ID: ALA4217754

Max Phase: Preclinical

Molecular Formula: C27H23ClFN3S

Molecular Weight: 476.02

Molecule Type: Small molecule

Representations

Canonical SMILES:  Fc1ccc2scc(-c3ccc(CNCCCNc4ccnc5cc(Cl)ccc45)cc3)c2c1

Standard InChI:  InChI=1S/C27H23ClFN3S/c28-20-6-8-22-25(10-13-32-26(22)14-20)31-12-1-11-30-16-18-2-4-19(5-3-18)24-17-33-27-9-7-21(29)15-23(24)27/h2-10,13-15,17,30H,1,11-12,16H2,(H,31,32)

Standard InChI Key:  OGKDSZQVPAJLSA-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: 476.02

Molecular Weight (Monoisotopic): 475.1285

AlogP: 7.50

#Rotatable Bonds: 8

Polar Surface Area: 36.95

Molecular Species: BASE

HBA: 4

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 3

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa:

CX Basic pKa: 9.25

CX LogP: 6.29

CX LogD: 4.22

Aromatic Rings: 5

Heavy Atoms: 33

QED Weighted: 0.23

Np Likeness Score: -1.56

References

1. Konstantinović J, Videnović M, Orsini S, Bogojević K, D'Alessandro S, Scaccabarozzi D, Terzić Jovanović N, Gradoni L, Basilico N, Šolaja BA..  (2018)  Novel Aminoquinoline Derivatives Significantly Reduce Parasite Load in Leishmania infantum Infected Mice.,  9  (7): [PMID:30034591] [10.1021/acsmedchemlett.8b00053]

2. Manzano JI, Konstantinović J, Scaccabarozzi D, Perea A, Pavić A, Cavicchini L, Basilico N, Gamarro F, Šolaja BA..  (2019)  4-Aminoquinoline-based compounds as antileishmanial agents that inhibit the energy metabolism of Leishmania.,  180  [PMID:31299585] [10.1016/j.ejmech.2019.07.010]

Source

Source(1):

• Scientific Literature