Ligand 7alpha-hydroxycholesterol

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Basic Ligand Information

Molecular Structure
Picture of 7alpha-hydroxycholesterol (click for magnification)
Molecular Formula
BRENDA Name
InChIKey
C27H46O2
7alpha-hydroxycholesterol
OYXZMSRRJOYLLO-RVOWOUOISA-N
Synonyms:
5-cholesten-3beta,7alpha-diol, 5-cholestene-3beta,7alpha-diol, 7-alpha-hydroxy-cholesterol, 7alpha-hydroxy-cholesterol, cholest-5-ene-3beta,7alpha-diol, cholesterol hydroxide


Show all pahtways known for Show all BRENDA pathways known for 7alpha-hydroxycholesterol

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
cholest-5-ene-3beta,7alpha-diol + NAD+ = 7alpha-hydroxycholest-4-en-3-one + NADH
show the reaction diagram
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5-cholestene-3beta,7alpha-diol + reduced adrenodoxin + O2 = 5-cholestene-3alpha,7alpha,26-triol + oxidized adrenodoxin + H2O
show the reaction diagram
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In Vivo Product in Enzyme-catalyzed Reactions (1 result)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
cholesterol + [reduced NADPH-hemoprotein reductase] + O2 = 7alpha-hydroxycholesterol + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
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Substrate in Enzyme-catalyzed Reactions (9 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
7alpha-hydroxycholesterol + NAD+ = 7alpha-hydroxy-4-cholesten-3-one + NADH
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7alpha-hydroxycholesterol + NADP+ = 7-oxocholesterol + NADPH
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cholest-5-ene-3beta,7alpha-diol + NAD+ = 7alpha-hydroxycholest-4-en-3-one + NADH
show the reaction diagram
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7alpha-hydroxy-cholesterol + O2 = 7alpha-hydroxy-cholest-4-en-3-one + H2O2
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5-cholestene-3beta,7alpha-diol + reduced adrenodoxin + O2 = 5-cholestene-3alpha,7alpha,26-triol + oxidized adrenodoxin + H2O
show the reaction diagram
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oleoyl-CoA + 7alpha-hydroxycholesterol = CoA + 7alpha-hydroxycholesteryl oleate
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3'-phosphoadenylyl sulfate + 7alpha-hydroxycholesterol = adenosine 3',5'-bisphosphate + 7alpha-hydroxycholesteryl sulfate
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Product in Enzyme-catalyzed Reactions (9 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
2 7-oxocholesterol + 2 NADPH + 2 H+ = 7beta-hydroxycholesterol + 7alpha-hydroxycholesterol + 2 NADPH
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glutathione + 3beta-hydroxycholest-5-ene-7alpha-hydroperoxide = cholest-5-ene-3beta,7alpha-diol + ?
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a [lipoyl-carrier protein]-N6-[(R)-dihydrolipoyl]-L-lysine + cholesterol hydroperoxide = a [lipoyl-carrier protein]-N6-lipoyl-L-lysine + H2O + cholesterol hydroxide
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cholesterol 7alpha-hydroperoxide + GSH = 7alpha-hydroxycholesterol + GSSG
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cholesterol + [reduced NADPH-hemoprotein reductase] + O2 = 7alpha-hydroxycholesterol + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
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Inhibitor in Enzyme-catalyzed Reactions (1 result)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE

3D Structure of Enzyme-Ligand-Complex (PDB) (28 results)

Enzyme Kinetic Parameters

KM Value (3 results)

EC NUMBER
KM VALUE [MM]
KM VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
0.0032
-
-
0.00049
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37°C, pH 7.4, in HEK-293 lysates expressing 11beta-HSD1
0.045
-
-

Ki Value (1 result)

EC NUMBER
KI VALUE [MM]
KI VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
0.0061
-
pH 7.4, 37°C

References & Links

Links to other databases for 7alpha-hydroxycholesterol

ChEBI
PubChem
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PubChem