ID: ALA1651866

Max Phase: Preclinical

Molecular Formula: C26H31Cl2N3O6

Molecular Weight: 434.37

Molecule Type: Small molecule

Representations

Synonyms (1): NPC1161B
Synonyms from Alternative Forms(1):

Canonical SMILES:  COc1cc(N[C@H](C)CCCN)c2nccc(C)c2c1Oc1ccc(Cl)c(Cl)c1.O=C(O)CCC(=O)O

Standard InChI:  InChI=1S/C22H25Cl2N3O2.C4H6O4/c1-13-8-10-26-21-18(27-14(2)5-4-9-25)12-19(28-3)22(20(13)21)29-15-6-7-16(23)17(24)11-15;5-3(6)1-2-4(7)8/h6-8,10-12,14,27H,4-5,9,25H2,1-3H3;1-2H2,(H,5,6)(H,7,8)/t14-;/m1./s1

Standard InChI Key:  VWFHXOIAXIAYQN-PFEQFJNWSA-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: 434.37

Molecular Weight (Monoisotopic): 433.1324

AlogP: 6.19

#Rotatable Bonds: 8

Polar Surface Area: 69.40

Molecular Species: BASE

HBA: 5

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 5

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 1

CX Acidic pKa:

CX Basic pKa: 10.20

CX LogP: 4.86

CX LogD: 2.26

Aromatic Rings: 3

Heavy Atoms: 29

QED Weighted: 0.44

Np Likeness Score: -0.39

References

1. Nanayakkara NP, Ager AL, Bartlett MS, Yardley V, Croft SL, Khan IA, McChesney JD, Walker LA..  (2008)  Antiparasitic activities and toxicities of individual enantiomers of the 8-aminoquinoline 8-[(4-amino-1-methylbutyl)amino]-6-methoxy-4-methyl-5-[3,4-dichlorophenoxy]quinoline succinate.,  52  (6): [PMID:18378716] [10.1128/aac.00645-07]

2. Dechy-Cabaret O, Benoit-Vical F..  (2012)  Effects of antimalarial molecules on the gametocyte stage of Plasmodium falciparum: the debate.,  55  (23): [PMID:23075290] [10.1021/jm3005898]

3. Flannery EL, Fidock DA, Winzeler EA..  (2013)  Using genetic methods to define the targets of compounds with antimalarial activity.,  56  (20): [PMID:23927658] [10.1021/jm400325j]

Source

Source(1):

• Scientific Literature