jiosephlee/chembl-endpoint-pair-clean-labels huggingface dataset:
## Endpoint to Predict
- Endpoint scope: assay
- Measurement type: Activity
- Label type: binary
- Binary semantics: activity
- Assay description: Binding affinity to PS1 Carboxy-terminal fragment in human HeLa cell membrane at 20 nM by photo-affinity in-gel fluorescence method
- Assay organism: Homo sapiens
- Assay cell type: HeLa
- Target name: Presenilin-1
- Target type: SINGLE PROTEIN
- Target organism: Homo sapiens

## Reference Molecule A
- Canonical SMILES: C#CCCCCNC(=O)[C@H](Cc1ccc(C(=O)c2ccccc2)cc1)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](Cc1ccccc1)C[C@@H](O)[C@H](Cc1ccccc1)NC(=O)OC(C)(C)C
- Properties:
- ChEMBL ID: CHEMBL2017499
- Molecule type: Small molecule
- Molecular weight: 857.1
- Heavy atoms: 63
- Hydrogen bond donors: 5
- Hydrogen bond acceptors: 7
- TPSA: 162.93
- LogP: 7.14
- Rotatable bonds: 23
- Ring count: 4
- Aromatic rings: 4
- Formal charge: 0
- Fraction Csp3: 0.4
- QED: 0.03

## 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: C#CCCCCNC(=O)[C@H](Cc1ccccc1)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](Cc1ccccc1)C[C@@H](O)[C@H](Cc1ccccc1)NC(=O)c1ccc(C(=O)c2ccccc2)cc1
- Properties:
- ChEMBL ID: CHEMBL2017498
- Molecule type: Small molecule
- Molecular weight: 861.1
- Heavy atoms: 64
- Hydrogen bond donors: 5
- Hydrogen bond acceptors: 6
- TPSA: 153.7
- LogP: 7.05
- Rotatable bonds: 24
- Ring count: 5
- Aromatic rings: 5
- Formal charge: 0
- Fraction Csp3: 0.31
- QED: 0.03

## Molecule Similarity
- Weighted Tanimoto: 0.8

Answer: 0
## Endpoint to Predict
- Endpoint scope: assay
- Measurement type: EC50
- Label type: continuous
- Binary semantics: pchembl
- Assay description: Antiviral activity against Herpes simplex virus 1 KOS infected in human HELF cells assessed as reduction in virus-induced cytopathogenicity incubated for 7 days by microscopic analysis
- Assay organism: Human alphaherpesvirus 1
- Target name: Human alphaherpesvirus 1
- Target type: ORGANISM
- Target organism: Human alphaherpesvirus 1

## Reference Molecule A
- Canonical SMILES: Nc1nc2c(ncn2COCCO)c(=O)[nH]1
- Properties:
- ChEMBL ID: CHEMBL184
- Preferred name: ACYCLOVIR
- Molecule type: Small molecule
- Max clinical phase: 4
- Molecular weight: 225.21
- Heavy atoms: 16
- Hydrogen bond donors: 3
- Hydrogen bond acceptors: 6
- TPSA: 119.05
- LogP: -1.33
- Rotatable bonds: 4
- Ring count: 2
- Aromatic rings: 2
- Formal charge: 0
- Fraction Csp3: 0.38
- QED: 0.55

## Known Reference Result on This Endpoint
- Molecule A clean result: median pChEMBL = 6.05
- This result is provided as context for predicting Molecule B on the same endpoint.

