ID: ALA254412

Max Phase: Preclinical

Molecular Formula: C16H14Cl2N6O

Molecular Weight: 377.24

Molecule Type: Small molecule

Representations

Canonical SMILES:  N#Cc1nc(NCc2ccc(Cl)c(Cl)c2)c2ncn(CCCO)c2n1

Standard InChI:  InChI=1S/C16H14Cl2N6O/c17-11-3-2-10(6-12(11)18)8-20-15-14-16(23-13(7-19)22-15)24(9-21-14)4-1-5-25/h2-3,6,9,25H,1,4-5,8H2,(H,20,22,23)

Standard InChI Key:  BDSGZPUKZJAYIB-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: 377.24

Molecular Weight (Monoisotopic): 376.0606

AlogP: 3.00

#Rotatable Bonds: 6

Polar Surface Area: 99.65

Molecular Species: NEUTRAL

HBA: 7

HBD: 2

#RO5 Violations: 0

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 0

CX Acidic pKa:

CX Basic pKa: 1.14

CX LogP: 2.90

CX LogD: 2.90

Aromatic Rings: 3

Heavy Atoms: 25

QED Weighted: 0.69

Np Likeness Score: -1.36

References

1. Mallari JP, Shelat AA, Obrien T, Caffrey CR, Kosinski A, Connelly M, Harbut M, Greenbaum D, McKerrow JH, Guy RK..  (2008)  Development of potent purine-derived nitrile inhibitors of the trypanosomal protease TbcatB.,  51  (3): [PMID:18173229] [10.1021/jm070760l]

2. Watts KR, Ratnam J, Ang KH, Tenney K, Compton JE, McKerrow J, Crews P..  (2010)  Assessing the trypanocidal potential of natural and semi-synthetic diketopiperazines from two deep water marine-derived fungi.,  18  (7): [PMID:20303767] [10.1016/j.bmc.2010.02.034]

3. Mallari JP, Zhu F, Lemoff A, Kaiser M, Lu M, Brun R, Guy RK..  (2010)  Optimization of purine-nitrile TbcatB inhibitors for use in vivo and evaluation of efficacy in murine models.,  18  (23): [PMID:21051236] [10.1016/j.bmc.2010.09.073]

4. PubChem BioAssay data set, 

Source

Source(2):

• Scientific Literature
• PubChem BioAssays