5-(4-Hydroxy-benzyl)-thiazolidine-2,4-dione

ID: ALA1061

Max Phase: Preclinical

Molecular Formula: C10H9NO3S

Molecular Weight: 223.25

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Glitazone

Canonical SMILES:  O=C1NC(=O)C(Cc2ccc(O)cc2)S1

Standard InChI:  InChI=1S/C10H9NO3S/c12-7-3-1-6(2-4-7)5-8-9(13)11-10(14)15-8/h1-4,8,12H,5H2,(H,11,13,14)

Standard InChI Key:  NKOHRVBBQISBSB-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 15 16  0  0  0  0  0  0  0  0999 V2000
    3.5792   -1.0125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0792   -0.3542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1042   -1.6875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3042   -0.6167    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.3167   -1.4417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3250    0.4375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3667   -2.4667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6542   -1.9375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9000   -1.6125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6208   -0.9625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2292   -2.1042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8000   -0.7917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5250   -1.7792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0417   -0.4667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3750   -0.6292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  1  1  0
  4  2  1  0
  5  3  1  0
  6  2  2  0
  7  3  2  0
  8  5  1  0
  9  8  1  0
 10 14  2  0
 11  9  1  0
 12  9  2  0
 13 11  2  0
 14 12  1  0
 15 10  1  0
  5  4  1  0
 13 10  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1061

   GLITAZONE

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: 223.25

Molecular Weight (Monoisotopic): 223.0303

AlogP: 1.29

#Rotatable Bonds: 2

Polar Surface Area: 66.40

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 6.61

CX Basic pKa: ┄

CX LogP: 1.64

CX LogD: 0.82

Aromatic Rings: 1

Heavy Atoms: 15

QED Weighted: 0.79

Np Likeness Score: 0.37

References

1. Fan YH, Chen H, Natarajan A, Guo Y, Harbinski F, Iyasere J, Christ W, Aktas H, Halperin JA..  (2004)  Structure-activity requirements for the antiproliferative effect of troglitazone derivatives mediated by depletion of intracellular calcium.,  14  (10): [PMID:15109648] [10.1016/j.bmcl.2004.02.087]

2. Carroll RT, Dluzen DE, Stinnett H, Awale PS, Funk MO, Geldenhuys WJ..  (2011)  Structure-activity relationship and docking studies of thiazolidinedione-type compounds with monoamine oxidase B.,  21  (16): [PMID:21742494] [10.1016/j.bmcl.2011.06.060]

3. Geldenhuys WJ, Funk MO, Awale PS, Lin L, Carroll RT..  (2011)  A novel binding assay identifies high affinity ligands to the rosiglitazone binding site of mitoNEET.,  21  (18): [PMID:21782425] [10.1016/j.bmcl.2011.06.111]

4. Hoffmann BR, El-Mansy MF, Sem DS, Greene AS..  (2012)  Chemical proteomics-based analysis of off-target binding profiles for rosiglitazone and pioglitazone: clues for assessing potential for cardiotoxicity.,  55  (19): [PMID:22970990] [10.1021/jm301204r]

5. Geldenhuys WJ, Yonutas HM, Morris DL, Sullivan PG, Darvesh AS, Leeper TC..  (2016)  Identification of small molecules that bind to the mitochondrial protein mitoNEET.,  26  (21): [PMID:27687671] [10.1016/j.bmcl.2016.09.009]

Source

Source(1):

• Scientific Literature