Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
Cc1cccc(Nc2nc(-c3ccc(-c4ccc(N(C)C)nc4)cc3)cs2)n1
InChiKey
NTSGHYPXGWAVRV-UHFFFAOYSA-N
Route Signature
481938a722d9662e3e6dd0548e30ecb154b65c347bc4f7e70129e21fa57b549e
Synthesis route with 4 steps (convergent)
Route tree structure (JSON format)
{
"route": {
"id": "sa_9295edbdedb37ac9c55f12ae",
"signature": "481938a722d9662e3e6dd0548e30ecb154b65c347bc4f7e70129e21fa57b549e",
"contentHash": "ad3e1cab0cc14df8577a6bea04a83ee1d5f5d672a09d8e68f8086f6038f928d6",
"length": 4,
"isConvergent": true
},
"target": {
"id": "sa_19f526b2b7254860deced46a",
"benchmarkSetId": "3895c2909c53593560c5ba610abc7e6df80513dfd8624165c560451735097d36",
"targetId": "n5-00707",
"moleculeId": "sa_d42e664c179a0fa7d52e7890",
"smiles": "Cc1cccc(Nc2nc(-c3ccc(-c4ccc(N(C)C)nc4)cc3)cs2)n1",
"routeLength": 4,
"isConvergent": true,
"metadata": null,
"molecule": {
"id": "sa_d42e664c179a0fa7d52e7890",
"inchikey": "NTSGHYPXGWAVRV-UHFFFAOYSA-N",
"smiles": "Cc1cccc(Nc2nc(-c3ccc(-c4ccc(N(C)C)nc4)cc3)cs2)n1"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "9696",
"routeId": "sa_9295edbdedb37ac9c55f12ae",
"moleculeId": "sa_d42e664c179a0fa7d52e7890",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_d42e664c179a0fa7d52e7890",
"inchikey": "NTSGHYPXGWAVRV-UHFFFAOYSA-N",
"smiles": "Cc1cccc(Nc2nc(-c3ccc(-c4ccc(N(C)C)nc4)cc3)cs2)n1"
},
"smiles": "Cc1cccc(Nc2nc(-c3ccc(-c4ccc(N(C)C)nc4)cc3)cs2)n1",
"reactionStepId": "sa_96b6d6b95f3dc60a829e0584",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20140329863A1;0764;1608319\",\"rsmi\":\"Br[c:15]1[cH:16][n:17][c:18]([N:19]([CH3:20])[CH3:21])[cH:22][cH:23]1.CC1(C)OB([c:14]2[cH:13][cH:12][c:11](-[c:10]3[n:9][c:8]([NH:7][c:6]4[cH:5][cH:4][cH:3][c:2]([CH3:1])[n:28]4)[s:27][cH:26]3)[cH:25][cH:24]2)OC1(C)C>C1COCCO1.Cl[Pd]Cl.O.O=C(O)O.[Fe+2].[K+].[K+]>[CH3:1][c:2]1[cH:3][cH:4][cH:5][c:6]([NH:7][c:8]2[n:9][c:10](-[c:11]3[cH:12][cH:13][c:14](-[c:15]4[cH:16][n:17][c:18]([N:19]([CH3:20])[CH3:21])[cH:22][cH:23]4)[cH:24][cH:25]3)[cH:26][s:27]2)[n:28]1\"},\"mapped_reaction_smiles\":\"Br[c:15]1[cH:16][n:17][c:18]([N:19]([CH3:20])[CH3:21])[cH:22][cH:23]1.CC1(C)OB([c:14]2[cH:13][cH:12][c:11](-[c:10]3[n:9][c:8]([NH:7][c:6]4[cH:5][cH:4][cH:3][c:2]([CH3:1])[n:28]4)[s:27][cH:26]3)[cH:25][cH:24]2)OC1(C)C>C1COCCO1.Cl[Pd]Cl.O.O=C(O)O.[Fe+2].[K+].[K+]>[CH3:1][c:2]1[cH:3][cH:4][cH:5][c:6]([NH:7][c:8]2[n:9][c:10](-[c:11]3[cH:12][cH:13][c:14](-[c:15]4[cH:16][n:17][c:18]([N:19]([CH3:20])[CH3:21])[cH:22][cH:23]4)[cH:24][cH:25]3)[cH:26][s:27]2)[n:28]1\"}",
"reactionStep": {
"id": "sa_96b6d6b95f3dc60a829e0584",
"reactionHash": "88ccb3010546d056a42bd30b8ddff60aacc2a04162328cfb13e8fafb8997f457"
},
"children": [
{
"id": "9697",
"routeId": "sa_9295edbdedb37ac9c55f12ae",
"moleculeId": "sa_0edd76eb274c7f9cf65c8d0a",
"parentId": "9696",
"isLeaf": false,
"molecule": {
"id": "sa_0edd76eb274c7f9cf65c8d0a",
"inchikey": "NEXUOSJHWSIGNJ-UHFFFAOYSA-N",
"smiles": "Cc1cccc(Nc2nc(-c3ccc(B4OC(C)(C)C(C)(C)O4)cc3)cs2)n1"
},
