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Home Carboxys (2S,3S,4S,5R,6S)-6-((5-(2,5-Dimethylphenoxy)-2,2-dimethylpentanoyl)oxy)-3,4,5-trihydroxytetrahydro-2H-pyran-2-carboxylic acid

(2S,3S,4S,5R,6S)-6-((5-(2,5-Dimethylphenoxy)-2,2-dimethylpentanoyl)oxy)-3,4,5-trihydroxytetrahydro-2H-pyran-2-carboxylic acid

CAS No.:
91683-38-4
Catalog Number:
AG006R9A
Molecular Formula:
C21H29O4
Molecular Weight:
345.4526
Pack Size
Purity
Availability
Location
Price(USD)
Quantity
  
1mg
≥85%
1 week
United States
$582
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Product Description
Catalog Number:
AG006R9A
Chemical Name:
(2S,3S,4S,5R,6S)-6-((5-(2,5-Dimethylphenoxy)-2,2-dimethylpentanoyl)oxy)-3,4,5-trihydroxytetrahydro-2H-pyran-2-carboxylic acid
CAS Number:
91683-38-4
Molecular Formula:
C21H29O4
Molecular Weight:
345.4526
MDL Number:
MFCD00870898
IUPAC Name:
(2S,3S,4S,5R,6S)-6-[5-(2,5-dimethylphenoxy)-2,2-dimethylpentanoyl]oxy-3,4,5-trihydroxyoxane-2-carboxylic acid
InChI:
InChI=1S/C21H30O9/c1-11-6-7-12(2)13(10-11)28-9-5-8-21(3,4)20(27)30-19-16(24)14(22)15(23)17(29-19)18(25)26/h6-7,10,14-17,19,22-24H,5,8-9H2,1-4H3,(H,25,26)/t14-,15-,16+,17-,19-/m0/s1
InChI Key:
CJMNXSKEVNPQOK-LVEJAMMSSA-N
SMILES:
C[C@@H]1[CH][CH][CH][C@@H](O1)OC(=O)C(CCCOc1cc(C)ccc1C)(C)C
UNII:
954F30WZ3Y
Properties
Complexity:
593  
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
5  
Defined Bond Stereocenter Count:
0
Exact Mass:
426.189g/mol
Formal Charge:
0
Heavy Atom Count:
30  
Hydrogen Bond Acceptor Count:
9  
Hydrogen Bond Donor Count:
4  
Isotope Atom Count:
0
Molecular Weight:
426.462g/mol
Monoisotopic Mass:
426.189g/mol
Rotatable Bond Count:
9  
Topological Polar Surface Area:
143A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
2.2  
Literature
Title Journal
Mechanism-based inactivation (MBI) of cytochrome P450 enzymes: structure-activity relationships and discovery strategies to mitigate drug-drug interaction risks. Journal of medicinal chemistry 20120614
Mechanism-based inactivation of CYP2C8 by gemfibrozil occurs rapidly in humans. Clinical pharmacology and therapeutics 20110401
The CYP2C8 inhibitor gemfibrozil does not affect the pharmacokinetics of zafirlukast. European journal of clinical pharmacology 20110201
CYP2C8 activity recovers within 96 hours after gemfibrozil dosing: estimation of CYP2C8 half-life using repaglinide as an in vivo probe. Drug metabolism and disposition: the biological fate of chemicals 20091201
Construction of triple-transfected cells [organic anion-transporting polypeptide (OATP) 1B1/multidrug resistance-associated protein (MRP) 2/MRP3 and OATP1B1/MRP2/MRP4] for analysis of the sinusoidal function of MRP3 and MRP4. Drug metabolism and disposition: the biological fate of chemicals 20091001
Benzylic oxidation of gemfibrozil-1-O-beta-glucuronide by P450 2C8 leads to heme alkylation and irreversible inhibition. Chemical research in toxicology 20090701
The effect of gemfibrozil on repaglinide pharmacokinetics persists for at least 12 h after the dose: evidence for mechanism-based inhibition of CYP2C8 in vivo. Clinical pharmacology and therapeutics 20080901
Glucuronidation converts gemfibrozil to a potent, metabolism-dependent inhibitor of CYP2C8: implications for drug-drug interactions. Drug metabolism and disposition: the biological fate of chemicals 20060101
The effects of the phytoestrogenic isoflavone genistein on the hepatic disposition of preformed and hepatically generated gemfibrozil 1-O-acyl glucuronide in the isolated perfused rat liver. The Journal of pharmacy and pharmacology 20031001
Self-micellization of gemfibrozil 1-O-beta acyl glucuronide in aqueous solution. Pharmaceutical research 20030301
Properties