Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
CCOC(=O)Cc1cccc(-c2ccc(-c3onc(C)c3NC(=O)OC(C)c3ccccc3Cl)cc2)c1
InChiKey
JBDKWZIYWDHNER-UHFFFAOYSA-N
Route Signature
42941050d56d2c6f0be21f2ad6440e94610bd8339ccf8b8c4267ac8d4cba478c
Synthesis route with 4 steps (convergent)
Route tree structure (JSON format)
{
"route": {
"id": "sa_7839560af755b4821aeb98b7",
"signature": "42941050d56d2c6f0be21f2ad6440e94610bd8339ccf8b8c4267ac8d4cba478c",
"contentHash": "d2a24499247c5abfcf308af2e3d25cd31fedd693b785ab71244b95648f85d2a3",
"length": 4,
"isConvergent": true
},
"target": {
"id": "sa_fe912124fd0b48d78cd3708b",
"benchmarkSetId": "3895c2909c53593560c5ba610abc7e6df80513dfd8624165c560451735097d36",
"targetId": "n5-05445",
"moleculeId": "sa_f3d591a05a7c1c9433b86b18",
"smiles": "CCOC(=O)Cc1cccc(-c2ccc(-c3onc(C)c3NC(=O)OC(C)c3ccccc3Cl)cc2)c1",
"routeLength": 4,
"isConvergent": true,
"metadata": null,
"molecule": {
"id": "sa_f3d591a05a7c1c9433b86b18",
"inchikey": "JBDKWZIYWDHNER-UHFFFAOYSA-N",
"smiles": "CCOC(=O)Cc1cccc(-c2ccc(-c3onc(C)c3NC(=O)OC(C)c3ccccc3Cl)cc2)c1"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "2789",
"routeId": "sa_7839560af755b4821aeb98b7",
"moleculeId": "sa_f3d591a05a7c1c9433b86b18",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_f3d591a05a7c1c9433b86b18",
"inchikey": "JBDKWZIYWDHNER-UHFFFAOYSA-N",
"smiles": "CCOC(=O)Cc1cccc(-c2ccc(-c3onc(C)c3NC(=O)OC(C)c3ccccc3Cl)cc2)c1"
},
"smiles": "CCOC(=O)Cc1cccc(-c2ccc(-c3onc(C)c3NC(=O)OC(C)c3ccccc3Cl)cc2)c1",
"reactionStepId": "sa_1fd34ad01611f61277feca1c",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20100152257A1;0259;898480\",\"rsmi\":\"Br[c:11]1[cH:10][cH:9][cH:8][c:7]([CH2:6][C:4]([O:3][CH2:2][CH3:1])=[O:5])[cH:37]1.CC1(C)OB([c:12]2[cH:13][cH:14][c:15](-[c:16]3[c:17]([NH:18][C:19](=[O:20])[O:21][CH:22]([CH3:23])[c:24]4[c:25]([Cl:26])[cH:27][cH:28][cH:29][cH:30]4)[c:31]([CH3:32])[n:33][o:34]3)[cH:35][cH:36]2)OC1(C)C>Cl[Pd]Cl.[Fe+2]>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][c:7]1[cH:8][cH:9][cH:10][c:11](-[c:12]2[cH:13][cH:14][c:15](-[c:16]3[c:17]([NH:18][C:19](=[O:20])[O:21][CH:22]([CH3:23])[c:24]4[c:25]([Cl:26])[cH:27][cH:28][cH:29][cH:30]4)[c:31]([CH3:32])[n:33][o:34]3)[cH:35][cH:36]2)[cH:37]1\"},\"mapped_reaction_smiles\":\"Br[c:11]1[cH:10][cH:9][cH:8][c:7]([CH2:6][C:4]([O:3][CH2:2][CH3:1])=[O:5])[cH:37]1.CC1(C)OB([c:12]2[cH:13][cH:14][c:15](-[c:16]3[c:17]([NH:18][C:19](=[O:20])[O:21][CH:22]([CH3:23])[c:24]4[c:25]([Cl:26])[cH:27][cH:28][cH:29][cH:30]4)[c:31]([CH3:32])[n:33][o:34]3)[cH:35][cH:36]2)OC1(C)C>Cl[Pd]Cl.[Fe+2]>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][c:7]1[cH:8][cH:9][cH:10][c:11](-[c:12]2[cH:13][cH:14][c:15](-[c:16]3[c:17]([NH:18][C:19](=[O:20])[O:21][CH:22]([CH3:23])[c:24]4[c:25]([Cl:26])[cH:27][cH:28][cH:29][cH:30]4)[c:31]([CH3:32])[n:33][o:34]3)[cH:35][cH:36]2)[cH:37]1\"}",
