22R-Hydroxycholesterol

22R-Hydroxycholesterol
Names
	IUPAC name (22R)-Cholest-5-ene-3β,22-diol
	Systematic IUPAC name (1R,3aS,3bS,7S,9aR,9bS,11aS)-1--9a,11a-dimethyl-2,3,3a,3b,4,6,7,8,9,9a,9b,10,11,11a-tetradecahydro-1H-cyclopentaphenanthren-7-ol
Identifiers
CAS Number	17711-16-9 [EPA];
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:166802;
ChEMBL	ChEMBL3218924;
ChemSpider	96893;
PubChem CID	107724;
UNII	TJ9HV8VPD2 ;
CompTox Dashboard (EPA)	DTXSID501313409 DTXSID30904340, DTXSID501313409 ;
	InChI InChI=1S/C27H46O2/c1-17(2)6-11-25(29)18(3)22-9-10-23-21-8-7-19-16-20(28)12-14-26(19,4)24(21)13-15-27(22,23)5/h7,17-18,20-25,28-29H,6,8-16H2,1-5H3/t18-,20-,21-,22+,23-,24-,25?,26-,27+/m0/s1 Key: RZPAXNJLEKLXNO-UKNNTIGFSA-N; InChI=1/C27H46O2/c1-17(2)6-11-25(29)18(3)22-9-10-23-21-8-7-19-16-20(28)12-14-26(19,4)24(21)13-15-27(22,23)5/h7,17-18,20-25,28-29H,6,8-16H2,1-5H3/t18-,20-,21-,22+,23-,24-,25?,26-,27+/m0/s1 Key: RZPAXNJLEKLXNO-UKNNTIGFBU;
	SMILES O4C/C3=C/C1(CC2(1CC2(C)C(O)CCC(C)C)C)3(C)CC4;
Properties
Chemical formula	C27H46O2
Molar mass	402.653 g/mol
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references

22R-Hydroxycholesterol, or (3β)-cholest-5-ene-3,22-diol is an endogenous, metabolic intermediate in the biosynthesis of the steroid hormones from cholesterol.^[1]^[2] 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),^[1]^[2] the precursor to the steroid hormones.

It is an agonist of the liver X receptor.

References

^ ^a ^b 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.
^ ^a ^b 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.

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[pmid13878470-1] 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.

[pmid6723652-2] 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.

[1]

[2]

v t e FXRTooltip Farnesoid X receptor and LXRTooltip liver X receptor modulators
FXRTooltip Farnesoid X receptor	Agonists: Bile acids Cafestol Chenodeoxycholic acid Cilofexor Fexaramine GW-4064 Ivermectin Nidufexor Obeticholic acid Tropifexor Antagonists: Guggulsterone
LXRTooltip Liver X receptor	Agonists: 22R-Hydroxycholesterol 24S-Hydroxycholesterol 27-Hydroxycholesterol Abequolixron Cholestenoic acid DMHCA GW-3965 Hypocholamide T-0901317 Antagonists: Efavirenz Larsucosterol
See also Receptor/signaling modulators

See also

References