Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
CCNC(=O)Nc1cc(C#Cc2ccccn2)c(-c2cncc(-c3n[nH]c(=O)o3)c2)cn1
InChiKey
KQWRYUZXDQTUSC-UHFFFAOYSA-N
Route Signature
f0e0136e7c5efbf8a8cf6adce30a7637af972dab410f07d816367e5e3a9d05a7
Synthesis route with 6 steps
Route tree structure (JSON format)
{
"route": {
"id": "sa_170adfb317f476998f66acac",
"signature": "f0e0136e7c5efbf8a8cf6adce30a7637af972dab410f07d816367e5e3a9d05a7",
"contentHash": "a7972f0728682dc09535898307a8e7c769165b6febecc4996ebd28cff1938f68",
"length": 6,
"isConvergent": false
},
"target": {
"id": "sa_81e0badd92cf51e22656e800",
"benchmarkSetId": "f925e688d731a0ad4e3aa6a505df094f6d3ca64ce3facc312bc5f64731921b33",
"targetId": "n5-00338",
"moleculeId": "sa_0f246011969d33f96bd99b7c",
"smiles": "CCNC(=O)Nc1cc(C#Cc2ccccn2)c(-c2cncc(-c3n[nH]c(=O)o3)c2)cn1",
"routeLength": 6,
"isConvergent": false,
"metadata": null,
"molecule": {
"id": "sa_0f246011969d33f96bd99b7c",
"inchikey": "KQWRYUZXDQTUSC-UHFFFAOYSA-N",
"smiles": "CCNC(=O)Nc1cc(C#Cc2ccccn2)c(-c2cncc(-c3n[nH]c(=O)o3)c2)cn1"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 2
},
"rootNode": {
"id": "4038",
"routeId": "sa_170adfb317f476998f66acac",
"moleculeId": "sa_0f246011969d33f96bd99b7c",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_0f246011969d33f96bd99b7c",
"inchikey": "KQWRYUZXDQTUSC-UHFFFAOYSA-N",
"smiles": "CCNC(=O)Nc1cc(C#Cc2ccccn2)c(-c2cncc(-c3n[nH]c(=O)o3)c2)cn1"
},
"smiles": "CCNC(=O)Nc1cc(C#Cc2ccccn2)c(-c2cncc(-c3n[nH]c(=O)o3)c2)cn1",
"reactionStepId": "sa_b6080747d3ee5674ac6f4b42",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20090325902A1;0312;814066\",\"rsmi\":\"Br[c:9]1[cH:8][c:7]([NH:6][C:4]([NH:3][CH2:2][CH3:1])=[O:5])[n:32][cH:31][c:18]1-[c:19]1[cH:20][c:21](-[c:22]2[n:23][nH:24][c:25](=[O:26])[o:27]2)[cH:28][n:29][cH:30]1.[CH:10]#[C:11][c:12]1[n:13][cH:14][cH:15][cH:16][cH:17]1>CC#N.CCN(CC)CC.Cl[Pd](Cl)([PH](c1ccccc1)(c1ccccc1)c1ccccc1)[PH](c1ccccc1)(c1ccccc1)c1ccccc1.[Cu]I>[CH3:1][CH2:2][NH:3][C:4](=[O:5])[NH:6][c:7]1[cH:8][c:9]([C:10]#[C:11][c:12]2[n:13][cH:14][cH:15][cH:16][cH:17]2)[c:18](-[c:19]2[cH:20][c:21](-[c:22]3[n:23][nH:24][c:25](=[O:26])[o:27]3)[cH:28][n:29][cH:30]2)[cH:31][n:32]1\"},\"mapped_reaction_smiles\":\"Br[c:9]1[cH:8][c:7]([NH:6][C:4]([NH:3][CH2:2][CH3:1])=[O:5])[n:32][cH:31][c:18]1-[c:19]1[cH:20][c:21](-[c:22]2[n:23][nH:24][c:25](=[O:26])[o:27]2)[cH:28][n:29][cH:30]1.[CH:10]#[C:11][c:12]1[n:13][cH:14][cH:15][cH:16][cH:17]1>CC#N.CCN(CC)CC.Cl[Pd](Cl)([PH](c1ccccc1)(c1ccccc1)c1ccccc1)[PH](c1ccccc1)(c1ccccc1)c1ccccc1.[Cu]I>[CH3:1][CH2:2][NH:3][C:4](=[O:5])[NH:6][c:7]1[cH:8][c:9]([C:10]#[C:11][c:12]2[n:13][cH:14][cH:15][cH:16][cH:17]2)[c:18](-[c:19]2[cH:20][c:21](-[c:22]3[n:23][nH:24][c:25](=[O:26])[o:27]3)[cH:28][n:29][cH:30]2)[cH:31][n:32]1\"}",
