(2S)-2-ethoxy-3-(4-{2-[4-(methanesulfonyloxy)phenyl]ethoxy}phenyl)propanoic acid

• ChemBase ID: 5048
• Molecular Formular: C20H24O7S
• Molecular Mass: 408.46536
• Monoisotopic Mass: 408.12427411
• SMILES: c1(C[C@H](OCC)C(=O)O)ccc(cc1)OCCc1ccc(cc1)OS(=O)(=O)C
• Canonical SMILES: CCO[C@H](C(=O)O)Cc1ccc(cc1)OCCc1ccc(cc1)OS(=O)(=O)C
• InChI: InChI=1S/C20H24O7S/c1-3-25-19(20(21)22)14-16-6-8-17(9-7-16)26-13-12-15-4-10-18(11-5-15)27-28(2,23)24/h4-11,19H,3,12-14H2,1-2H3,(H,21,22)/t19-/m0/s1
• InChIKey: CXGTZJYQWSUFET-IBGZPJMESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-ethoxy-3-(4-{2-[4-(methanesulfonyloxy)phenyl]ethoxy}phenyl)propanoic acid
• IUPAC Traditional name: galida
• Synonyms: (2S)-2-ETHOXY-3-[4-(2-{4-[(METHYLSULFONYL)OXY]PHENYL}ETHOXY)PHENYL]PROPANOIC ACID; (S)-2-Ethoxy-3-(4-(4-((methylsulfonyl)oxy)phenethoxy)phenyl)propanoic acid; (αS)-α-Ethoxy-4-[2-[4-[(methylsulfonyl)oxy]phenyl]ethoxy]benzenepropanoic Acid; (S)-2-Ethoxy-3-[4-[2-(4-methanesulfonyloxyphenyl)ethoxy]phenyl]propanoic Acid; AR-H 039242; AR-H 039242XX; AZ 242; Galida; Tesaglitazar

Database IDs

• CAS Number: 251565-85-2
• MDL Number: MFCD07784004
• PubChem SID: 162103350
• PubChem CID: 208901

CALCULATED PROPERTIES

JChem

• Acid pKa: 3.7301824
• H Acceptors: 6
• H Donor: 1
• LogD (pH = 5.5): 1.3725483
• LogD (pH = 7.4): -0.15086626
• Log P: 3.142194
• Molar Refractivity: 103.5228 cm^3
• Polarizability: 41.35227 Å^3
• Polar Surface Area: 99.13 Å^2
• Rotatable Bonds: 11
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 3.18
• LOG S: -5.07
• Solubility (Water): 3.51e-03 g/l

PROPERTIES

Product Information

• Purity: 95+%

DETAILS

DrugBank - DB07399

Drug information: experimental

Toronto Research Chemicals - T136000

Dual -acting peroxisome proliferator-activated receptor (PPAR) α and γ agonist. Antidiabetic.

REFERENCES

• Hegarty, B.D., et al.: Endocrinology, 145, 3158 (2004)
• Ericsson, H., et al.: Drug Metab. Dispos., 32, 923 (2004)
• Fagerberg, B., et al.: Diabetologia, 48, 1716 (2004)
• Kamber, N., et al.: Drugs, 8, 927 (2004)