2,4-Dibromo-N'-(2-hydroxy-5-trifluoromethoxybenzylidene)benzohydrazide

ID: ALA4538179

PubChem CID: 137362106

Max Phase: Preclinical

Molecular Formula: C15H9Br2F3N2O3

Molecular Weight: 482.05

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C(N/N=C/c1cc(OC(F)(F)F)ccc1O)c1ccc(Br)cc1Br

Standard InChI:  InChI=1S/C15H9Br2F3N2O3/c16-9-1-3-11(12(17)6-9)14(24)22-21-7-8-5-10(2-4-13(8)23)25-15(18,19)20/h1-7,23H,(H,22,24)/b21-7+

Standard InChI Key:  NWEMLTCAJDXJNM-QPSGOUHRSA-N

Molfile:  

 
     RDKit          2D

 25 26  0  0  0  0  0  0  0  0999 V2000
   27.0030  -20.9374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.0019  -21.7569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.7099  -22.1659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.4196  -21.7565    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.4168  -20.9338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.7081  -20.5285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.2939  -22.1650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.5865  -21.7558    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.8784  -22.1638    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.1711  -21.7547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.1717  -20.9375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.4630  -22.1627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.2952  -20.5290    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.7591  -21.7527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0516  -22.1601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0505  -22.9781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.7628  -23.3871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.4675  -22.9774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.7612  -20.9355    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   21.3430  -23.3871    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   29.1279  -22.1639    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.1292  -22.9811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.8376  -23.3886    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   28.4222  -23.3908    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   29.1217  -23.7976    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  1  1  0
  2  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
  1 13  1  0
 12 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 12  1  0
 14 19  1  0
 16 20  1  0
  4 21  1  0
 21 22  1  0
 22 23  1  0
 22 24  1  0
 22 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4538179

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 482.05

Molecular Weight (Monoisotopic): 479.8932

AlogP: 4.58

#Rotatable Bonds: 4

Polar Surface Area: 70.92

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.72

CX Basic pKa: ┄

CX LogP: 5.63

CX LogD: 5.61

Aromatic Rings: 2

Heavy Atoms: 25

QED Weighted: 0.50

Np Likeness Score: -1.39

References

1. Haranahalli K, Lazzarini C, Sun Y, Zambito J, Pathiranage S, McCarthy JB, Mallamo J, Del Poeta M, Ojima I..  (2019)  SAR Studies on Aromatic Acylhydrazone-Based Inhibitors of Fungal Sphingolipid Synthesis as Next-Generation Antifungal Agents.,  62  (17): [PMID:31369263] [10.1021/acs.jmedchem.9b01004]

Source

Source(1):

• Scientific Literature