Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
CC(C)(O)c1cccc(Nc2cc(N[C@@H]3CCCC[C@@H]3N)nnc2C(N)=O)n1
InChiKey
JIUISYCELSZDAY-NWDGAFQWSA-N
Route Signature
48ebaf8586b48e65f963fa426c1a625bb0c54f6f526de4960c789f2d45963190
Synthesis route with 6 steps
Route tree structure (JSON format)
{
"route": {
"id": "sa_197967e0702c5f3d2c78aeca",
"signature": "48ebaf8586b48e65f963fa426c1a625bb0c54f6f526de4960c789f2d45963190",
"contentHash": "f53df7d4438000aedd6485d200679d0156a8fba200f7b3542d8724746c88418d",
"length": 6,
"isConvergent": false
},
"target": {
"id": "sa_d0e16b05804890bb4b657137",
"benchmarkSetId": "f925e688d731a0ad4e3aa6a505df094f6d3ca64ce3facc312bc5f64731921b33",
"targetId": "n5-00515",
"moleculeId": "sa_44d442b431ced79e2fdd5507",
"smiles": "CC(C)(O)c1cccc(Nc2cc(N[C@@H]3CCCC[C@@H]3N)nnc2C(N)=O)n1",
"routeLength": 6,
"isConvergent": false,
"metadata": null,
"molecule": {
"id": "sa_44d442b431ced79e2fdd5507",
"inchikey": "JIUISYCELSZDAY-NWDGAFQWSA-N",
"smiles": "CC(C)(O)c1cccc(Nc2cc(N[C@@H]3CCCC[C@@H]3N)nnc2C(N)=O)n1"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 2
},
"rootNode": {
"id": "4388",
"routeId": "sa_197967e0702c5f3d2c78aeca",
"moleculeId": "sa_44d442b431ced79e2fdd5507",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_44d442b431ced79e2fdd5507",
"inchikey": "JIUISYCELSZDAY-NWDGAFQWSA-N",
"smiles": "CC(C)(O)c1cccc(Nc2cc(N[C@@H]3CCCC[C@@H]3N)nnc2C(N)=O)n1"
},
"smiles": "CC(C)(O)c1cccc(Nc2cc(N[C@@H]3CCCC[C@@H]3N)nnc2C(N)=O)n1",
"reactionStepId": "sa_2bbcec9a035af13872f97960",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20130178478A1;0472;1391296\",\"rsmi\":\"CC(C)(C)OC(=O)[NH:26][C@@H:25]1[C@H:20]([NH:19][c:18]2[n:17][n:16][c:12]([C:13]([NH2:14])=[O:15])[c:11]([NH:10][c:9]3[cH:8][cH:7][cH:6][c:5]([C:2]([CH3:1])([CH3:3])[OH:4])[n:28]3)[cH:27]2)[CH2:21][CH2:22][CH2:23][CH2:24]1>ClCCl.O=C(O)C(F)(F)F>[CH3:1][C:2]([CH3:3])([OH:4])[c:5]1[cH:6][cH:7][cH:8][c:9]([NH:10][c:11]2[c:12]([C:13]([NH2:14])=[O:15])[n:16][n:17][c:18]([NH:19][C@@H:20]3[CH2:21][CH2:22][CH2:23][CH2:24][C@@H:25]3[NH2:26])[cH:27]2)[n:28]1\"},\"mapped_reaction_smiles\":\"CC(C)(C)OC(=O)[NH:26][C@@H:25]1[C@H:20]([NH:19][c:18]2[n:17][n:16][c:12]([C:13]([NH2:14])=[O:15])[c:11]([NH:10][c:9]3[cH:8][cH:7][cH:6][c:5]([C:2]([CH3:1])([CH3:3])[OH:4])[n:28]3)[cH:27]2)[CH2:21][CH2:22][CH2:23][CH2:24]1>ClCCl.O=C(O)C(F)(F)F>[CH3:1][C:2]([CH3:3])([OH:4])[c:5]1[cH:6][cH:7][cH:8][c:9]([NH:10][c:11]2[c:12]([C:13]([NH2:14])=[O:15])[n:16][n:17][c:18]([NH:19][C@@H:20]3[CH2:21][CH2:22][CH2:23][CH2:24][C@@H:25]3[NH2:26])[cH:27]2)[n:28]1\"}",
"reactionStep": {
"id": "sa_2bbcec9a035af13872f97960",
"reactionHash": "85023574adc80d1faf33b00118c386eace21b3bffad992dd7286b3a863fa98b1"
},
"children": [
{
"id": "4389",
"routeId": "sa_197967e0702c5f3d2c78aeca",
"moleculeId": "sa_16ea18791e6bca413c05cec9",
"parentId": "4388",
"isLeaf": false,
"molecule": {
"id": "sa_16ea18791e6bca413c05cec9",
