHFFFAOYSA-N",
"smiles": "CC(c1ccc(-c2ccc3cccnc3c2)cc1)N1CCC2(CC1)CN(C1CC1)C(=O)CO2"
},
"smiles": "CC(c1ccc(-c2ccc3cccnc3c2)cc1)N1CCC2(CC1)CN(C1CC1)C(=O)CO2",
"reactionStepId": "sa_b3ecb3dd784ee72fca38f34d",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20140194415A1;0326;1548587\",\"rsmi\":\"Br[c:6]1[cH:5][cH:4][c:3]([CH:2]([CH3:1])[N:19]2[CH2:20][CH2:21][C:22]3([CH2:23][CH2:24]2)[CH2:25][N:26]([CH:27]2[CH2:28][CH2:29]2)[C:30](=[O:31])[CH2:32][O:33]3)[cH:18][cH:17]1.CC1(C)OB([c:7]2[cH:8][cH:9][c:10]3[cH:11][cH:12][cH:13][n:14][c:15]3[cH:16]2)OC1(C)C>C1COCCO1.ClCCl.Cl[Pd]Cl.O=C(O)O.[Fe+2].[K+].[K+]>[CH3:1][CH:2]([c:3]1[cH:4][cH:5][c:6](-[c:7]2[cH:8][cH:9][c:10]3[cH:11][cH:12][cH:13][n:14][c:15]3[cH:16]2)[cH:17][cH:18]1)[N:19]1[CH2:20][CH2:21][C:22]2([CH2:23][CH2:24]1)[CH2:25][N:26]([CH:27]1[CH2:28][CH2:29]1)[C:30](=[O:31])[CH2:32][O:33]2\"},\"mapped_reaction_smiles\":\"Br[c:6]1[cH:5][cH:4][c:3]([CH:2]([CH3:1])[N:19]2[CH2:20][CH2:21][C:22]3([CH2:23][CH2:24]2)[CH2:25][N:26]([CH:27]2[CH2:28][CH2:29]2)[C:30](=[O:31])[CH2:32][O:33]3)[cH:18][cH:17]1.CC1(C)OB([c:7]2[cH:8][cH:9][c:10]3[cH:11][cH:12][cH:13][n:14][c:15]3[cH:16]2)OC1(C)C>C1COCCO1.ClCCl.Cl[Pd]Cl.O=C(O)O.[Fe+2].[K+].[K+]>[CH3:1][CH:2]([c:3]1[cH:4][cH:5][c:6](-[c:7]2[cH:8][cH:9][c:10]3[cH:11][cH:12][cH:13][n:14][c:15]3[cH:16]2)[cH:17][cH:18]1)[N:19]1[CH2:20][CH2:21][C:22]2([CH2:23][CH2:24]1)[CH2:25][N:26]([CH:27]1[CH2:28][CH2:29]1)[C:30](=[O:31])[CH2:32][O:33]2\"}",
"reactionStep": {
"id": "sa_b3ecb3dd784ee72fca38f34d",
"reactionHash": "5bfed76fc0f74ed6a5e2e420818aeeb69327b5f58cce628b0f58d66e69b39ec7"
},
"children": [
{
"id": "9855",
"routeId": "sa_5d9f2757c669bebbb7c9de9a",
"moleculeId": "sa_4d7713a47da09b9ed0966656",
"parentId": "9854",
"isLeaf": false,
"molecule": {
"id": "sa_4d7713a47da09b9ed0966656",
"inchikey": "CIXVOEJAOCHQKS-UHFFFAOYSA-N",
"smiles": "CC1(C)OB(c2ccc3cccnc3c2)OC1(C)C"
},
"smiles": "CC1(C)OB(c2ccc3cccnc3c2)OC1(C)C",
"reactionStepId": "sa_4a47b1d03f3e14d686887db6",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20140194415A1;0296;1548573\",\"rsmi\":\"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.O=S(=O)(O[c:6]1[cH:7][cH:8][c:9]2[cH:10][cH:11][cH:12][n:13][c:14]2[cH:15]1)C(F)(F)F>C1COCCO1.CC(=O)O.CCOC(C)=O.ClCCl.Cl[Pd]Cl.[Fe+2].[Fe+2].[K+]>[CH3:1][C:2]1([CH3:3])[O:4][B:5]([c:6]2[cH:7][cH:8][c:9]3[cH:10][cH:11][cH:12][n:13][c:14]3[cH:15]2)[O:16][C:17]1([CH3:18])[CH3:19]\"},\"mapped_reaction_smiles\":\"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.O=S(=O)(O[c:6]1[cH:7][cH:8][c:9]2[cH:10][cH:11][cH:12][n:13][c:14]2[cH:15]1)C(F)(F)F>C1COCCO1.CC(=O)O.CCOC(C)=O.ClCCl.Cl[Pd]Cl.[Fe+2].[Fe+2].[K+]>[CH3:1][C:2]1([CH3:3])[O:4][B:5]([c:6]2[cH:7][cH:8][c:9]3[cH:10][cH:11][cH:12][n:13][c:14]3[cH:15]2)[O:16][C:17]1([CH3:18])[CH3:19]\"}",
"reactionStep": {
"id": "sa_4a47b1d03f3e14d686887db6",
