N'-(2-chlorobenzylidene)cinnamohydrazide

ID: ALA1170986

Cas Number: 25330-03-4

PubChem CID: 9554893

Max Phase: Preclinical

Molecular Formula: C16H13ClN2O

Molecular Weight: 284.75

Molecule Type: Small molecule

Names and Identifiers

Synonyms: N'-(2-Chlorobenzylidene)Cinnamohydrazide | NSC205474|25330-03-4|N'-(2-Chlorobenzylidene)Cinnamohydrazide|CHEMBL1170986|DTXSID10429607|AKOS024337354|NSC-205474|(2E)-N'-[(E)-(2-chlorophenyl)methylidene]-3-phenyl-2-propenohydrazide|(E)-N-[(E)-(2-Chlorophenyl)methylideneamino]-3-phenylprop-2-enamide

Canonical SMILES:  O=C(/C=C/c1ccccc1)N/N=C/c1ccccc1Cl

Standard InChI:  InChI=1S/C16H13ClN2O/c17-15-9-5-4-8-14(15)12-18-19-16(20)11-10-13-6-2-1-3-7-13/h1-12H,(H,19,20)/b11-10+,18-12+

Standard InChI Key:  OXUFKZCQXWZJJP-RJXLRZCOSA-N

Molfile:  

     RDKit          2D

 20 21  0  0  0  0  0  0  0  0999 V2000
   -3.9110    2.0322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7384    2.0302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1485    1.3138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7324    0.5989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9019    0.6050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4955    1.3219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6706    1.3275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2532    0.6159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4282    0.6215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0109   -0.0901    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0206    1.3388    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1956    1.3444    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2120    2.0617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0370    2.0673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4511    1.3566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2754    1.3619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6838    2.0797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2620    2.7937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4392    2.7849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0424    0.6400    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  9 10  2  0
  2  3  1  0
  9 11  1  0
  5  6  2  0
 11 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 18  1  0
  8  9  1  0
 18 19  2  0
 19 14  1  0
  4  5  1  0
 15 20  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1170986

   N'-(2-Chlorobenzylidene)Cinnamohydrazide

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: 284.75

Molecular Weight (Monoisotopic): 284.0716

AlogP: 3.50

#Rotatable Bonds: 4

Polar Surface Area: 41.46

Molecular Species: NEUTRAL

HBA: 2

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.96

CX Basic pKa: 1.19

CX LogP: 4.07

CX LogD: 4.07

Aromatic Rings: 2

Heavy Atoms: 20

QED Weighted: 0.52

Np Likeness Score: -1.24

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