"inchikey": "ZZIPUZQXGQVJCY-CABCVRRESA-N",
"smiles": "CC(C)(C)OC(=O)N[C@H]1CCCC[C@H]1Nc1cc(Nc2cccc(C(C)(C)O)n2)c(C(N)=O)nn1"
},
"smiles": "CC(C)(C)OC(=O)N[C@H]1CCCC[C@H]1Nc1cc(Nc2cccc(C(C)(C)O)n2)c(C(N)=O)nn1",
"reactionStepId": "sa_24ee1e7cc52d66ac32bb0cc5",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20130178478A1;0470;1391295\",\"rsmi\":\"Cl[c:16]1[cH:17][c:18]([NH:19][c:20]2[n:21][c:22]([C:23]([CH3:24])([CH3:25])[OH:26])[cH:27][cH:28][cH:29]2)[c:30]([C:31]([NH2:32])=[O:33])[n:34][n:35]1.[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][C@H:9]1[CH2:10][CH2:11][CH2:12][CH2:13][C@H:14]1[NH2:15]>CN1CCCC1=O>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][C@H:9]1[CH2:10][CH2:11][CH2:12][CH2:13][C@H:14]1[NH:15][c:16]1[cH:17][c:18]([NH:19][c:20]2[n:21][c:22]([C:23]([CH3:24])([CH3:25])[OH:26])[cH:27][cH:28][cH:29]2)[c:30]([C:31]([NH2:32])=[O:33])[n:34][n:35]1\"},\"mapped_reaction_smiles\":\"Cl[c:16]1[cH:17][c:18]([NH:19][c:20]2[n:21][c:22]([C:23]([CH3:24])([CH3:25])[OH:26])[cH:27][cH:28][cH:29]2)[c:30]([C:31]([NH2:32])=[O:33])[n:34][n:35]1.[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][C@H:9]1[CH2:10][CH2:11][CH2:12][CH2:13][C@H:14]1[NH2:15]>CN1CCCC1=O>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][C@H:9]1[CH2:10][CH2:11][CH2:12][CH2:13][C@H:14]1[NH:15][c:16]1[cH:17][c:18]([NH:19][c:20]2[n:21][c:22]([C:23]([CH3:24])([CH3:25])[OH:26])[cH:27][cH:28][cH:29]2)[c:30]([C:31]([NH2:32])=[O:33])[n:34][n:35]1\"}",
"reactionStep": {
"id": "sa_24ee1e7cc52d66ac32bb0cc5",
"reactionHash": "13bf361e98379ac3d4b0307749654159cd1101d517767ec467ecc052c00b7ed1"
},
"children": [
{
"id": "4390",
"routeId": "sa_197967e0702c5f3d2c78aeca",
"moleculeId": "sa_109d74885f56800b43cdc170",
"parentId": "4389",
"isLeaf": true,
"molecule": {
"id": "sa_109d74885f56800b43cdc170",
"inchikey": "AKVIZYGPJIWKOS-BDAKNGLRSA-N",
"smiles": "CC(C)(C)OC(=O)N[C@H]1CCCC[C@H]1N"
},
"smiles": "CC(C)(C)OC(=O)N[C@H]1CCCC[C@H]1N",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "4391",
"routeId": "sa_197967e0702c5f3d2c78aeca",
"moleculeId": "sa_fc2e8d824d77735c26e424e5",
"parentId": "4389",
"isLeaf": false,
"molecule": {
"id": "sa_fc2e8d824d77735c26e424e5",
"inchikey": "HGQBDLYYOZYUFE-UHFFFAOYSA-N",
"smiles": "CC(C)(O)c1cccc(Nc2cc(Cl)nnc2C(N)=O)n1"
},
"smiles": "CC(C)(O)c1cccc(Nc2cc(Cl)nnc2C(N)=O)n1",
"reactionStepId": "sa_a6855f646d92a4c2d371545e",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20130178478A1;0468;1391294\",\"rsmi\":\"CCO[C:13]([c:12]1[c:11]([NH:10][c:9]2[cH:8][cH:7][cH:6][c:5]([C:2]([CH3:1])([CH3:3])[OH:4])[n:21]2)[cH:20][c:18]([Cl:19])[n:17][n:16]1)=[O:15].[NH3:14]>CO>[CH3:1][C:2]([CH3:3])([OH:4])[c:5]1[cH:6][cH:7][cH:8][c:9]([NH:10][c:11]2[c:12]([C:13]([NH2:14])=[O:15])[n:16][n:17][c:18]([Cl:19])[cH:20]2)[n:21]1\"},\"mapped_reaction_smiles\":\"CCO[C:13]([c:12]1[c:11]([NH:10][c:9]2[cH:8][cH:7][cH:6][c:5]([C:2]([CH3:1])([CH3:3])[OH:4])[n:21]2)[cH:20][c:18]([Cl:19])[n:17][n:16]1)=[O:15].[NH3:14]>CO>[CH3:1][C:2]([CH3:3])([OH:4])[c:5]1[cH:6][cH:7][cH:8][c:9]([NH:10][c:11]2[c:12]([C:13]([NH2:14])=[O:15])[n:16][n:17][c:18]([Cl:19])[cH:20]2)[n:21]1\"}",
