Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
CCc1cnc(N(CCCN2CCc3ccc(CC(=O)O)cc3C2)Cc2ccc(OC(F)(F)F)cc2)nc1
InChiKey
PZKVTXQVHFUGAW-UHFFFAOYSA-N
Route Signature
056026cee6c245b158faad1a0ccc54ada1935dd40eaf2d46e7aad94b94b77088
Synthesis route with 4 steps (convergent)
Route tree structure (JSON format)
{
"route": {
"id": "sa_0d28d08f2e2f2ece01f8c4a9",
"signature": "056026cee6c245b158faad1a0ccc54ada1935dd40eaf2d46e7aad94b94b77088",
"contentHash": "7e881988633f41ca098ab3ee03dea5c8bf7f2e0c4a09cf983f63d9fe1c34d107",
"length": 4,
"isConvergent": true
},
"target": {
"id": "sa_9c219d4c94ca11f29fa21ae0",
"benchmarkSetId": "3895c2909c53593560c5ba610abc7e6df80513dfd8624165c560451735097d36",
"targetId": "n5-02144",
"moleculeId": "sa_5733c7b8b6347927a40d083d",
"smiles": "CCc1cnc(N(CCCN2CCc3ccc(CC(=O)O)cc3C2)Cc2ccc(OC(F)(F)F)cc2)nc1",
"routeLength": 4,
"isConvergent": true,
"metadata": null,
"molecule": {
"id": "sa_5733c7b8b6347927a40d083d",
"inchikey": "PZKVTXQVHFUGAW-UHFFFAOYSA-N",
"smiles": "CCc1cnc(N(CCCN2CCc3ccc(CC(=O)O)cc3C2)Cc2ccc(OC(F)(F)F)cc2)nc1"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "10639",
"routeId": "sa_0d28d08f2e2f2ece01f8c4a9",
"moleculeId": "sa_5733c7b8b6347927a40d083d",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_5733c7b8b6347927a40d083d",
"inchikey": "PZKVTXQVHFUGAW-UHFFFAOYSA-N",
"smiles": "CCc1cnc(N(CCCN2CCc3ccc(CC(=O)O)cc3C2)Cc2ccc(OC(F)(F)F)cc2)nc1"
},
"smiles": "CCc1cnc(N(CCCN2CCc3ccc(CC(=O)O)cc3C2)Cc2ccc(OC(F)(F)F)cc2)nc1",
"reactionStepId": "sa_1f55cfcbf4c68d6e5392a3ad",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20070219193A1;0202;496605\",\"rsmi\":\"C[O:21][C:19]([CH2:18][c:17]1[cH:16][cH:15][c:14]2[c:23]([cH:22]1)[CH2:24][N:11]([CH2:10][CH2:9][CH2:8][N:7]([c:6]1[n:5][cH:4][c:3]([CH2:2][CH3:1])[cH:38][n:37]1)[CH2:25][c:26]1[cH:27][cH:28][c:29]([O:30][C:31]([F:32])([F:33])[F:34])[cH:35][cH:36]1)[CH2:12][CH2:13]2)=[O:20]>C1CCOC1.CO.[Li+].O>[CH3:1][CH2:2][c:3]1[cH:4][n:5][c:6]([N:7]([CH2:8][CH2:9][CH2:10][N:11]2[CH2:12][CH2:13][c:14]3[cH:15][cH:16][c:17]([CH2:18][C:19](=[O:20])[OH:21])[cH:22][c:23]3[CH2:24]2)[CH2:25][c:26]2[cH:27][cH:28][c:29]([O:30][C:31]([F:32])([F:33])[F:34])[cH:35][cH:36]2)[n:37][cH:38]1\"},\"mapped_reaction_smiles\":\"C[O:21][C:19]([CH2:18][c:17]1[cH:16][cH:15][c:14]2[c:23]([cH:22]1)[CH2:24][N:11]([CH2:10][CH2:9][CH2:8][N:7]([c:6]1[n:5][cH:4][c:3]([CH2:2][CH3:1])[cH:38][n:37]1)[CH2:25][c:26]1[cH:27][cH:28][c:29]([O:30][C:31]([F:32])([F:33])[F:34])[cH:35][cH:36]1)[CH2:12][CH2:13]2)=[O:20]>C1CCOC1.CO.[Li+].O>[CH3:1][CH2:2][c:3]1[cH:4][n:5][c:6]([N:7]([CH2:8][CH2:9][CH2:10][N:11]2[CH2:12][CH2:13][c:14]3[cH:15][cH:16][c:17]([CH2:18][C:19](=[O:20])[OH:21])[cH:22][c:23]3[CH2:24]2)[CH2:25][c:26]2[cH:27][cH:28][c:29]([O:30][C:31]([F:32])([F:33])[F:34])[cH:35][cH:36]2)[n:37][cH:38]1\"}",
