Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
COc1ccc2ncc(=O)n(CCCCNC3CC(=O)N(c4ccc5c(c4)NC(=O)CO5)C3)c2c1
InChiKey
ZKNHOWVOIGRIJM-UHFFFAOYSA-N
Route Signature
f5d35df704946ee16002932514c9d54f214d9a33f9c3d32ff6a304238f7a0a20
Synthesis route with 4 steps (convergent)
Route tree structure (JSON format)
{
"route": {
"id": "sa_1fd79ba00328f01dc4313198",
"signature": "f5d35df704946ee16002932514c9d54f214d9a33f9c3d32ff6a304238f7a0a20",
"contentHash": "6409adf17c4b961a626b2a22b009fff361d92b0f098da46c239968f8f9ad1698",
"length": 4,
"isConvergent": true
},
"target": {
"id": "sa_58ba03b7d795d6915a88d9b3",
"benchmarkSetId": "3895c2909c53593560c5ba610abc7e6df80513dfd8624165c560451735097d36",
"targetId": "n5-02168",
"moleculeId": "sa_59ac0d3796caf6f7f4bf0578",
"smiles": "COc1ccc2ncc(=O)n(CCCCNC3CC(=O)N(c4ccc5c(c4)NC(=O)CO5)C3)c2c1",
"routeLength": 4,
"isConvergent": true,
"metadata": null,
"molecule": {
"id": "sa_59ac0d3796caf6f7f4bf0578",
"inchikey": "ZKNHOWVOIGRIJM-UHFFFAOYSA-N",
"smiles": "COc1ccc2ncc(=O)n(CCCCNC3CC(=O)N(c4ccc5c(c4)NC(=O)CO5)C3)c2c1"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "10647",
"routeId": "sa_1fd79ba00328f01dc4313198",
"moleculeId": "sa_59ac0d3796caf6f7f4bf0578",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_59ac0d3796caf6f7f4bf0578",
"inchikey": "ZKNHOWVOIGRIJM-UHFFFAOYSA-N",
"smiles": "COc1ccc2ncc(=O)n(CCCCNC3CC(=O)N(c4ccc5c(c4)NC(=O)CO5)C3)c2c1"
},
"smiles": "COc1ccc2ncc(=O)n(CCCCNC3CC(=O)N(c4ccc5c(c4)NC(=O)CO5)C3)c2c1",
"reactionStepId": "sa_31873deb3f5ff244f85b9e4c",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20140187542A1;0204;1545964\",\"rsmi\":\"O=[CH:15][CH2:14][CH2:13][CH2:12][n:11]1[c:9](=[O:10])[cH:8][n:7][c:6]2[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:35][c:34]21.[NH2:16][CH:17]1[CH2:18][C:19](=[O:20])[N:21]([c:22]2[cH:23][c:24]3[c:25]([cH:26][cH:27]2)[O:28][CH2:29][C:30](=[O:31])[NH:32]3)[CH2:33]1>CC(=O)OB(OC(C)=O)OC(C)=O.CO.ClC(Cl)Cl.[Na+]>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[n:7][cH:8][c:9](=[O:10])[n:11]([CH2:12][CH2:13][CH2:14][CH2:15][NH:16][CH:17]3[CH2:18][C:19](=[O:20])[N:21]([c:22]4[cH:23][c:24]5[c:25]([cH:26][cH:27]4)[O:28][CH2:29][C:30](=[O:31])[NH:32]5)[CH2:33]3)[c:34]2[cH:35]1\"},\"mapped_reaction_smiles\":\"O=[CH:15][CH2:14][CH2:13][CH2:12][n:11]1[c:9](=[O:10])[cH:8][n:7][c:6]2[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:35][c:34]21.[NH2:16][CH:17]1[CH2:18][C:19](=[O:20])[N:21]([c:22]2[cH:23][c:24]3[c:25]([cH:26][cH:27]2)[O:28][CH2:29][C:30](=[O:31])[NH:32]3)[CH2:33]1>CC(=O)OB(OC(C)=O)OC(C)=O.CO.ClC(Cl)Cl.[Na+]>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[n:7][cH:8][c:9](=[O:10])[n:11]([CH2:12][CH2:13][CH2:14][CH2:15][NH:16][CH:17]3[CH2:18][C:19](=[O:20])[N:21]([c:22]4[cH:23][c:24]5[c:25]([cH:26][cH:27]4)[O:28][CH2:29][C:30](=[O:31])[NH:32]5)[CH2:33]3)[c:34]2[cH:35]1\"}",
"reactionStep": {
"id": "sa_31873deb3f5ff244f85b9e4c",
"reactionHash": "7f6e8d9e90e08ce01c1539c4a7f63b600da2fe85ea23e8de799e55632cdc4d10"
},
"children": [
{
"id": "10648",
"routeId": "sa_1fd79ba00328f01dc4313198",
"moleculeId": "sa_2cb25fc5509498f6677cda2f",
"parentId": "10647",
"isLeaf": false,
"molecule": {
"id": "sa_2cb25fc5509498f6677cda2f",
