N,N'-(Ethane-1,2-diyl)bis(4-nitrobenzamide)

ID: ALA4543507

Cas Number: 33288-81-2

PubChem CID: 2134211

Max Phase: Preclinical

Molecular Formula: C16H14N4O6

Molecular Weight: 358.31

Molecule Type: Unknown

Names and Identifiers

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

Standard InChI:  InChI=1S/C16H14N4O6/c21-15(11-1-5-13(6-2-11)19(23)24)17-9-10-18-16(22)12-3-7-14(8-4-12)20(25)26/h1-8H,9-10H2,(H,17,21)(H,18,22)

Standard InChI Key:  KGDGPIKXAQPEMP-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 26 27  0  0  0  0  0  0  0  0999 V2000
   34.0111  -18.3744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.0099  -19.1939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.7180  -19.6029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.4276  -19.1934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.4248  -18.3708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.7162  -17.9655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.3019  -19.6020    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   32.5945  -19.1928    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   33.3013  -20.4191    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   36.1310  -17.9595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.8402  -18.3655    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   36.1279  -17.1423    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   37.5464  -17.9542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.2556  -18.3601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.9618  -17.9489    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   39.6710  -18.3548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.3772  -17.9435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.6741  -19.1720    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   41.0836  -18.3516    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.7893  -17.9410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.7866  -17.1230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.0724  -16.7172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.3697  -17.1301    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.4923  -16.7108    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   43.2020  -17.1157    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   42.4881  -15.8936    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
  2  7  1  0
  7  8  1  0
  7  9  2  0
  5 10  1  0
 10 11  1  0
 10 12  2  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  2  0
 17 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 17  1  0
 21 24  1  0
 24 25  1  0
 24 26  2  0
M  CHG  4   7   1   8  -1  24   1  25  -1
M  END

Alternative Forms

1. Parent:

   

   ALA4543507

   N,N'-bis(p-nitrobenzoyl)ethylenediamine

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: 358.31

Molecular Weight (Monoisotopic): 358.0913

AlogP: 1.66

#Rotatable Bonds: 7

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: 13.39

CX Basic pKa: ┄

CX LogP: 1.80

CX LogD: 1.80

Aromatic Rings: 2

Heavy Atoms: 26

QED Weighted: 0.44

Np Likeness Score: -0.90

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