7a-Hydroxydehydroepiandrosterone
IUPAC 名称
(1S,2R,5S,9S,10R,11S,15S)-5,9-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-14-one
描述
7a-Hydroxydehydroepiandrosterone is a major metabolite of dehydroepiandrosterone (DHEA), which is is 7alpha-hydroxylated by the cytochrome P450 7B1 (EC 1.14.13.100, 25-hydroxycholesterol 7alpha-hydroxylase, CYP7B1) in the human brain and liver microsomes. Exposure to the proinflammatory cytokines TNFalpha, IL-1alpha, IL-1beta, and IL-17 increases CYP7B activity in synovial tissue. Increased CYP7B activity leads to higher levels of the DHEA metabolite 7alpha-OH-DHEA in synovial fluid, which may contribute to the maintenance of the chronic inflammation observed in rheumatoid arthritis patients. The glucocorticoid dhydrocorticosterone inhibits the conversion of DHEA to 7a-Hydroxydehydroepiandrosterone. The total levels of 7a-Hydroxydehydroepiandrosterone are increased in serum of patients with Alzheimer's disease. (PMID: 17467270, 15751070, 12667489, 9520908) [HMDB]
异构
[H][C@@]12CCC(=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])[C@H](O)C=C2C[C@@H](O)CC[C@]12C
InChI标识符
InChI=1S/C19H28O3/c1-18-7-5-12(20)9-11(18)10-15(21)17-13-3-4-16(22)19(13,2)8-6-14(17)18/h10,12-15,17,20-21H,3-9H2,1-2H3/t12-,13-,14-,15+,17-,18-,19-/m0/s1
键
OLPSAOWBSPXZEA-JIEICEMKSA-N