Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
O=C(NO)c1cccc(CC(=O)N(CCO)c2ccccc2)c1
InChiKey
MSFDDWNQFRLDNL-UHFFFAOYSA-N
Route Signature
1e6e0a1e225eaeff6d728b7930b88ebc83a851f281733bc488be874b2ace25cd
Synthesis route with 5 steps (convergent)
Route tree structure (JSON format)
{
"route": {
"id": "sa_70887589f44dab2573aa2a37",
"signature": "1e6e0a1e225eaeff6d728b7930b88ebc83a851f281733bc488be874b2ace25cd",
"contentHash": "ce9e17e9b1affe8994aafdd99c136f76d0a48320f9666b25b212ea582aa95967",
"length": 5,
"isConvergent": true
},
"target": {
"id": "sa_5093d04c9b0432a6c4611ef1",
"benchmarkSetId": "3895c2909c53593560c5ba610abc7e6df80513dfd8624165c560451735097d36",
"targetId": "n5-01399",
"moleculeId": "sa_238ba07141fc7a1049ea3a3a",
"smiles": "O=C(NO)c1cccc(CC(=O)N(CCO)c2ccccc2)c1",
"routeLength": 5,
"isConvergent": true,
"metadata": null,
"molecule": {
"id": "sa_238ba07141fc7a1049ea3a3a",
"inchikey": "MSFDDWNQFRLDNL-UHFFFAOYSA-N",
"smiles": "O=C(NO)c1cccc(CC(=O)N(CCO)c2ccccc2)c1"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "10150",
"routeId": "sa_70887589f44dab2573aa2a37",
"moleculeId": "sa_238ba07141fc7a1049ea3a3a",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_238ba07141fc7a1049ea3a3a",
"inchikey": "MSFDDWNQFRLDNL-UHFFFAOYSA-N",
"smiles": "O=C(NO)c1cccc(CC(=O)N(CCO)c2ccccc2)c1"
},
"smiles": "O=C(NO)c1cccc(CC(=O)N(CCO)c2ccccc2)c1",
"reactionStepId": "sa_47ae1fb39f4f1e05b513dbda",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20140288119A1;0281;1588364\",\"rsmi\":\"CC(C)(C)[Si](C)(C)[O:14][CH2:13][CH2:12][N:11]([C:9]([CH2:8][c:7]1[cH:6][c:5]([C:2](=[O:1])[NH:3][OH:4])[cH:23][cH:22][cH:21]1)=[O:10])[c:15]1[cH:16][cH:17][cH:18][cH:19][cH:20]1>CCO.Cl>[O:1]=[C:2]([NH:3][OH:4])[c:5]1[cH:6][c:7]([CH2:8][C:9](=[O:10])[N:11]([CH2:12][CH2:13][OH:14])[c:15]2[cH:16][cH:17][cH:18][cH:19][cH:20]2)[cH:21][cH:22][cH:23]1\"},\"mapped_reaction_smiles\":\"CC(C)(C)[Si](C)(C)[O:14][CH2:13][CH2:12][N:11]([C:9]([CH2:8][c:7]1[cH:6][c:5]([C:2](=[O:1])[NH:3][OH:4])[cH:23][cH:22][cH:21]1)=[O:10])[c:15]1[cH:16][cH:17][cH:18][cH:19][cH:20]1>CCO.Cl>[O:1]=[C:2]([NH:3][OH:4])[c:5]1[cH:6][c:7]([CH2:8][C:9](=[O:10])[N:11]([CH2:12][CH2:13][OH:14])[c:15]2[cH:16][cH:17][cH:18][cH:19][cH:20]2)[cH:21][cH:22][cH:23]1\"}",
"reactionStep": {
"id": "sa_47ae1fb39f4f1e05b513dbda",
"reactionHash": "fad12e667d2b861e7de6ee18c31662383337e8a7f1f0b74341c9e708a76eed26"
},
"children": [
{
"id": "10151",
"routeId": "sa_70887589f44dab2573aa2a37",
"moleculeId": "sa_a2554c5839ae32e7a294841f",
"parentId": "10150",
"isLeaf": false,
"molecule": {
"id": "sa_a2554c5839ae32e7a294841f",
"inchikey": "VZDKYLYHECVLLJ-UHFFFAOYSA-N",
"smiles": "CC(C)(C)[Si](C)(C)OCCN(C(=O)Cc1cccc(C(=O)NO)c1)c1ccccc1"
},
