ID: ALA494163

Max Phase: Preclinical

Molecular Formula: C19H25ClN4O2

Molecular Weight: 340.43

Molecule Type: Small molecule

Representations

Synonyms (2): TCMDC-125857 | TCMDC-125857
Synonyms from Alternative Forms(2):

Canonical SMILES:  Cl.N=C(N)c1ccc(OCCCCCOc2ccc(C(=N)N)cc2)cc1

Standard InChI:  InChI=1S/C19H24N4O2.ClH/c20-18(21)14-4-8-16(9-5-14)24-12-2-1-3-13-25-17-10-6-15(7-11-17)19(22)23;/h4-11H,1-3,12-13H2,(H3,20,21)(H3,22,23);1H

Standard InChI Key:  WIJHFFBIVJGJJU-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: 340.43

Molecular Weight (Monoisotopic): 340.1899

AlogP: 2.88

#Rotatable Bonds: 10

Polar Surface Area: 118.20

Molecular Species: BASE

HBA: 4

HBD: 4

#RO5 Violations: 0

HBA (Lipinski): 6

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 1

CX Acidic pKa:

CX Basic pKa: 12.13

CX LogP: 2.32

CX LogD: -2.50

Aromatic Rings: 2

Heavy Atoms: 25

QED Weighted: 0.30

Np Likeness Score: -0.14

References

1. Tidwell RR, Jones SK, Geratz JD, Ohemeng KA, Cory M, Hall JE..  (1990)  Analogues of 1,5-bis(4-amidinophenoxy)pentane (pentamidine) in the treatment of experimental Pneumocystis carinii pneumonia.,  33  (4): [PMID:2319567] [10.1021/jm00166a026]

2. Bakunova SM, Bakunov SA, Patrick DA, Kumar EV, Ohemeng KA, Bridges AS, Wenzler T, Barszcz T, Jones SK, Werbovetz KA, Brun R, Tidwell RR..  (2009)  Structure-activity study of pentamidine analogues as antiprotozoal agents.,  52  (7): [PMID:19267462] [10.1021/jm801547t]

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. Maciejewska D, Żabiński J, Kaźmierczak P, Wójciuk K, Kruszewski M, Kruszewska H..  (2014)  In vitro screening of pentamidine analogs against bacterial and fungal strains.,  24  (13): [PMID:24830598] [10.1016/j.bmcl.2014.04.075]

Source

Source(2):

• Scientific Literature
• GSK Malaria Screening