Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
CN(C)C(=O)NC1Cc2c(n(Cc3cccc(F)n3)c3ccc(C#N)cc23)C1
InChiKey
AHRVHKYJVUKSST-UHFFFAOYSA-N
Route Signature
63a81b0d9008bfc28a56d96ded87a6d9de4fa7ba089e61d4b42d5aa56d7be145
Synthesis route with 4 steps (convergent)
Route tree structure (JSON format)
{
"route": {
"id": "sa_eea664b59eb61ef1ff0765bc",
"signature": "63a81b0d9008bfc28a56d96ded87a6d9de4fa7ba089e61d4b42d5aa56d7be145",
"contentHash": "146829205f76b287aec4ca59f66b51eddaf07e9efad8ebed6f4ecbeb96b49466",
"length": 4,
"isConvergent": true
},
"target": {
"id": "sa_dd46f81db7d140a22e09fd66",
"benchmarkSetId": "7390a9c2522b1c81605e80a42a8de7c7ad9a5797d028633b54904bc78f091bb8",
"targetId": "n5-01954",
"moleculeId": "sa_5bc8ea34756386b95cb3fc37",
"smiles": "CN(C)C(=O)NC1Cc2c(n(Cc3cccc(F)n3)c3ccc(C#N)cc23)C1",
"routeLength": 4,
"isConvergent": true,
"metadata": null,
"molecule": {
"id": "sa_5bc8ea34756386b95cb3fc37",
"inchikey": "AHRVHKYJVUKSST-UHFFFAOYSA-N",
"smiles": "CN(C)C(=O)NC1Cc2c(n(Cc3cccc(F)n3)c3ccc(C#N)cc23)C1"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 2
},
"rootNode": {
"id": "1627",
"routeId": "sa_eea664b59eb61ef1ff0765bc",
"moleculeId": "sa_5bc8ea34756386b95cb3fc37",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_5bc8ea34756386b95cb3fc37",
"inchikey": "AHRVHKYJVUKSST-UHFFFAOYSA-N",
"smiles": "CN(C)C(=O)NC1Cc2c(n(Cc3cccc(F)n3)c3ccc(C#N)cc23)C1"
},
"smiles": "CN(C)C(=O)NC1Cc2c(n(Cc3cccc(F)n3)c3ccc(C#N)cc23)C1",
"reactionStepId": "sa_6e7dd455a8d97844285528c1",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20100069404A1;0233;851621\",\"rsmi\":\"Cl[C:4]([N:2]([CH3:1])[CH3:3])=[O:5].[NH2:6][CH:7]1[CH2:8][c:9]2[c:10]([n:12]([CH2:13][c:14]3[n:15][c:16]([F:17])[cH:18][cH:19][cH:20]3)[c:21]3[c:22]2[cH:23][c:24]([C:25]#[N:26])[cH:27][cH:28]3)[CH2:11]1>CCN(C(C)C)C(C)C.ClCCl>[CH3:1][N:2]([CH3:3])[C:4](=[O:5])[NH:6][CH:7]1[CH2:8][c:9]2[c:10]([n:12]([CH2:13][c:14]3[n:15][c:16]([F:17])[cH:18][cH:19][cH:20]3)[c:21]3[c:22]2[cH:23][c:24]([C:25]#[N:26])[cH:27][cH:28]3)[CH2:11]1\"},\"mapped_reaction_smiles\":\"Cl[C:4]([N:2]([CH3:1])[CH3:3])=[O:5].[NH2:6][CH:7]1[CH2:8][c:9]2[c:10]([n:12]([CH2:13][c:14]3[n:15][c:16]([F:17])[cH:18][cH:19][cH:20]3)[c:21]3[c:22]2[cH:23][c:24]([C:25]#[N:26])[cH:27][cH:28]3)[CH2:11]1>CCN(C(C)C)C(C)C.ClCCl>[CH3:1][N:2]([CH3:3])[C:4](=[O:5])[NH:6][CH:7]1[CH2:8][c:9]2[c:10]([n:12]([CH2:13][c:14]3[n:15][c:16]([F:17])[cH:18][cH:19][cH:20]3)[c:21]3[c:22]2[cH:23][c:24]([C:25]#[N:26])[cH:27][cH:28]3)[CH2:11]1\"}",
"reactionStep": {
"id": "sa_6e7dd455a8d97844285528c1",
