Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
CCCCc1nnc(OC[C@@H]2CN(C(=O)OC(C)(C)C)CC[C@@H]2OC)cc1-c1ccc(OC2CCCCC2)cc1
InChiKey
SLZOSHAUNMMJFD-OUTSHDOLSA-N
Route Signature
291153dcec4b0f49aef9358e38d4c3da648ecd7e4f9067d5e35ef6b97fe56b83
Synthesis route with 4 steps (convergent)
Route tree structure (JSON format)
{
"route": {
"id": "sa_24c1f3be9b10c39af6560b3d",
"signature": "291153dcec4b0f49aef9358e38d4c3da648ecd7e4f9067d5e35ef6b97fe56b83",
"contentHash": "fa2da81807163320198928c28a23559499786ed73f79733250ca883d6e205be9",
"length": 4,
"isConvergent": true
},
"target": {
"id": "sa_052e6b4732b97c564d9aee6c",
"benchmarkSetId": "3895c2909c53593560c5ba610abc7e6df80513dfd8624165c560451735097d36",
"targetId": "n5-06431",
"moleculeId": "sa_ecf10d24f0213431ea20a807",
"smiles": "CCCCc1nnc(OC[C@@H]2CN(C(=O)OC(C)(C)C)CC[C@@H]2OC)cc1-c1ccc(OC2CCCCC2)cc1",
"routeLength": 4,
"isConvergent": true,
"metadata": null,
"molecule": {
"id": "sa_ecf10d24f0213431ea20a807",
"inchikey": "SLZOSHAUNMMJFD-OUTSHDOLSA-N",
"smiles": "CCCCc1nnc(OC[C@@H]2CN(C(=O)OC(C)(C)C)CC[C@@H]2OC)cc1-c1ccc(OC2CCCCC2)cc1"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "11595",
"routeId": "sa_24c1f3be9b10c39af6560b3d",
"moleculeId": "sa_ecf10d24f0213431ea20a807",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_ecf10d24f0213431ea20a807",
"inchikey": "SLZOSHAUNMMJFD-OUTSHDOLSA-N",
"smiles": "CCCCc1nnc(OC[C@@H]2CN(C(=O)OC(C)(C)C)CC[C@@H]2OC)cc1-c1ccc(OC2CCCCC2)cc1"
},
"smiles": "CCCCc1nnc(OC[C@@H]2CN(C(=O)OC(C)(C)C)CC[C@@H]2OC)cc1-c1ccc(OC2CCCCC2)cc1",
"reactionStepId": "sa_17a7c8005d20c92d051ea233",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20110230458A1;0499;1106462\",\"rsmi\":\"I[CH3:38].[CH3:1][CH2:2][CH2:3][CH2:4][c:5]1[c:6](-[c:7]2[cH:8][cH:9][c:10]([O:11][CH:12]3[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17]3)[cH:18][cH:19]2)[cH:20][c:21]([O:22][CH2:23][C@@H:24]2[CH2:25][N:26]([C:27](=[O:28])[O:29][C:30]([CH3:31])([CH3:32])[CH3:33])[CH2:34][CH2:35][C@@H:36]2[OH:37])[n:39][n:40]1>CCOC(C)=O.CN(C)C=O.[HH].[Na+]>[CH3:1][CH2:2][CH2:3][CH2:4][c:5]1[c:6](-[c:7]2[cH:8][cH:9][c:10]([O:11][CH:12]3[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17]3)[cH:18][cH:19]2)[cH:20][c:21]([O:22][CH2:23][C@@H:24]2[CH2:25][N:26]([C:27](=[O:28])[O:29][C:30]([CH3:31])([CH3:32])[CH3:33])[CH2:34][CH2:35][C@@H:36]2[O:37][CH3:38])[n:39][n:40]1\"},\"mapped_reaction_smiles\":\"I[CH3:38].[CH3:1][CH2:2][CH2:3][CH2:4][c:5]1[c:6](-[c:7]2[cH:8][cH:9][c:10]([O:11][CH:12]3[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17]3)[cH:18][cH:19]2)[cH:20][c:21]([O:22][CH2:23][C@@H:24]2[CH2:25][N:26]([C:27](=[O:28])[O:29][C:30]([CH3:31])([CH3:32])[CH3:33])[CH2:34][CH2:35][C@@H:36]2[OH:37])[n:39][n:40]1>CCOC(C)=O.CN(C)C=O.