jiosephlee/chembl-endpoint-pair-clean-labels huggingface dataset:
## Endpoint to Predict
- Endpoint scope: assay
- Measurement type: Activity
- Label type: binary
- Binary semantics: toxic
- Assay description: Genotoxicity in Salmonella Typhimurium Cytox pr1 at 0.1 to 10 uM measured every 5 mins for 4 hrs by vitotox assay in absence of S9 liver extract
- Assay organism: Salmonella enterica subsp. enterica serovar Typhimurium
- Target name: Salmonella typhimurium
- Target type: ORGANISM
- Target organism: Salmonella enterica subsp. enterica serovar Typhimurium

## Reference Molecule A
- Canonical SMILES: COc1ccc(-c2cc(O)c3c(c2)C(=O)c2ccccc2C3=O)cc1
- Properties:
- ChEMBL ID: CHEMBL2435253
- Molecule type: Small molecule
- Molecular weight: 330.34
- Heavy atoms: 25
- Hydrogen bond donors: 1
- Hydrogen bond acceptors: 4
- TPSA: 63.6
- LogP: 3.84
- Rotatable bonds: 2
- Ring count: 4
- Aromatic rings: 3
- Formal charge: 0
- Fraction Csp3: 0.05
- QED: 0.61

## 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: COc1ccc(-c2cc3c(c(/C=C/N(C)C)n2)C(=O)c2ccccc2C3=O)cc1
- Properties:
- ChEMBL ID: CHEMBL2435269
- Molecule type: Small molecule
- Molecular weight: 384.44
- Heavy atoms: 29
- Hydrogen bond donors: 0
- Hydrogen bond acceptors: 5
- TPSA: 59.5
- LogP: 4.06
- Rotatable bonds: 4
- Ring count: 4
- Aromatic rings: 3
- Formal charge: 0
- Fraction Csp3: 0.12
- QED: 0.53

## Molecule Similarity
- Weighted Tanimoto: 0.47

Answer: 0
## Endpoint to Predict
- Endpoint scope: assay
- Measurement type: Activity
- Label type: binary
- Binary semantics: activity
- Assay description: Inhibition of Plasmodium falciparum recombinant falcipain-2
- Assay organism: Plasmodium falciparum
- Target name: Falcipain 2
- Target type: SINGLE PROTEIN
- Target organism: Plasmodium falciparum

## Reference Molecule A
- Canonical SMILES: CC[C@H](C)[C@H](N)C(=O)N[C@@H](CO)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](C)C(=O)N[C@H](C(=O)N[C@@H](Cc1cnc[nH]1)C(=O)N[C@@H](C)C(=O)N[C@@H](C)C(=O)N[C@@H](Cc1cnc[nH]1)C(=O)N[C@@H](C)C(=O)N[C@@H](CCC(=O)O)C(=O)N[C@H](C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CCC(=O)O)C(=O)N[C@@H](C)C(=O)NCC(=O)N[C@@H](CCCNC(=N)N)C(=O)O)[C@@H](C)CC)C(C)C
- Properties:
- ChEMBL ID: CHEMBL525439
- Preferred name: ovalbumin peptide
- Molecule type: Protein
- Molecular weight: 1773.93
- Heavy atoms: 125
- Hydrogen bond donors: 28
- Hydrogen bond acceptors: 26
- TPSA: 829.19
- LogP: -10.31
- Rotatable bonds: 58
- Ring count: 2
- Aromatic rings: 2
- Formal charge: 0
- Fraction Csp3: 0.62
- QED: 0.02

## 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: CC[C@H](C)[C@H](NC(=O)[C@H](Cc1ccccc1)NC(=O)[C@@H](NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@H](Cc1ccccc1)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CC(N)=O)NC(=O)[C@@H](NC(=O)[C@H](Cc1c[nH]cn1)NC(=O)[C@H](CCC(=O)O)NC(=O)[C@@H](NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CCSC)NC(=O)[C@@H](N)CC(C)C)C(C)C)[C@@H](C)CC)[C@@H](C)O)C(=O)O
- Properties:
- ChEMBL ID: CHEMBL499512
- Molecule type: Protein
- Molecular weight: 1883.16
- Heavy atoms: 133
- Hydrogen bond donors: 24
- Hydrogen bond acceptors: 25
- TPSA: 749.52
- LogP: -4.73
- Rotatable bonds: 60
- Ring count: 4
- Aromatic rings: 4
- Formal charge: 0
- Fraction Csp3: 0.53
- QED: 0.02

