20α,22R-dihydroxycholesterol

20α,22R-Dihydroxycholesterol
Names

IUPAC name (3β)-Cholest-5-ene-3,20,22-triol
Identifiers
3D model (Jmol)	Interactive image
ChemSpider	4956189
PubChem	6453841
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/s1 Key: ISBSSBGEYIBVTO-TYKWNDPBSA-N
SMILES CC(C)CC[C@H]([C@@](C)([C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CC=C4[C@@]3(CC[C@@H](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 [77 °F], 100 kPa).
Infobox references

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 hydroxlated 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.