2-Fluoro-4-trifluoromethoxy-N'-(5-bromo-2-hydroxybenzylidene)benzohydrazide

ID: ALA4536097

PubChem CID: 137361740

Max Phase: Preclinical

Molecular Formula: C15H9BrF4N2O3

Molecular Weight: 421.14

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C(N/N=C/c1cc(Br)ccc1O)c1ccc(OC(F)(F)F)cc1F

Standard InChI:  InChI=1S/C15H9BrF4N2O3/c16-9-1-4-13(23)8(5-9)7-21-22-14(24)11-3-2-10(6-12(11)17)25-15(18,19)20/h1-7,23H,(H,22,24)/b21-7+

Standard InChI Key:  VFFBPUPBTZPRPV-QPSGOUHRSA-N

Molfile:  

 
     RDKit          2D

 25 26  0  0  0  0  0  0  0  0999 V2000
   27.5355  -13.6487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.5343  -14.4682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.2424  -14.8772    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.9520  -14.4678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.9492  -13.6451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.2406  -13.2398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.8263  -14.8763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.1189  -14.4671    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   25.4109  -14.8752    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.7035  -14.4660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.7041  -13.6488    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.9954  -14.8740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.8276  -13.2403    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.2915  -14.4640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.5840  -14.8714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.5829  -15.6894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.2953  -16.0984    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.9999  -15.6887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8754  -16.0984    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.8758  -16.9156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1684  -17.3246    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   22.5838  -17.3238    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   21.8702  -17.7306    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   29.6604  -14.8753    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   24.7093  -16.0943    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
 16 19  1  0
 19 20  1  0
 20 21  1  0
 20 22  1  0
 20 23  1  0
  4 24  1  0
 18 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4536097

   ---

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: 421.14

Molecular Weight (Monoisotopic): 419.9733

AlogP: 3.96

#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: 8.26

CX Basic pKa: ┄

CX LogP: 5.00

CX LogD: 4.95

Aromatic Rings: 2

Heavy Atoms: 25

QED Weighted: 0.45

Np Likeness Score: -1.72

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