Home Other Building Blocks rac Ketoprofen Acyl-β-D-glucuronide

rac Ketoprofen Acyl-β-D-glucuronide

CAS No.:
76690-94-3
Catalog Number:
AG008PH7
Molecular Formula:
C22H22O9
Molecular Weight:
430.4047
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Product Description
Catalog Number:
AG008PH7
Chemical Name:
rac Ketoprofen Acyl-β-D-glucuronide
CAS Number:
76690-94-3
Molecular Formula:
C22H22O9
Molecular Weight:
430.4047
MDL Number:
MFCD00870105
IUPAC Name:
(2S,3S,4S,5R,6S)-6-[2-(3-benzoylphenyl)propanoyloxy]-3,4,5-trihydroxyoxane-2-carboxylic acid
InChI:
InChI=1S/C22H22O9/c1-11(13-8-5-9-14(10-13)15(23)12-6-3-2-4-7-12)21(29)31-22-18(26)16(24)17(25)19(30-22)20(27)28/h2-11,16-19,22,24-26H,1H3,(H,27,28)/t11?,16-,17-,18+,19-,22-/m0/s1
InChI Key:
PBTXSZZKPHBHMA-LYFYOZKASA-N
SMILES:
O=C(C(c1cccc(c1)C(=O)c1ccccc1)C)O[C@@H]1OC(C(=O)O)[C@H](C([C@@H]1O)O)O
Properties
Complexity:
659  
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
5  
Defined Bond Stereocenter Count:
0
Exact Mass:
430.126g/mol
Formal Charge:
0
Heavy Atom Count:
31  
Hydrogen Bond Acceptor Count:
9  
Hydrogen Bond Donor Count:
4  
Isotope Atom Count:
0
Molecular Weight:
430.409g/mol
Monoisotopic Mass:
430.126g/mol
Rotatable Bond Count:
7  
Topological Polar Surface Area:
151A^2
Undefined Atom Stereocenter Count:
1  
Undefined Bond Stereocenter Count:
0
XLogP3:
1.7  
Literature
Title Journal
Toxicological evaluation of acyl glucuronides of nonsteroidal anti-inflammatory drugs using human embryonic kidney 293 cells stably expressing human UDP-glucuronosyltransferase and human hepatocytes. Drug metabolism and disposition: the biological fate of chemicals 20110101
Ketoprofen glucuronidation and bile excretion in carbon tetrachloride and alpha-naphthylisothiocyanate induced hepatic injury rats. Toxicology 20070212
Kinetic studies on the intramolecular acyl migration of beta-1-O-acyl glucuronides: application to the glucuronides of (R)- and (S)-ketoprofen, (R)- and (S)-hydroxy-ketoprofen metabolites, and tolmetin by 1H-NMR spectroscopy. Xenobiotica; the fate of foreign compounds in biological systems 20050701
Elucidation of the mechanism of inhibition of cyclooxygenases by acyl-coenzyme A and acylglucuronic conjugates of ketoprofen. Biochemical pharmacology 20041115
Stereospecific pH-dependent degradation kinetics of R- and S-naproxen-beta-l-O-acyl-glucuronide. Chirality 20020505
Evidence for significant differences in microsomal drug glucuronidation by canine and human liver and kidney. Drug metabolism and disposition: the biological fate of chemicals 20010201
Properties