3-(2-Ethylbutyl)-5-(4-hydroxy-3-trifluoromethylbenzylidene)-thiazolidine-2,4-dione

ID: ALA2057965

PubChem CID: 57413467

Max Phase: Preclinical

Molecular Formula: C17H18F3NO3S

Molecular Weight: 373.40

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCC(CC)CN1C(=O)S/C(=C\c2ccc(O)c(C(F)(F)F)c2)C1=O

Standard InChI:  InChI=1S/C17H18F3NO3S/c1-3-10(4-2)9-21-15(23)14(25-16(21)24)8-11-5-6-13(22)12(7-11)17(18,19)20/h5-8,10,22H,3-4,9H2,1-2H3/b14-8-

Standard InChI Key:  KQXTUMIUQMDJET-ZSOIEALJSA-N

Molfile:  

     RDKit          2D

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   -2.4735   -8.6855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7590   -8.2746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7576   -7.4487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4766   -7.0355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1881   -7.4488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0432   -7.0361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3290   -7.4485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3624   -8.2722    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.4119   -8.5571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9221   -7.9088    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4631   -7.2233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7475   -6.4488    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6365   -9.3510    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9003   -8.6787    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7465   -7.9404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1861   -7.2423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9039   -7.0386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9066   -6.2136    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6171   -7.4534    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6208   -6.6250    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    3.0105   -7.2739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4501   -6.5758    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8013   -6.5125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2409   -5.8144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 12  8  1  0
  6  1  1  0
 12 13  2  0
  1  2  2  0
 10 14  2  0
  4  7  1  0
  1 15  1  0
  3  4  2  0
 11 16  1  0
  7  8  2  0
 16 17  1  0
  8  9  1  0
  6 18  1  0
 18 19  1  0
  4  5  1  0
 18 20  1  0
  2  3  1  0
 18 21  1  0
  5  6  2  0
 17 22  1  0
  9 10  1  0
 22 23  1  0
 10 11  1  0
 17 24  1  0
 11 12  1  0
 24 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2057965

   (5Z)-3-(2-ethylbutyl)-5-[[4-hydroxy-3-(trifluoromethyl)phenyl]methylidene]-1,3-thiazolidine-2,4-dione

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: 373.40

Molecular Weight (Monoisotopic): 373.0959

AlogP: 4.88

#Rotatable Bonds: 5

Polar Surface Area: 57.61

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.14

CX Basic pKa: ┄

CX LogP: 4.78

CX LogD: 4.71

Aromatic Rings: 1

Heavy Atoms: 25

QED Weighted: 0.75

Np Likeness Score: -0.95

References

1. Wang D, Chu PC, Yang CN, Yan R, Chuang YC, Kulp SK, Chen CS..  (2012)  Development of a novel class of glucose transporter inhibitors.,  55  (8): [PMID:22468970] [10.1021/jm300015m]

Source

Source(1):

• Scientific Literature