ID: ALA21357

Max Phase: Preclinical

Molecular Formula: C11H11ClN4

Molecular Weight: 234.69

Molecule Type: Small molecule

Representations

Synonyms (2): TCMDC-138984 | TCMDC-138984
Synonyms from Alternative Forms(2):

Canonical SMILES:  Cc1nc(N)nc(N)c1-c1ccc(Cl)cc1

Standard InChI:  InChI=1S/C11H11ClN4/c1-6-9(10(13)16-11(14)15-6)7-2-4-8(12)5-3-7/h2-5H,1H3,(H4,13,14,15,16)

Standard InChI Key:  SNBBQZGVKQEBQT-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: 234.69

Molecular Weight (Monoisotopic): 234.0672

AlogP: 2.27

#Rotatable Bonds: 1

Polar Surface Area: 77.82

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: 0

HBA (Lipinski): 4

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 0

CX Acidic pKa:

CX Basic pKa: 7.94

CX LogP: 2.05

CX LogD: 1.41

Aromatic Rings: 2

Heavy Atoms: 16

QED Weighted: 0.79

Np Likeness Score: -0.81

References

1. Tarnchompoo B, Sirichaiwat C, Phupong W, Intaraudom C, Sirawaraporn W, Kamchonwongpaisan S, Vanichtanankul J, Thebtaranonth Y, Yuthavong Y..  (2002)  Development of 2,4-diaminopyrimidines as antimalarials based on inhibition of the S108N and C59R+S108N mutants of dihydrofolate reductase from pyrimethamine-resistant Plasmodium falciparum.,  45  (6): [PMID:11881993] [10.1021/jm010131q]

2. Parenti MD, Pacchioni S, Ferrari AM, Rastelli G..  (2004)  Three-dimensional quantitative structure-activity relationship analysis of a set of Plasmodium falciparum dihydrofolate reductase inhibitors using a pharmacophore generation approach.,  47  (17): [PMID:15293997] [10.1021/jm040769c]

3. 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]

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

5. Tropak MB, Zhang J, Yonekawa S, Rigat BA, Aulakh VS, Smith MR, Hwang HJ, Ciufolini MA, Mahuran DJ..  (2015)  Pyrimethamine Derivatives: Insight into Binding Mechanism and Improved Enhancement of Mutant β-N-acetylhexosaminidase Activity.,  58  (11): [PMID:25984755] [10.1021/jm5017895]

Source

Source(3):

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