[HH].[Na+]>[CH3:1][CH2:2][CH2:3][CH2:4][c:5]1[c:6](-[c:7]2[cH:8][cH:9][c:10]([O:11][CH:12]3[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17]3)[cH:18][cH:19]2)[cH:20][c:21]([O:22][CH2:23][C@@H:24]2[CH2:25][N:26]([C:27](=[O:28])[O:29][C:30]([CH3:31])([CH3:32])[CH3:33])[CH2:34][CH2:35][C@@H:36]2[O:37][CH3:38])[n:39][n:40]1\"}",
"reactionStep": {
"id": "sa_17a7c8005d20c92d051ea233",
"reactionHash": "3ecbd78b860f0ece4a551c6db083026492ce845e60dfe0aa75923a31b786d131"
},
"children": [
{
"id": "11596",
"routeId": "sa_24c1f3be9b10c39af6560b3d",
"moleculeId": "sa_82fdccf7d1cc329c9db73f21",
"parentId": "11595",
"isLeaf": true,
"molecule": {
"id": "sa_82fdccf7d1cc329c9db73f21",
"inchikey": "INQOMBQAUSQDDS-UHFFFAOYSA-N",
"smiles": "CI"
},
"smiles": "CI",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "11597",
"routeId": "sa_24c1f3be9b10c39af6560b3d",
"moleculeId": "sa_fd108708368ba9ae31534faa",
"parentId": "11595",
"isLeaf": false,
"molecule": {
"id": "sa_fd108708368ba9ae31534faa",
"inchikey": "MUXKSANAZXVFDA-FIPFOOKPSA-N",
"smiles": "CCCCc1nnc(OC[C@@H]2CN(C(=O)OC(C)(C)C)CC[C@@H]2O)cc1-c1ccc(OC2CCCCC2)cc1"
},
"smiles": "CCCCc1nnc(OC[C@@H]2CN(C(=O)OC(C)(C)C)CC[C@@H]2O)cc1-c1ccc(OC2CCCCC2)cc1",
"reactionStepId": "sa_baec7ace02310ba3bbfcacc6",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20110230458A1;0496;1106459\",\"rsmi\":\"COC[O:37][C@@H:36]1[C@H:24]([CH2:23][O:22][c:21]2[cH:20][c:6](-[c:7]3[cH:8][cH:9][c:10]([O:11][CH:12]4[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17]4)[cH:18][cH:19]3)[c:5]([CH2:4][CH2:3][CH2:2][CH3:1])[n:39][n:38]2)[CH2:25][N:26]([C:27](=[O:28])[O:29][C:30]([CH3:31])([CH3:32])[CH3:33])[CH2:34][CH2:35]1>C1COCCO1.CO.Cl.ClCCl>[CH3:1][CH2:2][CH2:3][CH2:4][c:5]1[c:6](-[c:7]2[cH:8][cH:9][c:10]([O:11][CH:12]3[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17]3)[cH:18][cH:19]2)[cH:20][c:21]([O:22][CH2:23][C@@H:24]2[CH2:25][N:26]([C:27](=[O:28])[O:29][C:30]([CH3:31])([CH3:32])[CH3:33])[CH2:34][CH2:35][C@@H:36]2[OH:37])[n:38][n:39]1\"},\"mapped_reaction_smiles\":\"COC[O:37][C@@H:36]1[C@H:24]([CH2:23][O:22][c:21]2[cH:20][c:6](-[c:7]3[cH:8][cH:9][c:10]([O:11][CH:12]4[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17]4)[cH:18][cH:19]3)[c:5]([CH2:4][CH2:3][CH2:2][CH3:1])[n:39][n:38]2)[CH2:25][N:26]([C:27](=[O:28])[O:29][C:30]([CH3:31])([CH3:32])[CH3:33])[CH2:34][CH2:35]1>C1COCCO1.CO.Cl.ClCCl>[CH3:1][CH2:2][CH2:3][CH2:4][c:5]1[c:6](-[c:7]2[cH:8][cH:9][c:10]([O:11][CH:12]3[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17]3)[cH:18][cH:19]2)[cH:20][c:21]([O:22][CH2:23][C@@H:24]2[CH2:25][N:26]([C:27](=[O:28])[O:29][C:30]([CH3:31])([CH3:32])[CH3:33])[CH2:34][CH2:35][C@@H:36]2[OH:37])[n:38][n:39]1\"}",
