Compound

(20R,22R)-20,22-dihydroxycholesterol

An oxysterol that is cholesterol substituted by hydroxy groups at positions 20 and 22 (the 20R,22R-stereoisomer).

Definition from ChEBI (CHEBI:1294), read 2026-09-23. CC BY 4.0.

CHEBI:1294ChEBI

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Structure

2D depiction · 3D model shown

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A generated conformer of (20R,22R)-20,22-dihydroxycholesterol — one low-energy arrangement PubChem computed, not a measured structure. Hydrogens are not drawn; the formula counts them.

Class: Organic compound
Formula: C27H46O3
Mass: 418.662 g/mol
Charge: 0
InChIKey: ISBSSBGEYIBVTO-TYKWNDPBSA-N
SMILES: [H][C@@]12CC=C3C[C@@H](O)CC[C@]3(C)[C@@]1([H])CC[C@@]1(C)[C@@]2([H])CC[C@]1([H])[C@@](C)(O)[C@H](O)CCC(C)C
Look it up: ChEBI PubChem By InChIKey

Identity from ChEBI, geometry from PubChem. Not evidence.

What it touches on the way

Mechanistic reach

1 entity

1 entities reached.

0 reported hops1 assembled from the scaffold

CYP11A1ProteinUNIPROT:P05108metabolized byInferred only60 paths30 endpoints

What the reference databases state

Statements

3 statements

3 statements · 2 reference databases · Subject: (20R,22R)-20,22-dihydroxycholesterol · Sources: Human-GEM, Rhea

Order

(22S)-22-hydroxycholesterol is converted to (20R,22R)-20,22-dihydroxycholesterolCompoundHuman-GEM MAR01928Inferred only
(20R,22R)-20,22-dihydroxycholesterol is metabolised by CYP11A1ProteinRhea RHEA:34343Inferred only
(20R,22R)-20,22-dihydroxycholesterol is metabolised by CYP11A1ProteinHuman-GEM MAR01929Inferred only

Reactions

5 reactions

(22S)-22-hydroxycholesterol+proton+NADPH(4-)+dioxygen(20R,22R)-20,22-dihydroxycholesterol+water+NADP(3-)
Catalysed by CYP11A1
Reaction pageLeft to rightBalancedEC 1.14.15.16GO:0005759
Human-GEM MAR01928CC BY 4.0Reference data
(20R,22R)-20,22-dihydroxycholesterol+proton+NADPH(4-)+dioxygen2water+4-methylpentanal+NADP(3-)+pregnenolone
Catalysed by CYP11A1
Reaction pageLeft to rightBalancedEC 1.14.15.16GO:0005759
Human-GEM MAR01929CC BY 4.0Reference data
MAM00592c+2proton+dioxygen+2reduced adrenodoxin(20R,22R)-20,22-dihydroxycholesterol+water+2MAM02663c
Catalysed by CYP11A1
Reaction pageLeft to rightBalance undeterminableEC 1.14.15.6GO:0005829
Human-GEM MAR01935CC BY 4.0Reference data
(22R)-hydroxycholesterol+2reduced [adrenodoxin]+dioxygen+2hydron(20R,22R)-20,22-dihydroxycholesterol+2oxidized [adrenodoxin]+water
Catalysed by CYP11A1
Reaction pageLeft to rightBalance undeterminable
Rhea RHEA:34339CC BY 4.0Reference data
(20R,22R)-20,22-dihydroxycholesterol+2reduced [adrenodoxin]+dioxygen+2hydron4-methylpentanal+pregnenolone+2oxidized [adrenodoxin]+2water
Catalysed by CYP11A1
Reaction pageLeft to rightBalance undeterminable
Rhea RHEA:34343CC BY 4.0Reference data

Other names

9 names

Resolves to: (20R,22R)-20,22-dihydroxycholesterol

Also called: (22R)-20alpha,22-Dihydroxycholesterol20,22-Dihydroxycholesterol20alpha,22beta-Dihydroxycholesterol20alpha,22R-Dihydroxycholesterol20R,22R-Dihydroxycholesterolcholest-5-en-3beta,20R,22R-triolST 27:1;O3
Systematic name: (22R)-cholest-5-ene-3beta,20,22-triol(22R)-cholest-5-ene-3β,20,22-triol