"smiles": "Cc1cccc(Nc2nc(-c3ccc(B4OC(C)(C)C(C)(C)O4)cc3)cs2)n1",
"reactionStepId": "sa_be5d195710e37e225170dfa2",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20140329863A1;0769;1608324\",\"rsmi\":\"Br[c:14]1[cH:13][cH:12][c:11](-[c:10]2[n:9][c:8]([NH:7][c:6]3[cH:5][cH:4][cH:3][c:2]([CH3:1])[n:28]3)[s:27][cH:26]2)[cH:25][cH:24]1.CC1(C)OB([B:15]2[O:16][C:17]([CH3:18])([CH3:19])[C:20]([CH3:21])([CH3:22])[O:23]2)OC1(C)C>C1COCCO1.CC(=O)O[K].Cl[Pd]Cl.[Fe+2]>[CH3:1][c:2]1[cH:3][cH:4][cH:5][c:6]([NH:7][c:8]2[n:9][c:10](-[c:11]3[cH:12][cH:13][c:14]([B:15]4[O:16][C:17]([CH3:18])([CH3:19])[C:20]([CH3:21])([CH3:22])[O:23]4)[cH:24][cH:25]3)[cH:26][s:27]2)[n:28]1\"},\"mapped_reaction_smiles\":\"Br[c:14]1[cH:13][cH:12][c:11](-[c:10]2[n:9][c:8]([NH:7][c:6]3[cH:5][cH:4][cH:3][c:2]([CH3:1])[n:28]3)[s:27][cH:26]2)[cH:25][cH:24]1.CC1(C)OB([B:15]2[O:16][C:17]([CH3:18])([CH3:19])[C:20]([CH3:21])([CH3:22])[O:23]2)OC1(C)C>C1COCCO1.CC(=O)O[K].Cl[Pd]Cl.[Fe+2]>[CH3:1][c:2]1[cH:3][cH:4][cH:5][c:6]([NH:7][c:8]2[n:9][c:10](-[c:11]3[cH:12][cH:13][c:14]([B:15]4[O:16][C:17]([CH3:18])([CH3:19])[C:20]([CH3:21])([CH3:22])[O:23]4)[cH:24][cH:25]3)[cH:26][s:27]2)[n:28]1\"}",
"reactionStep": {
"id": "sa_be5d195710e37e225170dfa2",
"reactionHash": "205b8c800ee78f074c3fb8ab5dd07b5a3084b21d02b14db4beabc9d92c752af5"
},
"children": [
{
"id": "9698",
"routeId": "sa_9295edbdedb37ac9c55f12ae",
"moleculeId": "sa_e6c301388ac142801d4af5a2",
"parentId": "9697",
"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": "9699",
"routeId": "sa_9295edbdedb37ac9c55f12ae",
"moleculeId": "sa_e93996d7cbf1eb586503d22d",
"parentId": "9697",
"isLeaf": false,
"molecule": {
"id": "sa_e93996d7cbf1eb586503d22d",
"inchikey": "VPSJTTNJJCQXLE-UHFFFAOYSA-N",
"smiles": "Cc1cccc(Nc2nc(-c3ccc(Br)cc3)cs2)n1"
},
"smiles": "Cc1cccc(Nc2nc(-c3ccc(Br)cc3)cs2)n1",
"reactionStepId": "sa_e846fed8e08fd0a6674dea7e",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20140329863A1;0769;1608323\",\"rsmi\":\"O=[C:10]([c:11]1[cH:12][cH:13][c:14]([Br:15])[cH:16][cH:17]1)[CH2:18]Br.[CH3:1][c:2]1[cH:3][cH:4][cH:5][c:6]([NH:7][C:8]([NH2:9])=[S:19])[n:20]1>CCO>[CH3:1][c:2]1[cH:3][cH:4][cH:5][c:6]([NH:7][c:8]2[n:9][c:10](-[c:11]3[cH:12][cH:13][c:14]([Br:15])[cH:16][cH:17]3)[cH:18][s:19]2)[n:20]1\"},\"mapped_reaction_smiles\":\"O=[C:10]([c:11]1[cH:12][cH:13][c:14]([Br:15])[cH:16][cH:17]1)[CH2:18]Br.[CH3:1][c:2]1[cH:3][cH:4][cH:5][c:6]([NH:7][C:8]([NH2:9])=[S:19])[n:20]1>CCO>[CH3:1][c:2]1[cH:3][cH:4][cH:5][c:6]([NH:7][c:8]2[n:9][c:10](-[c:11]3[cH:12][cH:13][c:14]([Br:15])[cH:16][cH:17]3)[cH:18][s:19]2)[n:20]1\"}",
"reactionStep": {
"id": "sa_e846fed8e08fd0a6674dea7e",
"reactionHash": "291128bcec2f63e931e3c071f67cdcda4f591964b66d8f0db8927d6add15233d"
},
"children": [
{
"id": "9700",
"routeId": "sa_9295edbdedb37ac9c55f12ae",
"moleculeId": "sa_083aec6797bb3df3ad05f67d",
"parentId": "9699",
"isLeaf": true,
"molecule": {
"id": "sa_083aec6797bb3df3ad05f67d",
"inchikey": "FKJSFKCZZIXQIP-UHFFFAOYSA-N",
"smiles": "O=C(CBr)c1ccc(Br)cc1"
},