## Reference Molecule A Other ChEMBL Evidence
- type EC50; relation =; value 900; units nM; pChEMBL 6.05

## Query Molecule B
- Canonical SMILES: O=c1[nH]c(=O)n([C@H]2C[C@H](O)[C@@H](CO)O2)cc1/C=C/Br
- Properties:
- ChEMBL ID: CHEMBL31634
- Preferred name: BRIVUDINE
- Molecule type: Small molecule
- Max clinical phase: 2
- Molecular weight: 333.14
- Heavy atoms: 19
- Hydrogen bond donors: 3
- Hydrogen bond acceptors: 5
- TPSA: 104.55
- LogP: -0.46
- Rotatable bonds: 3
- Ring count: 2
- Aromatic rings: 1
- Formal charge: 0
- Fraction Csp3: 0.45
- QED: 0.69

## Molecule Similarity
- Weighted Tanimoto: 0.18

Answer: 7.4
## Endpoint to Predict
- Endpoint scope: assay
- Measurement type: IC50
- Label type: continuous
- Binary semantics: pchembl
- Assay description: Inhibition of human CYP3A4
- Assay organism: Homo sapiens
- Target name: Cytochrome P450 3A4
- Target type: SINGLE PROTEIN
- Target organism: Homo sapiens

## Reference Molecule A
- Canonical SMILES: N#Cc1ccccc1Cn1c(N2CCC[C@@H](N)C2)nc2ccc(Cl)cc2c1=O
- Properties:
- ChEMBL ID: CHEMBL389074
- Molecule type: Small molecule
- Molecular weight: 393.88
- Heavy atoms: 28
- Hydrogen bond donors: 1
- Hydrogen bond acceptors: 5
- TPSA: 87.94
- LogP: 2.9
- Rotatable bonds: 3
- Ring count: 4
- Aromatic rings: 3
- Formal charge: 0
- Fraction Csp3: 0.29
- QED: 0.74

## Known Reference Result on This Endpoint
- Molecule A clean result: median pChEMBL = 6.6
- This result is provided as context for predicting Molecule B on the same endpoint.

## Reference Molecule A Other ChEMBL Evidence
- type IC50; relation =; value 250; units nM; pChEMBL 6.6

## Query Molecule B
- Canonical SMILES: N#Cc1ccccc1Cn1c(N2CCC[C@@H](N)C2)nc2cccc(F)c2c1=O
- Properties:
- ChEMBL ID: CHEMBL227464
- Molecule type: Small molecule
- Molecular weight: 377.42
- Heavy atoms: 28
- Hydrogen bond donors: 1
- Hydrogen bond acceptors: 5
- TPSA: 87.94
- LogP: 2.38
- Rotatable bonds: 3
- Ring count: 4
- Aromatic rings: 3
- Formal charge: 0
- Fraction Csp3: 0.29
- QED: 0.76

## Molecule Similarity
- Weighted Tanimoto: 0.71

Answer: 6.3
## Endpoint to Predict
- Endpoint scope: assay
- Measurement type: Activity
- Label type: binary
- Binary semantics: activity
- Assay description: Antiproliferative activity against human cisplatin resistant human MCF7-CR cells assessed as reduction in cell viability at 15 uM after 24 hrs by MTT assay relative to control
- Assay organism: Homo sapiens
- Assay cell type: MCF7
- Target name: MCF7
- Target type: CELL-LINE
- Target organism: Homo sapiens

## Reference Molecule A
- Canonical SMILES: CCOc1ccc(-c2nc(-c3ccccc3)c3cc(Cl)ccc3n2)cc1
- Properties:
- ChEMBL ID: CHEMBL5199250
- Molecular weight: 360.84
- Heavy atoms: 26
- Hydrogen bond donors: 0
- Hydrogen bond acceptors: 3
- TPSA: 35.01
- LogP: 6.02
- Rotatable bonds: 4
- Ring count: 4
- Aromatic rings: 4
- Formal charge: 0
- Fraction Csp3: 0.09
- QED: 0.45

## 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: Oc1ccccc1-c1nc(-c2ccccc2)c2cc(Cl)ccc2n1
- Properties:
- ChEMBL ID: CHEMBL5205664
- Molecular weight: 332.79
- Heavy atoms: 24
- Hydrogen bond donors: 1
- Hydrogen bond acceptors: 3
- TPSA: 46.01
- LogP: 5.32
- Rotatable bonds: 2
- Ring count: 4
- Aromatic rings: 4
- Formal charge: 0
- Fraction Csp3: 0
- QED: 0.54

