3,5-dimethyl-5-((2E,6E)-3,7,11-trimethyldodeca-2,6,10-trienyl)-4-hydroxy-5H-thiophen-2-one

ID: ALA199771

Max Phase: Preclinical

Molecular Formula: C21H32O2S

Molecular Weight: 348.55

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)=CCC/C(C)=C/CC/C(C)=C/CC1(C)SC(O)=C(C)C1=O

Standard InChI:  InChI=1S/C21H32O2S/c1-15(2)9-7-10-16(3)11-8-12-17(4)13-14-21(6)19(22)18(5)20(23)24-21/h9,11,13,23H,7-8,10,12,14H2,1-6H3/b16-11+,17-13+

Standard InChI Key:  VTJVDTDMBBEGHT-IUBLYSDUSA-N

Molfile:  

     RDKit          2D

 24 24  0  0  0  0  0  0  0  0999 V2000
    5.6844  -23.8685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5162  -24.6745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6939  -24.7594    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3605  -24.0049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9727  -23.4560    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    6.4389  -23.5309    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2814  -25.4752    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6446  -24.4174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9287  -24.0049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2129  -24.4174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5012  -24.0049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7853  -24.4174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0736  -24.0049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6423  -24.4174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3581  -24.0049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8716  -23.3395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0651  -25.2868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2118  -25.2424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6423  -25.2424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0722  -24.4180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7871  -24.0061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5012  -24.4192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2160  -24.0073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5005  -25.2442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  3  7  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
  4  8  1  0
  4 16  1  0
  2 17  1  0
 10 18  1  0
  1  2  2  0
 14 19  1  0
  2  3  1  0
 15 20  1  0
  3  4  1  0
 20 21  1  0
  4  5  1  0
 21 22  2  0
  1  5  1  0
 22 23  1  0
  1  6  1  0
 22 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA199771

   ---

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: 348.55

Molecular Weight (Monoisotopic): 348.2123

AlogP: 6.66

#Rotatable Bonds: 8

Polar Surface Area: 37.30

Molecular Species: NEUTRAL

HBA: 3

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 2

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 6.67

CX Basic pKa: ┄

CX LogP: 6.85

CX LogD: 6.05

Aromatic Rings: ┄

Heavy Atoms: 24

QED Weighted: 0.50

Np Likeness Score: 1.59

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