"reactionStep": {
"id": "sa_1f55cfcbf4c68d6e5392a3ad",
"reactionHash": "ec0d170888703cd93a7ef3bb07899313f96b57a3138f5d30f7cdf41a6d6e2327"
},
"children": [
{
"id": "10640",
"routeId": "sa_0d28d08f2e2f2ece01f8c4a9",
"moleculeId": "sa_53632c55d04856fe86e09bf3",
"parentId": "10639",
"isLeaf": false,
"molecule": {
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"inchikey": "QMCUKSUMSYQTFN-UHFFFAOYSA-N",
"smiles": "CCc1cnc(N(CCCN2CCc3ccc(CC(=O)OC)cc3C2)Cc2ccc(OC(F)(F)F)cc2)nc1"
},
"smiles": "CCc1cnc(N(CCCN2CCc3ccc(CC(=O)OC)cc3C2)Cc2ccc(OC(F)(F)F)cc2)nc1",
"reactionStepId": "sa_3f1fdaf55bacbda97848a298",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20070219193A1;0201;496604\",\"rsmi\":\"O=[CH:10][CH2:9][CH2:8][N:7]([c:6]1[n:5][cH:4][c:3]([CH2:2][CH3:1])[cH:39][n:38]1)[CH2:26][c:27]1[cH:28][cH:29][c:30]([O:31][C:32]([F:33])([F:34])[F:35])[cH:36][cH:37]1.[NH:11]1[CH2:12][CH2:13][c:14]2[cH:15][cH:16][c:17]([CH2:18][C:19](=[O:20])[O:21][CH3:22])[cH:23][c:24]2[CH2:25]1>CO.COC(OC)OC.B.[Na+]>[CH3:1][CH2:2][c:3]1[cH:4][n:5][c:6]([N:7]([CH2:8][CH2:9][CH2:10][N:11]2[CH2:12][CH2:13][c:14]3[cH:15][cH:16][c:17]([CH2:18][C:19](=[O:20])[O:21][CH3:22])[cH:23][c:24]3[CH2:25]2)[CH2:26][c:27]2[cH:28][cH:29][c:30]([O:31][C:32]([F:33])([F:34])[F:35])[cH:36][cH:37]2)[n:38][cH:39]1\"},\"mapped_reaction_smiles\":\"O=[CH:10][CH2:9][CH2:8][N:7]([c:6]1[n:5][cH:4][c:3]([CH2:2][CH3:1])[cH:39][n:38]1)[CH2:26][c:27]1[cH:28][cH:29][c:30]([O:31][C:32]([F:33])([F:34])[F:35])[cH:36][cH:37]1.[NH:11]1[CH2:12][CH2:13][c:14]2[cH:15][cH:16][c:17]([CH2:18][C:19](=[O:20])[O:21][CH3:22])[cH:23][c:24]2[CH2:25]1>CO.COC(OC)OC.B.[Na+]>[CH3:1][CH2:2][c:3]1[cH:4][n:5][c:6]([N:7]([CH2:8][CH2:9][CH2:10][N:11]2[CH2:12][CH2:13][c:14]3[cH:15][cH:16][c:17]([CH2:18][C:19](=[O:20])[O:21][CH3:22])[cH:23][c:24]3[CH2:25]2)[CH2:26][c:27]2[cH:28][cH:29][c:30]([O:31][C:32]([F:33])([F:34])[F:35])[cH:36][cH:37]2)[n:38][cH:39]1\"}",
"reactionStep": {
"id": "sa_3f1fdaf55bacbda97848a298",
"reactionHash": "3661126728845c6778c8f497525aa1517478e7108f69c2edcaf45bbea6d12870"
},
"children": [
{
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"routeId": "sa_0d28d08f2e2f2ece01f8c4a9",
"moleculeId": "sa_81cad7b0168a4b02ed256aba",
"parentId": "10640",
"isLeaf": false,
"molecule": {
"id": "sa_81cad7b0168a4b02ed256aba",
"inchikey": "BRWFWVULAGIBBN-UHFFFAOYSA-N",