## Molecule Similarity
- Weighted Tanimoto: 0.4

Answer: 1
## Endpoint to Predict
- Endpoint scope: assay
- Measurement type: IC50
- Label type: continuous
- Binary semantics: pchembl
- Assay description: SPA Assay: The assays were performed in U-bottom 384-well optiplates. The final assay volume was 15 ul prepared from 7.5 ul additions of microsomes (prepared as a high-speed pellet from homogenized HEK2 cells stably transfected with CYP17), substrates (3H-Pregnenolone and NADPH) and test compounds in assay buffer (50 mM Potassium phosphate pH 7.2, 10% glycerol). The reaction was initiated by the combination of the microsomes and substrates in wells containing compound. The reaction was incubated at room temperature for 45 minutes and terminated by adding 7.5 ul of 0.2N HCl to each well. Following an incubation period of 10 minutes, anti-DHEA-coated SPA beads were added to the terminated reaction. The plate was sealed and incubated overnight with shaking at 4 C. The beads were allowed to settle in the plate for 1 hour and the plate read on a TOPCOUNT (Perkin-Elmer) plate reader.Inhibition data were calculated by comparison to no enzyme control reactions for 100% inhibition.
- Assay organism: Homo sapiens
- Assay cell type: HEK2
- Target name: Steroid 17-alpha-hydroxylase/17,20 lyase
- Target type: SINGLE PROTEIN
- Target organism: Homo sapiens

## Reference Molecule A
- Canonical SMILES: Cc1ccncc1-c1cccc2c1ncn2-c1cnccn1
- Properties:
- ChEMBL ID: CHEMBL2147035
- Molecule type: Small molecule
- Molecular weight: 287.33
- Heavy atoms: 22
- Hydrogen bond donors: 0
- Hydrogen bond acceptors: 4
- TPSA: 56.49
- LogP: 3.19
- Rotatable bonds: 2
- Ring count: 4
- Aromatic rings: 4
- Formal charge: 0
- Fraction Csp3: 0.06
- QED: 0.57

## Known Reference Result on This Endpoint
- Molecule A clean result: median pChEMBL = 7.43
- This result is provided as context for predicting Molecule B on the same endpoint.

## Reference Molecule A Other ChEMBL Evidence
- type IC50; relation =; value 37; units nM; pChEMBL 7.43; comment 326836

## Query Molecule B
- Canonical SMILES: CCOc1ncncc1-c1cccc2c1ncn2CC(F)(F)F
- Properties:
- ChEMBL ID: CHEMBL2147046
- Molecule type: Small molecule
- Molecular weight: 322.29
- Heavy atoms: 23
- Hydrogen bond donors: 0
- Hydrogen bond acceptors: 4
- TPSA: 52.83
- LogP: 3.45
- Rotatable bonds: 4
- Ring count: 3
- Aromatic rings: 3
- Formal charge: 0
- Fraction Csp3: 0.27
- QED: 0.74

## Molecule Similarity
- Weighted Tanimoto: 0.33

Answer: 6.87
## Endpoint to Predict
- Endpoint scope: assay
- Measurement type: EC50
- Label type: continuous
- Binary semantics: pchembl
- Assay description: Antiproliferative activity against human A549 cells assessed as reduction in cell viability
- Assay organism: Homo sapiens
- Assay cell type: A549
- Target name: A549
- Target type: CELL-LINE
- Target organism: Homo sapiens

## Reference Molecule A
- Canonical SMILES: CCCCCCCN(C)Cc1ccc(-c2[nH]c3c(C#N)cnn3c(=O)c2C(C)C)cc1
- Properties:
- ChEMBL ID: CHEMBL5272926
- Molecular weight: 419.57
- Heavy atoms: 31
- Hydrogen bond donors: 1
- Hydrogen bond acceptors: 4
- TPSA: 77.19
- LogP: 5.09
- Rotatable bonds: 10
- Ring count: 3
- Aromatic rings: 3
- Formal charge: 0
- Fraction Csp3: 0.48
- QED: 0.46

## Known Reference Result on This Endpoint
- Molecule A clean result: median pChEMBL = 4.68
- This result is provided as context for predicting Molecule B on the same endpoint.