"smiles": "O=C(CBr)c1ccc(Br)cc1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "9701",
"routeId": "sa_9295edbdedb37ac9c55f12ae",
"moleculeId": "sa_5161862b4b7738afc5bf671e",
"parentId": "9699",
"isLeaf": false,
"molecule": {
"id": "sa_5161862b4b7738afc5bf671e",
"inchikey": "LEWSYNYKTYXRHP-UHFFFAOYSA-N",
"smiles": "Cc1cccc(NC(N)=S)n1"
},
"smiles": "Cc1cccc(NC(N)=S)n1",
"reactionStepId": "sa_266e88f339cb9849ac890024",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20140329863A1;0769;1608322\",\"rsmi\":\"O=C(c1ccccc1)[NH:9][C:8]([NH:7][c:6]1[cH:5][cH:4][cH:3][c:2]([CH3:1])[n:11]1)=[S:10]>C1CCOC1.[Na+].O>[CH3:1][c:2]1[cH:3][cH:4][cH:5][c:6]([NH:7][C:8]([NH2:9])=[S:10])[n:11]1\"},\"mapped_reaction_smiles\":\"O=C(c1ccccc1)[NH:9][C:8]([NH:7][c:6]1[cH:5][cH:4][cH:3][c:2]([CH3:1])[n:11]1)=[S:10]>C1CCOC1.[Na+].O>[CH3:1][c:2]1[cH:3][cH:4][cH:5][c:6]([NH:7][C:8]([NH2:9])=[S:10])[n:11]1\"}",
"reactionStep": {
"id": "sa_266e88f339cb9849ac890024",
"reactionHash": "d448bb651e4c7ba715f559a208e4afacee22a0de6b966327ebfc2aa4a4abeb3b"
},
"children": [
{
"id": "9702",
"routeId": "sa_9295edbdedb37ac9c55f12ae",
"moleculeId": "sa_3ec9393919fd67ee378bb689",
"parentId": "9701",
"isLeaf": true,
"molecule": {
"id": "sa_3ec9393919fd67ee378bb689",
"inchikey": "VWKPOGQHIDVZER-UHFFFAOYSA-N",
"smiles": "Cc1cccc(NC(=S)NC(=O)c2ccccc2)n1"
},
"smiles": "Cc1cccc(NC(=S)NC(=O)c2ccccc2)n1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
}
]
}
]
},
{
"id": "9703",
"routeId": "sa_9295edbdedb37ac9c55f12ae",
"moleculeId": "sa_60589e5f404130f064c324b3",
"parentId": "9696",
"isLeaf": false,
"molecule": {
"id": "sa_60589e5f404130f064c324b3",
"inchikey": "XIMCGXXYEMOWQP-UHFFFAOYSA-N",
"smiles": "CN(C)c1ccc(Br)cn1"
},
"smiles": "CN(C)c1ccc(Br)cn1",
"reactionStepId": "sa_e9005cbbdd148d519dd005dc",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20140329863A1;0767;1608320\",\"rsmi\":\"F[c:4]1[n:5][cH:6][c:7]([Br:8])[cH:9][cH:10]1.[CH3:1][NH:2][CH3:3]>C1CCOC1.O>[CH3:1][N:2]([CH3:3])[c:4]1[n:5][cH:6][c:7]([Br:8])[cH:9][cH:10]1\"},\"mapped_reaction_smiles\":\"F[c:4]1[n:5][cH:6][c:7]([Br:8])[cH:9][cH:10]1.[CH3:1][NH:2][CH3:3]>C1CCOC1.O>[CH3:1][N:2]([CH3:3])[c:4]1[n:5][cH:6][c:7]([Br:8])[cH:9][cH:10]1\"}",
"reactionStep": {
"id": "sa_e9005cbbdd148d519dd005dc",
"reactionHash": "806b2b4edcd3a7b227083c4fd5f656ded1c1bbd7b6781203fb8acc5fe12b8341"
},
"children": [
{
"id": "9704",
"routeId": "sa_9295edbdedb37ac9c55f12ae",
"moleculeId": "sa_8cc2e353f9aecde319fc1528",
"parentId": "9703",
"isLeaf": true,
"molecule": {
"id": "sa_8cc2e353f9aecde319fc1528",
"inchikey": "MYUQKYGWKHTRPG-UHFFFAOYSA-N",
"smiles": "Fc1ccc(Br)cn1"
},
"smiles": "Fc1ccc(Br)cn1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "9705",
"routeId": "sa_9295edbdedb37ac9c55f12ae",
"moleculeId": "sa_e2676e5c7c9d7a020ed1780e",
"parentId": "9703",
"isLeaf": true,
"molecule": {
"id": "sa_e2676e5c7c9d7a020ed1780e",
"inchikey": "ROSDSFDQCJNGOL-UHFFFAOYSA-N",
"smiles": "CNC"
},
"smiles": "CNC",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
}
]
}
}