"reactionStep": {
"id": "sa_1fd34ad01611f61277feca1c",
"reactionHash": "33813eb31987781c17b39dcbf9d8f3e9bf172abf6128f0ed5b83b57a48137d36"
},
"children": [
{
"id": "2790",
"routeId": "sa_7839560af755b4821aeb98b7",
"moleculeId": "sa_b178e32e86e3a0f416c512d2",
"parentId": "2789",
"isLeaf": false,
"molecule": {
"id": "sa_b178e32e86e3a0f416c512d2",
"inchikey": "CAERSDJFKGMKLY-UHFFFAOYSA-N",
"smiles": "CCOC(=O)Cc1cccc(Br)c1"
},
"smiles": "CCOC(=O)Cc1cccc(Br)c1",
"reactionStepId": "sa_dfbc4fc9741d09127388a3f1",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20100152257A1;0258;898479\",\"rsmi\":\"O[C:4](=[O:5])[CH2:6][c:7]1[cH:8][c:9]([Br:10])[cH:11][cH:12][cH:13]1.[CH3:1][CH2:2][OH:3]>O=S(=O)(O)O>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][c:7]1[cH:8][c:9]([Br:10])[cH:11][cH:12][cH:13]1\"},\"mapped_reaction_smiles\":\"O[C:4](=[O:5])[CH2:6][c:7]1[cH:8][c:9]([Br:10])[cH:11][cH:12][cH:13]1.[CH3:1][CH2:2][OH:3]>O=S(=O)(O)O>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][c:7]1[cH:8][c:9]([Br:10])[cH:11][cH:12][cH:13]1\"}",
"reactionStep": {
"id": "sa_dfbc4fc9741d09127388a3f1",
"reactionHash": "5bfb2f14f8f56c5103b1f5e902f1bb8aa3c4b9fd2d502bb88c63828af70af4b5"
},
"children": [
{
"id": "2791",
"routeId": "sa_7839560af755b4821aeb98b7",
"moleculeId": "sa_ecb888028ea09776b81a8f8f",
"parentId": "2790",
"isLeaf": true,
"molecule": {
"id": "sa_ecb888028ea09776b81a8f8f",
"inchikey": "KYNNBXCGXUOREX-UHFFFAOYSA-N",
"smiles": "O=C(O)Cc1cccc(Br)c1"
},
"smiles": "O=C(O)Cc1cccc(Br)c1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "2792",
"routeId": "sa_7839560af755b4821aeb98b7",
"moleculeId": "sa_afaca116b303dc7d01346819",
"parentId": "2790",
"isLeaf": true,
"molecule": {
"id": "sa_afaca116b303dc7d01346819",
"inchikey": "LFQSCWFLJHTTHZ-UHFFFAOYSA-N",
"smiles": "CCO"
},
"smiles": "CCO",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
},
{
"id": "2793",
"routeId": "sa_7839560af755b4821aeb98b7",
"moleculeId": "sa_b86c6c25b8269a773cfdd5fe",
"parentId": "2789",
"isLeaf": false,
"molecule": {
"id": "sa_b86c6c25b8269a773cfdd5fe",
"inchikey": "FMUYWQAVFBVVLU-UHFFFAOYSA-N",
"smiles": "Cc1noc(-c2ccc(B3OC(C)(C)C(C)(C)O3)cc2)c1NC(=O)OC(C)c1ccccc1Cl"
},
"smiles": "Cc1noc(-c2ccc(B3OC(C)(C)C(C)(C)O3)cc2)c1NC(=O)OC(C)c1ccccc1Cl",
