5-Fluoro-pyrazine-2-carboxylic acid methyl ester

ID: ALA117948

Cas Number: 169335-35-7

PubChem CID: 465060

Max Phase: Preclinical

Molecular Formula: C6H5FN2O2

Molecular Weight: 156.12

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COC(=O)c1cnc(F)cn1

Standard InChI:  InChI=1S/C6H5FN2O2/c1-11-6(10)4-2-9-5(7)3-8-4/h2-3H,1H3

Standard InChI Key:  OJSIPUSAMRJSND-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 11 11  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
    3.9875   -5.4917    0.0000 N   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   -7.1417    0.0000 N   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
    4.7042   -6.7292    0.0000 C   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
    3.2750   -5.9042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5542   -7.1417    0.0000 F   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
    6.8417   -5.4792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  1  1  0
  4  6  2  0
  5  4  1  0
  6  1  1  0
  7  3  2  0
  8  2  1  0
  9  5  1  0
 10  3  1  0
 11 10  1  0
  8  5  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA117948

   Methyl 5-fluoropyrazine-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: 156.12

Molecular Weight (Monoisotopic): 156.0335

AlogP: 0.40

#Rotatable Bonds: 1

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: 0.26

CX LogD: 0.26

Aromatic Rings: 1

Heavy Atoms: 11

QED Weighted: 0.55

Np Likeness Score: -1.14

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. Johannes Zuegg, Alysha Elliott, Maite Amado, Emma Cowie, Ali Hinton, Geraldine Kaeslin, Angela Kavanagh, Anne Kunert, Gabriell Lowe, Soumya Ramu, Janet Reid, Robin Trauer, Mathilde Desselle, Ruth Neale, Karl Hansford, Mark Blascovich, Matthew Cooper. CO-ADD screening of MMV (CH) - Small Polar Library,  [10.6019/CHEMBL4513160]

5. University of Dundee.  (2021)  University of Dundee, Small-Polar-MMV Screening Library,  [10.6019/CHEMBL3988442]

Source

Source(3):

• Scientific Literature
• Gates Library compound collection
• CO-ADD antimicrobial screening data