## Reference Molecule A Other ChEMBL Evidence
- type EC50; relation =; value 20900; units nM; pChEMBL 4.68

## Query Molecule B
- Canonical SMILES: CCOC(=O)c1c(O)c2ccncc2[nH]c1=O
- Properties:
- ChEMBL ID: CHEMBL4637168
- Molecule type: Unknown
- Molecular weight: 234.21
- Heavy atoms: 17
- Hydrogen bond donors: 2
- Hydrogen bond acceptors: 5
- TPSA: 92.28
- LogP: 0.81
- Rotatable bonds: 2
- Ring count: 2
- Aromatic rings: 2
- Formal charge: 0
- Fraction Csp3: 0.18
- QED: 0.75

## Molecule Similarity
- Weighted Tanimoto: 0.18

Answer: 4.4
## Endpoint to Predict
- Endpoint scope: assay
- Measurement type: EC50
- Label type: continuous
- Binary semantics: pchembl
- Assay description: Inhibition of MCP-1/CCL2-induced chemotaxis in human THP1 cells incubated for 3 hrs by Beckman Coulter counting based cell counting method
- Assay organism: Homo sapiens
- Assay cell type: THP-1
- Target name: THP-1
- Target type: CELL-LINE
- Target organism: Homo sapiens

## Reference Molecule A
- Canonical SMILES: CCCCCCc1ccc(C#Cc2ccc(CN(Cc3ccc(C(F)(F)F)cc3)C(=O)C(=O)O)cc2)cc1
- Properties:
- ChEMBL ID: CHEMBL4083629
- Molecule type: Small molecule
- Molecular weight: 521.58
- Heavy atoms: 38
- Hydrogen bond donors: 1
- Hydrogen bond acceptors: 2
- TPSA: 57.61
- LogP: 6.84
- Rotatable bonds: 9
- Ring count: 3
- Aromatic rings: 3
- Formal charge: 0
- Fraction Csp3: 0.29
- QED: 0.19

## 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 EC50; relation =; value 1000; units nM; pChEMBL 6

## Query Molecule B
- Canonical SMILES: CCCCCCN(Cc1ccc(C#Cc2ccc(CCCC)cc2)cc1)C(=O)c1ccc(O)c(C(=O)O)c1
- Properties:
- ChEMBL ID: CHEMBL4103320
- Molecule type: Small molecule
- Molecular weight: 511.66
- Heavy atoms: 38
- Hydrogen bond donors: 2
- Hydrogen bond acceptors: 3
- TPSA: 77.84
- LogP: 7.06
- Rotatable bonds: 12
- Ring count: 3
- Aromatic rings: 3
- Formal charge: 0
- Fraction Csp3: 0.33
- QED: 0.2

## Molecule Similarity
- Weighted Tanimoto: 0.47

Answer: 6
## Endpoint to Predict
- Endpoint scope: assay
- Measurement type: Ki
- Label type: continuous
- Binary semantics: pchembl
- Assay description: Displacement of [125I](+/-)DOI from rat 5HT2A after 1 hr by beta scintillation counting method
- Assay organism: Rattus norvegicus
- Target name: 5-hydroxytryptamine receptor 2A
- Target type: SINGLE PROTEIN
- Target organism: Rattus norvegicus

## Reference Molecule A
- Canonical SMILES: COc1cc([C@H](O)[C@@H](C)N)c(OC)cc1Br
- Properties:
- ChEMBL ID: CHEMBL364723
- Molecule type: Small molecule
- Molecular weight: 290.16
- Heavy atoms: 16
- Hydrogen bond donors: 2
- Hydrogen bond acceptors: 4
- TPSA: 64.71
- LogP: 1.85
- Rotatable bonds: 4
- Ring count: 1
- Aromatic rings: 1
- Formal charge: 0
- Fraction Csp3: 0.45
- QED: 0.89

## Known Reference Result on This Endpoint
- Molecule A clean result: median pChEMBL = 8.04
- This result is provided as context for predicting Molecule B on the same endpoint.

