5-octylthiazolidine-2,4-dione

ID: ALA448569

Max Phase: Preclinical

Molecular Formula: C11H19NO2S

Molecular Weight: 229.34

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCCCCCCC1SC(=O)NC1=O

Standard InChI:  InChI=1S/C11H19NO2S/c1-2-3-4-5-6-7-8-9-10(13)12-11(14)15-9/h9H,2-8H2,1H3,(H,12,13,14)

Standard InChI Key:  ZCRBNUCQSVGDLG-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 15 15  0  0  0  0  0  0  0  0999 V2000
   13.5916  -14.5709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4166  -14.5709    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.6734  -13.7867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0041  -13.3000    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   13.3391  -13.7867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5544  -13.5321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9415  -14.0845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1568  -13.8299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5439  -14.3822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7592  -14.1276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1464  -14.6799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3616  -14.4253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7488  -14.9776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1058  -15.2377    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.4584  -13.5329    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0
  7  8  1  0
  3  4  1  0
  8  9  1  0
  4  5  1  0
  9 10  1  0
  5  1  1  0
 10 11  1  0
  1  2  1  0
 11 12  1  0
  5  6  1  0
 12 13  1  0
  1 14  2  0
  6  7  1  0
  3 15  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA448569

   ---

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: 229.34

Molecular Weight (Monoisotopic): 229.1136

AlogP: 3.09

#Rotatable Bonds: 7

Polar Surface Area: 46.17

Molecular Species: NEUTRAL

HBA: 3

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 6.62

CX Basic pKa: ┄

CX LogP: 3.48

CX LogD: 2.66

Aromatic Rings: ┄

Heavy Atoms: 15

QED Weighted: 0.68

Np Likeness Score: 0.26

References

1. Bharate SB, Rodge A, Joshi RK, Kaur J, Srinivasan S, Kumar SS, Kulkarni-Almeida A, Balachandran S, Balakrishnan A, Vishwakarma RA..  (2008)  Discovery of diacylphloroglucinols as a new class of GPR40 (FFAR1) agonists.,  18  (24): [PMID:18993064] [10.1016/j.bmcl.2008.10.085]

2. Darwish KM, Salama I, Mostafa S, Gomaa MS, Helal MA..  (2016)  Design, synthesis, and biological evaluation of novel thiazolidinediones as PPARγ/FFAR1 dual agonists.,  109  [PMID:26774923] [10.1016/j.ejmech.2015.12.049]

Source

Source(1):

• Scientific Literature