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

ID: ALA113815

PubChem CID: 11324247

Max Phase: Preclinical

Molecular Formula: C15H9N5O3

Molecular Weight: 307.27

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  N#C/C(=C\c1ccc([N+](=O)[O-])o1)c1n[nH]c(-c2ccccc2)n1

Standard InChI:  InChI=1S/C15H9N5O3/c16-9-11(8-12-6-7-13(23-12)20(21)22)15-17-14(18-19-15)10-4-2-1-3-5-10/h1-8H,(H,17,18,19)/b11-8+

Standard InChI Key:  ASFXIWZYLRAKAV-DHZHZOJOSA-N

Molfile:  

     RDKit          2D

 23 25  0  0  0  0  0  0  0  0999 V2000
    4.1917   -4.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.6042   -3.2875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0292   -4.1125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7417   -4.5375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.4292   -3.2125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3792   -3.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0417   -2.6667    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3042   -3.0042    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.2750   -4.4375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9042   -3.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7292   -3.8125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9542   -3.2875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7792   -2.4625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1292   -1.7042    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.1500   -3.1042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7292   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.4667   -4.1292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7667   -4.3750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9792   -4.1125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9292   -5.1750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3167   -5.7292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3625   -4.6542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5292   -5.4667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  9  1  0
  4  3  1  0
  5  2  1  0
  6  1  2  0
  7  2  2  0
  8  6  1  0
  9 11  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  6  1  0
 19 18  2  0
 20 18  1  0
 21 20  2  0
 22 19  1  0
 23 21  1  0
  8  7  1  0
 22 23  2  0
  3 12  2  0
M  CHG  2   4   1  16  -1
M  END

Alternative Forms

1. Parent:

   

   ALA113815

   (E)-3-(5-nitrofuran-2-yl)-2-(3-phenyl-1H-1,2,4-triazol-5-yl)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: 307.27

Molecular Weight (Monoisotopic): 307.0705

AlogP: 3.04

#Rotatable Bonds: 4

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: 9.18

CX Basic pKa: 0.13

CX LogP: 3.75

CX LogD: 3.74

Aromatic Rings: 3

Heavy Atoms: 23

QED Weighted: 0.45

Np Likeness Score: -1.79

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]

Source

Source(1):

• Scientific Literature