ID: ALA478507

Max Phase: Preclinical

Molecular Formula: C28H22F3N3O2

Molecular Weight: 489.50

Molecule Type: Small molecule

Representations

Synonyms (1): JLK-1486
Synonyms from Alternative Forms(1):

Canonical SMILES:  Oc1ccc(CN(Cc2ccc(C(F)(F)F)cc2)Cc2ccc(O)c3ncccc23)c2cccnc12

Standard InChI:  InChI=1S/C28H22F3N3O2/c29-28(30,31)21-9-5-18(6-10-21)15-34(16-19-7-11-24(35)26-22(19)3-1-13-32-26)17-20-8-12-25(36)27-23(20)4-2-14-33-27/h1-14,35-36H,15-17H2

Standard InChI Key:  JZARXLRJMQKPON-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: 489.50

Molecular Weight (Monoisotopic): 489.1664

AlogP: 6.42

#Rotatable Bonds: 6

Polar Surface Area: 69.48

Molecular Species: BASE

HBA: 5

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 8.19

CX Basic pKa: 9.50

CX LogP: 4.94

CX LogD: 4.52

Aromatic Rings: 5

Heavy Atoms: 36

QED Weighted: 0.29

Np Likeness Score: -0.74

References

1. Moret V, Laras Y, Cresteil T, Aubert G, Ping DQ, Di C, Barthélémy-Requin M, Béclin C, Peyrot V, Allegro D, Rolland A, De Angelis F, Gatti E, Pierre P, Pasquini L, Petrucci E, Testa U, Kraus JL..  (2009)  Discovery of a new family of bis-8-hydroxyquinoline substituted benzylamines with pro-apoptotic activity in cancer cells: synthesis, structure-activity relationship, and action mechanism studies.,  44  (2): [PMID:18485536] [10.1016/j.ejmech.2008.03.042]

2. Madonna S, Béclin C, Laras Y, Moret V, Marcowycz A, Lamoral-Theys D, Dubois J, Barthelemy-Requin M, Lenglet G, Depauw S, Cresteil T, Aubert G, Monnier V, Kiss R, David-Cordonnier MH, Kraus JL..  (2010)  Structure-activity relationships and mechanism of action of antitumor bis 8-hydroxyquinoline substituted benzylamines.,  45  (2): [PMID:19931949] [10.1016/j.ejmech.2009.11.006]

3. Madonna S, Maher P, Kraus JL..  (2010)  N,N-Bis-(8-hydroxyquinoline-5-yl methyl)-benzyl substituted amines (HQNBA): peroxisome proliferator-activated receptor (PPAR-γ) agonists with neuroprotective properties.,  20  (23): [PMID:20971007] [10.1016/j.bmcl.2010.09.134]

4. Barthelemy-Requin M, Nugier J, Madonna S, Kraus J.  (2012)  Bloodbrain barrier permeability and transport studies of JLK1486: a new antiglioblastoma drug,  21  (7): [10.1007/s00044-011-9649-6]

Source

Source(1):

• Scientific Literature