"reactionHash": "1b29088fe95f3386848e1cc69af33a52415ad1bc1f609a783e98a0d3c40f1c23"
},
"children": [
{
"id": "9856",
"routeId": "sa_5d9f2757c669bebbb7c9de9a",
"moleculeId": "sa_bad2118c740146231e87b6c7",
"parentId": "9855",
"isLeaf": false,
"molecule": {
"id": "sa_bad2118c740146231e87b6c7",
"inchikey": "FPSAXXSFDJDIRR-UHFFFAOYSA-N",
"smiles": "O=S(=O)(Oc1ccc2cccnc2c1)C(F)(F)F"
},
"smiles": "O=S(=O)(Oc1ccc2cccnc2c1)C(F)(F)F",
"reactionStepId": "sa_f3fd09e9b808908b9d5dec15",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20140194415A1;0295;1548572\",\"rsmi\":\"O=S(=O)(O[S:2](=[O:1])(=[O:3])[C:15]([F:16])([F:17])[F:18])C(F)(F)F.[OH:4][c:5]1[cH:6][cH:7][c:8]2[cH:9][cH:10][cH:11][n:12][c:13]2[cH:14]1>ClCCl.c1ccncc1>[O:1]=[S:2](=[O:3])([O:4][c:5]1[cH:6][cH:7][c:8]2[cH:9][cH:10][cH:11][n:12][c:13]2[cH:14]1)[C:15]([F:16])([F:17])[F:18]\"},\"mapped_reaction_smiles\":\"O=S(=O)(O[S:2](=[O:1])(=[O:3])[C:15]([F:16])([F:17])[F:18])C(F)(F)F.[OH:4][c:5]1[cH:6][cH:7][c:8]2[cH:9][cH:10][cH:11][n:12][c:13]2[cH:14]1>ClCCl.c1ccncc1>[O:1]=[S:2](=[O:3])([O:4][c:5]1[cH:6][cH:7][c:8]2[cH:9][cH:10][cH:11][n:12][c:13]2[cH:14]1)[C:15]([F:16])([F:17])[F:18]\"}",
"reactionStep": {
"id": "sa_f3fd09e9b808908b9d5dec15",
"reactionHash": "725a867e376677de8afb9dd8c24fa9b784e2fe83cc11636148a8a13ce43773c0"
},
"children": [
{
"id": "9857",
"routeId": "sa_5d9f2757c669bebbb7c9de9a",
"moleculeId": "sa_d8869d189c1f39359fac1c8b",
"parentId": "9856",
"isLeaf": true,
"molecule": {
"id": "sa_d8869d189c1f39359fac1c8b",
"inchikey": "WJKHJLXJJJATHN-UHFFFAOYSA-N",
"smiles": "O=S(=O)(OS(=O)(=O)C(F)(F)F)C(F)(F)F"
},
"smiles": "O=S(=O)(OS(=O)(=O)C(F)(F)F)C(F)(F)F",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "9858",
"routeId": "sa_5d9f2757c669bebbb7c9de9a",
"moleculeId": "sa_012a8bd74d44e00fe48bfa62",
"parentId": "9856",
"isLeaf": true,
"molecule": {
"id": "sa_012a8bd74d44e00fe48bfa62",
"inchikey": "XCRPPAPDRUBKRJ-UHFFFAOYSA-N",
"smiles": "Oc1ccc2cccnc2c1"
},
"smiles": "Oc1ccc2cccnc2c1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
},
{
"id": "9859",
"routeId": "sa_5d9f2757c669bebbb7c9de9a",
"moleculeId": "sa_e6c301388ac142801d4af5a2",
"parentId": "9855",
"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": "9860",
"routeId": "sa_5d9f2757c669bebbb7c9de9a",
"moleculeId": "sa_cf26819999985e7b8f7e08c1",
"parentId": "9854",
"isLeaf": false,
"molecule": {
"id": "sa_cf26819999985e7b8f7e08c1",
"inchikey": "PSZLTEGFIDFHAO-UHFFFAOYSA-N",
"smiles": "CC(c1ccc(Br)cc1)N1CCC2(CC1)CN(C1CC1)C(=O)CO2"
},
"smiles": "CC(c1ccc(Br)cc1)N1CCC2(CC1)CN(C1CC1)C(=O)CO2",
