jiosephlee/chembl-endpoint-pair-clean-labels huggingface dataset:
## Endpoint to Predict
- Endpoint scope: assay
- Measurement type: Inhibition
- Label type: binary
- Binary semantics: activity
- Assay description: Inhibition of human leukocyte MPO peroxidase activity using hydrogen peroxide as substrate by fluorescence based analysis
- Assay organism: Homo sapiens
- Target name: Myeloperoxidase
- Target type: SINGLE PROTEIN
- Target organism: Homo sapiens

## Reference Molecule A
- Canonical SMILES: CN1CCc2nc3sc(C(=O)Nc4cccc(C#N)c4)c(N)c3cc2C1
- Properties:
- ChEMBL ID: CHEMBL1515494
- Molecule type: Small molecule
- Molecular weight: 363.45
- Heavy atoms: 26
- Hydrogen bond donors: 2
- Hydrogen bond acceptors: 6
- TPSA: 95.04
- LogP: 2.99
- Rotatable bonds: 2
- Ring count: 4
- Aromatic rings: 3
- Formal charge: 0
- Fraction Csp3: 0.21
- QED: 0.73

## Known Reference Result on This Endpoint
- Molecule A clean result: activity label = 0
- This result is provided as context for predicting Molecule B on the same endpoint.

## Reference Molecule A Other ChEMBL Evidence
- type Inhibition; units %; comment Not Active

## Query Molecule B
- Canonical SMILES: CN(C)CCc1c(C#N)c(=O)ncn1Cc1ccccc1
- Properties:
- ChEMBL ID: CHEMBL5564806
- Molecular weight: 282.35
- Heavy atoms: 21
- Hydrogen bond donors: 0
- Hydrogen bond acceptors: 4
- TPSA: 61.92
- LogP: 1.27
- Rotatable bonds: 5
- Ring count: 2
- Aromatic rings: 2
- Formal charge: 0
- Fraction Csp3: 0.31
- QED: 0.83

## Molecule Similarity
- Weighted Tanimoto: 0.18

Answer: 0
## Endpoint to Predict
- Endpoint scope: assay
- Measurement type: IC50
- Label type: continuous
- Binary semantics: pchembl
- Assay description: Inverse agonist activity at Gal4-fused human full length Nurr1 heterodimer transfected in HEK293T cells cotransfected with pFR-Luc-DR5 incubated for 16 hrs by firefly/renilla based Dual-Glo luciferase assay
- Assay organism: Homo sapiens
- Assay cell type: HEK293T
- Target name: Nuclear receptor subfamily 4 group A member 2
- Target type: SINGLE PROTEIN
- Target organism: Homo sapiens

## Reference Molecule A
- Canonical SMILES: CN(C)C(=O)CCc1nc(-c2ccccc2)c(-c2ccccc2)o1
- Properties:
- ChEMBL ID: CHEMBL5549932
- Molecular weight: 320.39
- Heavy atoms: 24
- Hydrogen bond donors: 0
- Hydrogen bond acceptors: 3
- TPSA: 46.34
- LogP: 4.03
- Rotatable bonds: 5
- Ring count: 3
- Aromatic rings: 3
- Formal charge: 0
- Fraction Csp3: 0.2
- QED: 0.71

## Known Reference Result on This Endpoint
- Molecule A clean result: median pChEMBL = 4.75
- This result is provided as context for predicting Molecule B on the same endpoint.

## Reference Molecule A Other ChEMBL Evidence
- type IC50; relation =; value 18000; units nM; pChEMBL 4.75

## Query Molecule B
- Canonical SMILES: O=C(O)/C=C/c1nc(-c2ccccc2)c(-c2ccccc2)o1
- Properties:
- ChEMBL ID: CHEMBL5417665
- Molecular weight: 291.31
- Heavy atoms: 22
- Hydrogen bond donors: 1
- Hydrogen bond acceptors: 3
- TPSA: 63.33
- LogP: 4.11
- Rotatable bonds: 4
- Ring count: 3
- Aromatic rings: 3
- Formal charge: 0
- Fraction Csp3: 0
- QED: 0.73