"reactionHash": "013402409962fc7f68c615f8a67b3809772080c1e809df7695c2659a775379f3"
},
"children": [
{
"id": "1628",
"routeId": "sa_eea664b59eb61ef1ff0765bc",
"moleculeId": "sa_56255c3cb905617dbe1447fe",
"parentId": "1627",
"isLeaf": false,
"molecule": {
"id": "sa_56255c3cb905617dbe1447fe",
"inchikey": "RJAGYZDHDFAFKV-UHFFFAOYSA-N",
"smiles": "N#Cc1ccc2c(c1)c1c(n2Cc2cccc(F)n2)CC(N)C1"
},
"smiles": "N#Cc1ccc2c(c1)c1c(n2Cc2cccc(F)n2)CC(N)C1",
"reactionStepId": "sa_1a5954a4e2ac12552632e481",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20100069404A1;0225;851619\",\"rsmi\":\"O=C1c2ccccc2C(=O)[N:22]1[CH:21]1[CH2:20][c:19]2[c:5]3[cH:4][c:3]([C:2]#[N:1])[cH:8][cH:7][c:6]3[n:9]([CH2:10][c:11]3[n:12][c:13]([F:14])[cH:15][cH:16][cH:17]3)[c:18]2[CH2:23]1>C1CCOC1.CCO.CCOC(C)=O.NN.O>[N:1]#[C:2][c:3]1[cH:4][c:5]2[c:6]([cH:7][cH:8]1)[n:9]([CH2:10][c:11]1[n:12][c:13]([F:14])[cH:15][cH:16][cH:17]1)[c:18]1[c:19]2[CH2:20][CH:21]([NH2:22])[CH2:23]1\"},\"mapped_reaction_smiles\":\"O=C1c2ccccc2C(=O)[N:22]1[CH:21]1[CH2:20][c:19]2[c:5]3[cH:4][c:3]([C:2]#[N:1])[cH:8][cH:7][c:6]3[n:9]([CH2:10][c:11]3[n:12][c:13]([F:14])[cH:15][cH:16][cH:17]3)[c:18]2[CH2:23]1>C1CCOC1.CCO.CCOC(C)=O.NN.O>[N:1]#[C:2][c:3]1[cH:4][c:5]2[c:6]([cH:7][cH:8]1)[n:9]([CH2:10][c:11]1[n:12][c:13]([F:14])[cH:15][cH:16][cH:17]1)[c:18]1[c:19]2[CH2:20][CH:21]([NH2:22])[CH2:23]1\"}",
"reactionStep": {
"id": "sa_1a5954a4e2ac12552632e481",
"reactionHash": "1e517d448c4b0c039d0adb7a54b16548b2a06996273ec2bea4ff8d428c46dcb4"
},
"children": [
{
"id": "1629",
"routeId": "sa_eea664b59eb61ef1ff0765bc",
"moleculeId": "sa_247331929be0f0b07b697f0c",
"parentId": "1628",
"isLeaf": false,
"molecule": {
"id": "sa_247331929be0f0b07b697f0c",
"inchikey": "CVFOFHLDSDLLRB-UHFFFAOYSA-N",
"smiles": "N#Cc1ccc2c(c1)c1c(n2Cc2cccc(F)n2)CC(N2C(=O)c3ccccc3C2=O)C1"
},
"smiles": "N#Cc1ccc2c(c1)c1c(n2Cc2cccc(F)n2)CC(N2C(=O)c3ccccc3C2=O)C1",
"reactionStepId": "sa_f282c16f081e974e343dde4c",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20100069404A1;0221;851617\",\"rsmi\":\"Br[CH2:10][c:11]1[n:12][c:13]([F:14])[cH:15][cH:16][cH:17]1.[N:1]#[C:2][c:3]1[cH:4][c:5]2[c:6]([cH:7][cH:8]1)[nH:9][c:18]1[c:19]2[CH2:20][CH:21]([N:22]2[C:23](=[O:24])[c:25]3[cH:26][cH:27][cH:28][cH:29][c:30]3[C:31]2=[O:32])[CH2:33]1>CCOC(C)=O.CN(C)C=O.O=C(O)O.[Cs+].[Cs+]>[N:1]#[C:2][c:3]1[cH:4][c:5]2[c:6]([cH:7][cH:8]1)[n:9]([CH2:10][c:11]1[n:12][c:13]([F:14])[cH:15][cH:16][cH:17]1)[c:18]1[c:19]2[CH2:20][CH:21]([N:22]2[C:23](=[O:24])[c:25]3[cH:26][cH:27][cH:28][cH:29][c:30]3[C:31]2=[O:32])[CH2:33]1\"},\"mapped_reaction_smiles\":\"Br[CH2:10][c:11]1[n:12][c:13]([F:14])[cH:15][cH:16][cH:17]1.