## Molecule Similarity
- Weighted Tanimoto: 0.55

Answer: 1
## Endpoint to Predict
- Endpoint scope: assay
- Measurement type: EC50
- Label type: continuous
- Binary semantics: pchembl
- Assay description: Antibacterial activity against Klebsiella pneumoniae ATCC 13883 after 6 to 8 hrs by bacterial proliferation assay
- Assay organism: Klebsiella pneumoniae
- Target name: Klebsiella pneumoniae
- Target type: ORGANISM
- Target organism: Klebsiella pneumoniae

## Reference Molecule A
- Canonical SMILES: CO[C@H]1/C=C/O[C@@]2(C)Oc3c(C)c(O)c4c(O)c(c(/C=N/N5CCN(C)CC5)c(O)c4c3C2=O)NC(=O)/C(C)=C\C=C\[C@H](C)[C@H](O)[C@@H](C)[C@@H](O)[C@@H](C)[C@H](OC(C)=O)[C@@H]1C
- Properties:
- ChEMBL ID: CHEMBL374478
- Preferred name: RIFAMPIN
- Molecule type: Small molecule
- Max clinical phase: 4
- Molecular weight: 822.95
- Heavy atoms: 59
- Hydrogen bond donors: 6
- Hydrogen bond acceptors: 15
- TPSA: 220.15
- LogP: 4.34
- Rotatable bonds: 4
- Ring count: 6
- Aromatic rings: 2
- Formal charge: 0
- Fraction Csp3: 0.53
- QED: 0.11

## Known Reference Result on This Endpoint
- Molecule A clean result: median pChEMBL = 4.96
- This result is provided as context for predicting Molecule B on the same endpoint.

## Reference Molecule A Other ChEMBL Evidence
- type EC50; relation =; value 11000; units nM; pChEMBL 4.96

## Query Molecule B
- Canonical SMILES: O=C(Nc1cccc(Cl)c1)c1cc(Br)cc(Br)c1O
- Properties:
- ChEMBL ID: CHEMBL1631668
- Molecule type: Small molecule
- Molecular weight: 405.47
- Heavy atoms: 19
- Hydrogen bond donors: 2
- Hydrogen bond acceptors: 2
- TPSA: 49.33
- LogP: 4.82
- Rotatable bonds: 2
- Ring count: 2
- Aromatic rings: 2
- Formal charge: 0
- Fraction Csp3: 0
- QED: 0.75

## Molecule Similarity
- Weighted Tanimoto: 0.08

Answer: 4.02
## Endpoint to Predict
- Endpoint scope: assay
- Measurement type: AC50
- Label type: continuous
- Binary semantics: pchembl
- Assay description: PUBCHEM_BIOASSAY: Inhibition of Human CDK5 Activity Measured in Biochemical System Using Microfluidics - 2046-12_Inhibitor_Dose_DryPowder_Activity_Set2. (Class of assay: confirmatory)
- Target name: Cyclin-dependent kinase 5/CDK5 activator 1
- Target type: PROTEIN COMPLEX
- Target organism: Homo sapiens

## Reference Molecule A
- Canonical SMILES: Cc1cccc(C(=O)N[C@H]2C[C@@H](n3cnc(NC(=O)Cc4cccc5ccccc45)c3)C2)n1
- Properties:
- ChEMBL ID: CHEMBL583658
- Molecule type: Small molecule
- Molecular weight: 439.52
- Heavy atoms: 33
- Hydrogen bond donors: 2
- Hydrogen bond acceptors: 4
- TPSA: 88.91
- LogP: 4.05
- Rotatable bonds: 6
- Ring count: 5
- Aromatic rings: 4
- Formal charge: 0
- Fraction Csp3: 0.23
- QED: 0.47

## Known Reference Result on This Endpoint
- Molecule A clean result: median pChEMBL = 7.42
- This result is provided as context for predicting Molecule B on the same endpoint.

