ID: ALA3219153

Max Phase: Preclinical

Molecular Formula: C24H25ClN4O

Molecular Weight: 420.94

Molecule Type: Small molecule

Representations

Canonical SMILES:  COc1cc(NC(C)CCCNc2ccnc3cc(Cl)ccc23)c2ncccc2c1

Standard InChI:  InChI=1S/C24H25ClN4O/c1-16(29-23-15-19(30-2)13-17-6-4-11-28-24(17)23)5-3-10-26-21-9-12-27-22-14-18(25)7-8-20(21)22/h4,6-9,11-16,29H,3,5,10H2,1-2H3,(H,26,27)

Standard InChI Key:  XGGLHZNSHPBQNK-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: 420.94

Molecular Weight (Monoisotopic): 420.1717

AlogP: 6.14

#Rotatable Bonds: 8

Polar Surface Area: 59.07

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa:

CX Basic pKa: 7.31

CX LogP: 4.48

CX LogD: 4.23

Aromatic Rings: 4

Heavy Atoms: 30

QED Weighted: 0.34

Np Likeness Score: -0.96

References

1. Pal C, Sarkar S, Mazumder S, Adhikari S, Bandyopadhyay U.  (2013)  Synthesis and biological evaluation of primaquinechloroquine twin drug: a novel heme-interacting molecule prevents free heme and hydroxyl radical-mediated protein degradation,  4  (4): [10.1039/C3MD00019B]

2. Mushtaque M, Shahjahan..  (2015)  Reemergence of chloroquine (CQ) analogs as multi-targeting antimalarial agents: a review.,  90  [PMID:25461328] [10.1016/j.ejmech.2014.11.022]

3. Oliveira R, Miranda D, Magalhães J, Capela R, Perry MJ, O'Neill PM, Moreira R, Lopes F..  (2015)  From hybrid compounds to targeted drug delivery in antimalarial therapy.,  23  (16): [PMID:25913864] [10.1016/j.bmc.2015.04.017]

4. Vandekerckhove S, D'hooghe M..  (2015)  Quinoline-based antimalarial hybrid compounds.,  23  (16): [PMID:25593097] [10.1016/j.bmc.2014.12.018]

Source

Source(1):

• Scientific Literature