"smiles": "CC(C)(C)[Si](C)(C)OCCN(C(=O)Cc1cccc(C(=O)NO)c1)c1ccccc1",
"reactionStepId": "sa_e32e291e80ccc9104f4d1072",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20140288119A1;0280;1588363\",\"rsmi\":\"CO[C:20]([c:19]1[cH:18][cH:17][cH:16][c:15]([CH2:14][C:12]([N:11]([CH2:10][CH2:9][O:8][Si:5]([C:2]([CH3:1])([CH3:3])[CH3:4])([CH3:6])[CH3:7])[c:25]2[cH:26][cH:27][cH:28][cH:29][cH:30]2)=[O:13])[cH:24]1)=[O:21].[NH2:22][OH:23]>C1CCOC1.CC(C)O.CO.Cl.ClC(Cl)Cl.C#N.Cl.[K+].N>[CH3:1][C:2]([CH3:3])([CH3:4])[Si:5]([CH3:6])([CH3:7])[O:8][CH2:9][CH2:10][N:11]([C:12](=[O:13])[CH2:14][c:15]1[cH:16][cH:17][cH:18][c:19]([C:20](=[O:21])[NH:22][OH:23])[cH:24]1)[c:25]1[cH:26][cH:27][cH:28][cH:29][cH:30]1\"},\"mapped_reaction_smiles\":\"CO[C:20]([c:19]1[cH:18][cH:17][cH:16][c:15]([CH2:14][C:12]([N:11]([CH2:10][CH2:9][O:8][Si:5]([C:2]([CH3:1])([CH3:3])[CH3:4])([CH3:6])[CH3:7])[c:25]2[cH:26][cH:27][cH:28][cH:29][cH:30]2)=[O:13])[cH:24]1)=[O:21].[NH2:22][OH:23]>C1CCOC1.CC(C)O.CO.Cl.ClC(Cl)Cl.C#N.Cl.[K+].N>[CH3:1][C:2]([CH3:3])([CH3:4])[Si:5]([CH3:6])([CH3:7])[O:8][CH2:9][CH2:10][N:11]([C:12](=[O:13])[CH2:14][c:15]1[cH:16][cH:17][cH:18][c:19]([C:20](=[O:21])[NH:22][OH:23])[cH:24]1)[c:25]1[cH:26][cH:27][cH:28][cH:29][cH:30]1\"}",
"reactionStep": {
"id": "sa_e32e291e80ccc9104f4d1072",
"reactionHash": "c3a316420475a10f2d5963872ed2568ea13706612f61792c04d1d91f173cde04"
},
"children": [
{
"id": "10152",
"routeId": "sa_70887589f44dab2573aa2a37",
"moleculeId": "sa_04a18e3f07bde82ca29399ee",
"parentId": "10151",
"isLeaf": true,
"molecule": {
"id": "sa_04a18e3f07bde82ca29399ee",
"inchikey": "AVXURJPOCDRRFD-UHFFFAOYSA-N",
"smiles": "NO"
},
"smiles": "NO",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "10153",
"routeId": "sa_70887589f44dab2573aa2a37",
"moleculeId": "sa_50d0191a5a5e2e183e09c96e",
"parentId": "10151",
"isLeaf": false,
"molecule": {
"id": "sa_50d0191a5a5e2e183e09c96e",
"inchikey": "KKZVXKUKYPROJY-UHFFFAOYSA-N",
"smiles": "COC(=O)c1cccc(CC(=O)N(CCO[Si](C)(C)C(C)(C)C)c2ccccc2)c1"
},
"smiles": "COC(=O)c1cccc(CC(=O)N(CCO[Si](C)(C)C(C)(C)C)c2ccccc2)c1",
"reactionStepId": "sa_db7a44894bf734f07f6107ef",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20140288119A1;0279;1588362\",\"rsmi\":\"O[C:9]([CH2:8][c:7]1[cH:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[cH:30][cH:29][cH:28]1)=[O:10].[NH:11]([CH2:12][CH2:13][O:14][Si:15]([CH3:16])([CH3:17])[C:18]([CH3:19])([CH3:20])[CH3:21])[c:22]1[cH:23][cH:24][cH:25][cH:26][cH:27]1>CC(C)O.ClC(Cl)Cl.ClCCCl.ClCCl>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]([CH2:8][C:9](=[O:10])[N:11]([CH2:12][CH2:13][O:14][Si:15]([CH3:16])([CH3:17])[C:18]([CH3:19])([CH3:20])[CH3:21])[c:22]2[cH:23][cH:24][cH:25][cH:26][cH:27]2)[cH:28][cH:29][cH:30]1\"},\"mapped_reaction_smiles\":\"O[C:9]([CH2:8][c:7]1[cH:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[cH:30][cH:29][cH:28]1)=[O:10].