## Molecule Similarity
- Weighted Tanimoto: 0.44

Answer: 5.4
## Endpoint to Predict
- Endpoint scope: target
- Measurement type: Inhibition
- Label type: binary
- Binary semantics: activity
- Target name: Histamine H2 receptor
- Target type: SINGLE PROTEIN
- Target organism: Cavia porcellus

## Reference Molecule A
- Canonical SMILES: Cc1cc2cc(/N=C(/NC#N)N[C@H]3CCCCN(CC(=O)N4CCCC4)C3=O)ccc2o1
- Properties:
- ChEMBL ID: CHEMBL551991
- Molecule type: Small molecule
- Molecular weight: 436.52
- Heavy atoms: 32
- Hydrogen bond donors: 2
- Hydrogen bond acceptors: 5
- TPSA: 113.97
- LogP: 2.39
- Rotatable bonds: 4
- Ring count: 4
- Aromatic rings: 2
- Formal charge: 0
- Fraction Csp3: 0.48
- QED: 0.33

## Known Reference Result on This Endpoint
- Molecule A clean result: activity label = 0
- This result is provided as context for predicting Molecule B on the same endpoint.

## Reference Molecule A Other ChEMBL Evidence
- type Inhibition; units %; comment Not Active

## Query Molecule B
- Canonical SMILES: Cc1c2c(c(C)n1-c1ccccc1)C(C)(C(N)=O)CC2(C)C
- Properties:
- ChEMBL ID: CHEMBL176413
- Molecule type: Small molecule
- Molecular weight: 296.41
- Heavy atoms: 22
- Hydrogen bond donors: 1
- Hydrogen bond acceptors: 1
- TPSA: 48.02
- LogP: 3.52
- Rotatable bonds: 2
- Ring count: 3
- Aromatic rings: 2
- Formal charge: 0
- Fraction Csp3: 0.42
- QED: 0.91

## Molecule Similarity
- Weighted Tanimoto: 0.13

Answer: 1
## Endpoint to Predict
- Endpoint scope: assay
- Measurement type: Ki
- Label type: continuous
- Binary semantics: pchembl
- Assay description: Inhibition of human plasma kallikrein catalytic domain E217R mutant after 15 mins using H-D-Pro-Phe-Arg-p-nitroanilide as substrate
- Assay organism: Homo sapiens
- Assay tissue: Plasma
- Target name: Plasma kallikrein
- Target type: SINGLE PROTEIN
- Target organism: Homo sapiens

## Reference Molecule A
- Canonical SMILES: CC(C)C[C@@H]1NC(=O)[C@H](C)NC(=O)[C@H](CC2CCN(C(=N)N)CC2)NC(=O)[C@H](Cc2ccccc2)NC(=O)[C@H](CCCNC(=N)N)NC(=O)[C@H](C)NC(=O)[C@@H]2CCCN2C(=O)[C@@H](N)CSSC[C@@H](C(=O)O)NC(=O)[C@H](Cc2c[nH]c3ccccc23)NC1=O
- Properties:
- ChEMBL ID: CHEMBL3735263
- Molecule type: Protein
- Molecular weight: 1260.56
- Heavy atoms: 88
- Hydrogen bond donors: 16
- Hydrogen bond acceptors: 15
- TPSA: 447.23
- LogP: -1.03
- Rotatable bonds: 13
- Ring count: 6
- Aromatic rings: 3
- Formal charge: 0
- Fraction Csp3: 0.55
- QED: 0.04

## Known Reference Result on This Endpoint
- Molecule A clean result: median pChEMBL = 6.78
- This result is provided as context for predicting Molecule B on the same endpoint.

