N,N'-(1,3-Cyclohexadiyl)bis(4-nitrobenzamide)

ID: ALA4560417

PubChem CID: 155558299

Max Phase: Preclinical

Molecular Formula: C20H20N4O6

Molecular Weight: 412.40

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C(NC1CCCC(NC(=O)c2ccc([N+](=O)[O-])cc2)C1)c1ccc([N+](=O)[O-])cc1

Standard InChI:  InChI=1S/C20H20N4O6/c25-19(13-4-8-17(9-5-13)23(27)28)21-15-2-1-3-16(12-15)22-20(26)14-6-10-18(11-7-14)24(29)30/h4-11,15-16H,1-3,12H2,(H,21,25)(H,22,26)

Standard InChI Key:  GOHCNNUQLXUZGZ-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 30 32  0  0  0  0  0  0  0  0999 V2000
   42.8133  -27.6024    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   43.5187  -27.1899    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.5141  -26.3727    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   44.2287  -27.5945    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   44.2199  -25.9636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   44.2157  -25.1472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.5051  -24.7418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.7974  -25.1588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.8051  -25.9738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.4994  -23.9246    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   44.2043  -23.5111    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   42.7889  -23.5210    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   38.5634  -25.1678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.5623  -25.9873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.2703  -26.3963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.9800  -25.9869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.9771  -25.1642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.2685  -24.7589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.8542  -26.3954    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   37.1468  -25.9862    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   37.8536  -27.2126    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   40.6833  -24.7529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.3925  -25.1589    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   40.6802  -23.9358    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   41.3956  -25.9761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.6889  -26.3808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.6900  -27.1944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.3974  -27.6042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.1054  -27.1941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.1059  -26.3743    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  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 29  1  1  0
M  CHG  4  10   1  11  -1  19   1  20  -1
M  END

Alternative Forms

1. Parent:

   

   ALA4560417

   ---

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: 412.40

Molecular Weight (Monoisotopic): 412.1383

AlogP: 2.97

#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: 13.51

CX Basic pKa: ┄

CX LogP: 2.83

CX LogD: 2.83

Aromatic Rings: 2

Heavy Atoms: 30

QED Weighted: 0.55

Np Likeness Score: -0.70

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