"reactionStep": {
"id": "sa_baec7ace02310ba3bbfcacc6",
"reactionHash": "28ce2a330fbaf5534e5873aa2ae61aa6b6fa7957510ab54555846d59bd34fb86"
},
"children": [
{
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"moleculeId": "sa_aa2c90ff23b65c047283f78c",
"parentId": "11597",
"isLeaf": false,
"molecule": {
"id": "sa_aa2c90ff23b65c047283f78c",
"inchikey": "NZWQGZLBSSHJFC-QCDSWUKFSA-N",
"smiles": "CCCCc1nnc(OC[C@@H]2CN(C(=O)OC(C)(C)C)CC[C@@H]2OCOC)cc1-c1ccc(OC2CCCCC2)cc1"
},
"smiles": "CCCCc1nnc(OC[C@@H]2CN(C(=O)OC(C)(C)C)CC[C@@H]2OCOC)cc1-c1ccc(OC2CCCCC2)cc1",
"reactionStepId": "sa_c5711dc966a213ad3cc31831",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20110230458A1;0495;1106458\",\"rsmi\":\"Cl[c:21]1[cH:20][c:6](-[c:7]2[cH:8][cH:9][c:10]([O:11][CH:12]3[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17]3)[cH:18][cH:19]2)[c:5]([CH2:4][CH2:3][CH2:2][CH3:1])[n:42][n:41]1.[OH:22][CH2:23][C@@H:24]1[CH2:25][N:26]([C:27](=[O:28])[O:29][C:30]([CH3:31])([CH3:32])[CH3:33])[CH2:34][CH2:35][C@@H:36]1[O:37][CH2:38][O:39][CH3:40]>C1CCOC1.CCOC(C)=O.CO.[HH].[Na+]>[CH3:1][CH2:2][CH2:3][CH2:4][c:5]1[c:6](-[c:7]2[cH:8][cH:9][c:10]([O:11][CH:12]3[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17]3)[cH:18][cH:19]2)[cH:20][c:21]([O:22][CH2:23][C@@H:24]2[CH2:25][N:26]([C:27](=[O:28])[O:29][C:30]([CH3:31])([CH3:32])[CH3:33])[CH2:34][CH2:35][C@@H:36]2[O:37][CH2:38][O:39][CH3:40])[n:41][n:42]1\"},\"mapped_reaction_smiles\":\"Cl[c:21]1[cH:20][c:6](-[c:7]2[cH:8][cH:9][c:10]([O:11][CH:12]3[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17]3)[cH:18][cH:19]2)[c:5]([CH2:4][CH2:3][CH2:2][CH3:1])[n:42][n:41]1.[OH:22][CH2:23][C@@H:24]1[CH2:25][N:26]([C:27](=[O:28])[O:29][C:30]([CH3:31])([CH3:32])[CH3:33])[CH2:34][CH2:35][C@@H:36]1[O:37][CH2:38][O:39][CH3:40]>C1CCOC1.CCOC(C)=O.CO.[HH].[Na+]>[CH3:1][CH2:2][CH2:3][CH2:4][c:5]1[c:6](-[c:7]2[cH:8][cH:9][c:10]([O:11][CH:12]3[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17]3)[cH:18][cH:19]2)[cH:20][c:21]([O:22][CH2:23][C@@H:24]2[CH2:25][N:26]([C:27](=[O:28])[O:29][C:30]([CH3:31])([CH3:32])[CH3:33])[CH2:34][CH2:35][C@@H:36]2[O:37][CH2:38][O:39][CH3:40])[n:41][n:42]1\"}",
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"children": [
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"routeId": "sa_24c1f3be9b10c39af6560b3d",
"moleculeId": "sa_3376bcaa56573dce11ffa136",
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"molecule": {
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"inchikey": "FHJNWVJPLKNYPR-QWRGUYRKSA-N",