## Reference Molecule A Other ChEMBL Evidence
- type Ki; relation =; value 9.2; units nM; pChEMBL 8.04

## Query Molecule B
- Canonical SMILES: COc1cc([C@@H](O)[C@H](C)N)c(OC)cc1Br
- Properties:
- ChEMBL ID: CHEMBL191286
- Molecule type: Small molecule
- Molecular weight: 290.16
- Heavy atoms: 16
- Hydrogen bond donors: 2
- Hydrogen bond acceptors: 4
- TPSA: 64.71
- LogP: 1.85
- Rotatable bonds: 4
- Ring count: 1
- Aromatic rings: 1
- Formal charge: 0
- Fraction Csp3: 0.45
- QED: 0.89

## Molecule Similarity
- Weighted Tanimoto: 1

Answer: 8.96
## Endpoint to Predict
- Endpoint scope: assay
- Measurement type: Kd
- Label type: continuous
- Binary semantics: pchembl
- Assay description: Binding affinity to BRD4 BD1 (unknown origin) assessed as dissociation constant by ITC analysis
- Assay organism: Homo sapiens
- Target name: Bromodomain-containing protein 4
- Target type: SINGLE PROTEIN
- Target organism: Homo sapiens

## Reference Molecule A
- Canonical SMILES: CC1=C(C)C2C(c3ccc(Cl)cc3)N[C@@](C)(CC(=O)NCCOCCOCCOCC(=O)N[C@H](C(=O)N3C[C@H](O)C[C@H]3C(=O)NCc3ccc(-c4scnc4C)cc3)C(C)(C)C)c3nnc(C)n3C2S1
- Properties:
- ChEMBL ID: CHEMBL5278246
- Molecular weight: 1020.72
- Heavy atoms: 70
- Hydrogen bond donors: 5
- Hydrogen bond acceptors: 14
- TPSA: 211.16
- LogP: 5.75
- Rotatable bonds: 20
- Ring count: 7
- Aromatic rings: 4
- Formal charge: 0
- Fraction Csp3: 0.54
- QED: 0.07

## Known Reference Result on This Endpoint
- Molecule A clean result: median pChEMBL = 6.42
- This result is provided as context for predicting Molecule B on the same endpoint.

## Reference Molecule A Other ChEMBL Evidence
- type Kd; relation =; value 382; units nM; pChEMBL 6.42

## Query Molecule B
- Canonical SMILES: CC(=O)N[C@H](CSCCCCCCNC(=O)C[C@H]1N=C(c2ccc(Cl)cc2)c2c(sc(C)c2C)-n2c(C)nnc21)C(=O)N1C[C@@H](O)C[C@@H]1C(=O)NCc1ccc(-c2scnc2C)cc1
- Properties:
- ChEMBL ID: CHEMBL5277866
- Molecular weight: 944.65
- Heavy atoms: 64
- Hydrogen bond donors: 4
- Hydrogen bond acceptors: 12
- TPSA: 183.8
- LogP: 6.81
- Rotatable bonds: 18
- Ring count: 7
- Aromatic rings: 5
- Formal charge: 0
- Fraction Csp3: 0.43
- QED: 0.07

## Molecule Similarity
- Weighted Tanimoto: 0.43

Answer: 7.36
## Endpoint to Predict
- Endpoint scope: assay
- Measurement type: IC50
- Label type: continuous
- Binary semantics: pchembl
- Assay description: Anticancer activity against human HelaM cells assessed as cell growth inhibition measured after 24 hrs by DAPI and propidium iodide staining based assay
- Assay organism: Homo sapiens
- Assay cell type: M-HeLa
- Target name: M-HeLa
- Target type: CELL-LINE
- Target organism: Homo sapiens

## Reference Molecule A
- Canonical SMILES: Oc1cc2c(cc1-c1ccccc1)OCO2
- Properties:
- ChEMBL ID: CHEMBL5395103
- Molecular weight: 214.22
- Heavy atoms: 16
- Hydrogen bond donors: 1
- Hydrogen bond acceptors: 3
- TPSA: 38.69
- LogP: 2.79
- Rotatable bonds: 1
- Ring count: 3
- Aromatic rings: 2
- Formal charge: 0
- Fraction Csp3: 0.08
- QED: 0.79

## Known Reference Result on This Endpoint
- Molecule A clean result: median pChEMBL = 4.83
- This result is provided as context for predicting Molecule B on the same endpoint.

