N,N'-(Butane-1,4-diyl)bis(4-nitrobenzamide)

ID: ALA4567423

Cas Number: 34062-77-6

PubChem CID: 4295048

Max Phase: Preclinical

Molecular Formula: C18H18N4O6

Molecular Weight: 386.36

Molecule Type: Unknown

Names and Identifiers

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

Standard InChI:  InChI=1S/C18H18N4O6/c23-17(13-3-7-15(8-4-13)21(25)26)19-11-1-2-12-20-18(24)14-5-9-16(10-6-14)22(27)28/h3-10H,1-2,11-12H2,(H,19,23)(H,20,24)

Standard InChI Key:  XNOBJDFFNIHUAI-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 28 29  0  0  0  0  0  0  0  0999 V2000
    8.6842  -25.9297    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.3934  -26.3356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0996  -25.9244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3965  -27.1528    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.8060  -26.3324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5117  -25.9219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5091  -25.1038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7948  -24.6981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0921  -25.1110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2147  -24.6916    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.9245  -25.0966    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.2105  -23.8744    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3181  -26.3606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3169  -27.1801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0250  -27.5891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7346  -27.1796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7318  -26.3570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0232  -25.9517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6089  -27.5881    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9015  -27.1790    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6083  -28.4053    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4380  -25.9457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1472  -26.3516    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4349  -25.1285    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8534  -25.9404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5626  -26.3463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2688  -25.9350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9780  -26.3410    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
 26 27  1  0
 27 28  1  0
 28  1  1  0
M  CHG  4  10   1  11  -1  19   1  20  -1
M  END

Alternative Forms

1. Parent:

   

   ALA4567423

   4-nitro-N-[4-[(4-nitrobenzoyl)amino]butyl]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: 386.36

Molecular Weight (Monoisotopic): 386.1226

AlogP: 2.44

#Rotatable Bonds: 9

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: 13.40

CX Basic pKa: ┄

CX LogP: 2.38

CX LogD: 2.38

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.38

Np Likeness Score: -0.83

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