(R)-N-(2-(4-chlorophenyl)-4-oxothiazolidin-3-yl)pyrazine-2-carboxamide

ID: ALA3792993

PubChem CID: 127053304

Max Phase: Preclinical

Molecular Formula: C14H11ClN4O2S

Molecular Weight: 334.79

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(NN1C(=O)CS[C@@H]1c1ccc(Cl)cc1)c1cnccn1

Standard InChI:  InChI=1S/C14H11ClN4O2S/c15-10-3-1-9(2-4-10)14-19(12(20)8-22-14)18-13(21)11-7-16-5-6-17-11/h1-7,14H,8H2,(H,18,21)/t14-/m1/s1

Standard InChI Key:  CZAIOTMABDAIEL-CQSZACIVSA-N

Molfile:  

     RDKit          2D

 22 24  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
   -8.0307   -4.6262    0.0000 Cl  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
 19 22  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3792993

   ---

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: 334.79

Molecular Weight (Monoisotopic): 334.0291

AlogP: 2.05

#Rotatable Bonds: 3

Polar Surface Area: 75.19

Molecular Species: ACID

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 5.59

CX Basic pKa: ┄

CX LogP: 1.12

CX LogD: 0.22

Aromatic Rings: 2

Heavy Atoms: 22

QED Weighted: 0.93

Np Likeness Score: -1.52

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