"reactionStep": {
"id": "sa_b6080747d3ee5674ac6f4b42",
"reactionHash": "76bd98666752ad6cb6a66f5d9df307eb4b424cff19aee7eaeb0dae70e9e8539f"
},
"children": [
{
"id": "4039",
"routeId": "sa_170adfb317f476998f66acac",
"moleculeId": "sa_3bb9eb23ed22ddd9fa105c0c",
"parentId": "4038",
"isLeaf": true,
"molecule": {
"id": "sa_3bb9eb23ed22ddd9fa105c0c",
"inchikey": "NHUBNHMFXQNNMV-UHFFFAOYSA-N",
"smiles": "C#Cc1ccccn1"
},
"smiles": "C#Cc1ccccn1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "4040",
"routeId": "sa_170adfb317f476998f66acac",
"moleculeId": "sa_370c0b2d5e6a86bfe7862638",
"parentId": "4038",
"isLeaf": false,
"molecule": {
"id": "sa_370c0b2d5e6a86bfe7862638",
"inchikey": "UZSPYCGGHXWAJQ-UHFFFAOYSA-N",
"smiles": "CCNC(=O)Nc1cc(Br)c(-c2cncc(-c3n[nH]c(=O)o3)c2)cn1"
},
"smiles": "CCNC(=O)Nc1cc(Br)c(-c2cncc(-c3n[nH]c(=O)o3)c2)cn1",
"reactionStepId": "sa_aabce73e5ce28489490b3d01",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20090325902A1;0325;814069\",\"rsmi\":\"CN(C)[CH:18]=[O:19].[CH3:1][CH2:2][NH:3][C:4](=[O:5])[NH:6][c:7]1[cH:8][c:9]([Br:10])[c:11](-[c:12]2[cH:13][c:14]([C:15]([NH:16][NH2:17])=[O:20])[cH:21][n:22][cH:23]2)[cH:24][n:25]1>CCN(C(C)C)C(C)C.O=C(n1ccnc1)n1ccnc1>[CH3:1][CH2:2][NH:3][C:4](=[O:5])[NH:6][c:7]1[cH:8][c:9]([Br:10])[c:11](-[c:12]2[cH:13][c:14](-[c:15]3[n:16][nH:17][c:18](=[O:19])[o:20]3)[cH:21][n:22][cH:23]2)[cH:24][n:25]1\"},\"mapped_reaction_smiles\":\"CN(C)[CH:18]=[O:19].[CH3:1][CH2:2][NH:3][C:4](=[O:5])[NH:6][c:7]1[cH:8][c:9]([Br:10])[c:11](-[c:12]2[cH:13][c:14]([C:15]([NH:16][NH2:17])=[O:20])[cH:21][n:22][cH:23]2)[cH:24][n:25]1>CCN(C(C)C)C(C)C.O=C(n1ccnc1)n1ccnc1>[CH3:1][CH2:2][NH:3][C:4](=[O:5])[NH:6][c:7]1[cH:8][c:9]([Br:10])[c:11](-[c:12]2[cH:13][c:14](-[c:15]3[n:16][nH:17][c:18](=[O:19])[o:20]3)[cH:21][n:22][cH:23]2)[cH:24][n:25]1\"}",
"reactionStep": {
"id": "sa_aabce73e5ce28489490b3d01",
"reactionHash": "057992a81c36a324e0f9e4d3b6cd4b7bbca8d8df0100b6e868b678f5c5f1c350"
},
"children": [
{
"id": "4041",
"routeId": "sa_170adfb317f476998f66acac",
"moleculeId": "sa_ec4f72c960948192b8d7b0f2",
"parentId": "4040",
"isLeaf": false,
"molecule": {
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"inchikey": "PBMNNPUPDDYXEX-UHFFFAOYSA-N",
"smiles": "CCNC(=O)Nc1cc(Br)c(-c2cncc(C(=O)NN)c2)cn1"
},
"smiles": "CCNC(=O)Nc1cc(Br)c(-c2cncc(C(=O)NN)c2)cn1",