## Reference Molecule A Other ChEMBL Evidence
- type Ki; relation =; value 166; units nM; pChEMBL 6.78

## Query Molecule B
- Canonical SMILES: CC(C)C[C@@H]1NC(=O)[C@H](Cc2ccc(O)cc2)NC(=O)[C@H](CC2CCN(C(=N)N)CC2)NC(=O)[C@H](CO)NC(=O)[C@H](Cc2ccc(O)cc2)NC(=O)[C@H](C)NC(=O)[C@@H]2CCCN2C(=O)[C@@H](N)CSSC[C@@H](C(=O)O)NC(=O)[C@H](CC(=O)O)NC1=O
- Properties:
- ChEMBL ID: CHEMBL3735080
- Molecule type: Protein
- Molecular weight: 1228.42
- Heavy atoms: 85
- Hydrogen bond donors: 16
- Hydrogen bond acceptors: 18
- TPSA: 467.53
- LogP: -2.91
- Rotatable bonds: 12
- Ring count: 5
- Aromatic rings: 2
- Formal charge: 0
- Fraction Csp3: 0.56
- QED: 0.06

## Molecule Similarity
- Weighted Tanimoto: 0.65

Answer: 5.77
## Endpoint to Predict
- Endpoint scope: assay
- Measurement type: Activity
- Label type: binary
- Binary semantics: activity
- Assay description: Induction of oligodendrocyte precursor cell differentiation isolated from Wistar rat fetal brain cortex at 0.03 uM after 3 days by anti O1-antibody immunostaining method
- Assay organism: Rattus norvegicus
- Target name: Unchecked
- Target type: UNCHECKED

## Reference Molecule A
- Canonical SMILES: Cc1cc(SCc2sc(-c3ccc(C(F)(F)F)cc3)nc2C)ccc1OCC(=O)O
- Properties:
- ChEMBL ID: CHEMBL38943
- Preferred name: GW501516
- Molecule type: Small molecule
- Max clinical phase: 2
- Molecular weight: 453.51
- Heavy atoms: 30
- Hydrogen bond donors: 1
- Hydrogen bond acceptors: 5
- TPSA: 59.42
- LogP: 6.2
- Rotatable bonds: 7
- Ring count: 3
- Aromatic rings: 3
- Formal charge: 0
- Fraction Csp3: 0.24
- QED: 0.43

## Known Reference Result on This Endpoint
- Molecule A clean result: activity label = 1
- This result is provided as context for predicting Molecule B on the same endpoint.

## Reference Molecule A Other ChEMBL Evidence
- type Activity; comment Active

## Query Molecule B
- Canonical SMILES: Cc1cc2c(CCc3sc(-c4ccc(C(F)(F)F)cc4)nc3C(C)C)noc2cc1OC(C)(C)C(=O)O
- Properties:
- ChEMBL ID: CHEMBL1778840
- Molecule type: Small molecule
- Molecular weight: 532.58
- Heavy atoms: 37
- Hydrogen bond donors: 1
- Hydrogen bond acceptors: 6
- TPSA: 85.45
- LogP: 7.43
- Rotatable bonds: 8
- Ring count: 4
- Aromatic rings: 4
- Formal charge: 0
- Fraction Csp3: 0.37
- QED: 0.25

## Molecule Similarity
- Weighted Tanimoto: 0.42

Answer: 1
## Endpoint to Predict
- Endpoint scope: assay
- Measurement type: Kd
- Label type: continuous
- Binary semantics: pchembl
- Assay description: Binding affinity to recombinant human carbonic anhydrase 12 (30 to 291 residues) expressed in Escherichia coli Rosetta 2 (DE3) strain assessed as intrinsic Kd by by isothermal titration calorimetry
- Assay organism: Homo sapiens
- Target name: Carbonic anhydrase 12
- Target type: SINGLE PROTEIN
- Target organism: Homo sapiens

## Reference Molecule A
- Canonical SMILES: NS(=O)(=O)c1cc(C(=O)NCCO)c(NC2CCCCC2)cc1Cl
- Properties:
- ChEMBL ID: CHEMBL4176828
- Molecule type: Small molecule
- Molecular weight: 375.88
- Heavy atoms: 24
- Hydrogen bond donors: 4
- Hydrogen bond acceptors: 5
- TPSA: 121.52
- LogP: 1.45
- Rotatable bonds: 6
- Ring count: 2
- Aromatic rings: 1
- Formal charge: 0
- Fraction Csp3: 0.53
- QED: 0.6

## Known Reference Result on This Endpoint
- Molecule A clean result: median pChEMBL = 10.72
- This result is provided as context for predicting Molecule B on the same endpoint.

