6-(3-Methoxyphenyl)-4-(methylthio)-2-oxo-1,2-dihydropyridine-3-carbonitrile

ID: ALA3394148

PubChem CID: 118725936

Max Phase: Preclinical

Molecular Formula: C14H12N2O2S

Molecular Weight: 272.33

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cccc(-c2cc(SC)c(C#N)c(=O)[nH]2)c1

Standard InChI:  InChI=1S/C14H12N2O2S/c1-18-10-5-3-4-9(6-10)12-7-13(19-2)11(8-15)14(17)16-12/h3-7H,1-2H3,(H,16,17)

Standard InChI Key:  TUVARXJSYRADOF-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 19 20  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 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
   -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
    2.5988    1.5004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6380    2.1004    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
   -0.0031    3.0008    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0432    3.5993    0.0000 C   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
   -6.4994   -0.7589    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5368   -1.3620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  1  6  1  0
  7  8  3  0
  2  7  1  0
  1  9  2  0
 10 11  1  0
  3 10  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 12 17  2  0
 18 19  1  0
 14 18  1  0
  5 12  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3394148

   ---

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: 272.33

Molecular Weight (Monoisotopic): 272.0619

AlogP: 2.64

#Rotatable Bonds: 3

Polar Surface Area: 65.88

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 6.96

CX Basic pKa: ┄

CX LogP: 1.47

CX LogD: 1.01

Aromatic Rings: 2

Heavy Atoms: 19

QED Weighted: 0.87

Np Likeness Score: -1.23

References

1. Naik M, Raichurkar A, Bandodkar BS, Varun BV, Bhat S, Kalkhambkar R, Murugan K, Menon R, Bhat J, Paul B, Iyer H, Hussein S, Tucker JA, Vogtherr M, Embrey KJ, McMiken H, Prasad S, Gill A, Ugarkar BG, Venkatraman J, Read J, Panda M..  (2015)  Structure guided lead generation for M. tuberculosis thymidylate kinase (Mtb TMK): discovery of 3-cyanopyridone and 1,6-naphthyridin-2-one as potent inhibitors.,  58  (2): [PMID:25486447] [10.1021/jm5012947]

2. Jian Y,Forbes HE,Hulpia F,Risseeuw MDP,Caljon G,Munier-Lehmann H,Boshoff HIM,Van Calenbergh S.  (2021)  2-((3,5-Dinitrobenzyl)thio)quinazolinones: Potent Antimycobacterial Agents Activated by Deazaflavin (F)-Dependent Nitroreductase (Ddn).,  64  (1.0): [PMID:33347317] [10.1021/acs.jmedchem.0c01374]

Source

Source(1):

• Scientific Literature