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74772-77-3 molecular structure
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5-({4-[(1-methylcyclohexyl)methoxy]phenyl}methyl)-1,3-thiazolidine-2,4-dione

ChemBase ID: 133657
Molecular Formular: C18H23NO3S
Molecular Mass: 333.44512
Monoisotopic Mass: 333.1398646
SMILES and InChIs

SMILES:
CC1(CCCCC1)COc1ccc(cc1)CC1C(=O)NC(=O)S1
Canonical SMILES:
O=C1NC(=O)C(S1)Cc1ccc(cc1)OCC1(C)CCCCC1
InChI:
InChI=1S/C18H23NO3S/c1-18(9-3-2-4-10-18)12-22-14-7-5-13(6-8-14)11-15-16(20)19-17(21)23-15/h5-8,15H,2-4,9-12H2,1H3,(H,19,20,21)
InChIKey:
YZFWTZACSRHJQD-UHFFFAOYSA-N

Cite this record

CBID:133657 http://www.chembase.cn/molecule-133657.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
5-({4-[(1-methylcyclohexyl)methoxy]phenyl}methyl)-1,3-thiazolidine-2,4-dione
IUPAC Traditional name
ciglitazone
Synonyms
(±)-5-[4-(1-Methylcyclohexylmethoxy)benzyl]thiazolidine-2,4-dione
Ciglitazone
Ciglitizone
(+/-)-5-[4-(1-methylcyclohexylmethoxy)benzyl]thiazolidine-2,4-dione
ADD-3878
Ciglitazone
2-amino-5-[[4-[(1-methylcyclohexyl)methoxy]phenyl]methyl]-4(5H)-thiazolone
rac 2-Imino-5-[4-(1-methylcyclohexylmethoxyl)benzyl]thiazolidine-4one
CAS Number
74772-77-3
85010-66-8
MDL Number
MFCD00865499
PubChem SID
24892661
162227934
PubChem CID
2750

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources
Data Source Data ID
PubChem 2750 external link

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem
Acid pKa 6.6135864  H Acceptors
H Donor LogD (pH = 5.5) 4.25011 
LogD (pH = 7.4) 3.459027  Log P 4.281939 
Molar Refractivity 91.2588 cm3 Polarizability 36.03663 Å3
Polar Surface Area 55.4 Å2 Rotatable Bonds
Lipinski's Rule of Five true 

PROPERTIES

PROPERTIES

Physical Property Safety Information Pharmacology Properties Product Information Bioassay(PubChem)
Solubility
Chloroform expand Show data source
DMSO expand Show data source
Ethanol expand Show data source
Apperance
White Powder expand Show data source
White Solid expand Show data source
Melting Point
130-131°C expand Show data source
264°C expand Show data source
Storage Condition
-20°C Freezer expand Show data source
RTECS
XJ5813700 expand Show data source
MSDS Link
Download expand Show data source
German water hazard class
3 expand Show data source
Personal Protective Equipment
Eyeshields, Gloves, half-mask respirator (US), multi-purpose combination respirator cartridge (US) expand Show data source
Gene Information
human ... PPARG(5468)mouse ... Pparg(19016) expand Show data source
Purity
≥99% (TLC) expand Show data source
Certificate of Analysis
Download expand Show data source

DETAILS

DETAILS

Sigma Aldrich Sigma Aldrich TRC TRC
Sigma Aldrich - C3974 external link
Biochem/physiol Actions
Selective peroxisome proliferator-activated receptor-γ (PPARγ) agonist (EC50 = 3 μM) and antihyperglycemic agent displaying activity in genetically obese C57 B1/6 ob/ob mice.
Toronto Research Chemicals - C441000 external link
Displays antihyperglycemic activity in genetically obese mice. It is a selective PPARg agonist.
Toronto Research Chemicals - I423750 external link
Displays antihyperglycemic activity in genetically obese mice. It is a selective PPARg agonist.

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • Clark, D.A., et al.: J. Med. Chem., 34, 319-325 (1991)
  • • Sohda, T., et al.: Chem. Pharm. Bull., 30(1991)
  • • 3580-3600, (1982)
  • • Clark, D.A., et al.: J. Med. Chem., 34, 319-325 (1991)
  • • Sohda, T., et al.: Chem. Pharm. Bull., 30(1991)
  • • 3580-3600, (1982)
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PATENTS

PATENTS

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INTERNET

INTERNET

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