ID: ALA533684

Max Phase: Preclinical

Molecular Formula: C15H13Cl2N5

Molecular Weight: 334.21

Molecule Type: Small molecule

Representations

Synonyms (2): TCMDC-141974 | TCMDC-141974
Synonyms from Alternative Forms(2):

Canonical SMILES:  Nc1nc(N)c2cc(CNc3ccc(Cl)c(Cl)c3)ccc2n1

Standard InChI:  InChI=1S/C15H13Cl2N5/c16-11-3-2-9(6-12(11)17)20-7-8-1-4-13-10(5-8)14(18)22-15(19)21-13/h1-6,20H,7H2,(H4,18,19,21,22)

Standard InChI Key:  LFMKPWQUJBLWEK-UHFFFAOYSA-N

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Properties

Molecular Weight: 334.21

Molecular Weight (Monoisotopic): 333.0548

AlogP: 3.71

#Rotatable Bonds: 3

Polar Surface Area: 89.85

Molecular Species: NEUTRAL

HBA: 5

HBD: 3

#RO5 Violations: 0

HBA (Lipinski): 5

HBD (Lipinski): 5

#RO5 Violations (Lipinski): 0

CX Acidic pKa:

CX Basic pKa: 6.99

CX LogP: 3.45

CX LogD: 3.31

Aromatic Rings: 3

Heavy Atoms: 22

QED Weighted: 0.68

Np Likeness Score: -1.42

References

1. Gamo FJ, Sanz LM, Vidal J, de Cozar C, Alvarez E, Lavandera JL, Vanderwall DE, Green DV, Kumar V, Hasan S, Brown JR, Peishoff CE, Cardon LR, Garcia-Bustos JF..  (2010)  Thousands of chemical starting points for antimalarial lead identification.,  465  (7296): [PMID:20485427] [10.1038/nature09107]

2. Chen BK, Horváth C, Bertino JR..  (1979)  Multivariate analysis and quantitative structure-activity relationships. Inhibition of dihydrofolate reductase and thymidylate synthetase by quinazolines.,  22  (5): [PMID:110930] [10.1021/jm00191a005]

3. Hansch C, Fukunaga JY, Jow PY..  (1977)  Quantitative structure-activity relationships of antimalarial and dihydrofolate reductase inhibition by quinazolines and 5-substituted benzyl-2,4-diaminopyrimidines.,  20  (1): [PMID:319234] [10.1021/jm00211a020]

4. St. Jude Leishmania screening dataset.,  [10.6019/CHEMBL3433997]

5. Bibi M,Qureshi NA,Sadiq A,Farooq U,Hassan A,Shaheen N,Asghar I,Umer D,Ullah A,Khan FA,Salman M,Bibi A,Rashid U.  (2021)  Exploring the ability of dihydropyrimidine-5-carboxamide and 5-benzyl-2,4-diaminopyrimidine-based analogues for the selective inhibition of L. major dihydrofolate reductase.,  210  [PMID:33187806] [10.1016/j.ejmech.2020.112986]

Source

Source(3):

• Scientific Literature
• GSK Malaria Screening
• St Jude Leishmania Screening