"reactionStep": {
"id": "sa_a6855f646d92a4c2d371545e",
"reactionHash": "8707f1840db3c11f175a57d0edee864a02b1086851387ecf66dfcdb2d2778d06"
},
"children": [
{
"id": "4392",
"routeId": "sa_197967e0702c5f3d2c78aeca",
"moleculeId": "sa_ac484c636b02ce315b06717b",
"parentId": "4391",
"isLeaf": false,
"molecule": {
"id": "sa_ac484c636b02ce315b06717b",
"inchikey": "CQPQUFHJDXRGOV-UHFFFAOYSA-N",
"smiles": "CCOC(=O)c1nnc(Cl)cc1Nc1cccc(C(C)(C)O)n1"
},
"smiles": "CCOC(=O)c1nnc(Cl)cc1Nc1cccc(C(C)(C)O)n1",
"reactionStepId": "sa_dd9e856835bedb931cfd5ea8",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20130178478A1;0466;1391293\",\"rsmi\":\"Cl[c:7]1[c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[n:23][n:22][c:20]([Cl:21])[cH:19]1.[NH2:8][c:9]1[n:10][c:11]([C:12]([CH3:13])([CH3:14])[OH:15])[cH:16][cH:17][cH:18]1>CC#N>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[c:7]([NH:8][c:9]2[n:10][c:11]([C:12]([CH3:13])([CH3:14])[OH:15])[cH:16][cH:17][cH:18]2)[cH:19][c:20]([Cl:21])[n:22][n:23]1\"},\"mapped_reaction_smiles\":\"Cl[c:7]1[c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[n:23][n:22][c:20]([Cl:21])[cH:19]1.[NH2:8][c:9]1[n:10][c:11]([C:12]([CH3:13])([CH3:14])[OH:15])[cH:16][cH:17][cH:18]1>CC#N>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[c:7]([NH:8][c:9]2[n:10][c:11]([C:12]([CH3:13])([CH3:14])[OH:15])[cH:16][cH:17][cH:18]2)[cH:19][c:20]([Cl:21])[n:22][n:23]1\"}",
"reactionStep": {
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"reactionHash": "bb6fafeaa2f5c62caf571ed1a7a38dfe85400f315b26e1767e1d803daa75e88b"
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"children": [
{
"id": "4393",
"routeId": "sa_197967e0702c5f3d2c78aeca",
"moleculeId": "sa_0d43968d426c6ef56afe5dd6",
"parentId": "4392",
"isLeaf": true,
"molecule": {
"id": "sa_0d43968d426c6ef56afe5dd6",
"inchikey": "MOWPWJUYSRHMHS-UHFFFAOYSA-N",
"smiles": "CCOC(=O)c1nnc(Cl)cc1Cl"
},
"smiles": "CCOC(=O)c1nnc(Cl)cc1Cl",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "4394",
"routeId": "sa_197967e0702c5f3d2c78aeca",
"moleculeId": "sa_e0b10cb9a09327aea45205a6",
"parentId": "4392",
"isLeaf": false,
"molecule": {
"id": "sa_e0b10cb9a09327aea45205a6",
"inchikey": "SZAXGTZCBQFNBF-UHFFFAOYSA-N",
"smiles": "CC(C)(O)c1cccc(N)n1"
},
"smiles": "CC(C)(O)c1cccc(N)n1",
"reactionStepId": "sa_ace46caf19c0c8fbfda668ab",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20130178478A1;0464;1391292\",\"rsmi\":\"Br[c:7]1[n:6][c:5]([C:2]([CH3:1])([CH3:3])[OH:4])[cH:11][cH:10][cH:9]1.[NH3:8]>CN(C)CCN.O=C(O)O.O=[CuH].OCCO.[K+].[K+].O>[CH3:1][C:2]([CH3:3])([OH:4])[c:5]1[n:6][c:7]([NH2:8])[cH:9][cH:10][cH:11]1\"},\"mapped_reaction_smiles\":\"Br[c:7]1[n:6][c:5]([C:2]([CH3:1])([CH3:3])[OH:4])[cH:11][cH:10][cH:9]1.[NH3:8]>CN(C)CCN.O=C(O)O.O=[CuH].OCCO.[K+].[K+].O>[CH3:1][C:2]([CH3:3])([OH:4])[c:5]1[n:6][c:7]([NH2:8])[cH:9][cH:10][cH:11]1\"}",