"inchikey": "UPKTUGQOHDITIM-UHFFFAOYSA-N",
"smiles": "NC1CC(=O)N(c2ccc3c(c2)NC(=O)CO3)C1"
},
"smiles": "NC1CC(=O)N(c2ccc3c(c2)NC(=O)CO3)C1",
"reactionStepId": "sa_a3568379b5f33ff19997568f",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20140187542A1;0200;1545963\",\"rsmi\":\"CC(C)(C)OC(=O)[NH:1][CH:2]1[CH2:3][C:4](=[O:5])[N:6]([c:7]2[cH:8][c:9]3[c:10]([cH:11][cH:12]2)[O:13][CH2:14][C:15](=[O:16])[NH:17]3)[CH2:18]1>ClCCl.O=C(O)C(F)(F)F>[NH2:1][CH:2]1[CH2:3][C:4](=[O:5])[N:6]([c:7]2[cH:8][c:9]3[c:10]([cH:11][cH:12]2)[O:13][CH2:14][C:15](=[O:16])[NH:17]3)[CH2:18]1\"},\"mapped_reaction_smiles\":\"CC(C)(C)OC(=O)[NH:1][CH:2]1[CH2:3][C:4](=[O:5])[N:6]([c:7]2[cH:8][c:9]3[c:10]([cH:11][cH:12]2)[O:13][CH2:14][C:15](=[O:16])[NH:17]3)[CH2:18]1>ClCCl.O=C(O)C(F)(F)F>[NH2:1][CH:2]1[CH2:3][C:4](=[O:5])[N:6]([c:7]2[cH:8][c:9]3[c:10]([cH:11][cH:12]2)[O:13][CH2:14][C:15](=[O:16])[NH:17]3)[CH2:18]1\"}",
"reactionStep": {
"id": "sa_a3568379b5f33ff19997568f",
"reactionHash": "683e15ff90e8f4f07bfe61f2bcbcb951de7a7cb91b8626a6cec4a92d21bf102c"
},
"children": [
{
"id": "10649",
"routeId": "sa_1fd79ba00328f01dc4313198",
"moleculeId": "sa_ff82deedbf97bbbefd620ba1",
"parentId": "10648",
"isLeaf": true,
"molecule": {
"id": "sa_ff82deedbf97bbbefd620ba1",
"inchikey": "BANLWOQJUXCYQV-UHFFFAOYSA-N",
"smiles": "CC(C)(C)OC(=O)NC1CC(=O)N(c2ccc3c(c2)NC(=O)CO3)C1"
},
"smiles": "CC(C)(C)OC(=O)NC1CC(=O)N(c2ccc3c(c2)NC(=O)CO3)C1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
},
{
"id": "10650",
"routeId": "sa_1fd79ba00328f01dc4313198",
"moleculeId": "sa_bf168e19b882dafa9e249dc8",
"parentId": "10647",
"isLeaf": false,
"molecule": {
"id": "sa_bf168e19b882dafa9e249dc8",
"inchikey": "WGNZSCOMXPLYNJ-UHFFFAOYSA-N",
"smiles": "COc1ccc2ncc(=O)n(CCCC=O)c2c1"
},
"smiles": "COc1ccc2ncc(=O)n(CCCC=O)c2c1",
"reactionStepId": "sa_fc526162e2f8d3daeb024b56",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20140187542A1;0188;1545960\",\"rsmi\":\"[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[n:7][cH:8][c:9](=[O:10])[n:11]([CH2:12][CH2:13][CH2:14][CH2:15][OH:16])[c:17]2[cH:18]1>CCN(CC)CC.CS(C)=O.ClCCl.O=C(Cl)C(=O)Cl.Cl.N>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[n:7][cH:8][c:9](=[O:10])[n:11]([CH2:12][CH2:13][CH2:14][CH:15]=[O:16])[c:17]2[cH:18]1\"},\"mapped_reaction_smiles\":\"[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[n:7][cH:8][c:9](=[O:10])[n:11]([CH2:12][CH2:13][CH2:14][CH2:15][OH:16])[c:17]2[cH:18]1>CCN(CC)CC.CS(C)=O.ClCCl.O=C(Cl)C(=O)Cl.Cl.N>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[n:7][cH:8][c:9](=[O:10])[n:11]([CH2:12][CH2:13][CH2:14][CH:15]=[O:16])[c:17]2[cH:18]1\"}",
"reactionStep": {
"id": "sa_fc526162e2f8d3daeb024b56",
"reactionHash": "553d375a3795258c46b6e7b137a465c0d8e80d555fa3bca4d3edf65123676cbc"
},
"children": [
{
"id": "10651",
"routeId": "sa_1fd79ba00328f01dc4313198",
"moleculeId": "sa_5a4984e03dca95f17ec01eca",
"parentId": "10650",
"isLeaf": false,
"molecule": {
"id": "sa_5a4984e03dca95f17ec01eca",
"inchikey": "XOEHPXUPSNAJHV-UHFFFAOYSA-N",
"smiles": "COc1ccc2ncc(=O)n(CCCCO)c2c1"
},
"smiles": "COc1ccc2ncc(=O)n(CCCCO)c2c1",
