[(RS)-5-{4-[(6-methoxy-1-methyl-1H-benzimidazol-2-yl)methoxy]benzyl}-1,3-thiazolidine-2,4-dione monohydrochloride]

ID: ALA3526905

Cas Number: 299176-11-7

PubChem CID: 9889104

Max Phase: Preclinical

Molecular Formula: C20H20ClN3O4S

Molecular Weight: 397.46

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc2nc(COc3ccc(CC4SC(=O)NC4=O)cc3)n(C)c2c1.Cl

Standard InChI:  InChI=1S/C20H19N3O4S.ClH/c1-23-16-10-14(26-2)7-8-15(16)21-18(23)11-27-13-5-3-12(4-6-13)9-17-19(24)22-20(25)28-17;/h3-8,10,17H,9,11H2,1-2H3,(H,22,24,25);1H

Standard InChI Key:  LKKAMJRUPIIUTC-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 29 31  0  0  0  0  0  0  0  0999 V2000
    2.3257    1.9113    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -4.0983   -0.3083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0971   -1.1356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3870   -1.5485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3852    0.1122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6673   -0.3047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6638   -1.1356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8724   -1.3878    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3904   -0.7126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8812   -0.0433    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8087    0.1043    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8085    0.9292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6315    0.7488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5654   -0.7078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1488   -1.4197    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6821   -1.4149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0967   -2.1265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9209   -2.1220    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3300   -1.4046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9088   -0.6902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0860   -0.6983    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1549   -1.3986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5725   -2.1100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2451   -2.8648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8622   -3.4124    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5736   -2.9948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3961   -2.1892    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.3297   -3.3248    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4396   -3.0432    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  2  0
  3  4  1  0
  4  7  2  0
  6  5  2  0
  5  2  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10  6  1  0
  2 11  1  0
 11 12  1  0
 10 13  1  0
  9 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 16  1  0
 19 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 23  1  0
 26 28  2  0
 24 29  2  0
M  END

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: 397.46

Molecular Weight (Monoisotopic): 397.1096

AlogP: 3.06

#Rotatable Bonds: 6

Polar Surface Area: 82.45

Molecular Species: NEUTRAL

HBA: 7

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 6.62

CX Basic pKa: 4.66

CX LogP: 2.83

CX LogD: 2.12

Aromatic Rings: 3

Heavy Atoms: 28

QED Weighted: 0.69

Np Likeness Score: -0.82

References

1. Uchiyama M, Iwabuchi H, Tsuruta F, Abe K, Takahashi M, Koda H, Oguchi M, Okazaki O, Izumi T..  (2011)  Pharmacokinetics, metabolism, and disposition of rivoglitazone, a novel peroxisome proliferator-activated receptor γ agonist, in rats and monkeys.,  39  (4): [PMID:21177486] [10.1124/dmd.110.036194]

2. Uchiyama M, Koda H, Fischer T, Mueller J, Yamamura N, Oguchi M, Iwabuchi H, Okazaki O, Izumi T..  (2011)  In vitro metabolism of rivoglitazone, a novel peroxisome proliferator-activated receptor γ agonist, in rat, monkey, and human liver microsomes and freshly isolated hepatocytes.,  39  (7): [PMID:21511943] [10.1124/dmd.111.038729]

Source

Source(1):

• Scientific Literature