2-(2-Fluorobiphenyl-4-yl)-N'-[(4-nitrophenyl)methylene]propanehydrazide

ID: ALA2281792

PubChem CID: 76334355

Max Phase: Preclinical

Molecular Formula: C22H18FN3O3

Molecular Weight: 391.40

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C(=O)N/N=C/c1ccc([N+](=O)[O-])cc1)c1ccc(-c2ccccc2)c(F)c1

Standard InChI:  InChI=1S/C22H18FN3O3/c1-15(18-9-12-20(21(23)13-18)17-5-3-2-4-6-17)22(27)25-24-14-16-7-10-19(11-8-16)26(28)29/h2-15H,1H3,(H,25,27)/b24-14+

Standard InChI Key:  BOTIVXGJTHIKFS-ZVHZXABRSA-N

Molfile:  

     RDKit          2D

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   10.5301   -2.7469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2382   -3.1559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9478   -2.7464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9450   -1.9238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2364   -1.5185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6481   -1.5138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3577   -1.9214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0634   -1.5109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0607   -0.6928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3465   -0.2871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6437   -0.7000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7663   -0.2806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4761   -0.6856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7622    0.5448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4803   -1.5028    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.1817   -0.2734    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.8915   -0.6784    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.3599   -2.7386    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   17.5971   -0.2662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3069   -0.6712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3057   -1.4869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0146   -1.8918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7212   -1.4795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7144   -0.6581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0049   -0.2569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4341   -1.8841    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.1391   -1.4709    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.4393   -2.7012    0.0000 O   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
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12  7  1  0
  5  7  1  0
 10 13  1  0
 13 14  1  0
 13 15  1  0
 14 16  2  0
 14 17  1  0
 17 18  1  0
  8 19  1  0
 18 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 21  1  0
 27 28  2  0
 27 29  1  0
 24 27  1  0
M  CHG  2  27   1  29  -1
M  END

Alternative Forms

1. Parent:

   

   ALA2281792

   2-(3-fluoro-4-phenylphenyl)-N-[(E)-(4-nitrophenyl)methylideneamino]propanamide

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: 391.40

Molecular Weight (Monoisotopic): 391.1332

AlogP: 4.65

#Rotatable Bonds: 6

Polar Surface Area: 84.60

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.78

CX Basic pKa: 1.07

CX LogP: 5.22

CX LogD: 5.22

Aromatic Rings: 3

Heavy Atoms: 29

QED Weighted: 0.38

Np Likeness Score: -1.47

References

1. Ckla P, Tatar E, Kucukguzel I, Sahin F, Yurdakul D, Basu A, Krishnan R, Nichols DB, Kaushik-Basu N, Kucukguzel SG.  (2013)  Synthesis and characterization of flurbiprofen hydrazide derivatives as potential anti-HCV, anticancer and antimicrobial agents,  22  (12): [10.1007/s00044-013-0550-3]

Source

Source(1):

• Scientific Literature