## Reference Molecule A Other ChEMBL Evidence
- type IC50; relation =; value 14700; units nM; pChEMBL 4.83

## Query Molecule B
- Canonical SMILES: Oc1cc2c(cc1-c1ccc(F)cc1)OCO2
- Properties:
- ChEMBL ID: CHEMBL5396257
- Molecular weight: 232.21
- Heavy atoms: 17
- Hydrogen bond donors: 1
- Hydrogen bond acceptors: 3
- TPSA: 38.69
- LogP: 2.93
- Rotatable bonds: 1
- Ring count: 3
- Aromatic rings: 2
- Formal charge: 0
- Fraction Csp3: 0.08
- QED: 0.82

## Molecule Similarity
- Weighted Tanimoto: 0.7

Answer: 4.83
## Endpoint to Predict
- Endpoint scope: assay
- Measurement type: Bacterial Biotransformation
- Label type: binary
- Binary semantics: metabolized
- Assay description: The drug is tested on the gut metagenome community of A-02 with ENA study accession number: PRJEB31790 for biotransformation under microaerobic condition. The drug concentrations were measured over 7 timepoints collected between 0 and 12 hours of incubation by liquid-chromatography-coupled mass spectrometry (LC–MS)
- Assay organism: gut metagenome
- Target name: ADMET
- Target type: ADMET

## Reference Molecule A
- Canonical SMILES: C[C@@H]1C[C@H]2[C@@H]3CCC4=CC(=O)C=C[C@]4(C)[C@@]3(F)[C@@H](O)C[C@]2(C)[C@@]1(O)C(=O)CO
- Properties:
- ChEMBL ID: CHEMBL384467
- Preferred name: DEXAMETHASONE
- Molecule type: Small molecule
- Max clinical phase: 4
- Molecular weight: 392.47
- Heavy atoms: 28
- Hydrogen bond donors: 3
- Hydrogen bond acceptors: 5
- TPSA: 94.83
- LogP: 1.9
- Rotatable bonds: 2
- Ring count: 4
- Aromatic rings: 0
- Formal charge: 0
- Fraction Csp3: 0.73
- QED: 0.67

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

## Reference Molecule A Other ChEMBL Evidence
- type Bacterial Biotransformation; text Compound metabolized; comment Putative Metabolite Identification: The Drug Dexamethasone Is Biotransformed By A-02 And A Corresponding Drug Metabolite With M/Z 333.19 At Retention Time 4.07 Minutes Is Detected. The Source Of The Metabolite Suggests The Following: Doi: 10.1/S41586-019-1291-3

## Query Molecule B
- Canonical SMILES: CO[C@H]1C[C@@H]2CC[C@@H](C)[C@@](O)(O2)C(=O)C(=O)N2CCCC[C@H]2C(=O)O[C@H]([C@H](C)C[C@@H]2CC[C@@H](OCCO)[C@H](OC)C2)CC(=O)[C@H](C)/C=C(\C)[C@@H](O)[C@@H](OC)C(=O)[C@H](C)C[C@H](C)/C=C/C=C/C=C/1C
- Properties:
- ChEMBL ID: CHEMBL1908360
- Preferred name: EVEROLIMUS
- Molecule type: Small molecule
- Max clinical phase: 4
- Molecular weight: 958.24
- Heavy atoms: 68
- Hydrogen bond donors: 3
- Hydrogen bond acceptors: 14
- TPSA: 204.66
- LogP: 6.2
- Rotatable bonds: 9
- Ring count: 4
- Aromatic rings: 0
- Formal charge: 0
- Fraction Csp3: 0.75
- QED: 0.13

## Molecule Similarity
- Weighted Tanimoto: 0.13

Answer: 1
## Endpoint to Predict
- Endpoint scope: assay
- Measurement type: IC50
- Label type: continuous
- Binary semantics: pchembl
- Assay description: Inhibition of recombinant human PDE3A using [3H]cAMP after 1 hr by scintillation proximity assay
- Assay organism: Homo sapiens
- Target name: cGMP-inhibited 3',5'-cyclic phosphodiesterase 3A
- Target type: SINGLE PROTEIN
- Target organism: Homo sapiens

## Reference Molecule A
- Canonical SMILES: COc1ccc2nc(C)c3c(C)nc(-c4sccc4C)n3c2n1
- Properties:
- ChEMBL ID: CHEMBL1915906
- Molecule type: Small molecule
- Molecular weight: 324.41
- Heavy atoms: 23
- Hydrogen bond donors: 0
- Hydrogen bond acceptors: 5
- TPSA: 52.31
- LogP: 3.94
- Rotatable bonds: 2
- Ring count: 4
- Aromatic rings: 4
- Formal charge: 0
- Fraction Csp3: 0.24
- QED: 0.56

## Known Reference Result on This Endpoint
- Molecule A clean result: median pChEMBL = 5.16
- This result is provided as context for predicting Molecule B on the same endpoint.

