3-amino-N-(2-(3-nitrophenyl)-4-oxothiazolidin-3-yl)pyrazine-2-carboxamide

ID: ALA3792799

PubChem CID: 127031494

Max Phase: Preclinical

Molecular Formula: C14H12N6O4S

Molecular Weight: 360.36

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Nc1nccnc1C(=O)NN1C(=O)CSC1c1cccc([N+](=O)[O-])c1

Standard InChI:  InChI=1S/C14H12N6O4S/c15-12-11(16-4-5-17-12)13(22)18-19-10(21)7-25-14(19)8-2-1-3-9(6-8)20(23)24/h1-6,14H,7H2,(H2,15,17)(H,18,22)

Standard InChI Key:  MGUUXPHXIBDHHC-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 25 27  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
   -2.5973    1.5031    0.0000 C   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
   -3.8933    3.7570    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0312    5.2378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4984    5.5497    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2484    4.2507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2447    3.1359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4873    1.9607    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9100    6.2354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4585    5.8783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4206    6.9612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8394    8.4015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2962    8.7590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3341    7.6761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3383   -1.3500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7182   10.1992    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8841   10.4835    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8894   11.0670    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  1  1  0
  4  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 10  1  0
 14 15  2  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 16  1  0
 11 16  1  0
  5 22  1  0
 23 24  2  0
 23 25  1  0
 20 23  1  0
M  CHG  2  23   1  25  -1
M  END

Alternative Forms

1. Parent:

   

   ALA3792799

   ---

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: 360.36

Molecular Weight (Monoisotopic): 360.0641

AlogP: 0.89

#Rotatable Bonds: 4

Polar Surface Area: 144.35

Molecular Species: ACID

HBA: 8

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 10

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 6.02

CX Basic pKa: 1.01

CX LogP: 0.87

CX LogD: 0.04

Aromatic Rings: 2

Heavy Atoms: 25

QED Weighted: 0.60

Np Likeness Score: -1.39

References

1. Chitre TS, Asgaonkar KD, Miniyar PB, Dharme AB, Arkile MA, Yeware A, Sarkar D, Khedkar VM, Jha PC..  (2016)  Synthesis and docking studies of pyrazine-thiazolidinone hybrid scaffold targeting dormant tuberculosis.,  26  (9): [PMID:27017114] [10.1016/j.bmcl.2016.03.055]

Source

Source(1):

• Scientific Literature