(R)-5-methyl-N-(2-(3-nitrophenyl)-4-oxothiazolidin-3-yl)pyrazine-2-carboxamide

ID: ALA3794212

PubChem CID: 127053299

Max Phase: Preclinical

Molecular Formula: C15H13N5O4S

Molecular Weight: 359.37

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1cnc(C(=O)NN2C(=O)CS[C@@H]2c2cccc([N+](=O)[O-])c2)cn1

Standard InChI:  InChI=1S/C15H13N5O4S/c1-9-6-17-12(7-16-9)14(22)18-19-13(21)8-25-15(19)10-3-2-4-11(5-10)20(23)24/h2-7,15H,8H2,1H3,(H,18,22)/t15-/m1/s1

Standard InChI Key:  VKYJDNOZSHCKJM-OAHLLOKOSA-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
   -2.6003    1.4977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6024    2.6977    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8990    0.7455    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2003    1.4932    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5517    0.8722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5554    1.9869    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8054    3.2859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3382    2.9741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4417    3.7717    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8550   -0.5976    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8200   -1.6761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2388   -3.1164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6956   -3.4739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7336   -2.3910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3147   -0.9507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.1919   -2.7457    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  -11.0210   -1.8782    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  -10.5290   -3.8973    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3383   -1.3500    0.0000 C   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  1
 22 23  2  0
 22 24  1  0
 20 22  1  0
  1 25  1  0
M  CHG  2  22   1  24  -1
M  END

Alternative Forms

1. Parent:

   

   ALA3794212

   ---

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: 359.37

Molecular Weight (Monoisotopic): 359.0688

AlogP: 1.61

#Rotatable Bonds: 4

Polar Surface Area: 118.33

Molecular Species: ACID

HBA: 7

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 5.85

CX Basic pKa: ┄

CX LogP: 0.58

CX LogD: -0.28

Aromatic Rings: 2

Heavy Atoms: 25

QED Weighted: 0.65

Np Likeness Score: -1.62

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