## Reference Molecule A Other ChEMBL Evidence
- type Kd; relation =; value 0.02; units nM; pChEMBL 10.72

## Query Molecule B
- Canonical SMILES: COCCNC(=O)c1cc(S(N)(=O)=O)c(Cl)cc1NC1CCCCC1
- Properties:
- ChEMBL ID: CHEMBL4162451
- Molecule type: Small molecule
- Molecular weight: 389.91
- Heavy atoms: 25
- Hydrogen bond donors: 3
- Hydrogen bond acceptors: 5
- TPSA: 110.52
- LogP: 2.11
- Rotatable bonds: 7
- Ring count: 2
- Aromatic rings: 1
- Formal charge: 0
- Fraction Csp3: 0.56
- QED: 0.62

## Molecule Similarity
- Weighted Tanimoto: 0.78

Answer: 10.85
## Endpoint to Predict
- Endpoint scope: assay
- Measurement type: Activity
- Label type: binary
- Binary semantics: activity
- Assay description: Inhibition of bovine hyaluronidase up to 13 mM at pH 5
- Assay organism: Bos taurus
- Target name: Unchecked
- Target type: UNCHECKED

## Reference Molecule A
- Canonical SMILES: O=C1O[C@H]([C@@H](O)CO)C2=C1OCCO2
- Properties:
- ChEMBL ID: CHEMBL219306
- Molecule type: Small molecule
- Molecular weight: 202.16
- Heavy atoms: 14
- Hydrogen bond donors: 2
- Hydrogen bond acceptors: 6
- TPSA: 85.22
- LogP: -1.48
- Rotatable bonds: 2
- Ring count: 2
- Aromatic rings: 0
- Formal charge: 0
- Fraction Csp3: 0.62
- QED: 0.53

## Known Reference Result on This Endpoint
- Molecule A clean result: activity label = 0
- This result is provided as context for predicting Molecule B on the same endpoint.

## Reference Molecule A Other ChEMBL Evidence
- type Activity; comment Not Active

## Query Molecule B
- Canonical SMILES: O=C1O[C@H]([C@@H](O)CO)C(OCc2ccccc2)=C1OCc1ccccc1
- Properties:
- ChEMBL ID: CHEMBL441706
- Molecule type: Small molecule
- Molecular weight: 356.37
- Heavy atoms: 26
- Hydrogen bond donors: 2
- Hydrogen bond acceptors: 6
- TPSA: 85.22
- LogP: 1.91
- Rotatable bonds: 8
- Ring count: 3
- Aromatic rings: 2
- Formal charge: 0
- Fraction Csp3: 0.25
- QED: 0.7

## Molecule Similarity
- Weighted Tanimoto: 0.42

Answer: 0
## Endpoint to Predict
- Endpoint scope: assay
- Measurement type: EC50
- Label type: continuous
- Binary semantics: pchembl
- Assay description: Cytotoxicity against human HepG2 cells
- Assay organism: Homo sapiens
- Assay cell type: HepG2
- Target name: HepG2
- Target type: CELL-LINE
- Target organism: Homo sapiens

## Reference Molecule A
- Canonical SMILES: COc1ccc2c(c1)C1CC1(C(=O)N1C3CC1CN(Cc1ccccc1)C3)Cn1c-2c(C2CCCCC2)c2ccc(C(=O)NS(=O)(=O)N(C)C)cc21
- Properties:
- ChEMBL ID: CHEMBL3126836
- Molecule type: Small molecule
- Molecular weight: 721.92
- Heavy atoms: 52
- Hydrogen bond donors: 1
- Hydrogen bond acceptors: 6
- TPSA: 104.19
- LogP: 5.87
- Rotatable bonds: 8
- Ring count: 10
- Aromatic rings: 4
- Formal charge: 0
- Fraction Csp3: 0.46
- QED: 0.24

## Known Reference Result on This Endpoint
- Molecule A clean result: median pChEMBL = 4.66
- This result is provided as context for predicting Molecule B on the same endpoint.

