ID: ALA1290599

Max Phase: Preclinical

Molecular Formula: C27H29ClN4O

Molecular Weight: 425.56

Molecule Type: Small molecule

Representations

Canonical SMILES:  CCN(CC)Cc1ccc(Nc2c3ccccc3[n+](C)c3c2[nH]c2ccccc23)cc1O.[Cl-]

Standard InChI:  InChI=1S/C27H28N4O.ClH/c1-4-31(5-2)17-18-14-15-19(16-24(18)32)28-25-21-11-7-9-13-23(21)30(3)27-20-10-6-8-12-22(20)29-26(25)27;/h6-16H,4-5,17H2,1-3H3,(H2,28,29,32);1H

Standard InChI Key:  WVPCEQDWJHUGPJ-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: 425.56

Molecular Weight (Monoisotopic): 425.2336

AlogP: 5.59

#Rotatable Bonds: 6

Polar Surface Area: 55.17

Molecular Species: BASE

HBA: 3

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 5

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 8.45

CX Basic pKa: 10.25

CX LogP: -0.47

CX LogD: -1.36

Aromatic Rings: 5

Heavy Atoms: 32

QED Weighted: 0.31

Np Likeness Score: -0.20

References

1. Lavrado J, Reszka AP, Moreira R, Neidle S, Paulo A..  (2010)  C-11 diamino cryptolepine derivatives NSC748392, NSC748393, and NSC748394: anticancer profile and G-quadruplex stabilization.,  20  (23): [PMID:20952194] [10.1016/j.bmcl.2010.09.110]

2. Lavrado J, Cabal GG, Prudêncio M, Mota MM, Gut J, Rosenthal PJ, Díaz C, Guedes RC, dos Santos DJ, Bichenkova E, Douglas KT, Moreira R, Paulo A..  (2011)  Incorporation of basic side chains into cryptolepine scaffold: structure-antimalarial activity relationships and mechanistic studies.,  54  (3): [PMID:21207937] [10.1021/jm101383f]

3. Lavrado J, Mackey Z, Hansell E, McKerrow JH, Paulo A, Moreira R..  (2012)  Antitrypanosomal and cysteine protease inhibitory activities of alkyldiamine cryptolepine derivatives.,  22  (19): [PMID:22926067] [10.1016/j.bmcl.2012.07.104]

Source

Source(1):

• Scientific Literature