[N:1]#[C:2][c:3]1[cH:4][c:5]2[c:6]([cH:7][cH:8]1)[nH:9][c:18]1[c:19]2[CH2:20][CH:21]([N:22]2[C:23](=[O:24])[c:25]3[cH:26][cH:27][cH:28][cH:29][c:30]3[C:31]2=[O:32])[CH2:33]1>CCOC(C)=O.CN(C)C=O.O=C(O)O.[Cs+].[Cs+]>[N:1]#[C:2][c:3]1[cH:4][c:5]2[c:6]([cH:7][cH:8]1)[n:9]([CH2:10][c:11]1[n:12][c:13]([F:14])[cH:15][cH:16][cH:17]1)[c:18]1[c:19]2[CH2:20][CH:21]([N:22]2[C:23](=[O:24])[c:25]3[cH:26][cH:27][cH:28][cH:29][c:30]3[C:31]2=[O:32])[CH2:33]1\"}",
"reactionStep": {
"id": "sa_f282c16f081e974e343dde4c",
"reactionHash": "a52cffb865fc72d4b8e00a41432a97084ebf8fe97ae83bbda9728ecb36874d0e"
},
"children": [
{
"id": "1630",
"routeId": "sa_eea664b59eb61ef1ff0765bc",
"moleculeId": "sa_f9090d7109fb2f9c95c91171",
"parentId": "1629",
"isLeaf": false,
"molecule": {
"id": "sa_f9090d7109fb2f9c95c91171",
"inchikey": "ADYKBYXVMBDQQX-UHFFFAOYSA-N",
"smiles": "Fc1cccc(CBr)n1"
},
"smiles": "Fc1cccc(CBr)n1",
"reactionStepId": "sa_735c398a307a38e6161b0365",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20100069404A1;0187;851608\",\"rsmi\":\"O=C1CCC(=O)N1[Br:8].[F:1][c:2]1[cH:3][cH:4][cH:5][c:6]([CH3:7])[n:9]1>CC(C)(C#N)N=NC(C)(C)C#N.CCCCCC.CCOC(C)=O>[F:1][c:2]1[cH:3][cH:4][cH:5][c:6]([CH2:7][Br:8])[n:9]1\"},\"mapped_reaction_smiles\":\"O=C1CCC(=O)N1[Br:8].[F:1][c:2]1[cH:3][cH:4][cH:5][c:6]([CH3:7])[n:9]1>CC(C)(C#N)N=NC(C)(C)C#N.CCCCCC.CCOC(C)=O>[F:1][c:2]1[cH:3][cH:4][cH:5][c:6]([CH2:7][Br:8])[n:9]1\"}",
"reactionStep": {
"id": "sa_735c398a307a38e6161b0365",
"reactionHash": "450354e3d70ef3398b9b1f94ac79af8f6ff0266416047ae65644c96dbf223fee"
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"children": [
{
"id": "1631",
"routeId": "sa_eea664b59eb61ef1ff0765bc",
"moleculeId": "sa_ccdcf23ac83e7a68bfa4f2e5",
"parentId": "1630",
"isLeaf": true,
"molecule": {
"id": "sa_ccdcf23ac83e7a68bfa4f2e5",
"inchikey": "PCLIMKBDDGJMGD-UHFFFAOYSA-N",
"smiles": "O=C1CCC(=O)N1Br"
},
"smiles": "O=C1CCC(=O)N1Br",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "1632",
"routeId": "sa_eea664b59eb61ef1ff0765bc",
"moleculeId": "sa_89a13944ffb45c1393ca9b23",
"parentId": "1630",
"isLeaf": true,
"molecule": {
"id": "sa_89a13944ffb45c1393ca9b23",
"inchikey": "UDMNVTJFUISBFD-UHFFFAOYSA-N",
"smiles": "Cc1cccc(F)n1"
},
"smiles": "Cc1cccc(F)n1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
},
{
"id": "1633",
"routeId": "sa_eea664b59eb61ef1ff0765bc",
"moleculeId": "sa_d4c9d0cd70c5d64dba6ed5ba",
"parentId": "1629",
"isLeaf": false,
"molecule": {