## Reference Molecule A Other ChEMBL Evidence
- type EC50; relation =; value 22000; units nM; pChEMBL 4.66

## Query Molecule B
- Canonical SMILES: CCN1CC2CC(C1)N2C(=O)[C@]12C[C@H]1c1cc(OC)ccc1-c1c(C3CCCCC3)c3ccc(C(=O)NS(=O)(=O)N(C)C)cc3n1C2
- Properties:
- ChEMBL ID: CHEMBL3126835
- Molecule type: Small molecule
- Molecular weight: 659.85
- Heavy atoms: 47
- Hydrogen bond donors: 1
- Hydrogen bond acceptors: 6
- TPSA: 104.19
- LogP: 4.69
- Rotatable bonds: 7
- Ring count: 9
- Aromatic rings: 3
- Formal charge: 0
- Fraction Csp3: 0.56
- QED: 0.39

## Molecule Similarity
- Weighted Tanimoto: 0.86

Answer: 4.72
## Endpoint to Predict
- Endpoint scope: assay
- Measurement type: Activity
- Label type: binary
- Binary semantics: activity
- Assay description: Binding affinity to amyloid beta (1 to 42) aggregate in Alzheimer disease patient brain by immunohistochemical staining using amyloid beta antibody
- Assay organism: Homo sapiens
- Target name: Amyloid-beta precursor protein
- Target type: SINGLE PROTEIN
- Target organism: Homo sapiens

## Reference Molecule A
- Canonical SMILES: CNc1ccc(/C=C/C(=O)/C=C/c2ccc(OCCOCCOCC[18F])cc2)cc1
- Properties:
- ChEMBL ID: CHEMBL1767210
- Molecule type: Small molecule
- Molecular weight: 412.49
- Heavy atoms: 30
- Hydrogen bond donors: 1
- Hydrogen bond acceptors: 5
- TPSA: 56.79
- LogP: 4.41
- Rotatable bonds: 14
- Ring count: 2
- Aromatic rings: 2
- Formal charge: 0
- Fraction Csp3: 0.29
- QED: 0.37

## Known Reference Result on This Endpoint
- Molecule A clean result: activity label = 1
- This result is provided as context for predicting Molecule B on the same endpoint.

## Reference Molecule A Other ChEMBL Evidence
- type Activity; comment Active

## Query Molecule B
- Canonical SMILES: CN(C)c1ccc(/C=C/C(=O)/C=C/c2ccc(OCCOCCOCC[18F])cc2)cc1
- Properties:
- ChEMBL ID: CHEMBL1767209
- Molecule type: Small molecule
- Molecular weight: 426.52
- Heavy atoms: 31
- Hydrogen bond donors: 0
- Hydrogen bond acceptors: 5
- TPSA: 48
- LogP: 4.43
- Rotatable bonds: 14
- Ring count: 2
- Aromatic rings: 2
- Formal charge: 0
- Fraction Csp3: 0.32
- QED: 0.33

## Molecule Similarity
- Weighted Tanimoto: 0.71

Answer: 1
## Endpoint to Predict
- Endpoint scope: target
- Measurement type: Kd
- Label type: continuous
- Binary semantics: pchembl
- Target name: C5a anaphylatoxin chemotactic receptor 1
- Target type: SINGLE PROTEIN
- Target organism: Homo sapiens

## Reference Molecule A
- Canonical SMILES: Cc1cccc(F)c1N1CCC(N2Cc3ccccc3N(Cc3ccccc3C(F)(F)F)C2=O)CC1
- Properties:
- ChEMBL ID: CHEMBL5573973
- Molecular weight: 497.54
- Heavy atoms: 36
- Hydrogen bond donors: 0
- Hydrogen bond acceptors: 2
- TPSA: 26.79
- LogP: 6.76
- Rotatable bonds: 4
- Ring count: 5
- Aromatic rings: 3
- Formal charge: 0
- Fraction Csp3: 0.32
- QED: 0.37

## Known Reference Result on This Endpoint
- Molecule A clean result: median pChEMBL = 7.82
- This result is provided as context for predicting Molecule B on the same endpoint.