"reactionStepId": "sa_82948e94685e8b9644a4bb61",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20100152257A1;0252;898473\",\"rsmi\":\"Br[c:9]1[cH:8][cH:7][c:6](-[c:5]2[o:4][n:3][c:2]([CH3:1])[c:21]2[NH:22][C:23](=[O:24])[O:25][CH:26]([CH3:27])[c:28]2[c:29]([Cl:30])[cH:31][cH:32][cH:33][cH:34]2)[cH:20][cH:19]1.CC1(C)OB([B:10]2[O:11][C:12]([CH3:13])([CH3:14])[C:15]([CH3:16])([CH3:17])[O:18]2)OC1(C)C>C1COCCO1.CC(=O)O.Cl[Pd]Cl.O.[Fe+2].[K+]>[CH3:1][c:2]1[n:3][o:4][c:5](-[c:6]2[cH:7][cH:8][c:9]([B:10]3[O:11][C:12]([CH3:13])([CH3:14])[C:15]([CH3:16])([CH3:17])[O:18]3)[cH:19][cH:20]2)[c:21]1[NH:22][C:23](=[O:24])[O:25][CH:26]([CH3:27])[c:28]1[c:29]([Cl:30])[cH:31][cH:32][cH:33][cH:34]1\"},\"mapped_reaction_smiles\":\"Br[c:9]1[cH:8][cH:7][c:6](-[c:5]2[o:4][n:3][c:2]([CH3:1])[c:21]2[NH:22][C:23](=[O:24])[O:25][CH:26]([CH3:27])[c:28]2[c:29]([Cl:30])[cH:31][cH:32][cH:33][cH:34]2)[cH:20][cH:19]1.CC1(C)OB([B:10]2[O:11][C:12]([CH3:13])([CH3:14])[C:15]([CH3:16])([CH3:17])[O:18]2)OC1(C)C>C1COCCO1.CC(=O)O.Cl[Pd]Cl.O.[Fe+2].[K+]>[CH3:1][c:2]1[n:3][o:4][c:5](-[c:6]2[cH:7][cH:8][c:9]([B:10]3[O:11][C:12]([CH3:13])([CH3:14])[C:15]([CH3:16])([CH3:17])[O:18]3)[cH:19][cH:20]2)[c:21]1[NH:22][C:23](=[O:24])[O:25][CH:26]([CH3:27])[c:28]1[c:29]([Cl:30])[cH:31][cH:32][cH:33][cH:34]1\"}",
"reactionStep": {
"id": "sa_82948e94685e8b9644a4bb61",
"reactionHash": "09f37782b10a85310a0d0b062933bd7b6ef69c36dced8b1a3be84671eb12d1ad"
},
"children": [
{
"id": "2794",
"routeId": "sa_7839560af755b4821aeb98b7",
"moleculeId": "sa_e6c301388ac142801d4af5a2",
"parentId": "2793",
"isLeaf": true,
"molecule": {
"id": "sa_e6c301388ac142801d4af5a2",
"inchikey": "IPWKHHSGDUIRAH-UHFFFAOYSA-N",
"smiles": "CC1(C)OB(B2OC(C)(C)C(C)(C)O2)OC1(C)C"
},
"smiles": "CC1(C)OB(B2OC(C)(C)C(C)(C)O2)OC1(C)C",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "2795",
"routeId": "sa_7839560af755b4821aeb98b7",
"moleculeId": "sa_fca1f3bacdec0a3e17f30179",
"parentId": "2793",
"isLeaf": false,
"molecule": {
"id": "sa_fca1f3bacdec0a3e17f30179",
"inchikey": "ZUWQMMFXMFXJEY-UHFFFAOYSA-N",
"smiles": "Cc1noc(-c2ccc(Br)cc2)c1NC(=O)OC(C)c1ccccc1Cl"
},
"smiles": "Cc1noc(-c2ccc(Br)cc2)c1NC(=O)OC(C)c1ccccc1Cl",
"reactionStepId": "sa_8d274465e87e5e6fafc3730e",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20100152257A1;0249;898470\",\"rsmi\":\"O[C:15]([c:13]1[c:2]([CH3:1])[n:3][o:4][c:5]1-[c:6]1[cH:7][cH:8][c:9]([Br:10])[cH:11][cH:12]1)=[O:16].[N-]=[N+]=[N:14]P(=O)(c1ccccc1)c1ccccc1.[OH:17][CH:18]([CH3:19])[c:20]1[c:21]([Cl:22])[cH:23][cH:24][cH:25][cH:26]1>CCN(CC)CC.CCOC(C)=O.Cc1ccccc1>[CH3:1][c:2]1[n:3][o:4][c:5](-[c:6]2[cH:7][cH:8][c:9]([Br:10])[cH:11][cH:12]2)[c:13]1[NH:14][C:15](=[O:16])[O:17][CH:18]([CH3:19])[c:20]1[c:21]([Cl:22])[cH:23][cH:24][cH:25][cH:26]1\"},\"mapped_reaction_smiles\":\"O[C:15]([c:13]1[c:2]([CH3:1])[n:3][o:4][c:5]1-[c:6]1[cH:7][cH:8][c:9]([Br:10])[cH:11][cH:12]1)=[O:16].[N-]=[N+]=[N:14]P(=O)(c1ccccc1)c1ccccc1.[OH:17][CH:18]([CH3:19])[c:20]1[c:21]([Cl:22])[cH:23][cH:24][cH:25][cH:26]1>CCN(CC)CC.CCOC(C)=O.Cc1ccccc1>[CH3:1][c:2]1[n:3][o:4][c:5](-[c:6]2[cH:7][cH:8][c:9]([Br:10])[cH:11][cH:12]2)[c:13]1[NH:14][C:15](=[O:16])[O:17][CH:18]([CH3:19])[c:20]1[c:21]([Cl:22])[cH:23][cH:24][cH:25][cH:26]1\"}",