## Reference Molecule A Other ChEMBL Evidence
- type AC50; relation =; value 38; units nM; pChEMBL 7.42; comment active

## Query Molecule B
- Canonical SMILES: COc1cccc(/C=C2/Sc3ccc(C(=O)NCCCN4CCCC4)cc3NC2=O)c1
- Properties:
- ChEMBL ID: CHEMBL1339810
- Molecule type: Small molecule
- Molecular weight: 437.57
- Heavy atoms: 31
- Hydrogen bond donors: 2
- Hydrogen bond acceptors: 5
- TPSA: 70.67
- LogP: 4
- Rotatable bonds: 7
- Ring count: 4
- Aromatic rings: 2
- Formal charge: 0
- Fraction Csp3: 0.33
- QED: 0.51

## Molecule Similarity
- Weighted Tanimoto: 0.16

Answer: 5.1
## Endpoint to Predict
- Endpoint scope: assay
- Measurement type: Activity
- Label type: binary
- Binary semantics: activity
- Assay description: Antibacterial activity against Pseudomonas aeruginosa NCIM 2036 up to 300 ug/ml by standard agar method
- Assay organism: Pseudomonas aeruginosa
- Target name: Pseudomonas aeruginosa
- Target type: ORGANISM
- Target organism: Pseudomonas aeruginosa

## Reference Molecule A
- Canonical SMILES: COc1cccc(N)c1/C=N/NC(=O)CN1CCc2sccc2C1
- Properties:
- ChEMBL ID: CHEMBL3127390
- Molecule type: Small molecule
- Molecular weight: 344.44
- Heavy atoms: 24
- Hydrogen bond donors: 2
- Hydrogen bond acceptors: 6
- TPSA: 79.95
- LogP: 1.85
- Rotatable bonds: 5
- Ring count: 3
- Aromatic rings: 2
- Formal charge: 0
- Fraction Csp3: 0.29
- QED: 0.49

## 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: CN(C)c1ccc(/C=N/NC(=O)CN2CCc3sccc3C2)cc1
- Properties:
- ChEMBL ID: CHEMBL3127391
- Molecule type: Small molecule
- Molecular weight: 342.47
- Heavy atoms: 24
- Hydrogen bond donors: 1
- Hydrogen bond acceptors: 5
- TPSA: 47.94
- LogP: 2.32
- Rotatable bonds: 5
- Ring count: 3
- Aromatic rings: 2
- Formal charge: 0
- Fraction Csp3: 0.33
- QED: 0.67

## Molecule Similarity
- Weighted Tanimoto: 0.61

Answer: 0
## Endpoint to Predict
- Endpoint scope: assay
- Measurement type: Activity
- Label type: binary
- Binary semantics: toxic
- Assay description: Cytotoxicity against human K562 cells assessed as cell viability at 25 ug/ml after 24 hrs by MTT assay
- Assay organism: Homo sapiens
- Assay cell type: K562
- Target name: NON-PROTEIN TARGET
- Target type: NON-MOLECULAR

## Reference Molecule A
- Canonical SMILES: NCCCC[C@H](N)C(=O)N[C@@H](Cc1ccccc1)CN(CC(=O)NCc1ccc(-c2ccccc2)cc1)C(=O)CC12CC3CC(CC(C3)C1)C2
- Properties:
- ChEMBL ID: CHEMBL3959135
- Molecule type: Small molecule
- Molecular weight: 677.93
- Heavy atoms: 50
- Hydrogen bond donors: 4
- Hydrogen bond acceptors: 5
- TPSA: 130.55
- LogP: 5.59
- Rotatable bonds: 17
- Ring count: 7
- Aromatic rings: 3
- Formal charge: 0
- Fraction Csp3: 0.5
- QED: 0.14

## Known Reference Result on This Endpoint
- Molecule A clean result: toxic 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 Non-Toxic