## Reference Molecule A Other ChEMBL Evidence
- type Kd; relation =; value 15; units nM; pChEMBL 7.82

## Query Molecule B
- Canonical SMILES: CC[C@H](C)[C@H](NC(=O)[C@H](CO)NC(=O)[C@H](CCC(=O)O)NC(=O)[C@H](CCCNC(=N)N)NC(=O)[C@@H]1CCCN1C(=O)[C@H](Cc1ccccc1)NC(=O)[C@H](CC(=O)O)NC(=O)[C@H](CCCNC(=N)N)NC(=O)[C@H](CCCCN)NC(=O)[C@H](Cc1c[nH]c2ccccc12)NC(=O)[C@H](CCSC)NC(=O)[C@H](CCC(=O)O)NC(=O)[C@H](CC(=O)O)NC(=O)[C@H](CC(C)C)NC(=O)CNC(=O)[C@@H]1CCCN1C(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CC(=O)O)NC(=O)[C@H](CCCNC(=N)N)NC(=O)[C@@H](NC(=O)[C@H](Cc1cnc[nH]1)NC(=O)[C@H](CCC(=O)O)NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CC(C)C)NC(C)=O)C(C)C)C(=O)N[C@@H](CCCNC(=N)N)C(=O)N[C@H](C(=O)N[C@@H](Cc1cnc[nH]1)C(=O)N[C@H](C(=O)N[C@@H](C)C(N)=O)[C@@H](C)O)[C@@H](C)O
- Properties:
- ChEMBL ID: CHEMBL5594087
- Molecular weight: 3739.16
- Heavy atoms: 264
- Hydrogen bond donors: 57
- Hydrogen bond acceptors: 51
- TPSA: 1636.18
- LogP: -15.81
- Rotatable bonds: 121
- Ring count: 8
- Aromatic rings: 6
- Formal charge: 0
- Fraction Csp3: 0.58
- QED: 0.01

## Molecule Similarity
- Weighted Tanimoto: 0.09

Answer: 6.94
## Endpoint to Predict
- Endpoint scope: assay
- Measurement type: IC50
- Label type: continuous
- Binary semantics: pchembl
- Assay description: Inhibition of PDE11
- Target name: Dual 3',5'-cyclic-AMP and -GMP phosphodiesterase 11A
- Target type: SINGLE PROTEIN
- Target organism: Homo sapiens

## Reference Molecule A
- Canonical SMILES: COc1ccc(-c2nc(C(=O)N3CCN(C(=O)c4cc(C)[nH]n4)CC3)c(CN)o2)c2ccc(C(F)(F)F)nc12
- Properties:
- ChEMBL ID: CHEMBL250137
- Molecule type: Small molecule
- Molecular weight: 543.51
- Heavy atoms: 39
- Hydrogen bond donors: 2
- Hydrogen bond acceptors: 8
- TPSA: 143.47
- LogP: 3.01
- Rotatable bonds: 5
- Ring count: 5
- Aromatic rings: 4
- Formal charge: 0
- Fraction Csp3: 0.32
- QED: 0.39

## Known Reference Result on This Endpoint
- Molecule A clean result: median pChEMBL = 6
- This result is provided as context for predicting Molecule B on the same endpoint.

