5-(Butylamino)-N-(2-chlorophenyl)pyrazine-2-carboxamide

ID: ALA3355707

PubChem CID: 109272646

Max Phase: Preclinical

Molecular Formula: C15H17ClN4O

Molecular Weight: 304.78

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCCNc1cnc(C(=O)Nc2ccccc2Cl)cn1

Standard InChI:  InChI=1S/C15H17ClN4O/c1-2-3-8-17-14-10-18-13(9-19-14)15(21)20-12-7-5-4-6-11(12)16/h4-7,9-10H,2-3,8H2,1H3,(H,17,19)(H,20,21)

Standard InChI Key:  WSKWLLPVZCJAAK-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 21 22  0  0  0  0  0  0  0  0999 V2000
   20.2085  -19.9741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6171  -20.6832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3913  -19.9741    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.2085  -21.3882    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.3913  -21.3882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9827  -20.6832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6171  -19.2692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2085  -18.5601    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.4343  -19.2692    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.8429  -19.9741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6601  -19.9741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.0687  -20.6832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6601  -21.3882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8429  -21.3882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4343  -20.6832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.0687  -19.2692    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   18.9827  -22.0973    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.1655  -22.0973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7569  -21.3882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9397  -21.3882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5311  -20.6832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  3  2  0
  2  4  2  0
  4  5  1  0
  5  6  2  0
  3  6  1  0
  7  8  2  0
  7  9  1  0
  1  7  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 10 15  2  0
 11 16  1  0
  9 10  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 17 18  1  0
  5 17  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3355707

   5-(butylamino)-N-(2-chlorophenyl)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: 304.78

Molecular Weight (Monoisotopic): 304.1091

AlogP: 3.59

#Rotatable Bonds: 6

Polar Surface Area: 66.91

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 1.54

CX LogP: 3.01

CX LogD: 3.01

Aromatic Rings: 2

Heavy Atoms: 21

QED Weighted: 0.80

Np Likeness Score: -1.96

References

1. Zitko J, Servusová B, Janoutová A, Paterová P, Mandíková J, Garaj V, Vejsová M, Marek J, Doležal M, Doležal M..  (2015)  Synthesis and antimycobacterial evaluation of 5-alkylamino-N-phenylpyrazine-2-carboxamides.,  23  (1): [PMID:25438883] [10.1016/j.bmc.2014.11.014]

Source

Source(1):

• Scientific Literature