2,5-Dibromo-N'-(4-bromo-2-hydroxybenzylidene)benzohydrazide

ID: ALA4537436

PubChem CID: 154588473

Max Phase: Preclinical

Molecular Formula: C14H9Br3N2O2

Molecular Weight: 476.95

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C(N/N=C/c1ccc(Br)cc1O)c1cc(Br)ccc1Br

Standard InChI:  InChI=1S/C14H9Br3N2O2/c15-9-3-4-12(17)11(5-9)14(21)19-18-7-8-1-2-10(16)6-13(8)20/h1-7,20H,(H,19,21)/b18-7+

Standard InChI Key:  ODWZHUPHIVLDTK-CNHKJKLMSA-N

Molfile:  

 
     RDKit          2D

 21 22  0  0  0  0  0  0  0  0999 V2000
   16.3713  -21.7546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3702  -22.5741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0782  -22.9831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7879  -22.5736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7850  -21.7510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0764  -21.3457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6621  -22.9822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9547  -22.5730    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.2467  -22.9810    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.5393  -22.5719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5400  -21.7547    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.8313  -22.9799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1274  -22.5699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4198  -22.9772    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4187  -23.7953    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1311  -24.2043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8357  -23.7946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6635  -21.3462    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7126  -22.5677    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   13.5452  -24.2002    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   18.4912  -21.3397    0.0000 Br  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
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 12  1  0
  1 18  1  0
 14 19  1  0
 17 20  1  0
  5 21  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4537436

   ---

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: 476.95

Molecular Weight (Monoisotopic): 473.8214

AlogP: 4.44

#Rotatable Bonds: 3

Polar Surface Area: 61.69

Molecular Species: NEUTRAL

HBA: 3

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.06

CX Basic pKa: ┄

CX LogP: 4.97

CX LogD: 4.88

Aromatic Rings: 2

Heavy Atoms: 21

QED Weighted: 0.51

Np Likeness Score: -1.37

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