## Reference Molecule A Other ChEMBL Evidence
- type IC50; relation =; value 1000; units nM; pChEMBL 6

## Query Molecule B
- Canonical SMILES: COc1ccc(-c2nc(C(=O)N3CC[C@@H](NC(=O)OC(C)(C)C)C3)c(CN)o2)c2ccc(C(F)(F)F)nc12
- Properties:
- ChEMBL ID: CHEMBL399298
- Molecule type: Small molecule
- Molecular weight: 535.52
- Heavy atoms: 38
- Hydrogen bond donors: 2
- Hydrogen bond acceptors: 8
- TPSA: 132.81
- LogP: 4.12
- Rotatable bonds: 5
- Ring count: 4
- Aromatic rings: 3
- Formal charge: 0
- Fraction Csp3: 0.44
- QED: 0.5

## Molecule Similarity
- Weighted Tanimoto: 0.62

Answer: 6.09
## Endpoint to Predict
- Endpoint scope: assay
- Measurement type: EC50
- Label type: continuous
- Binary semantics: pchembl
- Assay description: Inhibition of forskolin-induced cAMP accumulation in CHO-K1 cells expressing human sst5 receptor
- Assay organism: Homo sapiens
- Assay cell type: CHO-K1
- Target name: Somatostatin receptor type 5
- Target type: SINGLE PROTEIN
- Target organism: Homo sapiens

## Reference Molecule A
- Canonical SMILES: Cc1cccc2c(CCSc3nnc(-c4ccc5ccccc5n4)n3CCCCN)c[nH]c12
- Properties:
- ChEMBL ID: CHEMBL187768
- Molecule type: Small molecule
- Molecular weight: 456.62
- Heavy atoms: 33
- Hydrogen bond donors: 2
- Hydrogen bond acceptors: 5
- TPSA: 85.41
- LogP: 5.36
- Rotatable bonds: 9
- Ring count: 5
- Aromatic rings: 5
- Formal charge: 0
- Fraction Csp3: 0.27
- QED: 0.23

## Known Reference Result on This Endpoint
- Molecule A clean result: median pChEMBL = 7.47
- This result is provided as context for predicting Molecule B on the same endpoint.

## Reference Molecule A Other ChEMBL Evidence
- type EC50; relation =; value 34; units nM; pChEMBL 7.47

## Query Molecule B
- Canonical SMILES: NCCCCn1c(SCCc2c[nH]c3cc(F)ccc23)nnc1-c1ccc2ccccc2n1
- Properties:
- ChEMBL ID: CHEMBL363092
- Molecule type: Small molecule
- Molecular weight: 460.58
- Heavy atoms: 33
- Hydrogen bond donors: 2
- Hydrogen bond acceptors: 5
- TPSA: 85.41
- LogP: 5.19
- Rotatable bonds: 9
- Ring count: 5
- Aromatic rings: 5
- Formal charge: 0
- Fraction Csp3: 0.24
- QED: 0.23

## Molecule Similarity
- Weighted Tanimoto: 0.72

Answer: 7.36
## Endpoint to Predict
- Endpoint scope: assay
- Measurement type: Activity
- Label type: binary
- Binary semantics: activity
- Assay description: Binding affinity to sulfonylurea receptor in pancreatic islet beta cell membranes
- Target name: Sulfonylurea receptor 1, Kir6.2
- Target type: PROTEIN COMPLEX
- Target organism: Homo sapiens

## Reference Molecule A
- Canonical SMILES: COc1ccc2c(c1)C(=O)N(CCc1ccc(S(=O)(=O)NC(=O)NC3CCCCC3)cc1)C(=O)C2(C)C
- Properties:
- ChEMBL ID: CHEMBL383634
- Preferred name: GLIQUIDONE
- Molecule type: Small molecule
- Max clinical phase: 2
- Molecular weight: 527.64
- Heavy atoms: 37
- Hydrogen bond donors: 2
- Hydrogen bond acceptors: 6
- TPSA: 121.88
- LogP: 3.52
- Rotatable bonds: 7
- Ring count: 4
- Aromatic rings: 2
- Formal charge: 0
- Fraction Csp3: 0.44
- QED: 0.53

## Known Reference Result on This Endpoint
- Molecule A clean result: activity label = 1
- This result is provided as context for predicting Molecule B on the same endpoint.