"id": "sa_d4c9d0cd70c5d64dba6ed5ba",
"inchikey": "NBNLXVDIURVLAP-UHFFFAOYSA-N",
"smiles": "N#Cc1ccc2[nH]c3c(c2c1)CC(N1C(=O)c2ccccc2C1=O)C3"
},
"smiles": "N#Cc1ccc2[nH]c3c(c2c1)CC(N1C(=O)c2ccccc2C1=O)C3",
"reactionStepId": "sa_2398b79edc6a89e9c7d05a5b",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20100069404A1;0174;851601\",\"rsmi\":\"N[NH:9][c:6]1[cH:5][cH:4][c:3]([C:2]#[N:1])[cH:8][cH:7]1.O=[C:10]1[CH2:11][CH2:12][CH:13]([N:14]2[C:15](=[O:16])[c:17]3[cH:18][cH:19][cH:20][cH:21][c:22]3[C:23]2=[O:24])[CH2:25]1>C1COCCO1.CC(=O)O.Cl.Cl.O>[N:1]#[C:2][c:3]1[cH:4][c:5]2[c:6]([cH:7][cH:8]1)[nH:9][c:10]1[c:11]2[CH2:12][CH:13]([N:14]2[C:15](=[O:16])[c:17]3[cH:18][cH:19][cH:20][cH:21][c:22]3[C:23]2=[O:24])[CH2:25]1\"},\"mapped_reaction_smiles\":\"N[NH:9][c:6]1[cH:5][cH:4][c:3]([C:2]#[N:1])[cH:8][cH:7]1.O=[C:10]1[CH2:11][CH2:12][CH:13]([N:14]2[C:15](=[O:16])[c:17]3[cH:18][cH:19][cH:20][cH:21][c:22]3[C:23]2=[O:24])[CH2:25]1>C1COCCO1.CC(=O)O.Cl.Cl.O>[N:1]#[C:2][c:3]1[cH:4][c:5]2[c:6]([cH:7][cH:8]1)[nH:9][c:10]1[c:11]2[CH2:12][CH:13]([N:14]2[C:15](=[O:16])[c:17]3[cH:18][cH:19][cH:20][cH:21][c:22]3[C:23]2=[O:24])[CH2:25]1\"}",
"reactionStep": {
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"reactionHash": "4277770af7ed7c1c2aedc58fb01c12ce5f32eeacf7cf1c06830fd670af48b1bc"
},
"children": [
{
"id": "1634",
"routeId": "sa_eea664b59eb61ef1ff0765bc",
"moleculeId": "sa_20033418e7cd6bdd9d6750aa",
"parentId": "1633",
"isLeaf": true,
"molecule": {
"id": "sa_20033418e7cd6bdd9d6750aa",
"inchikey": "DZUUSHCOMPROCJ-UHFFFAOYSA-N",
"smiles": "N#Cc1ccc(NN)cc1"
},
"smiles": "N#Cc1ccc(NN)cc1",
"reactionStepId": null,
"template": null,
"metadata": null,
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"children": []
},
{
"id": "1635",
"routeId": "sa_eea664b59eb61ef1ff0765bc",
"moleculeId": "sa_0dad9fd1bb9132622ef144ce",
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"molecule": {
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"inchikey": "RTIZJQCGWLDNKT-UHFFFAOYSA-N",
"smiles": "O=C1CCC(N2C(=O)c3ccccc3C2=O)C1"
},
"smiles": "O=C1CCC(N2C(=O)c3ccccc3C2=O)C1",
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}
]
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]
}
]
},
{
"id": "1636",
"routeId": "sa_eea664b59eb61ef1ff0765bc",
"moleculeId": "sa_f8aaf8bdcec39f45af300125",
"parentId": "1627",
"isLeaf": true,
"molecule": {
"id": "sa_f8aaf8bdcec39f45af300125",
"inchikey": "YIIMEMSDCNDGTB-UHFFFAOYSA-N",
"smiles": "CN(C)C(=O)Cl"
},
"smiles": "CN(C)C(=O)Cl",
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}
]
}
}