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

ID: ALA4457334

Cas Number: 5922-25-8

PubChem CID: 3092115

Max Phase: Preclinical

Molecular Formula: C20H14N4O6

Molecular Weight: 406.35

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C(Nc1ccc(NC(=O)c2ccc([N+](=O)[O-])cc2)cc1)c1ccc([N+](=O)[O-])cc1

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

Standard InChI Key:  NPYZUPPARJCROL-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 30 32  0  0  0  0  0  0  0  0999 V2000
   35.5904   -6.1797    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   36.2997   -6.5856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.0058   -6.1744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.3027   -7.4028    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   37.7122   -6.5824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.4179   -6.1719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.4153   -5.3538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.7011   -4.9481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.9983   -5.3610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.1209   -4.9416    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   39.8307   -5.3466    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   39.1167   -4.1244    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.7564   -2.9262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.7553   -3.7457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.4633   -4.1547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.1730   -3.7452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.1701   -2.9226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.4615   -2.5173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.0472   -4.1537    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   31.3398   -3.7446    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.0466   -4.9709    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   34.8763   -2.5113    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.5855   -2.9172    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   34.8732   -1.6941    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   35.5886   -3.7344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.8819   -4.1391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.8830   -4.9528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.5904   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.2984   -4.9525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.2989   -4.1327    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
 28  1  1  0
M  CHG  4  10   1  11  -1  19   1  20  -1
M  END

Alternative Forms

1. Parent:

   

   ALA4457334

   4-nitro-N-[4-[(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: 13.77

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