Pyrazine-2-carboxylic acid isobutyl ester

ID: ALA326351

Cas Number: 158905-14-7

PubChem CID: 465056

Max Phase: Preclinical

Molecular Formula: C9H12N2O2

Molecular Weight: 180.21

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Pyrazine-2-Carboxylic Acid Isobutyl Ester | 2-Methylpropyl pyrazine-2-carboxylate|158905-14-7|CHEMBL326351|isobutyl pyrazine-2-carboxylate|SCHEMBL9407322|DTXSID70332764|Pyrazine-2-carboxylic acid isobutyl ester

Canonical SMILES:  CC(C)COC(=O)c1cnccn1

Standard InChI:  InChI=1S/C9H12N2O2/c1-7(2)6-13-9(12)8-5-10-3-4-11-8/h3-5,7H,6H2,1-2H3

Standard InChI Key:  USUPZWMFSOZLLN-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 13 13  0  0  0  0  0  0  0  0999 V2000
    4.7042   -5.9042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4167   -5.4875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9875   -5.4917    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.1292   -5.8917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4125   -4.6625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9875   -7.1417    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.7042   -6.7292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8417   -5.4792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2750   -5.9042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2750   -6.7292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5625   -5.8917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2750   -5.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5625   -6.7167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  1  2  0
  4  2  1  0
  5  2  2  0
  6  7  2  0
  7  1  1  0
  8  4  1  0
  9  3  1  0
 10  6  1  0
 11  8  1  0
 12 11  1  0
 13 11  1  0
  9 10  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA326351

   2-Methylpropyl pyrazine-2-carboxylate

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: 180.21

Molecular Weight (Monoisotopic): 180.0899

AlogP: 1.29

#Rotatable Bonds: 3

Polar Surface Area: 52.08

Molecular Species: NEUTRAL

HBA: 4

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 0.97

CX LogD: 0.97

Aromatic Rings: 1

Heavy Atoms: 13

QED Weighted: 0.66

Np Likeness Score: -1.22

References

1. Bergmann KE, Cynamon MH, Welch JT..  (1996)  Quantitative structure-activity relationships for the in vitro antimycobacterial activity of pyrazinoic acid esters.,  39  (17): [PMID:8765523] [10.1021/jm950538t]

2. Bergmann KE, Cynamon MH, Welch JT..  (1996)  Quantitative structure-activity relationships for the in vitro antimycobacterial activity of pyrazinoic acid esters.,  39  (17): [PMID:8765523] [10.1021/jm950538t]

3. Cynamon MH, Gimi R, Gyenes F, Sharpe CA, Bergmann KE, Han HJ, Gregor LB, Rapolu R, Luciano G, Welch JT..  (1995)  Pyrazinoic acid esters with broad spectrum in vitro antimycobacterial activity.,  38  (20): [PMID:7562923] [10.1021/jm00020a003]

4. Fernandes GFDS, de Souza PC, Marino LB, Chegaev K, Guglielmo S, Lazzarato L, Fruttero R, Chung MC, Pavan FR, Dos Santos JL..  (2016)  Synthesis and biological activity of furoxan derivatives against Mycobacterium tuberculosis.,  123  [PMID:27508879] [10.1016/j.ejmech.2016.07.039]

Source

Source(1):

• Scientific Literature