N,N'-(1,2-Phenylene)bis(4-nitrobenzamide)

ID: ALA4454897

PubChem CID: 3570851

Max Phase: Preclinical

Molecular Formula: C20H14N4O6

Molecular Weight: 406.35

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C(Nc1ccccc1NC(=O)c1ccc([N+](=O)[O-])cc1)c1ccc([N+](=O)[O-])cc1

Standard InChI:  InChI=1S/C20H14N4O6/c25-19(13-5-9-15(10-6-13)23(27)28)21-17-3-1-2-4-18(17)22-20(26)14-7-11-16(12-8-14)24(29)30/h1-12H,(H,21,25)(H,22,26)

Standard InChI Key:  XLLSAFDUMYKCBU-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 30 32  0  0  0  0  0  0  0  0999 V2000
   16.8074   -4.3183    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.5166   -4.7243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2228   -4.3130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5197   -5.5414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.9292   -4.7211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6349   -4.3105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6323   -3.4924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9180   -3.0867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2153   -3.4996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3379   -3.0802    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.0477   -3.4852    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.3337   -2.2630    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.5619   -3.5246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5607   -4.3442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2688   -4.7531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9784   -4.3437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9756   -3.5210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2670   -3.1158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8527   -4.7522    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.1453   -4.3430    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.8520   -5.5694    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.6818   -3.1098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3910   -3.5157    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.6787   -2.2926    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.3941   -4.3329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6873   -4.7376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6885   -5.5512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3959   -5.9610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1039   -5.5509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1044   -4.7311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  0
  3  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9  3  1  0
  7 10  1  0
 10 11  1  0
 10 12  2  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 13  1  0
 14 19  1  0
 19 20  1  0
 19 21  2  0
 17 22  1  0
 22 23  1  0
 22 24  2  0
 23 25  1  0
 25 26  1  0
 25 30  2  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
 29 30  1  0
 30  1  1  0
M  CHG  4  10   1  11  -1  19   1  20  -1
M  END

Alternative Forms

1. Parent:

   

   ALA4454897

   4-nitro-N-[2-[(4-nitrobenzoyl)amino]phenyl]benzamide

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: 406.35

Molecular Weight (Monoisotopic): 406.0913

AlogP: 4.01

#Rotatable Bonds: 6

Polar Surface Area: 144.48

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 10

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.45

CX Basic pKa: ┄

CX LogP: 4.04

CX LogD: 4.04

Aromatic Rings: 3

Heavy Atoms: 30

QED Weighted: 0.47

Np Likeness Score: -0.98

References

1. Güngör T, Önder FC, Tokay E, Gülhan ÜG, Hacıoğlu N, Tok TT, Çelik A, Köçkar F, Ay M..  (2019)  PRODRUGS FOR NITROREDUCTASE BASED CANCER THERAPY- 2: Novel amide/Ntr combinations targeting PC3 cancer cells.,  171  [PMID:30928710] [10.1016/j.ejmech.2019.03.035]

Source

Source(1):

• Scientific Literature