"reactionStepId": "sa_579b79afa931f8e298687280",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20090325902A1;0330;814070\",\"rsmi\":\"CCO[C:15]([c:14]1[cH:13][c:12](-[c:11]2[c:9]([Br:10])[cH:8][c:7]([NH:6][C:4]([NH:3][CH2:2][CH3:1])=[O:5])[n:23][cH:22]2)[cH:21][n:20][cH:19]1)=[O:16].[NH2:17][NH2:18]>CCO.CCOC(C)=O.O>[CH3:1][CH2:2][NH:3][C:4](=[O:5])[NH:6][c:7]1[cH:8][c:9]([Br:10])[c:11](-[c:12]2[cH:13][c:14]([C:15](=[O:16])[NH:17][NH2:18])[cH:19][n:20][cH:21]2)[cH:22][n:23]1\"},\"mapped_reaction_smiles\":\"CCO[C:15]([c:14]1[cH:13][c:12](-[c:11]2[c:9]([Br:10])[cH:8][c:7]([NH:6][C:4]([NH:3][CH2:2][CH3:1])=[O:5])[n:23][cH:22]2)[cH:21][n:20][cH:19]1)=[O:16].[NH2:17][NH2:18]>CCO.CCOC(C)=O.O>[CH3:1][CH2:2][NH:3][C:4](=[O:5])[NH:6][c:7]1[cH:8][c:9]([Br:10])[c:11](-[c:12]2[cH:13][c:14]([C:15](=[O:16])[NH:17][NH2:18])[cH:19][n:20][cH:21]2)[cH:22][n:23]1\"}",
"reactionStep": {
"id": "sa_579b79afa931f8e298687280",
"reactionHash": "3abdb364741906469e219c22bedc19654c565828056a8ca1f68b102e28b6daaa"
},
"children": [
{
"id": "4042",
"routeId": "sa_170adfb317f476998f66acac",
"moleculeId": "sa_681b90bfe3789a310096845b",
"parentId": "4041",
"isLeaf": true,
"molecule": {
"id": "sa_681b90bfe3789a310096845b",
"inchikey": "OAKJQQAXSVQMHS-UHFFFAOYSA-N",
"smiles": "NN"
},
"smiles": "NN",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "4043",
"routeId": "sa_170adfb317f476998f66acac",
"moleculeId": "sa_da652a0d14a33e1e915c1eda",
"parentId": "4041",
"isLeaf": false,
"molecule": {
"id": "sa_da652a0d14a33e1e915c1eda",
"inchikey": "QYCVPHJUWCJODF-UHFFFAOYSA-N",
"smiles": "CCNC(=O)Nc1cc(Br)c(-c2cncc(C(=O)OCC)c2)cn1"
},
"smiles": "CCNC(=O)Nc1cc(Br)c(-c2cncc(C(=O)OCC)c2)cn1",
"reactionStepId": "sa_fa736dd91a8632ecb2170889",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20090325902A1;0335;814071\",\"rsmi\":\"CC1(C)OB([c:12]2[cH:13][c:14]([C:15](=[O:16])[O:17][CH2:18][CH3:19])[cH:20][n:21][cH:22]2)OC1(C)C.I[c:11]1[c:9]([Br:10])[cH:8][c:7]([NH:6][C:4]([NH:3][CH2:2][CH3:1])=[O:5])[n:24][cH:23]1>CN(C)C=O.O.O=C(O)O.[K+].[K+]>[CH3:1][CH2:2][NH:3][C:4](=[O:5])[NH:6][c:7]1[cH:8][c:9]([Br:10])[c:11](-[c:12]2[cH:13][c:14]([C:15](=[O:16])[O:17][CH2:18][CH3:19])[cH:20][n:21][cH:22]2)[cH:23][n:24]1\"},\"mapped_reaction_smiles\":\"CC1(C)OB([c:12]2[cH:13][c:14]([C:15](=[O:16])[O:17][CH2:18][CH3:19])[cH:20][n:21][cH:22]2)OC1(C)C.I[c:11]1[c:9]([Br:10])[cH:8][c:7]([NH:6][C:4]([NH:3][CH2:2][CH3:1])=[O:5])[n:24][cH:23]1>CN(C)C=O.O.O=C(O)O.[K+].[K+]>[CH3:1][CH2:2][NH:3][C:4](=[O:5])[NH:6][c:7]1[cH:8][c:9]([Br:10])[c:11](-[c:12]2[cH:13][c:14]([C:15](=[O:16])[O:17][CH2:18][CH3:19])[cH:20][n:21][cH:22]2)[cH:23][n:24]1\"}",