"reactionStep": {
"id": "sa_8d274465e87e5e6fafc3730e",
"reactionHash": "42a6ab4d4ad3729af705c299a0a766e88d4185acfd223ad74b671775e80083e7"
},
"children": [
{
"id": "2796",
"routeId": "sa_7839560af755b4821aeb98b7",
"moleculeId": "sa_e78c1c06854ca6aedd57e275",
"parentId": "2795",
"isLeaf": true,
"molecule": {
"id": "sa_e78c1c06854ca6aedd57e275",
"inchikey": "DDUBOVLGCYUYFX-UHFFFAOYSA-N",
"smiles": "CC(O)c1ccccc1Cl"
},
"smiles": "CC(O)c1ccccc1Cl",
"reactionStepId": null,
"template": null,
"metadata": null,
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"children": []
},
{
"id": "2797",
"routeId": "sa_7839560af755b4821aeb98b7",
"moleculeId": "sa_062a6f2c2748d6688da1dc5e",
"parentId": "2795",
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"molecule": {
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"inchikey": "GFLKZFOUAHOGJF-UHFFFAOYSA-N",
"smiles": "Cc1noc(-c2ccc(Br)cc2)c1C(=O)O"
},
"smiles": "Cc1noc(-c2ccc(Br)cc2)c1C(=O)O",
"reactionStepId": "sa_7f591136601c708e2bacb2e8",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20100152257A1;0234;898463\",\"rsmi\":\"C[O:16][C:14]([c:13]1[c:2]([CH3:1])[n:3][o:4][c:5]1-[c:6]1[cH:7][cH:8][c:9]([Br:10])[cH:11][cH:12]1)=[O:15]>CO.O.[Li+].O>[CH3:1][c:2]1[n:3][o:4][c:5](-[c:6]2[cH:7][cH:8][c:9]([Br:10])[cH:11][cH:12]2)[c:13]1[C:14](=[O:15])[OH:16]\"},\"mapped_reaction_smiles\":\"C[O:16][C:14]([c:13]1[c:2]([CH3:1])[n:3][o:4][c:5]1-[c:6]1[cH:7][cH:8][c:9]([Br:10])[cH:11][cH:12]1)=[O:15]>CO.O.[Li+].O>[CH3:1][c:2]1[n:3][o:4][c:5](-[c:6]2[cH:7][cH:8][c:9]([Br:10])[cH:11][cH:12]2)[c:13]1[C:14](=[O:15])[OH:16]\"}",
"reactionStep": {
"id": "sa_7f591136601c708e2bacb2e8",
"reactionHash": "201c2b499b6a3414478a716aeed26e4070f413b77bb86096be3574bad8408b4d"
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"children": [
{
"id": "2798",
"routeId": "sa_7839560af755b4821aeb98b7",
"moleculeId": "sa_6b8769c3f3913f5ef2cdffcf",
"parentId": "2797",
"isLeaf": true,
"molecule": {
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"inchikey": "YVWJQDKQALEQHO-UHFFFAOYSA-N",
"smiles": "COC(=O)c1c(C)noc1-c1ccc(Br)cc1"
},
"smiles": "COC(=O)c1c(C)noc1-c1ccc(Br)cc1",
"reactionStepId": null,
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}
]
},
{
"id": "2799",
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"molecule": {
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"inchikey": "MKRTXPORKIRPDG-UHFFFAOYSA-N",
"smiles": "[N-]=[N+]=NP(=O)(c1ccccc1)c1ccccc1"
},
"smiles": "[N-]=[N+]=NP(=O)(c1ccccc1)c1ccccc1",
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}
]
}
]
}
]
}
}