Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
CC1(C)CN(CCCOc2ccc(Cl)cc2C(N)=O)CCC1(O)Cc1ccc(Cl)cc1
InChiKey
OHADQSPORRHJRS-UHFFFAOYSA-N
Route Signature
11e4173d9c2f52b2577a58a0fb4b952cf9e8c6905e2ce23d9a65f025bde968c2
Synthesis route with 4 steps (convergent)
Route tree structure (JSON format)
{
"route": {
"id": "sa_2574c13ffae7b043cef4596f",
"signature": "11e4173d9c2f52b2577a58a0fb4b952cf9e8c6905e2ce23d9a65f025bde968c2",
"contentHash": "71d0b3d56e37e56ae3f2da9c7075108a4de12e127ffbe0a3885bdbc086dd98a7",
"length": 4,
"isConvergent": true
},
"target": {
"id": "sa_aa4e4c01037af12975d1ade5",
"benchmarkSetId": "3895c2909c53593560c5ba610abc7e6df80513dfd8624165c560451735097d36",
"targetId": "n5-01678",
"moleculeId": "sa_16427ae878d3e044675fd78e",
"smiles": "CC1(C)CN(CCCOc2ccc(Cl)cc2C(N)=O)CCC1(O)Cc1ccc(Cl)cc1",
"routeLength": 4,
"isConvergent": true,
"metadata": null,
"molecule": {
"id": "sa_16427ae878d3e044675fd78e",
"inchikey": "OHADQSPORRHJRS-UHFFFAOYSA-N",
"smiles": "CC1(C)CN(CCCOc2ccc(Cl)cc2C(N)=O)CCC1(O)Cc1ccc(Cl)cc1"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "1534",
"routeId": "sa_2574c13ffae7b043cef4596f",
"moleculeId": "sa_16427ae878d3e044675fd78e",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_16427ae878d3e044675fd78e",
"inchikey": "OHADQSPORRHJRS-UHFFFAOYSA-N",
"smiles": "CC1(C)CN(CCCOc2ccc(Cl)cc2C(N)=O)CCC1(O)Cc1ccc(Cl)cc1"
},
"smiles": "CC1(C)CN(CCCOc2ccc(Cl)cc2C(N)=O)CCC1(O)Cc1ccc(Cl)cc1",
"reactionStepId": "sa_ffa299b698b19c1e26b9350e",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20100168080A1;0648;905413\",\"rsmi\":\"CO[C:12]([c:11]1[c:10]([O:9][CH2:8][CH2:7][CH2:6][N:5]2[CH2:4][C:2]([CH3:1])([CH3:3])[C:22]([OH:23])([CH2:24][c:25]3[cH:26][cH:27][c:28]([Cl:29])[cH:30][cH:31]3)[CH2:21][CH2:20]2)[cH:19][cH:18][c:16]([Cl:17])[cH:15]1)=[O:14].[NH3:13]>CO>[CH3:1][C:2]1([CH3:3])[CH2:4][N:5]([CH2:6][CH2:7][CH2:8][O:9][c:10]2[c:11]([C:12]([NH2:13])=[O:14])[cH:15][c:16]([Cl:17])[cH:18][cH:19]2)[CH2:20][CH2:21][C:22]1([OH:23])[CH2:24][c:25]1[cH:26][cH:27][c:28]([Cl:29])[cH:30][cH:31]1\"},\"mapped_reaction_smiles\":\"CO[C:12]([c:11]1[c:10]([O:9][CH2:8][CH2:7][CH2:6][N:5]2[CH2:4][C:2]([CH3:1])([CH3:3])[C:22]([OH:23])([CH2:24][c:25]3[cH:26][cH:27][c:28]([Cl:29])[cH:30][cH:31]3)[CH2:21][CH2:20]2)[cH:19][cH:18][c:16]([Cl:17])[cH:15]1)=[O:14].[NH3:13]>CO>[CH3:1][C:2]1([CH3:3])[CH2:4][N:5]([CH2:6][CH2:7][CH2:8][O:9][c:10]2[c:11]([C:12]([NH2:13])=[O:14])[cH:15][c:16]([Cl:17])[cH:18][cH:19]2)[CH2:20][CH2:21][C:22]1([OH:23])[CH2:24][c:25]1[cH:26][cH:27][c:28]([Cl:29])[cH:30][cH:31]1\"}",
