5-(4-(4-hydroxy-3-isopropylphenoxy)-3,5-diisopropylbenzyl)thiazolidine-2,4-dione

ID: ALA245462

PubChem CID: 44441147

Max Phase: Preclinical

Molecular Formula: C25H31NO4S

Molecular Weight: 441.59

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)c1cc(Oc2c(C(C)C)cc(CC3SC(=O)NC3=O)cc2C(C)C)ccc1O

Standard InChI:  InChI=1S/C25H31NO4S/c1-13(2)18-12-17(7-8-21(18)27)30-23-19(14(3)4)9-16(10-20(23)15(5)6)11-22-24(28)26-25(29)31-22/h7-10,12-15,22,27H,11H2,1-6H3,(H,26,28,29)

Standard InChI Key:  MAVVKYQSGOSEET-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 31 33  0  0  0  0  0  0  0  0999 V2000
    6.5444  -17.2500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5432  -18.0773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2581  -18.4902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9716  -17.2463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2563  -16.8372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6846  -16.8311    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.4006  -17.2409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4003  -18.0636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1155  -18.4733    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1079  -16.8228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8284  -18.4893    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8298  -16.8376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8296  -16.0126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1155  -17.2503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8278  -17.2257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8290  -18.0583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5445  -18.4691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2580  -18.0550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0147  -18.3951    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   13.5607  -17.7804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1359  -17.0583    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.3418  -17.2386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7243  -16.6915    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.3818  -17.8605    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9714  -18.0658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9833  -18.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1584  -18.7696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3911  -19.4922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0981  -15.9979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8076  -15.5769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3788  -15.5939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 12 14  1  0
 15 16  1  0
  3 25  2  0
  6  7  1  0
  1  2  2  0
 16 17  1  0
  7  8  2  0
 18 17  1  0
 25  4  1  0
  8  9  1  0
  9 16  2  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 18  1  0
 18 19  1  0
 15 10  2  0
 22 23  2  0
 10  7  1  0
 20 24  2  0
  4  5  2  0
  2 11  1  0
  8 26  1  0
  5  1  1  0
 26 27  1  0
  1 12  1  0
 26 28  1  0
  2  3  1  0
 10 29  1  0
 12 13  1  0
 29 30  1  0
  4  6  1  0
 29 31  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA245462

   5-[[4-(4-Hydroxy-3-propan-2-ylphenoxy)-3,5-di(propan-2-yl)phenyl]methyl]-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: 441.59

Molecular Weight (Monoisotopic): 441.1974

AlogP: 6.45

#Rotatable Bonds: 7

Polar Surface Area: 75.63

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 6.61

CX Basic pKa: ┄

CX LogP: 6.88

CX LogD: 6.06

Aromatic Rings: 2

Heavy Atoms: 31

QED Weighted: 0.52

Np Likeness Score: 0.35

References

1. Haning H, Mueller U, Schmidt G, Schmeck C, Voehringer V, Kretschmer A, Bischoff H..  (2007)  Novel heterocyclic thyromimetics. Part 2.,  17  (14): [PMID:17499989] [10.1016/j.bmcl.2007.04.085]

Source

Source(1):

• Scientific Literature