5b-Cholestane-3a,7a,12a,25-tetrol
IUPAC 名称
(1S,2S,5R,7S,9R,10R,11S,15R,16S)-14-[(2R)-6-hydroxy-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecane-5,9,16-triol
描述
5b-Cholestane-3a,7a,12a,25-tetrol is an intermediates in the bile acid synthetic pathway, and is secreted into the bile and urine following glucuronidation and does not undergo enterohepatic circulation. In cerebrotendinous xanthomatosis (CTX), a bile acid synthesis disorder caused by sterol 27-hydroxylase (CYP27) deficiency, early intermediates and cholestanol accumulate in a variety of tissues, and glucuronides of 25-hydroxylated bile alcohols are released in bile, blood, and urine. Bile acid synthesis from cholesterol is tightly regulated via a feedback mechanism mediated by the farnesoid X receptor (FXR), a nuclear receptor activated by bile acids. Synthesis via the classic pathway is initiated by a series of cholesterol ring modifications and followed by the side chain cleavage. The enhanced cholesterol 7a-hydroxylase (CYP7A1) expression in CYP27 deficiency may be the result of decreased flux of bile acids and bile alcohols into the liver, while production of FXR-activating 5b-Cholestane-3a,7a,12a,25-tetrol is increased. (PMID 15145977) [HMDB]
异构
[H][C@@]12CCC([C@H](C)CCCC(C)(C)O)[C@@]1(C)[C@@H](O)C[C@@]1([H])[C@@]2([H])[C@H](O)C[C@]2([H])C[C@H](O)CC[C@]12C
InChI标识符
InChI=1S/C27H48O4/c1-16(7-6-11-25(2,3)31)19-8-9-20-24-21(15-23(30)27(19,20)5)26(4)12-10-18(28)13-17(26)14-22(24)29/h16-24,28-31H,6-15H2,1-5H3/t16-,17+,18-,19?,20+,21+,22-,23+,24+,26+,27-/m1/s1
键
NTIXPPFPXLYJCT-RUYUEJGQSA-N