"reactionStep": {
"id": "sa_ffa299b698b19c1e26b9350e",
"reactionHash": "5863f5f9cbd35449ddc5426ad392592b0b344e819a25ec37292c15819ac6f880"
},
"children": [
{
"id": "1535",
"routeId": "sa_2574c13ffae7b043cef4596f",
"moleculeId": "sa_c7cc0db5a91117c67562f76f",
"parentId": "1534",
"isLeaf": false,
"molecule": {
"id": "sa_c7cc0db5a91117c67562f76f",
"inchikey": "PBXFVAXVWGOLMA-UHFFFAOYSA-N",
"smiles": "COC(=O)c1cc(Cl)ccc1OCCCN1CCC(O)(Cc2ccc(Cl)cc2)C(C)(C)C1"
},
"smiles": "COC(=O)c1cc(Cl)ccc1OCCCN1CCC(O)(Cc2ccc(Cl)cc2)C(C)(C)C1",
"reactionStepId": "sa_5dd96dcbe632ec974d6a85ab",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20100168080A1;0645;905411\",\"rsmi\":\"Br[CH2:10][CH2:9][CH2:8][O:7][c:6]1[c:5]([C:3]([O:2][CH3:1])=[O:4])[cH:32][c:30]([Cl:31])[cH:29][cH:28]1.[NH:11]1[CH2:12][CH2:13][C:14]([OH:15])([CH2:16][c:17]2[cH:18][cH:19][c:20]([Cl:21])[cH:22][cH:23]2)[C:24]([CH3:25])([CH3:26])[CH2:27]1>CN(C)C=O.O.O=C(O)O.[K+].[K+]>[CH3:1][O:2][C:3](=[O:4])[c:5]1[c:6]([O:7][CH2:8][CH2:9][CH2:10][N:11]2[CH2:12][CH2:13][C:14]([OH:15])([CH2:16][c:17]3[cH:18][cH:19][c:20]([Cl:21])[cH:22][cH:23]3)[C:24]([CH3:25])([CH3:26])[CH2:27]2)[cH:28][cH:29][c:30]([Cl:31])[cH:32]1\"},\"mapped_reaction_smiles\":\"Br[CH2:10][CH2:9][CH2:8][O:7][c:6]1[c:5]([C:3]([O:2][CH3:1])=[O:4])[cH:32][c:30]([Cl:31])[cH:29][cH:28]1.[NH:11]1[CH2:12][CH2:13][C:14]([OH:15])([CH2:16][c:17]2[cH:18][cH:19][c:20]([Cl:21])[cH:22][cH:23]2)[C:24]([CH3:25])([CH3:26])[CH2:27]1>CN(C)C=O.O.O=C(O)O.[K+].[K+]>[CH3:1][O:2][C:3](=[O:4])[c:5]1[c:6]([O:7][CH2:8][CH2:9][CH2:10][N:11]2[CH2:12][CH2:13][C:14]([OH:15])([CH2:16][c:17]3[cH:18][cH:19][c:20]([Cl:21])[cH:22][cH:23]3)[C:24]([CH3:25])([CH3:26])[CH2:27]2)[cH:28][cH:29][c:30]([Cl:31])[cH:32]1\"}",
"reactionStep": {
"id": "sa_5dd96dcbe632ec974d6a85ab",
"reactionHash": "7493cd0aa92ec84f7edb3dcd22822e595813dc886ac37d9d48af14ecf2d4687f"
},
"children": [
{
"id": "1536",
"routeId": "sa_2574c13ffae7b043cef4596f",
"moleculeId": "sa_354f392b952f29bfa014538d",
"parentId": "1535",
"isLeaf": false,
"molecule": {
"id": "sa_354f392b952f29bfa014538d",
"inchikey": "IRYADPLSERFDCW-UHFFFAOYSA-N",
"smiles": "COC(=O)c1cc(Cl)ccc1OCCCBr"
},
"smiles": "COC(=O)c1cc(Cl)ccc1OCCCBr",
