5-tert-Butyl-6-chloro-N-(2-chloro-5-hydroxyphenyl)-pyrazine-2-carboxamide

ID: ALA523893

PubChem CID: 24881799

Max Phase: Preclinical

Molecular Formula: C15H15Cl2N3O2

Molecular Weight: 340.21

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)(C)c1ncc(C(=O)Nc2cc(O)ccc2Cl)nc1Cl

Standard InChI:  InChI=1S/C15H15Cl2N3O2/c1-15(2,3)12-13(17)19-11(7-18-12)14(22)20-10-6-8(21)4-5-9(10)16/h4-7,21H,1-3H3,(H,20,22)

Standard InChI Key:  DXJGOACPONQOMY-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 22 23  0  0  0  0  0  0  0  0999 V2000
   -2.7389  -24.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7401  -25.2523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0253  -25.6652    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3088  -25.2519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3117  -24.4213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0271  -24.0122    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5988  -24.0061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1172  -24.4159    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6019  -23.1811    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8302  -24.0008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5446  -24.4140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2570  -23.9995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2543  -23.1736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5333  -22.7640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8238  -23.1808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4549  -25.6643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1750  -26.0708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0461  -26.3809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8619  -24.9467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4535  -24.0126    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.5456  -25.2390    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.5273  -21.9390    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 10 11  2  0
  5  6  2  0
 11 12  1  0
  6  1  1  0
 12 13  2  0
  1  2  2  0
 13 14  1  0
  5  7  1  0
 14 15  2  0
 15 10  1  0
  3  4  2  0
  2 16  1  0
  7  8  1  0
 16 17  1  0
 16 18  1  0
  7  9  2  0
 16 19  1  0
  4  5  1  0
  1 20  1  0
  8 10  1  0
 11 21  1  0
  2  3  1  0
 14 22  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA523893

   5-tert-butyl-6-chloro-N-(2-chloro-5-hydroxyphenyl)pyrazine-2-carboxamide

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: 340.21

Molecular Weight (Monoisotopic): 339.0541

AlogP: 4.04

#Rotatable Bonds: 2

Polar Surface Area: 75.11

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.75

CX Basic pKa: ┄

CX LogP: 4.07

CX LogD: 4.05

Aromatic Rings: 2

Heavy Atoms: 22

QED Weighted: 0.87

Np Likeness Score: -1.24

References

1. Dolezal M, Dolezal M, Cmedlova P, Palek L, Vinsova J, Kunes J, Buchta V, Jampilek J, Kralova K..  (2008)  Synthesis and antimycobacterial evaluation of substituted pyrazinecarboxamides.,  43  (5): [PMID:17870211] [10.1016/j.ejmech.2007.07.013]

Source

Source(1):

• Scientific Literature