"reactionStep": {
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"reactionHash": "e0bcc4b745df0aed06f6dc95d3c0e46b6dd3e6a5b5012346e8ffe96a4061831e"
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"children": [
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"routeId": "sa_197967e0702c5f3d2c78aeca",
"moleculeId": "sa_1d99ef4be6fc3bd84b9652bd",
"parentId": "4394",
"isLeaf": false,
"molecule": {
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"inchikey": "OXSDDDKLMCHNHF-UHFFFAOYSA-N",
"smiles": "CC(C)(O)c1cccc(Br)n1"
},
"smiles": "CC(C)(O)c1cccc(Br)n1",
"reactionStepId": "sa_98982765bd2d9a665afc47c9",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20130178478A1;0462;1391291\",\"rsmi\":\"Br[c:5]1[n:6][c:7]([Br:8])[cH:9][cH:10][cH:11]1.[CH3:1][C:2]([CH3:3])=[O:4]>C1CCOC1.CCCCCC.O=C=O.Cl.N>[CH3:1][C:2]([CH3:3])([OH:4])[c:5]1[n:6][c:7]([Br:8])[cH:9][cH:10][cH:11]1\"},\"mapped_reaction_smiles\":\"Br[c:5]1[n:6][c:7]([Br:8])[cH:9][cH:10][cH:11]1.[CH3:1][C:2]([CH3:3])=[O:4]>C1CCOC1.CCCCCC.O=C=O.Cl.N>[CH3:1][C:2]([CH3:3])([OH:4])[c:5]1[n:6][c:7]([Br:8])[cH:9][cH:10][cH:11]1\"}",
"reactionStep": {
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"reactionHash": "da577568b6a2e5e1436bd07db05df112f5e168a34683cc4df3f16b4f79421e44"
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"children": [
{
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"moleculeId": "sa_7cde33951f00315079459adb",
"parentId": "4395",
"isLeaf": true,
"molecule": {
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"inchikey": "CSCPPACGZOOCGX-UHFFFAOYSA-N",
"smiles": "CC(C)=O"
},
"smiles": "CC(C)=O",
"reactionStepId": null,
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},
{
"id": "4397",
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"parentId": "4395",
"isLeaf": true,
"molecule": {
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"inchikey": "FEYDZHNIIMENOB-UHFFFAOYSA-N",
"smiles": "Brc1cccc(Br)n1"
},
"smiles": "Brc1cccc(Br)n1",
"reactionStepId": null,
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}
]
},
{
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"molecule": {
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"inchikey": "QGZKDVFQNNGYKY-UHFFFAOYSA-N",
"smiles": "N"
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"smiles": "N",
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}
]
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]
},
{
"id": "4399",
"routeId": "sa_197967e0702c5f3d2c78aeca",
"moleculeId": "sa_c9679fdd876f32f86b77fb69",
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"molecule": {
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"inchikey": "QGZKDVFQNNGYKY-UHFFFAOYSA-N",
"smiles": "N"
},
"smiles": "N",
"reactionStepId": null,
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"children": []
}
]
}
]
}
]
}
}