## Query Molecule B
- Canonical SMILES: NCCCC[C@H](N)C(=O)N[C@@H](Cc1ccccc1)CN(CC(=O)NCc1cc(C(F)(F)F)cc(C(F)(F)F)c1)C(=O)CC12CC3CC(CC(C3)C1)C2
- Properties:
- ChEMBL ID: CHEMBL3985700
- Molecule type: Small molecule
- Molecular weight: 737.83
- Heavy atoms: 52
- Hydrogen bond donors: 4
- Hydrogen bond acceptors: 5
- TPSA: 130.55
- LogP: 5.96
- Rotatable bonds: 16
- Ring count: 6
- Aromatic rings: 2
- Formal charge: 0
- Fraction Csp3: 0.61
- QED: 0.12

## Molecule Similarity
- Weighted Tanimoto: 0.8

Answer: 0
## Endpoint to Predict
- Endpoint scope: target
- Measurement type: IC50
- Label type: continuous
- Binary semantics: pchembl
- Target name: Cytochrome P450 2C9
- Target type: SINGLE PROTEIN
- Target organism: Homo sapiens

## Reference Molecule A
- Canonical SMILES: CC(C)(C)Sc1c(CC(C)(C)C(=O)O)n(Cc2ccc(Cl)cc2)c2ccc(OCc3ccc4ccccc4n3)cc12
- Properties:
- ChEMBL ID: CHEMBL16596
- Preferred name: QUIFLAPON
- Molecule type: Small molecule
- Max clinical phase: 2
- Molecular weight: 587.19
- Heavy atoms: 41
- Hydrogen bond donors: 1
- Hydrogen bond acceptors: 4
- TPSA: 64.35
- LogP: 9.01
- Rotatable bonds: 9
- Ring count: 5
- Aromatic rings: 5
- Formal charge: 0
- Fraction Csp3: 0.29
- QED: 0.17

## Known Reference Result on This Endpoint
- Molecule A clean result: median pChEMBL = 9.3
- This result is provided as context for predicting Molecule B on the same endpoint.

## Reference Molecule A Other ChEMBL Evidence
- type IC50; relation =; value 0.5; units nM; pChEMBL 9.3

## Query Molecule B
- Canonical SMILES: O=C(O)Cc1ccc(-n2nc(C(F)(F)F)cc2-c2ccc(C(F)(F)F)cc2)cc1
- Properties:
- ChEMBL ID: CHEMBL388226
- Molecule type: Small molecule
- Molecular weight: 414.31
- Heavy atoms: 29
- Hydrogen bond donors: 1
- Hydrogen bond acceptors: 2
- TPSA: 55.12
- LogP: 5.2
- Rotatable bonds: 4
- Ring count: 3
- Aromatic rings: 3
- Formal charge: 0
- Fraction Csp3: 0.16
- QED: 0.6

## Molecule Similarity
- Weighted Tanimoto: 0.15

Answer: 4.6
## Endpoint to Predict
- Endpoint scope: assay
- Measurement type: Activity
- Label type: binary
- Binary semantics: toxic
- Assay description: Toxicity in Wistar rat assessed as incidence of convulsion at 200 mg/kg, po measured after 24 hrs
- Assay organism: Rattus norvegicus
- Target name: Rattus norvegicus
- Target type: ORGANISM
- Target organism: Rattus norvegicus

## Reference Molecule A
- Canonical SMILES: Cc1nc(=O)[nH]c2c1c(=O)[nH]c1ccccc12
- Properties:
- ChEMBL ID: CHEMBL1288778
- Molecule type: Small molecule
- Molecular weight: 227.22
- Heavy atoms: 17
- Hydrogen bond donors: 2
- Hydrogen bond acceptors: 3
- TPSA: 78.61
- LogP: 1.07
- Rotatable bonds: 0
- Ring count: 3
- Aromatic rings: 3
- Formal charge: 0
- Fraction Csp3: 0.08
- QED: 0.56