"reactionStepId": "sa_89540260a38e6758ae117f73",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20140187542A1;0184;1545959\",\"rsmi\":\"CC(C)(C)[Si](C)(C)[O:16][CH2:15][CH2:14][CH2:13][CH2:12][n:11]1[c:9](=[O:10])[cH:8][n:7][c:6]2[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:18][c:17]21>C1CCOC1.CCCC[N+](CCCC)(CCCC)CCCC.CCOC(C)=O.F>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[n:7][cH:8][c:9](=[O:10])[n:11]([CH2:12][CH2:13][CH2:14][CH2:15][OH:16])[c:17]2[cH:18]1\"},\"mapped_reaction_smiles\":\"CC(C)(C)[Si](C)(C)[O:16][CH2:15][CH2:14][CH2:13][CH2:12][n:11]1[c:9](=[O:10])[cH:8][n:7][c:6]2[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:18][c:17]21>C1CCOC1.CCCC[N+](CCCC)(CCCC)CCCC.CCOC(C)=O.F>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[n:7][cH:8][c:9](=[O:10])[n:11]([CH2:12][CH2:13][CH2:14][CH2:15][OH:16])[c:17]2[cH:18]1\"}",
"reactionStep": {
"id": "sa_89540260a38e6758ae117f73",
"reactionHash": "d8a4f11a4c42e5f4a06ec22ff6772fb4d0f4eb683828877dea4dd48da1d06e3b"
},
"children": [
{
"id": "10652",
"routeId": "sa_1fd79ba00328f01dc4313198",
"moleculeId": "sa_dba952d134e65ee997a0cd43",
"parentId": "10651",
"isLeaf": false,
"molecule": {
"id": "sa_dba952d134e65ee997a0cd43",
"inchikey": "RDIPOELZNDQDKR-UHFFFAOYSA-N",
"smiles": "COc1ccc2ncc(=O)n(CCCCO[Si](C)(C)C(C)(C)C)c2c1"
},
"smiles": "COc1ccc2ncc(=O)n(CCCCO[Si](C)(C)C(C)(C)C)c2c1",
"reactionStepId": "sa_ef491aec90aca10c68f29440",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20140187542A1;0180;1545958\",\"rsmi\":\"Br[CH2:12][CH2:13][CH2:14][CH2:15][O:16][Si:17]([CH3:18])([CH3:19])[C:20]([CH3:21])([CH3:22])[CH3:23].[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[n:7][cH:8][c:9](=[O:10])[nH:11][c:24]2[cH:25]1>CCOC(C)=O.CN(C)C=O.[HH].I.[Li+].[Na+]>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[n:7][cH:8][c:9](=[O:10])[n:11]([CH2:12][CH2:13][CH2:14][CH2:15][O:16][Si:17]([CH3:18])([CH3:19])[C:20]([CH3:21])([CH3:22])[CH3:23])[c:24]2[cH:25]1\"},\"mapped_reaction_smiles\":\"Br[CH2:12][CH2:13][CH2:14][CH2:15][O:16][Si:17]([CH3:18])([CH3:19])[C:20]([CH3:21])([CH3:22])[CH3:23].[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[n:7][cH:8][c:9](=[O:10])[nH:11][c:24]2[cH:25]1>CCOC(C)=O.CN(C)C=O.[HH].I.[Li+].[Na+]>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[n:7][cH:8][c:9](=[O:10])[n:11]([CH2:12][CH2:13][CH2:14][CH2:15][O:16][Si:17]([CH3:18])([CH3:19])[C:20]([CH3:21])([CH3:22])[CH3:23])[c:24]2[cH:25]1\"}",
"reactionStep": {
"id": "sa_ef491aec90aca10c68f29440",
"reactionHash": "e44b1150b4511baa03cf37365fcc72103832c58a39b15fe1034126f5c752da3e"
},
"children": [
{
"id": "10653",
"routeId": "sa_1fd79ba00328f01dc4313198",
"moleculeId": "sa_01aab14e6a4602ae6232d6bd",
"parentId": "10652",
"isLeaf": true,
"molecule": {
"id": "sa_01aab14e6a4602ae6232d6bd",
"inchikey": "GVERQUMLAYWTMA-UHFFFAOYSA-N",
"smiles": "COc1ccc2ncc(=O)[nH]c2c1"
},
"smiles": "COc1ccc2ncc(=O)[nH]c2c1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "10654",
"routeId": "sa_1fd79ba00328f01dc4313198",
"moleculeId": "sa_5601f4aa7e8f15c267098b5a",
"parentId": "10652",
"isLeaf": true,
"molecule": {
"id": "sa_5601f4aa7e8f15c267098b5a",
"inchikey": "YORLKVKBZRVNMZ-UHFFFAOYSA-N",
"smiles": "CC(C)(C)[Si](C)(C)OCCCCBr"
},
"smiles": "CC(C)(C)[Si](C)(C)OCCCCBr",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
}
]
}
]
}
]
}
}