(S)-6-chloro-5-(2,6-difluorophenyl)-N-methyl-4-(2-methylbutyl)-3-oxo-3,4-dihydropyrazine-2-carboxamide

ID: ALA3739834

PubChem CID: 127039177

Max Phase: Preclinical

Molecular Formula: C17H18ClF2N3O2

Molecular Weight: 369.80

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC[C@H](C)Cn1c(-c2c(F)cccc2F)c(Cl)nc(C(=O)NC)c1=O

Standard InChI:  InChI=1S/C17H18ClF2N3O2/c1-4-9(2)8-23-14(12-10(19)6-5-7-11(12)20)15(18)22-13(17(23)25)16(24)21-3/h5-7,9H,4,8H2,1-3H3,(H,21,24)/t9-/m0/s1

Standard InChI Key:  VGTMWNYEWISZNU-VIFPVBQESA-N

Molfile:  

     RDKit          2D

 25 26  0  0  0  0  0  0  0  0999 V2000
    1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.5000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.5000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3383   -1.3500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3383    1.3500    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -2.5987   -1.5004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8991   -0.7525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1969   -1.5046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1945   -3.0046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8943   -3.7525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5964   -3.0004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9010    0.4475    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0031   -3.0008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2947   -3.7547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2916   -5.2556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3353   -3.1572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3292   -5.8583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5972    1.5031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5563   -3.5988    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    3.6375    0.9049    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5951    3.0039    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6331    3.6061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  6  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  1  7  2  0
  4  8  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14  9  1  0
  5  9  1  0
 10 15  1  0
  6 16  1  0
 16 17  1  0
 17 18  1  0
 17 19  1  1
 18 20  1  0
  2 21  1  0
 14 22  1  0
 21 23  2  0
 21 24  1  0
 24 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3739834

   ---

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: 369.80

Molecular Weight (Monoisotopic): 369.1056

AlogP: 3.25

#Rotatable Bonds: 5

Polar Surface Area: 63.99

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.80

CX Basic pKa: ┄

CX LogP: 3.22

CX LogD: 3.22

Aromatic Rings: 2

Heavy Atoms: 25

QED Weighted: 0.88

Np Likeness Score: -0.97

References

1. Taggi AE, Stevenson TM, Bereznak JF, Sharpe PL, Gutteridge S, Forman R, Bisaha JJ, Cordova D, Crompton M, Geist L, Kovacs P, Marshall E, Sheth R, Stavis C, Tseng CP..  (2016)  Tubulin modulating antifungal and antiproliferative pyrazinone derivatives.,  24  (3): [PMID:26386818] [10.1016/j.bmc.2015.08.038]

Source

Source(1):

• Scientific Literature