4-{[(3-{[3-(dimethylamino)propyl]amino}-6-nitroquinoxalin-2-yl)amino]methyl}benzonitrile

ID: ALA5179793

PubChem CID: 168273304

Max Phase: Preclinical

Molecular Formula: C21H23N7O2

Molecular Weight: 405.46

Names and Identifiers

Canonical SMILES:  CN(C)CCCNc1nc2cc([N+](=O)[O-])ccc2nc1NCc1ccc(C#N)cc1

Standard InChI:  InChI=1S/C21H23N7O2/c1-27(2)11-3-10-23-20-21(24-14-16-6-4-15(13-22)5-7-16)25-18-9-8-17(28(29)30)12-19(18)26-20/h4-9,12H,3,10-11,14H2,1-2H3,(H,23,26)(H,24,25)

Standard InChI Key:  GWCHVPVKANTRFR-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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   -3.2593   -0.0078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5463   -0.4196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8339   -0.0036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8346    0.8208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5481    1.2288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1260    1.2338    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4120    0.8275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4072    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1205   -0.4134    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3065   -0.4085    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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    1.7303   -1.2241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4437   -1.6327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1557   -1.2184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1498   -0.3914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4359    0.0133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2977    1.2434    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0128    0.8362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7229    1.2522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4380    0.8449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1481    1.2609    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8632    0.8537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1430    2.0836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9716    1.2281    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6841    0.8166    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9718    2.0510    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8682   -1.6298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6841   -2.0836    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  5  4  1  0
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  5  6  2  0
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  9 11  1  0
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 16 17  1  0
 17 18  2  0
 18 13  1  0
  8 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 23 25  1  0
  1 26  1  0
 26 27  2  0
 26 28  1  0
 16 29  1  0
 29 30  3  0
M  CHG  2  26   1  28  -1
M  END

Alternative Forms

1. Parent:

   

   ALA5179793

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type:

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 405.46

Molecular Weight (Monoisotopic): 405.1913

AlogP: 3.39

#Rotatable Bonds: 9

Polar Surface Area: 120.01

Molecular Species: BASE

HBA: 8

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 9.40

CX LogP: 3.03

CX LogD: 1.04

Aromatic Rings: 3

Heavy Atoms: 30

QED Weighted: 0.32

Np Likeness Score: -1.69

References

1. Pal R, Chakraborty J, Mukhopadhyay TK, Kanungo A, Saha R, Chakraborty A, Patra D, Datta A, Dutta S..  (2022)  Substituent effect of benzyl moiety in nitroquinoxaline small molecules upon DNA binding: Cumulative destacking of DNA nucleobases leading to histone eviction.,  229  [PMID:34802835] [10.1016/j.ejmech.2021.113995]

Source

Source(1):

• Scientific Literature