"smiles": "CCc1cnc(N(CCC=O)Cc2ccc(OC(F)(F)F)cc2)nc1"
},
"smiles": "CCc1cnc(N(CCC=O)Cc2ccc(OC(F)(F)F)cc2)nc1",
"reactionStepId": "sa_b7d939d0945c412cefe833fb",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20070219193A1;0200;496603\",\"rsmi\":\"[CH3:1][CH2:2][c:3]1[cH:4][n:5][c:6]([N:7]([CH2:8][CH2:9][CH2:10][OH:11])[CH2:12][c:13]2[cH:14][cH:15][c:16]([O:17][C:18]([F:19])([F:20])[F:21])[cH:22][cH:23]2)[n:24][cH:25]1>CC(=O)OI1(OC(C)=O)(OC(C)=O)OC(=O)c2ccccc21.ClCCl>[CH3:1][CH2:2][c:3]1[cH:4][n:5][c:6]([N:7]([CH2:8][CH2:9][CH:10]=[O:11])[CH2:12][c:13]2[cH:14][cH:15][c:16]([O:17][C:18]([F:19])([F:20])[F:21])[cH:22][cH:23]2)[n:24][cH:25]1\"},\"mapped_reaction_smiles\":\"[CH3:1][CH2:2][c:3]1[cH:4][n:5][c:6]([N:7]([CH2:8][CH2:9][CH2:10][OH:11])[CH2:12][c:13]2[cH:14][cH:15][c:16]([O:17][C:18]([F:19])([F:20])[F:21])[cH:22][cH:23]2)[n:24][cH:25]1>CC(=O)OI1(OC(C)=O)(OC(C)=O)OC(=O)c2ccccc21.ClCCl>[CH3:1][CH2:2][c:3]1[cH:4][n:5][c:6]([N:7]([CH2:8][CH2:9][CH:10]=[O:11])[CH2:12][c:13]2[cH:14][cH:15][c:16]([O:17][C:18]([F:19])([F:20])[F:21])[cH:22][cH:23]2)[n:24][cH:25]1\"}",
"reactionStep": {
"id": "sa_b7d939d0945c412cefe833fb",
"reactionHash": "910ed7b1c619cf41e73396c2bb7fe9168dd86e9c0c137e47d978053e2cebf1b6"
},
"children": [
{
"id": "10642",
"routeId": "sa_0d28d08f2e2f2ece01f8c4a9",
"moleculeId": "sa_27e45465fc8289647f788812",
"parentId": "10641",
"isLeaf": false,
"molecule": {
"id": "sa_27e45465fc8289647f788812",
"inchikey": "KGZMZVDCLYOXSA-UHFFFAOYSA-N",
"smiles": "CCc1cnc(N(CCCO)Cc2ccc(OC(F)(F)F)cc2)nc1"
},
"smiles": "CCc1cnc(N(CCCO)Cc2ccc(OC(F)(F)F)cc2)nc1",
"reactionStepId": "sa_d1b86c16db6ed78fdfb07bbf",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20070219193A1;0199;496602\",\"rsmi\":\"Cl[c:6]1[n:5][cH:4][c:3]([CH2:2][CH3:1])[cH:25][n:24]1.[NH:7]([CH2:8][CH2:9][CH2:10][OH:11])[CH2:12][c:13]1[cH:14][cH:15][c:16]([O:17][C:18]([F:19])([F:20])[F:21])[cH:22][cH:23]1>CCOC(C)=O.CN(C)C=O.O=C(O)O.[K+].[K+]>[CH3:1][CH2:2][c:3]1[cH:4][n:5][c:6]([N:7]([CH2:8][CH2:9][CH2:10][OH:11])[CH2:12][c:13]2[cH:14][cH:15][c:16]([O:17][C:18]([F:19])([F:20])[F:21])[cH:22][cH:23]2)[n:24][cH:25]1\"},\"mapped_reaction_smiles\":\"Cl[c:6]1[n:5][cH:4][c:3]([CH2:2][CH3:1])[cH:25][n:24]1.[NH:7]([CH2:8][CH2:9][CH2:10][OH:11])[CH2:12][c:13]1[cH:14][cH:15][c:16]([O:17][C:18]([F:19])([F:20])[F:21])[cH:22][cH:23]1>CCOC(C)=O.CN(C)C=O.O=C(O)O.[K+].[K+]>[CH3:1][CH2:2][c:3]1[cH:4][n:5][c:6]([N:7]([CH2:8][CH2:9][CH2:10][OH:11])[CH2:12][c:13]2[cH:14][cH:15][c:16]([O:17][C:18]([F:19])([F:20])[F:21])[cH:22][cH:23]2)[n:24][cH:25]1\"}",
"reactionStep": {