"reactionStep": {
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"children": [
{
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"moleculeId": "sa_72b45b46b277ff28e28b488d",
"parentId": "4043",
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"molecule": {
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"inchikey": "PZRUPQBXMCYNTG-UHFFFAOYSA-N",
"smiles": "CCNC(=O)Nc1cc(Br)c(I)cn1"
},
"smiles": "CCNC(=O)Nc1cc(Br)c(I)cn1",
"reactionStepId": "sa_776624256433ade57884166c",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20090325902A1;0340;814072\",\"rsmi\":\"[CH3:1][CH2:2][N:3]=[C:4]=[O:5].[NH2:6][c:7]1[n:8][cH:9][c:10]([I:11])[c:12]([Br:13])[cH:14]1>CCCCCC.ClC(Cl)Cl>[CH3:1][CH2:2][NH:3][C:4](=[O:5])[NH:6][c:7]1[n:8][cH:9][c:10]([I:11])[c:12]([Br:13])[cH:14]1\"},\"mapped_reaction_smiles\":\"[CH3:1][CH2:2][N:3]=[C:4]=[O:5].[NH2:6][c:7]1[n:8][cH:9][c:10]([I:11])[c:12]([Br:13])[cH:14]1>CCCCCC.ClC(Cl)Cl>[CH3:1][CH2:2][NH:3][C:4](=[O:5])[NH:6][c:7]1[n:8][cH:9][c:10]([I:11])[c:12]([Br:13])[cH:14]1\"}",
"reactionStep": {
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"children": [
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"molecule": {
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"smiles": "Nc1cc(Br)c(I)cn1",
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"metadata": "{\"annotations\":{\"ID\":\"US20090325902A1;0345;814073\",\"rsmi\":\"O=C1CCC(=O)N1[I:6].[NH2:1][c:2]1[n:3][cH:4][cH:5][c:7]([Br:8])[cH:9]1>CN(C)C=O.ClC(Cl)Cl>[NH2:1][c:2]1[n:3][cH:4][c:5]([I:6])[c:7]([Br:8])[cH:9]1\"},\"mapped_reaction_smiles\":\"O=C1CCC(=O)N1[I:6].[NH2:1][c:2]1[n:3][cH:4][cH:5][c:7]([Br:8])[cH:9]1>CN(C)C=O.ClC(Cl)Cl>[NH2:1][c:2]1[n:3][cH:4][c:5]([I:6])[c:7]([Br:8])[cH:9]1\"}",
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"children": [
{
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"molecule": {
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"smiles": "Nc1cc(Br)ccn1"
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{
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{
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"molecule": {
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{
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},
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{
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"smiles": "CN(C)C=O"
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}
]
}
]
}
}