Ligand cholesterol

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Basic Ligand Information

Molecular Structure
Picture of cholesterol (click for magnification)
Molecular Formula
BRENDA Name
InChIKey
C27H46O
cholesterol
HVYWMOMLDIMFJA-DPAQBDIFSA-N
Synonyms:
cholest-5-en-3-beta-ol, cholest-5-en-3beta-ol, cholesterol[side 1], cholesterol[side 2]


Show all pahtways known for Show all BRENDA pathways known for cholesterol

Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (36 results)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
cholesterol + [reduced NADPH-hemoprotein reductase] + O2 = 12-hydroxycholesterol + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
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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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cholest-5-en-3-beta-ol + 6 reduced [2Fe-2S] ferredoxin + 3 O2 = (25S)-3beta-hydroxycholest-5-en-26-oate + 6 oxidized [2Fe-2S] ferredoxin + 4 H2O
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cholesterol + AH2 + O2 = 25-hydroxycholesterol + A + H2O
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UDP-glucose + cholesterol = UDP + cholesterol 3-beta-D-glucoside
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ATP + H2O + cholesterol[side 1] = ADP + phosphate + cholesterol[side 2]
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In Vivo Product in Enzyme-catalyzed Reactions (14 results)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
5alpha-cholestan-3beta-ol + ferrocytochrome b5 + H+ + O2 = cholest-5-en-3beta-ol + ferricytochrome b5 + 2 H2O
show the reaction diagram
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cholesterol sulfate + H2O = cholesterol + sulfate
show the reaction diagram
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-

Substrate in Enzyme-catalyzed Reactions (105 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
cholesterol + NAD+ = cholest-5-en-3-one + NADH
show the reaction diagram
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cholesterol + [reduced NADPH-hemoprotein reductase] + O2 = 12-hydroxycholesterol + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
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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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cholesterol + AH2 + O2 = 25-hydroxycholesterol + A + H2O
show the reaction diagram
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cholesterol + NADPH + H+ + O2 = 22-hydroxy-cholesterol + NADP+ + H2O
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cholesterol + acceptor = ?
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cholesterol + S-adenosyl-L-methionine = ?
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cholesterol + 1,2-diacyl-sn-glycerol = monoacylglycerol + cholesterol-3-O-acyl ester
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ATP + H2O + cholesterol[side 1] = ADP + phosphate + cholesterol[side 2]
show the reaction diagram

Product in Enzyme-catalyzed Reactions (67 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
5alpha-cholestan-3beta-ol + ferrocytochrome b5 + H+ + O2 = cholest-5-en-3beta-ol + ferricytochrome b5 + 2 H2O
show the reaction diagram
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cholesterol oleate + H2O = cholesterol + oleic acid
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cholesteryl palmitate + H2O = cholesterol + palmitate
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cholesteryl oleate + H2O = oleate + cholesterol
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cholesteryl oleate + H2O = cholesterol + oleate
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cholesteryl oleate + H2O = cholesterol + oleate
show the reaction diagram
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cholesteryl beta-D-glucoside + H2O = cholesterol + beta-D-glucose
show the reaction diagram
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Activator in Enzyme-catalyzed Reactions (29 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
high levels of DHCR24 are associated with elevated cholesterol concentrations
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DGKalpha can be activated in vitro in a Ca2+-independent manner by lipids such cholesterol
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about 125% activity at 0.1 mM
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0.01 mM, isoform SphK2, 107% of initial activity
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concentration dependent activation of alkaline phosphatase grown in low phosphate medium
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phospholipase C is enhanced by cholesterol and by lipids with an intrinsic negative curvature, e.g. phosphatidylethanolamine
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in phosphatidylcholine/phosphatidylserine vesicles, cholesterol enhances Factor Va inactivation and the rate of cleavage by enzyme both at R506 and R306
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activation, acetone-washed membrane-bound enzyme
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maximum activity at 20% (w/v)
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the transport activity of P-glycoprotein is elevated by about 40% cholesterol
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presence of cholesterol in liposomes increases the binding affinity of small drug substrates with molecular masses below 500 Da, does not affect that of drugs with molecular mass of between 800 and 900 Da, and suppresses that of valinomycin with a molecular mass greater than 1000. Cholesterol enhances paclitaxel-stimulated ATPase activity of enzyme

Inhibitor in Enzyme-catalyzed Reactions (24 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
oxidase: 18.6% inhibition at 0.1 mM, reductase: 7.4% inhibition at 0.1 mM
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substrate inhibition of mutant V191A
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addition to a membrane preperation in vitro reduces 5-lipoxygenase activity by half. Cholesterol sulfate can inhibit 5-lipoxygenase in intact cells
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inhibition above 0.003 mM, mitochondrial
enzyme suppressed by feeding 5% cholesterol, 70% decrease in enzyme activity
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cholesterol sensitivity of PI4KIIalpha
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slight inhibition of CES1, not CES2
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80-100% inhibition at 0.01-0.15 mM
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strong inhibition in the presence of 0.4 mM linoleic acid
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1 mM, 57% inhibition
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hydrolysis of cholesteryl glucoside
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IC50 is above 0.125 mM
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membranes isolated from mouse brain with endogenous reduced levels of cholesterol due to targeted deletion of one seladin-I allele show a reduced amount of IDE
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inhibits the first cleavage of SREBP and indirectly S2P cleavage
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0.08 mM or below, decreases the hydrolysis of ceramide by a maximum of two-thirds
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an increased cholesterol level suppresses the expression of 2,3-oxidosqualene cyclase
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the transport activity of P-glycoprotein decreases by about 20% cholesterol
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3D Structure of Enzyme-Ligand-Complex (PDB) (46 results)

Enzyme Kinetic Parameters

kcat Value (Turnover Number) (74 results)

EC NUMBER
TURNOVER NUMBER [1/S]
TURNOVER NUMBER MAXIMUM [1/S]
COMMENTARY
LITERATURE
0.0117
-
-

KM Value (121 results)

EC NUMBER
KM VALUE [MM]
KM VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
0.0077
-
21°C, pH 7.4
0.0107
-
pH and temperature not specified in the publication

Ki Value (1 result)

EC NUMBER
KI VALUE [MM]
KI VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
0.62
-
37°C

IC50 Value (2 results)

EC NUMBER
IC50 VALUE
IC50 VALUE MAXIMUM
COMMENTARY
LITERATURE
2.8
-
pH 5.0, 40°C
0.125
-
IC50 is above 0.125 mM

References & Links

Links to other databases for cholesterol

ChEBI
PubChem
ChEBI
PubChem