## Known Reference Result on This Endpoint
- Molecule A clean result: toxic 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 Toxic

## Query Molecule B
- Canonical SMILES: CC1=NNC(=S)Nc2c1c(=O)[nH]c1ccccc21
- Properties:
- ChEMBL ID: CHEMBL1287821
- Molecule type: Small molecule
- Molecular weight: 258.31
- Heavy atoms: 18
- Hydrogen bond donors: 3
- Hydrogen bond acceptors: 3
- TPSA: 69.28
- LogP: 1.55
- Rotatable bonds: 0
- Ring count: 3
- Aromatic rings: 2
- Formal charge: 0
- Fraction Csp3: 0.08
- QED: 0.63

## Molecule Similarity
- Weighted Tanimoto: 0.37

Answer: 1
## Endpoint to Predict
- Endpoint scope: assay
- Measurement type: EC50
- Label type: continuous
- Binary semantics: pchembl
- Assay description: Agonist activity at Kv7.5 (unknown origin) expressed in CHO cells co-expressing GFP
- Assay organism: Homo sapiens
- Assay cell type: CHO
- Target name: Potassium voltage-gated channel subfamily KQT member 5
- Target type: SINGLE PROTEIN
- Target organism: Homo sapiens

## Reference Molecule A
- Canonical SMILES: CCOC(=O)Nc1cc(F)c(NCc2ccc(C(F)(F)F)cc2)c(F)c1N
- Properties:
- ChEMBL ID: CHEMBL5185685
- Molecular weight: 389.32
- Heavy atoms: 27
- Hydrogen bond donors: 3
- Hydrogen bond acceptors: 4
- TPSA: 76.38
- LogP: 4.75
- Rotatable bonds: 5
- Ring count: 2
- Aromatic rings: 2
- Formal charge: 0
- Fraction Csp3: 0.24
- QED: 0.51

## Known Reference Result on This Endpoint
- Molecule A clean result: median pChEMBL = 5.97
- This result is provided as context for predicting Molecule B on the same endpoint.

## Reference Molecule A Other ChEMBL Evidence
- type EC50; relation =; value 1060; units nM; pChEMBL 5.97

## Query Molecule B
- Canonical SMILES: Nc1c(NC(=O)OC2CC2)ccc(NCc2ccc(C(F)(F)F)cc2)c1F
- Properties:
- ChEMBL ID: CHEMBL4458793
- Molecule type: Unknown
- Molecular weight: 383.35
- Heavy atoms: 27
- Hydrogen bond donors: 3
- Hydrogen bond acceptors: 4
- TPSA: 76.38
- LogP: 4.75
- Rotatable bonds: 5
- Ring count: 3
- Aromatic rings: 2
- Formal charge: 0
- Fraction Csp3: 0.28
- QED: 0.51

## Molecule Similarity
- Weighted Tanimoto: 0.57

Answer: 5.42
## Endpoint to Predict
- Endpoint scope: assay
- Measurement type: Activity
- Label type: binary
- Binary semantics: activity
- Assay description: Antiproliferative activity against human A549/CDDP cells assessed as decrease in cell viability at 10 to 20 uM after 96 hrs in presence of 0.5 uM CDDP by tetrazolium-dye based assay
- Assay organism: Homo sapiens
- Assay cell type: A549/CDDP
- Target name: A549/CDDP
- Target type: CELL-LINE
- Target organism: Homo sapiens

## Reference Molecule A
- Canonical SMILES: O=C(NCCCc1ccc(O)cc1)c1cc2ccc(O)cc2oc1=O
- Properties:
- ChEMBL ID: CHEMBL4081954
- Molecule type: Small molecule
- Molecular weight: 339.35
- Heavy atoms: 25
- Hydrogen bond donors: 3
- Hydrogen bond acceptors: 5
- TPSA: 99.77
- LogP: 2.57
- Rotatable bonds: 5
- Ring count: 3
- Aromatic rings: 3
- Formal charge: 0
- Fraction Csp3: 0.16
- QED: 0.49

