2-(Benzimidazol-1-yl)-3-(3-nitrophenyl)-acrylonitrile

ID: ALA451824

PubChem CID: 25111568

Max Phase: Preclinical

Molecular Formula: C16H10N4O2

Molecular Weight: 290.28

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  N#C/C(=C\c1cccc([N+](=O)[O-])c1)n1cnc2ccccc21

Standard InChI:  InChI=1S/C16H10N4O2/c17-10-14(9-12-4-3-5-13(8-12)20(21)22)19-11-18-15-6-1-2-7-16(15)19/h1-9,11H/b14-9+

Standard InChI Key:  MRHNLTXTEQMWHL-NTEUORMPSA-N

Molfile:  

     RDKit          2D

 22 24  0  0  0  0  0  0  0  0999 V2000
   -0.3056  -24.2125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3068  -25.0398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4081  -25.4527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4063  -23.7997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1216  -24.2088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1265  -25.0399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9184  -25.2921    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4030  -24.6168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9105  -23.9475    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1779  -26.0752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6294  -26.6915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9859  -26.2420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0808  -27.3079    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2454  -27.0251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6946  -27.6406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9535  -28.4231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7622  -28.5906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3115  -27.9693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0497  -27.1892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1259  -28.1334    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.6722  -27.5152    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3882  -28.9156    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  6  1  0
 10 11  1  0
 10 12  2  0
  2  3  1  0
 11 13  3  0
  3  6  2  0
 12 14  1  0
  1  2  2  0
 14 15  2  0
  5  4  2  0
 15 16  1  0
  6  7  1  0
 16 17  2  0
  7  8  1  0
 17 18  1  0
  8  9  2  0
 18 19  2  0
 19 14  1  0
  9  5  1  0
  4  1  1  0
  7 10  1  0
 20 21  2  0
 20 22  1  0
 18 20  1  0
M  CHG  2  20   1  22  -1
M  END

Alternative Forms

1. Parent:

   

   ALA451824

   (E)-2-(benzimidazol-1-yl)-3-(3-nitrophenyl)prop-2-enenitrile

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: 290.28

Molecular Weight (Monoisotopic): 290.0804

AlogP: 3.47

#Rotatable Bonds: 3

Polar Surface Area: 84.75

Molecular Species: NEUTRAL

HBA: 5

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 4.77

CX LogP: 3.25

CX LogD: 3.25

Aromatic Rings: 3

Heavy Atoms: 22

QED Weighted: 0.42

Np Likeness Score: -1.48

References

1. Saczewski F, Stencel A, Bieńczak AM, Langowska KA, Michaelis M, Werel W, Hałasa R, Reszka P, Bednarski PJ..  (2008)  Structure-activity relationships of novel heteroaryl-acrylonitriles as cytotoxic and antibacterial agents.,  43  (9): [PMID:18187237] [10.1016/j.ejmech.2007.11.017]

Source

Source(1):

• Scientific Literature