N'-(2-chlorobenzylidene)-3,5-dinitrobenzohydrazide

ID: ALA1171793

PubChem CID: 46839094

Max Phase: Preclinical

Molecular Formula: C14H9ClN4O5

Molecular Weight: 348.70

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(N/N=C/c1ccccc1Cl)c1cc([N+](=O)[O-])cc([N+](=O)[O-])c1

Standard InChI:  InChI=1S/C14H9ClN4O5/c15-13-4-2-1-3-9(13)8-16-17-14(20)10-5-11(18(21)22)7-12(6-10)19(23)24/h1-8H,(H,17,20)/b16-8+

Standard InChI Key:  YSZCQZUMXQHNAJ-LZYBPNLTSA-N

Molfile:  

     RDKit          2D

 24 25  0  0  0  0  0  0  0  0999 V2000
    6.7694   -6.1500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7682   -6.9773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4831   -7.3902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1995   -6.9769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1966   -6.1463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4813   -5.7372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4788   -4.9122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7631   -4.5018    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.7606   -3.6768    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.0449   -3.2665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0425   -2.4415    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3317   -3.6811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6194   -3.2666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9066   -3.6805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9086   -4.5064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6294   -4.9166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3392   -4.5003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0548   -5.7376    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.1859   -3.2688    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4725   -3.6831    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1839   -2.4439    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6339   -5.7462    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.3510   -6.1540    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9221   -6.1633    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  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
  1 18  1  0
  8  9  1  0
  4  5  1  0
  9 10  1  0
 19 20  2  0
 19 21  1  0
 14 19  1  0
  2  3  1  0
 10 11  2  0
  5  6  2  0
 22 23  2  0
 22 24  1  0
 16 22  1  0
M  CHG  4  19   1  21  -1  22   1  24  -1
M  END

Alternative Forms

1. Parent:

   

   ALA1171793

   N-[(E)-(2-chlorophenyl)methylideneamino]-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: 348.70

Molecular Weight (Monoisotopic): 348.0261

AlogP: 2.92

#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: ┄

CX LogP: 3.45

CX LogD: 3.42

Aromatic Rings: 2

Heavy Atoms: 24

QED Weighted: 0.50

Np Likeness Score: -1.96

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