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20α,22R-Dihydroxycholesterol

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20α,22R-Dihydroxycholesterol
Names
IUPAC name (22R)-Cholest-5-ene-3β,20,22-triol
Systematic IUPAC name (2R,3R)-2-phenanthren-1-yl]-6-methylheptane-2,3-diol
Identifiers
CAS Number
3D model (JSmol)
Beilstein Reference 2339391
ChEBI
ChEMBL
ChemSpider
KEGG
PubChem CID
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C27H46O3/c1-17(2)6-11-24(29)27(5,30)23-10-9-21-20-8-7-18-16-19(28)12-14-25(18,3)22(20)13-15-26(21,23)4/h7,17,19-24,28-30H,6,8-16H2,1-5H3/t19-,20-,21-,22-,23-,24+,25-,26-,27+/m0/s1Key: ISBSSBGEYIBVTO-TYKWNDPBSA-N
SMILES
  • CC(C)CC((C)(1CC21(CC32CC=C43(CC(C4)O)C)C)O)O
Properties
Chemical formula C27H46O3
Molar mass 418.652 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references
Chemical compound

20α,22R-Dihydroxycholesterol, or (3β)-cholest-5-ene-3,20,22-triol is an endogenous, metabolic intermediate in the biosynthesis of the steroid hormones from cholesterol. Cholesterol ((3β)-cholest-5-en-3-ol) is hydroxylated by cholesterol side-chain cleavage enzyme (P450scc) to form 22R-hydroxycholesterol, which is subsequently hydroxylated again by P450scc to form 20α,22R-dihydroxycholesterol, and finally the bond between carbons 20 and 22 is cleaved by P450scc to form pregnenolone ((3β)-3-hydroxypregn-5-en-20-one), the precursor to the steroid hormones.

See also

References

  1. ^ CHAUDHURI AC, HARADA Y, SHIMIZU K, GUT M, DORFMAN RI (March 1962). "Biosynthesis of pregnenolone from 22-hydroxycholesterol". The Journal of Biological Chemistry. 237 (3): 703–4. doi:10.1016/S0021-9258(18)60359-X. PMID 13878470.
  2. ^ Hume R, Kelly RW, Taylor PL, Boyd GS (May 1984). "The catalytic cycle of cytochrome P-450scc and intermediates in the conversion of cholesterol to pregnenolone". European Journal of Biochemistry. 140 (3): 583–91. doi:10.1111/j.1432-1033.1984.tb08142.x. PMID 6723652.
Cholesterol and steroid metabolic intermediates
Mevalonate pathway
to HMG-CoA
Ketone bodies
to DMAPP
Geranyl-
Carotenoid
Non-mevalonate pathway
To Cholesterol
From Cholesterol
to Steroid hormones
Nonhuman
To Sitosterol
To Ergocalciferol
Endogenous steroids
Precursors
Corticosteroids
Glucocorticoids
Mineralocorticoids
Sex steroids
Androgens
Estrogens
Progestogens
Neurosteroids
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