[NH:11]([CH2:12][CH2:13][O:14][Si:15]([CH3:16])([CH3:17])[C:18]([CH3:19])([CH3:20])[CH3:21])[c:22]1[cH:23][cH:24][cH:25][cH:26][cH:27]1>CC(C)O.ClC(Cl)Cl.ClCCCl.ClCCl>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]([CH2:8][C:9](=[O:10])[N:11]([CH2:12][CH2:13][O:14][Si:15]([CH3:16])([CH3:17])[C:18]([CH3:19])([CH3:20])[CH3:21])[c:22]2[cH:23][cH:24][cH:25][cH:26][cH:27]2)[cH:28][cH:29][cH:30]1\"}",
"reactionStep": {
"id": "sa_db7a44894bf734f07f6107ef",
"reactionHash": "cf16a497ca44898d9b7cec7f7518b5763341b86259cdf47de827274a5d48a40b"
},
"children": [
{
"id": "10154",
"routeId": "sa_70887589f44dab2573aa2a37",
"moleculeId": "sa_0c18faae387f504c83035332",
"parentId": "10153",
"isLeaf": false,
"molecule": {
"id": "sa_0c18faae387f504c83035332",
"inchikey": "BRVFSWBAAITLFH-UHFFFAOYSA-N",
"smiles": "CC(C)(C)[Si](C)(C)OCCNc1ccccc1"
},
"smiles": "CC(C)(C)[Si](C)(C)OCCNc1ccccc1",
"reactionStepId": "sa_1cf90b1a24ee8ff49424dbd4",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20140288119A1;0250;1588350\",\"rsmi\":\"Cl[Si:5]([C:2]([CH3:1])([CH3:3])[CH3:4])([CH3:6])[CH3:7].[OH:8][CH2:9][CH2:10][NH:11][c:12]1[cH:13][cH:14][cH:15][cH:16][cH:17]1>ClCCl.c1c[nH]cn1>[CH3:1][C:2]([CH3:3])([CH3:4])[Si:5]([CH3:6])([CH3:7])[O:8][CH2:9][CH2:10][NH:11][c:12]1[cH:13][cH:14][cH:15][cH:16][cH:17]1\"},\"mapped_reaction_smiles\":\"Cl[Si:5]([C:2]([CH3:1])([CH3:3])[CH3:4])([CH3:6])[CH3:7].[OH:8][CH2:9][CH2:10][NH:11][c:12]1[cH:13][cH:14][cH:15][cH:16][cH:17]1>ClCCl.c1c[nH]cn1>[CH3:1][C:2]([CH3:3])([CH3:4])[Si:5]([CH3:6])([CH3:7])[O:8][CH2:9][CH2:10][NH:11][c:12]1[cH:13][cH:14][cH:15][cH:16][cH:17]1\"}",
"reactionStep": {
"id": "sa_1cf90b1a24ee8ff49424dbd4",
"reactionHash": "ac497ca3d9ae1203fb72d2e91f7ab5383e94bf677b08e620254eeba466ef0f7c"
},
"children": [
{
"id": "10155",
"routeId": "sa_70887589f44dab2573aa2a37",
"moleculeId": "sa_1785e67b778eb91f7e04c15a",
"parentId": "10154",
"isLeaf": true,
"molecule": {
"id": "sa_1785e67b778eb91f7e04c15a",
"inchikey": "BCNZYOJHNLTNEZ-UHFFFAOYSA-N",
"smiles": "CC(C)(C)[Si](C)(C)Cl"
},
"smiles": "CC(C)(C)[Si](C)(C)Cl",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "10156",
"routeId": "sa_70887589f44dab2573aa2a37",
"moleculeId": "sa_e4e56f304996c47cb01269a1",
"parentId": "10154",
"isLeaf": false,
"molecule": {
"id": "sa_e4e56f304996c47cb01269a1",
"inchikey": "MWGATWIBSKHFMR-UHFFFAOYSA-N",
"smiles": "OCCNc1ccccc1"
},
"smiles": "OCCNc1ccccc1",
