Compound

25-hydroxycholesterol

CHEBI:42977ChEBI

Structure

2D depiction · 3D model shown

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A generated conformer of 25-hydroxycholesterol — one low-energy arrangement PubChem computed, not a measured structure. Hydrogens are not drawn; the formula counts them.

Class: Organic compound
Formula: C27H46O2
Mass: 402.663 g/mol
Charge: 0
InChIKey: INBGSXNNRGWLJU-ZHHJOTBYSA-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@H](C)CCCC(C)(C)O
Look it up: ChEBI PubChem By InChIKey

Identity from ChEBI, geometry from PubChem. Not evidence.

What it touches on the way

Mechanistic reach

2 entities

2 entities reached.

0 reported hops2 assembled from the scaffold

What the reference databases state

Chemical structure

25-hydroxycholesterol has the functional parent cholesterolCompoundChEBI CHEBI:42977Inferred only

Statements

8 statements

8 statements · 2 reference databases · Subject: 25-hydroxycholesterol · Sources: Human-GEM, Rhea

Order

7alpha-hydroxycholest-4-en-3-one is converted to 25-hydroxycholesterolCompoundHuman-GEM MAR02184Inferred only
25-hydroxycholesterol is converted to 7alpha-hydroxycholest-4-en-3-oneCompoundHuman-GEM MAR02184Inferred only
25-hydroxycholesterol is converted to 7alpha,25-dihydroxycholesterolCompoundHuman-GEM MAR01777Inferred only
CHEBI:1307929 is converted to 25-hydroxycholesterolCompoundHuman-GEM MAR01776Inferred only
cholesterol is converted to 25-hydroxycholesterolCompoundRhea RHEA:46132Inferred only
25-hydroxycholesterol is metabolised by CYP7B1ProteinHuman-GEM MAR01777Inferred only
25-hydroxycholesterol is metabolised by CYP7B1ProteinRhea RHEA:24308Inferred only
25-hydroxycholesterol is a substrate of HSD3B7ProteinHuman-GEM MAR02184Inferred only

Reactions

10 reactions

CHEBI:1307929+proton+NADPH(4-)+dioxygen25-hydroxycholesterol+water+NADP(3-)
Catalysed by CH25H
Reaction pageLeft to rightBalancedEC 1.14.99.38endoplasmic reticulum
Human-GEM MAR01776CC BY 4.0Reference data
25-hydroxycholesterol+proton+NADPH(4-)+dioxygen7alpha,25-dihydroxycholesterol+water+NADP(3-)
Catalysed by CYP7B1
Reaction pageLeft to rightBalancedEC 1.14.14.29endoplasmic reticulum
Human-GEM MAR01777CC BY 4.0Reference data
25-hydroxycholesterol+NADP(3-)7alpha-hydroxycholest-4-en-3-one+proton+NADPH(4-)
Catalysed by HSD3B7
Reaction pageReversibleBalancedEC 1.1.1.181endoplasmic reticulum
Human-GEM MAR02184CC BY 4.0Reference data
25-hydroxycholesterol25-hydroxycholesterol
Reaction pageLeft to rightBalancedendoplasmic reticulum, cytosol
Human-GEM MAR11882CC BY 4.0Reference data
25-hydroxycholesterol25-hydroxycholesterol
Reaction pageLeft to rightBalancedcytosol, extracellular space
Human-GEM MAR11883CC BY 4.0Reference data
25-hydroxycholesterol
Reaction pageReversibleBalance undeterminableextracellular space
Human-GEM MAR11884CC BY 4.0Reference data
cholesterol+AH2+dioxygen25-hydroxycholesterol+A+water
Catalysed by CH25H
Reaction pageLeft to rightBalanced
Rhea RHEA:21104CC BY 4.0Reference data
25-hydroxycholesterol+reduced [NADPH--hemoprotein reductase]+dioxygen7alpha,25-dihydroxycholesterol+oxidized [NADPH--hemoprotein reductase]+water+hydron
Catalysed by CYP7B1
Reaction pageLeft to rightBalance undeterminable
Rhea RHEA:24308CC BY 4.0Reference data
cholesterol+NADPH(4-)+dioxygen+hydron25-hydroxycholesterol+NADP(3-)+water
Catalysed by CH25H
Reaction pageLeft to rightBalanced
Rhea RHEA:46132CC BY 4.0Reference data
cholesterol+reduced [NADPH--hemoprotein reductase]+dioxygen25-hydroxycholesterol+oxidized [NADPH--hemoprotein reductase]+water+hydron
Catalysed by CYP1A2 or CYP3A4 or CYP2D6 or CYP2C9
Reaction pageLeft to rightBalance undeterminable
Rhea RHEA:50256CC BY 4.0Reference data

Other names

7 names

Resolves to: 25-hydroxycholesterol

Also called: 25-hydroxy-cholesterol25-OHC5-Cholestene-3beta,25-diolcholest-5-en-3beta,25-diolST 27:1;O2
Systematic name: cholest-5-ene-3beta,25-diolcholest-5-ene-3β,25-diol