"reactionStepId": "sa_ca1d1d54a15b425669365f92",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20140194415A1;0325;1548586\",\"rsmi\":\"Br[CH:2]([CH3:1])[c:3]1[cH:4][cH:5][c:6]([Br:7])[cH:8][cH:9]1.[NH:10]1[CH2:11][CH2:12][C:13]2([CH2:14][CH2:15]1)[CH2:16][N:17]([CH:18]1[CH2:19][CH2:20]1)[C:21](=[O:22])[CH2:23][O:24]2>CN(C)C=O.Cl.O.O=C(O)O.[K+].[K+]>[CH3:1][CH:2]([c:3]1[cH:4][cH:5][c:6]([Br:7])[cH:8][cH:9]1)[N:10]1[CH2:11][CH2:12][C:13]2([CH2:14][CH2:15]1)[CH2:16][N:17]([CH:18]1[CH2:19][CH2:20]1)[C:21](=[O:22])[CH2:23][O:24]2\"},\"mapped_reaction_smiles\":\"Br[CH:2]([CH3:1])[c:3]1[cH:4][cH:5][c:6]([Br:7])[cH:8][cH:9]1.[NH:10]1[CH2:11][CH2:12][C:13]2([CH2:14][CH2:15]1)[CH2:16][N:17]([CH:18]1[CH2:19][CH2:20]1)[C:21](=[O:22])[CH2:23][O:24]2>CN(C)C=O.Cl.O.O=C(O)O.[K+].[K+]>[CH3:1][CH:2]([c:3]1[cH:4][cH:5][c:6]([Br:7])[cH:8][cH:9]1)[N:10]1[CH2:11][CH2:12][C:13]2([CH2:14][CH2:15]1)[CH2:16][N:17]([CH:18]1[CH2:19][CH2:20]1)[C:21](=[O:22])[CH2:23][O:24]2\"}",
"reactionStep": {
"id": "sa_ca1d1d54a15b425669365f92",
"reactionHash": "81973a2b65c0cce58ab44d5c73d763d858e7f3f20bd9f8de6c2292e8e48cd3e9"
},
"children": [
{
"id": "9861",
"routeId": "sa_5d9f2757c669bebbb7c9de9a",
"moleculeId": "sa_634030df771b5e93ac26c6ee",
"parentId": "9860",
"isLeaf": true,
"molecule": {
"id": "sa_634030df771b5e93ac26c6ee",
"inchikey": "OLSWQVUTSZUDJD-UHFFFAOYSA-N",
"smiles": "O=C1COC2(CCNCC2)CN1C1CC1"
},
"smiles": "O=C1COC2(CCNCC2)CN1C1CC1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "9862",
"routeId": "sa_5d9f2757c669bebbb7c9de9a",
"moleculeId": "sa_c39f6c5cca760077321b493c",
"parentId": "9860",
"isLeaf": false,
"molecule": {
"id": "sa_c39f6c5cca760077321b493c",
"inchikey": "QQIOJAHQDFJQSJ-UHFFFAOYSA-N",
"smiles": "CC(Br)c1ccc(Br)cc1"
},
"smiles": "CC(Br)c1ccc(Br)cc1",
"reactionStepId": "sa_406e95e9757f189a889c077f",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20140194415A1;0324;1548585\",\"rsmi\":\"BrP(Br)[Br:3].O[CH:2]([CH3:1])[c:4]1[cH:5][cH:6][c:7]([Br:8])[cH:9][cH:10]1>ClCCl>[CH3:1][CH:2]([Br:3])[c:4]1[cH:5][cH:6][c:7]([Br:8])[cH:9][cH:10]1\"},\"mapped_reaction_smiles\":\"BrP(Br)[Br:3].O[CH:2]([CH3:1])[c:4]1[cH:5][cH:6][c:7]([Br:8])[cH:9][cH:10]1>ClCCl>[CH3:1][CH:2]([Br:3])[c:4]1[cH:5][cH:6][c:7]([Br:8])[cH:9][cH:10]1\"}",
"reactionStep": {
"id": "sa_406e95e9757f189a889c077f",
"reactionHash": "218d0efaa71bc3a0ed53a2372f237cc58aa0e0a60265579cb8dbd4413b59df6a"
},
"children": [
{
"id": "9863",
"routeId": "sa_5d9f2757c669bebbb7c9de9a",
"moleculeId": "sa_dffdccbce5a44ffb8b04e1d2",
"parentId": "9862",
"isLeaf": true,
"molecule": {
"id": "sa_dffdccbce5a44ffb8b04e1d2",
"inchikey": "IPNPIHIZVLFAFP-UHFFFAOYSA-N",
"smiles": "BrP(Br)Br"
},
"smiles": "BrP(Br)Br",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "9864",
"routeId": "sa_5d9f2757c669bebbb7c9de9a",
"moleculeId": "sa_2f3f45e7d76b2b648dae3e96",
"parentId": "9862",
"isLeaf": true,
"molecule": {
"id": "sa_2f3f45e7d76b2b648dae3e96",
"inchikey": "XTDTYSBVMBQIBT-UHFFFAOYSA-N",
"smiles": "CC(O)c1ccc(Br)cc1"
},
"smiles": "CC(O)c1ccc(Br)cc1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
}
]
}
]
}
}