11beta-Hydroxy-3,20-dioxopregn-4-en-21-oic acid
IUPAC 名称
3-hydroxy-3-[(2R,15S,17S)-17-hydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-en-14-yl]propanoic acid
描述
11b-hydroxy-3,20-dioxopregn-4-en-21-oic acid or HDOPA is a major metabolite of corticosterone that is typically elevated in the liver. The in vivo conversion of corticosterone to DHOPA and then to HDOPA is thought to proceed via the aldehyde intermediate 11b-hydroxy-3,20-dioxopregn-4-en-21-al. Cytochrome P450 3A4 (CYP3A4), is known to convert corticosterone to the gem-diol form of the aldehyde. Because CYP3A4 is highly abundant in the liver, the conversion of corticosterone to its aldehyde presumably occurs readily, and the formation of DHOPA by isomerization of the aldehyde. Subsequent dehydrogenation of DHOPA to HDOPA may be done by one of several liver specfici dehydrogenases. Possible candidates include aldehyde dehydrogenase type 3, lactate dehydrogenase A4, or 11b-hydroxysteroid dehydrogenase I. HDOPA has also been identified as a biomarker that is elevated (3700 X) in animals that have been treated with PPARalpha agonists. Peroxisome proliferator-activated receptor alpha (PPARalpha) is a nuclear receptor with manifold effects on intermediary metabolism (PMID: 17550978). [HMDB]
异构
C[C@]12C[C@H](O)C3C(CCC4=CC(=O)CC[C@]34C)C1CCC2C(O)CC(O)=O
InChI标识符
InChI=1S/C22H32O5/c1-21-8-7-13(23)9-12(21)3-4-14-15-5-6-16(17(24)10-19(26)27)22(15,2)11-18(25)20(14)21/h9,14-18,20,24-25H,3-8,10-11H2,1-2H3,(H,26,27)/t14?,15?,16?,17?,18-,20?,21-,22-/m0/s1
键
MSUMOHDXPKCNSB-ZUNXIJJCSA-N