1-(2-(4'-nitrobiphenyl-4-yl)-1H-benzo[d]imidazol-5-yl)ethanone

ID: ALA2037268

PubChem CID: 70696498

Max Phase: Preclinical

Molecular Formula: C21H15N3O3

Molecular Weight: 357.37

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(=O)c1ccc2[nH]c(-c3ccc(-c4ccc([N+](=O)[O-])cc4)cc3)nc2c1

Standard InChI:  InChI=1S/C21H15N3O3/c1-13(25)17-8-11-19-20(12-17)23-21(22-19)16-4-2-14(3-5-16)15-6-9-18(10-7-15)24(26)27/h2-12H,1H3,(H,22,23)

Standard InChI Key:  ZTBHGCYEVHKCHT-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 27 30  0  0  0  0  0  0  0  0999 V2000
    0.6634   -6.2773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1749   -5.6122    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6094   -5.8722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6037   -6.7005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1848   -6.9493    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3271   -5.4664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0383   -5.8850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0317   -6.7092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3148   -7.1191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4844   -6.2689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1340   -6.2584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7119   -5.5445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8890   -5.5536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7259   -6.9765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9056   -6.9782    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9572   -6.2516    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3752   -6.9642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1995   -6.9575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6067   -6.2388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1836   -5.5255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3607   -5.5358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4336   -6.2292    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.8390   -5.5105    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8533   -6.9396    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7562   -5.4782    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7629   -4.6531    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4672   -5.8966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 12 13  2  0
 13 10  1  0
  1 10  1  0
  4  5  1  0
  1  5  1  0
 14 15  1  0
  6  7  1  0
  7  8  2  0
 16 17  2  0
  8  9  1  0
 17 18  1  0
  4  9  2  0
 18 19  2  0
  3  6  2  0
 19 20  1  0
 20 21  2  0
 21 16  1  0
 11 16  1  0
 10 15  2  0
  1  2  2  0
 14 11  2  0
 22 23  2  0
 22 24  1  0
 19 22  1  0
  2  3  1  0
  7 25  1  0
 11 12  1  0
 25 26  2  0
  3  4  1  0
 25 27  1  0
M  CHG  2  22   1  24  -1
M  END

Alternative Forms

1. Parent:

   

   ALA2037268

   1-[2-[4-(4-nitrophenyl)phenyl]-3H-benzimidazol-5-yl]ethanone

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 357.37

Molecular Weight (Monoisotopic): 357.1113

AlogP: 5.01

#Rotatable Bonds: 4

Polar Surface Area: 88.89

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 10.94

CX Basic pKa: 4.27

CX LogP: 4.43

CX LogD: 4.43

Aromatic Rings: 4

Heavy Atoms: 27

QED Weighted: 0.32

Np Likeness Score: -1.14

References

1. Vitale G, Corona P, Loriga M, Carta A, Paglietti G, Giliberti G, Sanna G, Farci P, Marongiu ME, La Colla P..  (2012)  5-acetyl-2-arylbenzimidazoles as antiviral agents. Part 4.,  53  [PMID:22513121] [10.1016/j.ejmech.2012.03.038]

Source

Source(1):

• Scientific Literature