"reactionStepId": "sa_a15555931004d93882c4ffba",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20140288119A1;0249;1588349\",\"rsmi\":\"O=[CH:3][CH2:2][OH:1].[NH2:4][c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1>CC(=O)OB(OC(C)=O)OC(C)=O.ClCCCl.[Na+]>[OH:1][CH2:2][CH2:3][NH:4][c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1\"},\"mapped_reaction_smiles\":\"O=[CH:3][CH2:2][OH:1].[NH2:4][c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1>CC(=O)OB(OC(C)=O)OC(C)=O.ClCCCl.[Na+]>[OH:1][CH2:2][CH2:3][NH:4][c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1\"}",
"reactionStep": {
"id": "sa_a15555931004d93882c4ffba",
"reactionHash": "5e5732c24bfc5d8cf97c079d7bfcd62b6ec4166f385fb25d85dade5c91b32b2f"
},
"children": [
{
"id": "10157",
"routeId": "sa_70887589f44dab2573aa2a37",
"moleculeId": "sa_257ba819b453f9a0e7fa3c07",
"parentId": "10156",
"isLeaf": true,
"molecule": {
"id": "sa_257ba819b453f9a0e7fa3c07",
"inchikey": "PAYRUJLWNCNPSJ-UHFFFAOYSA-N",
"smiles": "Nc1ccccc1"
},
"smiles": "Nc1ccccc1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "10158",
"routeId": "sa_70887589f44dab2573aa2a37",
"moleculeId": "sa_55994ecf08ce7c7954a1a0e2",
"parentId": "10156",
"isLeaf": true,
"molecule": {
"id": "sa_55994ecf08ce7c7954a1a0e2",
"inchikey": "WGCNASOHLSPBMP-UHFFFAOYSA-N",
"smiles": "O=CCO"
},
"smiles": "O=CCO",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
}
]
},
{
"id": "10159",
"routeId": "sa_70887589f44dab2573aa2a37",
"moleculeId": "sa_8343639834d0497f1d7f7fd2",
"parentId": "10153",
"isLeaf": false,
"molecule": {
"id": "sa_8343639834d0497f1d7f7fd2",
"inchikey": "DLWWJGQWXNOQCE-UHFFFAOYSA-N",
"smiles": "COC(=O)c1cccc(CC(=O)O)c1"
},
"smiles": "COC(=O)c1cccc(CC(=O)O)c1",
"reactionStepId": "sa_fe513b27c949bcdc8b2b5207",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20140288119A1;0278;1588361\",\"rsmi\":\"C[O:13][C:11]([CH2:10][c:9]1[cH:8][cH:7][cH:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[cH:14]1)=[O:12]>CO.O.O=C(O)O.[K+].[K+]>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][cH:8][c:9]([CH2:10][C:11](=[O:12])[OH:13])[cH:14]1\"},\"mapped_reaction_smiles\":\"C[O:13][C:11]([CH2:10][c:9]1[cH:8][cH:7][cH:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[cH:14]1)=[O:12]>CO.O.O=C(O)O.[K+].[K+]>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][cH:8][c:9]([CH2:10][C:11](=[O:12])[OH:13])[cH:14]1\"}",
"reactionStep": {
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"reactionHash": "94545bc3d689be7a792f87b9bd39aa064b43c5bd4a05a94590e5a568e847a58e"
},
"children": [
{
"id": "10160",
"routeId": "sa_70887589f44dab2573aa2a37",
"moleculeId": "sa_4f258d9c283dbbf5e31e61ac",
"parentId": "10159",
"isLeaf": true,
"molecule": {
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"inchikey": "XYJVSCYQGXVUKN-UHFFFAOYSA-N",
"smiles": "COC(=O)Cc1cccc(C(=O)OC)c1"
},
"smiles": "COC(=O)Cc1cccc(C(=O)OC)c1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
}
]
}
]
}
]
}
}