5-Chloro-pyrazine-2-carboxylic acid 1-methyl-1-pentyl-heptyl ester

ID: ALA117600

PubChem CID: 465054

Max Phase: Preclinical

Molecular Formula: C18H29ClN2O2

Molecular Weight: 340.90

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCCCCC(C)(CCCCC)OC(=O)c1cnc(Cl)cn1

Standard InChI:  InChI=1S/C18H29ClN2O2/c1-4-6-8-10-12-18(3,11-9-7-5-2)23-17(22)15-13-21-16(19)14-20-15/h13-14H,4-12H2,1-3H3

Standard InChI Key:  DNTNRKCCPBOWEL-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 23 23  0  0  0  0  0  0  0  0999 V2000
    4.1042   -5.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8292   -5.0042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3917   -5.0125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3917   -6.6625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.5417   -5.4167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6792   -6.2500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1042   -6.2500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8292   -4.1792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5417   -6.2500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6792   -5.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9542   -6.6667    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    5.5417   -7.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3667   -6.2500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7167   -6.2500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8292   -7.4875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7792   -6.9625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0250   -7.6750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1167   -9.5542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1167   -8.7292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6125   -6.9625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8292   -8.3167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4042   -9.9667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8542   -7.6750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  1  2  0
  4  7  2  0
  5  2  1  0
  6  4  1  0
  7  1  1  0
  8  2  2  0
  9  5  1  0
 10  3  1  0
 11  6  1  0
 12  9  1  0
 13  9  1  0
 14  9  1  0
 15 12  1  0
 16 13  1  0
 17 20  1  0
 18 19  1  0
 19 21  1  0
 20 16  1  0
 21 15  1  0
 22 18  1  0
 23 17  1  0
  6 10  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA117600

   1-Methyl-1-pentylheptyl 5-chloropyrazine-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: 340.90

Molecular Weight (Monoisotopic): 340.1918

AlogP: 5.60

#Rotatable Bonds: 11

Polar Surface Area: 52.08

Molecular Species: NEUTRAL

HBA: 4

HBD: ┄

#RO5 Violations: 1

HBA (Lipinski): 4

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 5.76

CX LogD: 5.76

Aromatic Rings: 1

Heavy Atoms: 23

QED Weighted: 0.39

Np Likeness Score: -0.16

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]

Source

Source(1):

• Scientific Literature