"smiles": "COCO[C@H]1CCN(C(=O)OC(C)(C)C)C[C@H]1CO"
},
"smiles": "COCO[C@H]1CCN(C(=O)OC(C)(C)C)C[C@H]1CO",
"reactionStepId": "sa_32b7675aecb6f53964ca1db1",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20110230458A1;0495;1106457\",\"rsmi\":\"CO[C:18]([C@H:17]1[C@@H:5]([O:4][CH2:3][O:2][CH3:1])[CH2:6][CH2:7][N:8]([C:9](=[O:10])[O:11][C:12]([CH3:13])([CH3:14])[CH3:15])[CH2:16]1)=[O:19]>CCOCC.[Al+3].[HH].[HH].[HH].[HH].[Li+]>[CH3:1][O:2][CH2:3][O:4][C@H:5]1[CH2:6][CH2:7][N:8]([C:9](=[O:10])[O:11][C:12]([CH3:13])([CH3:14])[CH3:15])[CH2:16][C@H:17]1[CH2:18][OH:19]\"},\"mapped_reaction_smiles\":\"CO[C:18]([C@H:17]1[C@@H:5]([O:4][CH2:3][O:2][CH3:1])[CH2:6][CH2:7][N:8]([C:9](=[O:10])[O:11][C:12]([CH3:13])([CH3:14])[CH3:15])[CH2:16]1)=[O:19]>CCOCC.[Al+3].[HH].[HH].[HH].[HH].[Li+]>[CH3:1][O:2][CH2:3][O:4][C@H:5]1[CH2:6][CH2:7][N:8]([C:9](=[O:10])[O:11][C:12]([CH3:13])([CH3:14])[CH3:15])[CH2:16][C@H:17]1[CH2:18][OH:19]\"}",
"reactionStep": {
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"children": [
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"molecule": {
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},
"smiles": "COCO[C@H]1CCN(C(=O)OC(C)(C)C)C[C@H]1C(=O)OC",
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},
{
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"inchikey": "IYLGLHZZHCZGAT-UHFFFAOYSA-N",
"smiles": "CCCCc1nnc(Cl)cc1-c1ccc(OC2CCCCC2)cc1"
},
"smiles": "CCCCc1nnc(Cl)cc1-c1ccc(OC2CCCCC2)cc1",
"reactionStepId": "sa_fae4ff2930ae7b27eb41cb21",
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"metadata": "{\"annotations\":{\"ID\":\"US20110230458A1;0418;1106402\",\"rsmi\":\"O=P(Cl)(Cl)[Cl:22].O=[c:21]1[cH:20][c:6](-[c:7]2[cH:8][cH:9][c:10]([O:11][CH:12]3[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17]3)[cH:18][cH:19]2)[c:5]([CH2:4][CH2:3][CH2:2][CH3:1])[n:24][nH:23]1>>[CH3:1][CH2:2][CH2:3][CH2:4][c:5]1[c:6](-[c:7]2[cH:8][cH:9][c:10]([O:11][CH:12]3[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17]3)[cH:18][cH:19]2)[cH:20][c:21]([Cl:22])[n:23][n:24]1\"},\"mapped_reaction_smiles\":\"O=P(Cl)(Cl)[Cl:22].O=[c:21]1[cH:20][c:6](-[c:7]2[cH:8][cH:9][c:10]([O:11][CH:12]3[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17]3)[cH:18][cH:19]2)[c:5]([CH2:4][CH2:3][CH2:2][CH3:1])[n:24][nH:23]1>>[CH3:1][CH2:2][CH2:3][CH2:4][c:5]1[c:6](-[c:7]2[cH:8][cH:9][c:10]([O:11][CH:12]3[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17]3)[cH:18][cH:19]2)[cH:20][c:21]([Cl:22])[n:23][n:24]1\"}",
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{
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]
}
}