## 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: O=C(NCCCc1ccc(F)cc1)c1cc2ccc(O)cc2oc1=O
- Properties:
- ChEMBL ID: CHEMBL4089817
- Molecule type: Small molecule
- Molecular weight: 341.34
- Heavy atoms: 25
- Hydrogen bond donors: 2
- Hydrogen bond acceptors: 4
- TPSA: 79.54
- LogP: 3
- Rotatable bonds: 5
- Ring count: 3
- Aromatic rings: 3
- Formal charge: 0
- Fraction Csp3: 0.16
- QED: 0.55

## Molecule Similarity
- Weighted Tanimoto: 0.87

Answer: 1
## Endpoint to Predict
- Endpoint scope: assay
- Measurement type: IC50
- Label type: continuous
- Binary semantics: pchembl
- Assay description: Inhibition of human recombinant MARK4 expressed in Escherichia coli M15 cells after 2 hrs in presence of [gamma-32-P]ATP by TLC analysis based ATPase assay
- Assay organism: Homo sapiens
- Target name: MAP/microtubule affinity-regulating kinase 4
- Target type: SINGLE PROTEIN
- Target organism: Homo sapiens

## Reference Molecule A
- Canonical SMILES: COc1ccc(Cn2cc(C(=O)N/N=C3/C(=O)Nc4ccc(F)c(Cl)c43)nn2)cc1
- Properties:
- ChEMBL ID: CHEMBL4543139
- Molecule type: Unknown
- Molecular weight: 428.81
- Heavy atoms: 30
- Hydrogen bond donors: 2
- Hydrogen bond acceptors: 6
- TPSA: 110.5
- LogP: 2.21
- Rotatable bonds: 5
- Ring count: 4
- Aromatic rings: 3
- Formal charge: 0
- Fraction Csp3: 0.11
- QED: 0.61

## Known Reference Result on This Endpoint
- Molecule A clean result: median pChEMBL = 4.99
- This result is provided as context for predicting Molecule B on the same endpoint.

## Reference Molecule A Other ChEMBL Evidence
- type IC50; relation =; value 10220; units nM; pChEMBL 4.99

## Query Molecule B
- Canonical SMILES: COc1ccc(Cn2cc(C(=O)N/N=C3/C(=O)Nc4c(C)cccc43)nn2)cc1
- Properties:
- ChEMBL ID: CHEMBL4529234
- Molecule type: Unknown
- Molecular weight: 390.4
- Heavy atoms: 29
- Hydrogen bond donors: 2
- Hydrogen bond acceptors: 6
- TPSA: 110.5
- LogP: 1.73
- Rotatable bonds: 5
- Ring count: 4
- Aromatic rings: 3
- Formal charge: 0
- Fraction Csp3: 0.15
- QED: 0.64

## Molecule Similarity
- Weighted Tanimoto: 0.65

Answer: 5.81
## Endpoint to Predict
- Endpoint scope: assay
- Measurement type: IC50
- Label type: continuous
- Binary semantics: pchembl
- Assay description: Inhibition of Histone Deacetylase Enzymatic Assay: For deacetylase assays, 20,000 cpm of the [3H]-metabolically labeled acetylated histone substrate (M. Yoshida et al., J. Biol. Chem. 265(28): 17174-17179 (1990)) is incubated with 30 ug of H446 nuclear extract or an equivalent amount of the cloned recombinant hHDAC-1 for 10 minutes at 37 C. The reaction is stopped by adding acetic acid (0.04 M, final concentration) and HCl (250 mM, final concentration). The mixture is extracted with ethyl acetate and the released [3H]-acetic acid was quantified by scintillation counting. For inhibition studies, the enzyme is preincubated with compounds at 4 C. for 30 minutes prior to initiation of the enzymatic assay. IC50 values for HDAC enzyme inhibitors are determined by performing dose response curves with individual compounds and determining the concentration of inhibitor producing fifty percent of the maximal inhibition. Alternatively, the following protocol is used to assay the compounds of the invention.
- Assay organism: Homo sapiens
- Target name: Histone deacetylase 8
- Target type: SINGLE PROTEIN
- Target organism: Homo sapiens