## Reference Molecule A Other ChEMBL Evidence
- type IC50; relation =; value 6900; units nM; pChEMBL 5.16

## Query Molecule B
- Canonical SMILES: COc1ccc2nc(C)c3c(C)nc(-c4sc(C)nc4C)n3c2n1
- Properties:
- ChEMBL ID: CHEMBL1915912
- Molecule type: Small molecule
- Molecular weight: 339.42
- Heavy atoms: 24
- Hydrogen bond donors: 0
- Hydrogen bond acceptors: 6
- TPSA: 65.2
- LogP: 3.64
- Rotatable bonds: 2
- Ring count: 4
- Aromatic rings: 4
- Formal charge: 0
- Fraction Csp3: 0.29
- QED: 0.56

## Molecule Similarity
- Weighted Tanimoto: 0.67

Answer: 5.28
## Endpoint to Predict
- Endpoint scope: assay
- Measurement type: EC50
- Label type: continuous
- Binary semantics: pchembl
- Assay description: Antimicrobial activity against chloroquine-sensitive Plasmodium falciparum D10 after 48 hrs
- Assay organism: Plasmodium falciparum
- Target name: Plasmodium falciparum
- Target type: ORGANISM
- Target organism: Plasmodium falciparum

## Reference Molecule A
- Canonical SMILES: CC(C)(C)NC(=O)[C@@H]1C[C@@H]2CCCC[C@@H]2CN1C[C@@H](O)[C@H](Cc1ccccc1)NC(=O)[C@H](CC(N)=O)NC(=O)c1ccc2ccccc2n1
- Properties:
- ChEMBL ID: CHEMBL114
- Preferred name: SAQUINAVIR
- Molecule type: Small molecule
- Max clinical phase: 4
- Molecular weight: 670.86
- Heavy atoms: 49
- Hydrogen bond donors: 5
- Hydrogen bond acceptors: 7
- TPSA: 166.75
- LogP: 3.09
- Rotatable bonds: 12
- Ring count: 5
- Aromatic rings: 3
- Formal charge: 0
- Fraction Csp3: 0.5
- QED: 0.2

## Known Reference Result on This Endpoint
- Molecule A clean result: median pChEMBL = 5.52
- This result is provided as context for predicting Molecule B on the same endpoint.

## Reference Molecule A Other ChEMBL Evidence
- type EC50; relation =; value 3000; units nM; pChEMBL 5.52

## Query Molecule B
- Canonical SMILES: CCN(CC)CCCC(C)Nc1ccnc2cc(Cl)ccc12
- Properties:
- ChEMBL ID: CHEMBL76
- Preferred name: CHLOROQUINE
- Molecule type: Small molecule
- Max clinical phase: 4
- Molecular weight: 319.88
- Heavy atoms: 22
- Hydrogen bond donors: 1
- Hydrogen bond acceptors: 3
- TPSA: 28.16
- LogP: 4.81
- Rotatable bonds: 8
- Ring count: 2
- Aromatic rings: 2
- Formal charge: 0
- Fraction Csp3: 0.5
- QED: 0.76

## Molecule Similarity
- Weighted Tanimoto: 0.12

Answer: 7.64
## Endpoint to Predict
- Endpoint scope: assay
- Measurement type: IC50
- Label type: continuous
- Binary semantics: pchembl
- Assay description: Antiproliferative activity against human K562/ADR cells after 72 hrs by MTT assay
- Assay organism: Homo sapiens
- Assay cell type: K562/Adr
- Target name: K562/Adr
- Target type: CELL-LINE
- Target organism: Homo sapiens

## Reference Molecule A
- Canonical SMILES: COc1cc2c3c(c4ccc(O)cc4c2cc1OC)CN1CCCC[C@@H]1C3
- Properties:
- ChEMBL ID: CHEMBL3356793
- Molecule type: Small molecule
- Molecular weight: 363.46
- Heavy atoms: 27
- Hydrogen bond donors: 1
- Hydrogen bond acceptors: 4
- TPSA: 41.93
- LogP: 4.63
- Rotatable bonds: 2
- Ring count: 5
- Aromatic rings: 3
- Formal charge: 0
- Fraction Csp3: 0.39
- QED: 0.67

## Known Reference Result on This Endpoint
- Molecule A clean result: median pChEMBL = 8.59
- This result is provided as context for predicting Molecule B on the same endpoint.

