3,5-dimethyl-4-hydroxy-5-(2-methoxybenzyl)-5H-thiophen-2-one

ID: ALA199810

Max Phase: Preclinical

Molecular Formula: C14H16O3S

Molecular Weight: 264.35

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccccc1CC1(C)SC(O)=C(C)C1=O

Standard InChI:  InChI=1S/C14H16O3S/c1-9-12(15)14(2,18-13(9)16)8-10-6-4-5-7-11(10)17-3/h4-7,16H,8H2,1-3H3

Standard InChI Key:  NXWQXQMALARPAW-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 18 19  0  0  0  0  0  0  0  0999 V2000
   13.9305  -25.0965    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   13.5160  -26.3781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3341  -26.3776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5947  -25.5930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3861  -25.3419    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.0242  -27.0436    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.8165  -27.0468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2708  -25.5250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2667  -24.6958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5183  -25.8629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8025  -25.4527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8017  -24.6278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0867  -24.2178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3727  -24.6327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3781  -25.4620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0936  -25.8683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5154  -24.2140    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.5139  -23.3890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  8  9  1  0
  4  1  1  0
  8 10  1  0
 10 11  1  0
  4  5  1  0
 11 12  2  0
  1  8  1  0
 12 13  1  0
  2  6  2  0
 13 14  2  0
  8  2  1  0
 14 15  1  0
  3  7  1  0
 15 16  2  0
 16 11  1  0
  2  3  1  0
 12 17  1  0
  3  4  2  0
 17 18  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA199810

   ---

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: 264.35

Molecular Weight (Monoisotopic): 264.0820

AlogP: 3.10

#Rotatable Bonds: 3

Polar Surface Area: 46.53

Molecular Species: ACID

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 6.34

CX Basic pKa: ┄

CX LogP: 3.74

CX LogD: 2.64

Aromatic Rings: 1

Heavy Atoms: 18

QED Weighted: 0.91

Np Likeness Score: 0.23

References

1. 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