"reactionStepId": "sa_df3762a42402369bbfdb2242",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20100168080A1;0644;905410\",\"rsmi\":\"O[c:16]1[c:5]([C:3]([O:2][CH3:1])=[O:4])[cH:6][cH:12][cH:13][c:14]1[Cl:15].[OH:7][CH2:8][CH2:9][CH2:10][Br:11]>C1CCOC1.CC(C)OC(=O)/N=N/C(=O)OC(C)C.c1ccc(P(c2ccccc2)c2ccccc2)cc1>[CH3:1][O:2][C:3](=[O:4])[c:5]1[c:6]([O:7][CH2:8][CH2:9][CH2:10][Br:11])[cH:12][cH:13][c:14]([Cl:15])[cH:16]1\"},\"mapped_reaction_smiles\":\"O[c:16]1[c:5]([C:3]([O:2][CH3:1])=[O:4])[cH:6][cH:12][cH:13][c:14]1[Cl:15].[OH:7][CH2:8][CH2:9][CH2:10][Br:11]>C1CCOC1.CC(C)OC(=O)/N=N/C(=O)OC(C)C.c1ccc(P(c2ccccc2)c2ccccc2)cc1>[CH3:1][O:2][C:3](=[O:4])[c:5]1[c:6]([O:7][CH2:8][CH2:9][CH2:10][Br:11])[cH:12][cH:13][c:14]([Cl:15])[cH:16]1\"}",
"reactionStep": {
"id": "sa_df3762a42402369bbfdb2242",
"reactionHash": "4c27d66837c65efc149d67527a879adab0a114068f5fd9a9031c06167943ca7f"
},
"children": [
{
"id": "1537",
"routeId": "sa_2574c13ffae7b043cef4596f",
"moleculeId": "sa_7933ae3fdf1322c6c78f89ae",
"parentId": "1536",
"isLeaf": true,
"molecule": {
"id": "sa_7933ae3fdf1322c6c78f89ae",
"inchikey": "MVXSDDGVZSEOIS-UHFFFAOYSA-N",
"smiles": "COC(=O)c1cccc(Cl)c1O"
},
"smiles": "COC(=O)c1cccc(Cl)c1O",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "1538",
"routeId": "sa_2574c13ffae7b043cef4596f",
"moleculeId": "sa_4e0739973446652372900716",
"parentId": "1536",
"isLeaf": true,
"molecule": {
"id": "sa_4e0739973446652372900716",
"inchikey": "RQFUZUMFPRMVDX-UHFFFAOYSA-N",
"smiles": "OCCCBr"
},
"smiles": "OCCCBr",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
},
{
"id": "1539",
"routeId": "sa_2574c13ffae7b043cef4596f",
"moleculeId": "sa_eb1ccd8d215b0d8906e9e3c0",
"parentId": "1535",
"isLeaf": false,
"molecule": {
"id": "sa_eb1ccd8d215b0d8906e9e3c0",
"inchikey": "NUUMJZMDCXPUBV-UHFFFAOYSA-N",
"smiles": "CC1(C)CNCCC1(O)Cc1ccc(Cl)cc1"
},
"smiles": "CC1(C)CNCCC1(O)Cc1ccc(Cl)cc1",
"reactionStepId": "sa_7e63d09ac7e3ecb6b9c7ddf4",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20100168080A1;0567;905386\",\"rsmi\":\"CC(C)(C)OC(=O)[N:5]1[CH2:4][C:2]([CH3:1])([CH3:3])[C:8]([OH:9])([CH2:10][c:11]2[cH:12][cH:13][c:14]([Cl:15])[cH:16][cH:17]2)[CH2:7][CH2:6]1>ClCCl.O=C(O)C(F)(F)F>[CH3:1][C:2]1([CH3:3])[CH2:4][NH:5][CH2:6][CH2:7][C:8]1([OH:9])[CH2:10][c:11]1[cH:12][cH:13][c:14]([Cl:15])[cH:16][cH:17]1\"},\"mapped_reaction_smiles\":\"CC(C)(C)OC(=O)[N:5]1[CH2:4][C:2]([CH3:1])([CH3:3])[C:8]([OH:9])([CH2:10][c:11]2[cH:12][cH:13][c:14]([Cl:15])[cH:16][cH:17]2)[CH2:7][CH2:6]1>ClCCl.O=C(O)C(F)(F)F>[CH3:1][C:2]1([CH3:3])[CH2:4][NH:5][CH2:6][CH2:7][C:8]1([OH:9])[CH2:10][c:11]1[cH:12][cH:13][c:14]([Cl:15])[cH:16][cH:17]1\"}",
"reactionStep": {
"id": "sa_7e63d09ac7e3ecb6b9c7ddf4",
"reactionHash": "4dd5a03a46806e2cfad238a42eced02b2967a9f0f335d9b2088537f1ad26fe89"
},
"children": [
{
"id": "1540",
"routeId": "sa_2574c13ffae7b043cef4596f",