## Reference Molecule A Other ChEMBL Evidence
- type IC50; relation =; value 2.6; units nM; pChEMBL 8.59

## Query Molecule B
- Canonical SMILES: COc1cccc2c1C(=O)c1c(O)c3c(c(O)c1C2=O)C[C@@](O)(C(=O)CO)C[C@@H]3O[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1.Cl
- Properties:
- ChEMBL ID: CHEMBL359744
- Preferred name: DOXORUBICIN HYDROCHLORIDE
- Molecule type: Small molecule
- Max clinical phase: 4
- Molecular weight: 579.99
- Heavy atoms: 40
- Hydrogen bond donors: 6
- Hydrogen bond acceptors: 12
- TPSA: 206.07
- LogP: 0.42
- Rotatable bonds: 5
- Ring count: 5
- Aromatic rings: 2
- Formal charge: 0
- Fraction Csp3: 0.44
- QED: 0.23

## Molecule Similarity
- Weighted Tanimoto: 0.16

Answer: 5.48
## Endpoint to Predict
- Endpoint scope: assay
- Measurement type: Activity
- Label type: binary
- Binary semantics: toxic
- Assay description: Hepatotoxicity in monkey assessed as effect on ALT levels at 5 mg/kg, po qd for 5 days
- Assay organism: Macaca mulatta
- Target name: Rhesus monkey
- Target type: ORGANISM
- Target organism: Macaca mulatta

## Reference Molecule A
- Canonical SMILES: Cc1nsc(-c2nnc3n2CCN(C(=O)c2ccc(F)cc2)C3)n1
- Properties:
- ChEMBL ID: CHEMBL3608684
- Molecule type: Small molecule
- Molecular weight: 344.38
- Heavy atoms: 24
- Hydrogen bond donors: 0
- Hydrogen bond acceptors: 6
- TPSA: 76.8
- LogP: 1.9
- Rotatable bonds: 2
- Ring count: 4
- Aromatic rings: 3
- Formal charge: 0
- Fraction Csp3: 0.27
- QED: 0.71

## 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: Cc1nsc(-c2nnc3n2CCN(C(=O)c2ccc(F)cc2)[C@@H]3C)n1
- Properties:
- ChEMBL ID: CHEMBL3608680
- Preferred name: FEZOLINETANT
- Molecule type: Small molecule
- Max clinical phase: 4
- Molecular weight: 358.4
- Heavy atoms: 25
- Hydrogen bond donors: 0
- Hydrogen bond acceptors: 6
- TPSA: 76.8
- LogP: 2.46
- Rotatable bonds: 2
- Ring count: 4
- Aromatic rings: 3
- Formal charge: 0
- Fraction Csp3: 0.31
- QED: 0.7

## Molecule Similarity
- Weighted Tanimoto: 0.66

Answer: 0
## Endpoint to Predict
- Endpoint scope: assay
- Measurement type: Activity
- Label type: binary
- Binary semantics: activity
- Assay description: Cytotoxicity against human NUGC cells at 10 uM
- Assay organism: Homo sapiens
- Assay cell type: NUGC
- Target name: NUGC
- Target type: CELL-LINE
- Target organism: Homo sapiens

## Reference Molecule A
- Canonical SMILES: C#CC(O)/C=C/CCCCCCCCCCCCC#CCCCCCCCCCCC#CC#CCO
- Properties:
- ChEMBL ID: CHEMBL492821
- Preferred name: DURISSIMOL B
- Molecule type: Small molecule
- Molecular weight: 492.79
- Heavy atoms: 36
- Hydrogen bond donors: 2
- Hydrogen bond acceptors: 2
- TPSA: 40.46
- LogP: 8.12
- Rotatable bonds: 22
- Ring count: 0
- Aromatic rings: 0
- Formal charge: 0
- Fraction Csp3: 0.71
- QED: 0.09

## 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#CC(O)/C=C/CCCCCCCCC/C=C\CCCCCCCCC/C=C/C(O)C#C
- Properties:
- ChEMBL ID: CHEMBL492822
- Molecule type: Small molecule
- Molecular weight: 440.71
- Heavy atoms: 32
- Hydrogen bond donors: 2
- Hydrogen bond acceptors: 2
- TPSA: 40.46
- LogP: 7.67
- Rotatable bonds: 22
- Ring count: 0
- Aromatic rings: 0
- Formal charge: 0
- Fraction Csp3: 0.67
- QED: 0.1

## Molecule Similarity
- Weighted Tanimoto: 0.63

Answer: 1