## Reference Molecule A
- Canonical SMILES: O=C(Cc1ccc(CCCCc2ccc3[nH]ccc3c2)cc1)NO
- Properties:
- ChEMBL ID: CHEMBL3698521
- Molecule type: Small molecule
- Molecular weight: 322.41
- Heavy atoms: 24
- Hydrogen bond donors: 3
- Hydrogen bond acceptors: 2
- TPSA: 65.12
- LogP: 3.78
- Rotatable bonds: 7
- Ring count: 3
- Aromatic rings: 3
- Formal charge: 0
- Fraction Csp3: 0.25
- QED: 0.35

## Known Reference Result on This Endpoint
- Molecule A clean result: median pChEMBL = 6.39
- This result is provided as context for predicting Molecule B on the same endpoint.

## Reference Molecule A Other ChEMBL Evidence
- type IC50; relation =; value 410; units nM; pChEMBL 6.39; comment 258839

## Query Molecule B
- Canonical SMILES: O=C(Cc1ccc(CCCCc2cc(F)c(F)cc2F)cc1)NO
- Properties:
- ChEMBL ID: CHEMBL3698520
- Molecule type: Small molecule
- Molecular weight: 337.34
- Heavy atoms: 24
- Hydrogen bond donors: 2
- Hydrogen bond acceptors: 2
- TPSA: 49.33
- LogP: 3.72
- Rotatable bonds: 7
- Ring count: 2
- Aromatic rings: 2
- Formal charge: 0
- Fraction Csp3: 0.28
- QED: 0.35

## Molecule Similarity
- Weighted Tanimoto: 0.51

Answer: 6.28
## Endpoint to Predict
- Endpoint scope: target
- Measurement type: IC50
- Label type: continuous
- Binary semantics: pchembl
- Target name: Eukaryotic translation initiation factor 2-alpha kinase 3
- Target type: SINGLE PROTEIN
- Target organism: Homo sapiens

## Reference Molecule A
- Canonical SMILES: COc1c(C)cc(S(=O)(=O)Nc2cccc(-c3cn(C)c4ncnc(N)c34)c2F)cc1C
- Properties:
- ChEMBL ID: CHEMBL5997013
- Molecular weight: 455.52
- Heavy atoms: 32
- Hydrogen bond donors: 2
- Hydrogen bond acceptors: 6
- TPSA: 112.13
- LogP: 3.78
- Rotatable bonds: 5
- Ring count: 4
- Aromatic rings: 4
- Formal charge: 0
- Fraction Csp3: 0.18
- QED: 0.47

## Known Reference Result on This Endpoint
- Molecule A clean result: median pChEMBL = 7.48
- This result is provided as context for predicting Molecule B on the same endpoint.

## Reference Molecule A Other ChEMBL Evidence
- type IC50; relation =; value 33; units nM; pChEMBL 7.48; comment 1223552

## Query Molecule B
- Canonical SMILES: NCCCc1n[nH]c2c(Cl)ccc(Nc3c(-c4ncccn4)oc4cnccc34)c12
- Properties:
- ChEMBL ID: CHEMBL1667865
- Molecule type: Small molecule
- Molecular weight: 419.88
- Heavy atoms: 30
- Hydrogen bond donors: 3
- Hydrogen bond acceptors: 7
- TPSA: 118.54
- LogP: 4.45
- Rotatable bonds: 6
- Ring count: 5
- Aromatic rings: 5
- Formal charge: 0
- Fraction Csp3: 0.14
- QED: 0.37

## Molecule Similarity
- Weighted Tanimoto: 0.11

Answer: 5.89