4-Hydroxy-3,5-dimethyl-5-(4-methyl-benzyl)-5H-thiophen-2-one

ID: ALA432983

Max Phase: Preclinical

Molecular Formula: C14H16O2S

Molecular Weight: 248.35

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC1=C(O)C(C)(Cc2ccc(C)cc2)SC1=O

Standard InChI:  InChI=1S/C14H16O2S/c1-9-4-6-11(7-5-9)8-14(3)12(15)10(2)13(16)17-14/h4-7,15H,8H2,1-3H3

Standard InChI Key:  RGYUMIUCPQIDNE-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 17 18  0  0  0  0  0  0  0  0999 V2000
    2.6500    0.6458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5667    1.4333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9042    1.4333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8250    0.6458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2375    1.9208    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.9792    0.8500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6917    1.6875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3375   -0.0167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1292   -0.0167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1875    1.0708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9792    2.0208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4000    1.5125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0208    1.8708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3958    0.4958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1958    0.7083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8125    2.0958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1958    1.7333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  4  1  0
  3  1  1  0
  4  1  2  0
  5  3  1  0
  6  2  1  0
  7  3  2  0
  8  4  1  0
  9  1  1  0
 10  6  1  0
 11  2  1  0
 12 15  1  0
 13 10  2  0
 14 10  1  0
 15 14  2  0
 16 13  1  0
 17 12  1  0
  2  5  1  0
 12 16  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA432983

   ---

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: 248.35

Molecular Weight (Monoisotopic): 248.0871

AlogP: 3.40

#Rotatable Bonds: 2

Polar Surface Area: 37.30

Molecular Species: NEUTRAL

HBA: 3

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 2

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 7.08

CX Basic pKa: ┄

CX LogP: 3.57

CX LogD: 3.08

Aromatic Rings: 1

Heavy Atoms: 17

QED Weighted: 0.87

Np Likeness Score: 0.37

References

1. Senior SJ, Illarionov PA, Gurcha SS, Campbell IB, Schaeffer ML, Minnikin DE, Besra GS..  (2003)  Biphenyl-based analogues of thiolactomycin, active against Mycobacterium tuberculosis mtFabH fatty acid condensing enzyme.,  13  (21): [PMID:14552758] [10.1016/j.bmcl.2003.08.015]

2. Kim P, Zhang YM, Shenoy G, Nguyen QA, Boshoff HI, Manjunatha UH, Goodwin MB, Lonsdale J, Price AC, Miller DJ, Duncan K, White SW, Rock CO, Barry CE, Dowd CS..  (2006)  Structure-activity relationships at the 5-position of thiolactomycin: an intact (5R)-isoprene unit is required for activity against the condensing enzymes from Mycobacterium tuberculosis and Escherichia coli.,  49  (1): [PMID:16392800] [10.1021/jm050825p]

Source

Source(1):

• Scientific Literature