N'-benzylidene-3,5-dinitrobenzohydrazide

ID: ALA1170778

Cas Number: 39575-23-0

PubChem CID: 5332138

Max Phase: Preclinical

Molecular Formula: C14H10N4O5

Molecular Weight: 314.26

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(N/N=C/c1ccccc1)c1cc([N+](=O)[O-])cc([N+](=O)[O-])c1

Standard InChI:  InChI=1S/C14H10N4O5/c19-14(16-15-9-10-4-2-1-3-5-10)11-6-12(17(20)21)8-13(7-11)18(22)23/h1-9H,(H,16,19)/b15-9+

Standard InChI Key:  VIQQTDMDKNJWHO-OQLLNIDSSA-N

Molfile:  

     RDKit          2D

 23 24  0  0  0  0  0  0  0  0999 V2000
   12.2902  -15.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2891  -15.8398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0039  -16.2527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7203  -15.8394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7175  -15.0088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0021  -14.5997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9996  -13.7747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2839  -13.3643    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.2815  -12.5393    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.5658  -12.1290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5633  -11.3040    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.8525  -12.5436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1402  -12.1291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4275  -12.5430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4295  -13.3689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1502  -13.7791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8600  -13.3628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7068  -12.1313    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.9933  -12.5456    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7047  -11.3064    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.1547  -14.6087    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.8719  -15.0165    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.4430  -15.0258    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  6  2  0
 10 12  1  0
  6  1  1  0
 12 13  2  0
  1  2  2  0
 13 14  1  0
  6  7  1  0
 14 15  2  0
  3  4  2  0
 15 16  1  0
  7  8  2  0
 16 17  2  0
 17 12  1  0
  8  9  1  0
  4  5  1  0
 18 19  2  0
 18 20  1  0
 14 18  1  0
  9 10  1  0
  2  3  1  0
 10 11  2  0
 21 22  2  0
 21 23  1  0
 16 21  1  0
M  CHG  4  18   1  20  -1  21   1  23  -1
M  END

Alternative Forms

1. Parent:

   

   ALA1170778

   N-[(E)-benzylideneamino]-3,5-dinitrobenzamide

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

Calculated Properties

Molecular Weight: 314.26

Molecular Weight (Monoisotopic): 314.0651

AlogP: 2.27

#Rotatable Bonds: 5

Polar Surface Area: 127.74

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.50

CX Basic pKa: 0.66

CX LogP: 2.84

CX LogD: 2.81

Aromatic Rings: 2

Heavy Atoms: 23

QED Weighted: 0.51

Np Likeness Score: -1.72

References

1. Kumar D, Judge V, Narang R, Sangwan S, De Clercq E, Balzarini J, Narasimhan B..  (2010)  Benzylidene/2-chlorobenzylidene hydrazides: synthesis, antimicrobial activity, QSAR studies and antiviral evaluation.,  45  (7): [PMID:20347509] [10.1016/j.ejmech.2010.03.002]

Source

Source(1):

• Scientific Literature