2-(5-Benzyl-1H-[1,2,4]triazol-3-yl)-3-(5-nitro-furan-2-yl)-acrylonitrile

ID: ALA116696

PubChem CID: 5472657

Max Phase: Preclinical

Molecular Formula: C16H11N5O3

Molecular Weight: 321.30

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  N#C/C(=C\c1ccc([N+](=O)[O-])o1)c1n[nH]c(Cc2ccccc2)n1

Standard InChI:  InChI=1S/C16H11N5O3/c17-10-12(9-13-6-7-15(24-13)21(22)23)16-18-14(19-20-16)8-11-4-2-1-3-5-11/h1-7,9H,8H2,(H,18,19,20)/b12-9+

Standard InChI Key:  NTIDGBCKTXTYPD-FMIVXFBMSA-N

Molfile:  

     RDKit          2D

 24 26  0  0  0  0  0  0  0  0999 V2000
    0.0917   -1.6917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3208   -2.4042    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5250   -2.5167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2375   -2.9417    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9167   -1.6167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4625   -1.0792    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1250   -2.2292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7667   -2.8417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2083   -1.4125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3917   -2.2917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2167   -2.2167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4500   -1.6917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2667   -0.8667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6167   -0.1167    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6417   -1.5125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2250   -3.7667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9542   -2.5417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7458   -2.7792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5250   -2.5167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6875   -1.7167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1333   -3.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9208   -2.8167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4708   -1.4542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0958   -2.0042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  8  1  0
  4  3  1  0
  5  1  1  0
  6  1  2  0
  7  2  2  0
  8 11  1  0
  9  6  1  0
 10  5  2  0
 11 10  1  0
 12 15  1  0
 13  5  1  0
 14 13  3  0
 15 11  2  0
 16  4  1  0
 17  4  2  0
 18  7  1  0
 19 18  1  0
 20 19  2  0
 21 19  1  0
 22 21  2  0
 23 20  1  0
 24 22  1  0
  9  7  1  0
  3 12  2  0
 23 24  2  0
M  CHG  2   4   1  16  -1
M  END

Alternative Forms

1. Parent:

   

   ALA116696

   3-(5-Nitro-2-furyl)-2-(benzyl-1,4-triazol-2-yl)-acrylonitr ile

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: 321.30

Molecular Weight (Monoisotopic): 321.0862

AlogP: 2.96

#Rotatable Bonds: 5

Polar Surface Area: 121.64

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.81

CX Basic pKa: 0.71

CX LogP: 3.71

CX LogD: 3.71

Aromatic Rings: 3

Heavy Atoms: 24

QED Weighted: 0.44

Np Likeness Score: -1.63

References

1. Saczewski F, Reszka P, Gdaniec M, Grünert R, Bednarski PJ..  (2004)  Synthesis, X-ray crystal structures, stabilities, and in vitro cytotoxic activities of new heteroarylacrylonitriles.,  47  (13): [PMID:15189040] [10.1021/jm0311036]

2. PubChem BioAssay data set, 

Source

Source(2):

• Scientific Literature
• PubChem BioAssays