## Reference Molecule A Other ChEMBL Evidence
- type Activity; comment Active

## Query Molecule B
- Canonical SMILES: COc1ccc2c[n+]3c(cc2c1)-c1cc2c(cc1CC3)OCO2
- Properties:
- ChEMBL ID: CHEMBL203895
- Molecule type: Small molecule
- Molecular weight: 306.34
- Heavy atoms: 23
- Hydrogen bond donors: 0
- Hydrogen bond acceptors: 3
- TPSA: 31.57
- LogP: 3.09
- Rotatable bonds: 1
- Ring count: 5
- Aromatic rings: 3
- Formal charge: 1
- Fraction Csp3: 0.21
- QED: 0.65

## Molecule Similarity
- Weighted Tanimoto: 0.17

Answer: 0
## Endpoint to Predict
- Endpoint scope: assay
- Measurement type: Ki
- Label type: continuous
- Binary semantics: pchembl
- Assay description: fluorescence polarization competition assay (FPCA): Molecular modeling and SILCS functional group affinity mapping (FragMaps) of the Mcl-1 binding site indicated that the carboxylic acid of designed molecule 3a (FIG. 1C) would occupy an energetically favorable region, associated with a salt bridge interaction with R263 of the Mcl-1 binding site, while the ring of the naphthyl core would bind in the p3 pocket demarcated by a favorable non-polar FragMap. The aniline was directed into the hydrophobic p2 pocket, which is also demarcated by a nonpolar FragMap. With the molecular modeling data in hand, compound 3a was then synthesized according to Scheme 1-2.Briefly, commercially available 1-hydroxy-2-naphthoic acid (4) was regioselectively 4-chlorosulfonylated to yield 5, which was isolated by pouring over ice and used without further purification. Sulfonyl chloride 5 was next reacted with 4-bromoaniline to furnish the target molecule 3a in excellent overall yield (83%). Evaluation of 3a in a fluorescence polarization competition assay (FPCA) indicated that it disrupted the Mcl-1-Bak-BH3 PPI with an IC50 of 10.9 μM, corresponding to a Ki of 2.76 μM. Given the ability of 3a to inhibit Mcl-1, a structure-activity relationship (SAR) study was developed, the results of which are presented in the tables below.
- Assay organism: Homo sapiens
- Target name: Induced myeloid leukemia cell differentiation protein Mcl-1
- Target type: SINGLE PROTEIN
- Target organism: Homo sapiens

## Reference Molecule A
- Canonical SMILES: COc1c(C(=O)O)cc(S(=O)(=O)N(CC(C)C)c2ccc(Br)cc2)c2ccccc12
- Properties:
- ChEMBL ID: CHEMBL3779915
- Molecule type: Small molecule
- Molecular weight: 492.39
- Heavy atoms: 30
- Hydrogen bond donors: 1
- Hydrogen bond acceptors: 4
- TPSA: 83.91
- LogP: 5.16
- Rotatable bonds: 7
- Ring count: 3
- Aromatic rings: 3
- Formal charge: 0
- Fraction Csp3: 0.23
- QED: 0.49

## Known Reference Result on This Endpoint
- Molecule A clean result: median pChEMBL = 4.63
- This result is provided as context for predicting Molecule B on the same endpoint.

## Reference Molecule A Other ChEMBL Evidence
- type Ki; relation =; value 23400; units nM; pChEMBL 4.63; comment 982804

## Query Molecule B
- Canonical SMILES: O=C(O)c1cc(S(=O)(=O)NCC2CCCCC2)c2ccccc2c1O
- Properties:
- ChEMBL ID: CHEMBL3780058
- Molecule type: Small molecule
- Molecular weight: 363.44
- Heavy atoms: 25
- Hydrogen bond donors: 3
- Hydrogen bond acceptors: 4
- TPSA: 103.7
- LogP: 3.1
- Rotatable bonds: 5
- Ring count: 3
- Aromatic rings: 2
- Formal charge: 0
- Fraction Csp3: 0.39
- QED: 0.76

## Molecule Similarity
- Weighted Tanimoto: 0.31

Answer: 5.14