"moleculeId": "sa_964c52a1f2ef43e4b294e485",
"parentId": "1539",
"isLeaf": false,
"molecule": {
"id": "sa_964c52a1f2ef43e4b294e485",
"inchikey": "XCKMBTVTEXLKOS-UHFFFAOYSA-N",
"smiles": "CC(C)(C)OC(=O)N1CCC(O)(Cc2ccc(Cl)cc2)C(C)(C)C1"
},
"smiles": "CC(C)(C)OC(=O)N1CCC(O)(Cc2ccc(Cl)cc2)C(C)(C)C1",
"reactionStepId": "sa_2faa882f733337b0e5af836f",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20100168080A1;0566;905385\",\"rsmi\":\"Br[CH2:13][c:14]1[cH:15][cH:16][c:17]([Cl:18])[cH:19][cH:20]1.[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][C:11](=[O:12])[C:21]([CH3:22])([CH3:23])[CH2:24]1>C1CCOC1.CCOCC.Cl.N>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][C:11]([OH:12])([CH2:13][c:14]2[cH:15][cH:16][c:17]([Cl:18])[cH:19][cH:20]2)[C:21]([CH3:22])([CH3:23])[CH2:24]1\"},\"mapped_reaction_smiles\":\"Br[CH2:13][c:14]1[cH:15][cH:16][c:17]([Cl:18])[cH:19][cH:20]1.[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][C:11](=[O:12])[C:21]([CH3:22])([CH3:23])[CH2:24]1>C1CCOC1.CCOCC.Cl.N>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][C:11]([OH:12])([CH2:13][c:14]2[cH:15][cH:16][c:17]([Cl:18])[cH:19][cH:20]2)[C:21]([CH3:22])([CH3:23])[CH2:24]1\"}",
"reactionStep": {
"id": "sa_2faa882f733337b0e5af836f",
"reactionHash": "0615343e387c7a1ee945c62d463caca07cf031f66c7fe04853ab11c43a01f8c8"
},
"children": [
{
"id": "1541",
"routeId": "sa_2574c13ffae7b043cef4596f",
"moleculeId": "sa_7a40ae693253cd172e27da9f",
"parentId": "1540",
"isLeaf": true,
"molecule": {
"id": "sa_7a40ae693253cd172e27da9f",
"inchikey": "KQNBRMUBPRGXSL-UHFFFAOYSA-N",
"smiles": "Clc1ccc(CBr)cc1"
},
"smiles": "Clc1ccc(CBr)cc1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "1542",
"routeId": "sa_2574c13ffae7b043cef4596f",
"moleculeId": "sa_af669ed195f4a8d96f248f3d",
"parentId": "1540",
"isLeaf": true,
"molecule": {
"id": "sa_af669ed195f4a8d96f248f3d",
"inchikey": "MXCAGVCUIHYAGH-UHFFFAOYSA-N",
"smiles": "CC(C)(C)OC(=O)N1CCC(=O)C(C)(C)C1"
},
"smiles": "CC(C)(C)OC(=O)N1CCC(=O)C(C)(C)C1",
"reactionStepId": null,
"template": null,
"metadata": null,
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}
]
}
]
}
]
},
{
"id": "1543",
"routeId": "sa_2574c13ffae7b043cef4596f",
"moleculeId": "sa_c9679fdd876f32f86b77fb69",
"parentId": "1534",
"isLeaf": true,
"molecule": {
"id": "sa_c9679fdd876f32f86b77fb69",
"inchikey": "QGZKDVFQNNGYKY-UHFFFAOYSA-N",
"smiles": "N"
},
"smiles": "N",
"reactionStepId": null,
"template": null,
"metadata": null,
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"children": []
}
]
}
}