Ligand 25-hydroxycholesterol

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Basic Ligand Information

Molecular Structure
Picture of 25-hydroxycholesterol (click for magnification)
Molecular Formula
BRENDA Name
InChIKey
C27H46O2
25-hydroxycholesterol
INBGSXNNRGWLJU-ZHHJOTBYSA-N
Synonyms:
25-hydroxy-cholesterol, cholest-5-ene-3beta,25-diol
Pathway Source
Pathways

Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (2 results)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE

In Vivo Product in Enzyme-catalyzed Reactions (1 result)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
cholesterol + AH2 + O2 = 25-hydroxycholesterol + A + H2O
show the reaction diagram
-
-

Substrate in Enzyme-catalyzed Reactions (7 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
25-hydroxycholesterol + O2 = 25-hydroxycholest-5-en-3-one + H2O2
show the reaction diagram
-
25-hydroxycholesterol + [reduced NADPH-hemoprotein reductase] + O2 = ?
show the reaction diagram
-
3'-phosphoadenylylsulfate + 25-hydroxycholesterol = adenosine 3',5'-bisphosphate + 25-hydroxycholesterol sulfate
show the reaction diagram
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Product in Enzyme-catalyzed Reactions (2 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
cholesterol + reduced adrenodoxin + O2 = 25-hydroxycholesterol + oxidized adrenodoxin + H2O
show the reaction diagram
-
-
cholesterol + AH2 + O2 = 25-hydroxycholesterol + A + H2O
show the reaction diagram
-
-

Activator in Enzyme-catalyzed Reactions (6 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
activates Golgi/endosome-associated PI4K activity, PI4K activation by 25-hydroxycholesterol is dependent on oxysterol binding protein, overview
-

Inhibitor in Enzyme-catalyzed Reactions (3 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
IC50: 0.45 mM
-
expression of mevalonate kinase is regulated by sterol response element-binding protein-1, which is sensitive to the cllular concentration of 25-hydroxycholesterol. Presence of 25-hydroxycholesterol inhibits mevalonate kinase expression and subsequently its binding to luteinizing hormone receptor mRNA
-
slight inhibition of CES1, not CES2
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Enzyme Kinetic Parameters

kcat Value (Turnover Number) (1 result)

EC NUMBER
TURNOVER NUMBER [1/S]
TURNOVER NUMBER MAXIMUM [1/S]
COMMENTARY
LITERATURE
0.015
-
pH 7.2, 37°C, wild-type enzyme

KM Value (2 results)

EC NUMBER
KM VALUE [MM]
KM VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
0.0015
-
-
0.001
-
pH 7.4, 37°C

IC50 Value (1 result)

EC NUMBER
IC50 VALUE
IC50 VALUE MAXIMUM
COMMENTARY
LITERATURE
0.45
-
IC50: 0.45 mM

References & Links

Links to other databases for 25-hydroxycholesterol

ChEBI
PubChem
ChEBI
PubChem