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"reactionHash": "ba288c0b7e8e8fa29adcb43778a5ce6f23ee6965654cb9bca6fec3a12af150bd"
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"children": [
{
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"routeId": "sa_0d28d08f2e2f2ece01f8c4a9",
"moleculeId": "sa_b7bf82c61690ec3a9ded2925",
"parentId": "10642",
"isLeaf": true,
"molecule": {
"id": "sa_b7bf82c61690ec3a9ded2925",
"inchikey": "BGLLZQRUXJGTAD-UHFFFAOYSA-N",
"smiles": "CCc1cnc(Cl)nc1"
},
"smiles": "CCc1cnc(Cl)nc1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
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},
{
"id": "10644",
"routeId": "sa_0d28d08f2e2f2ece01f8c4a9",
"moleculeId": "sa_21a358629b0e1be067c203f6",
"parentId": "10642",
"isLeaf": true,
"molecule": {
"id": "sa_21a358629b0e1be067c203f6",
"inchikey": "PGVJONMUSMZKBY-UHFFFAOYSA-N",
"smiles": "OCCCNCc1ccc(OC(F)(F)F)cc1"
},
"smiles": "OCCCNCc1ccc(OC(F)(F)F)cc1",
"reactionStepId": null,
"template": null,
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}
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},
{
"id": "10645",
"routeId": "sa_0d28d08f2e2f2ece01f8c4a9",
"moleculeId": "sa_9e6096a6e028281321517df0",
"parentId": "10640",
"isLeaf": false,
"molecule": {
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"inchikey": "SBWHIZQSENZAMH-UHFFFAOYSA-N",
"smiles": "COC(=O)Cc1ccc2c(c1)CNCC2"
},
"smiles": "COC(=O)Cc1ccc2c(c1)CNCC2",
"reactionStepId": "sa_08838b134842528cc5f63e59",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20070219193A1;0197;496601\",\"rsmi\":\"O=C(C(F)(F)F)[N:12]1[CH2:11][CH2:10][c:9]2[cH:8][cH:7][c:6]([CH2:5][C:3]([O:2][CH3:1])=[O:4])[cH:15][c:14]2[CH2:13]1>CO.B.[Na+]>[CH3:1][O:2][C:3](=[O:4])[CH2:5][c:6]1[cH:7][cH:8][c:9]2[c:14]([cH:15]1)[CH2:13][NH:12][CH2:11][CH2:10]2\"},\"mapped_reaction_smiles\":\"O=C(C(F)(F)F)[N:12]1[CH2:11][CH2:10][c:9]2[cH:8][cH:7][c:6]([CH2:5][C:3]([O:2][CH3:1])=[O:4])[cH:15][c:14]2[CH2:13]1>CO.B.[Na+]>[CH3:1][O:2][C:3](=[O:4])[CH2:5][c:6]1[cH:7][cH:8][c:9]2[c:14]([cH:15]1)[CH2:13][NH:12][CH2:11][CH2:10]2\"}",
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"children": [
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"moleculeId": "sa_f17605518ca7edb9f4002898",
"parentId": "10645",
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"molecule": {
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"inchikey": "OGXOBFXOXHGPRG-UHFFFAOYSA-N",
"smiles": "COC(=O)Cc1ccc2c(c1)CN(C(=O)C(F)(F)F)CC2"
},
"smiles": "COC(=O)Cc1ccc2c(c1)CN(C(=O)C(F)(F)F)CC2",
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]
}
]
}
}