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Enzyme Kinetic Parameters
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Ligand (24S)-24-hydroxycholesterol

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Basic Ligand Information

Molecular Structure

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Molecular Formula

BRENDA Name

InChIKey

C₂₇H₄₆O₂

(24S)-24-hydroxycholesterol

IOWMKBFJCNLRTC-XWXSNNQWSA-N

Synonyms:

(24S)-cholest-5-ene-3beta,24-diol, (24S)-hydroxycholesterol, 24(S)-hydroxycholesterol, 24-hydroxycholesterol, 24S-hydroxycholesterol, Cerebrosterol

Pathway Source

Pathways

KEGG

Primary bile acid biosynthesis

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Roles as Enzyme Ligand

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

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Show Natural Substrate (1 entry)

EC NUMBER

PROVEN IN VIVO REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

2.3.1.43

phosphatidylcholine + cerebrosterol = 1-acylglycerophosphocholine + cerebrosteryl ester

736674

In Vivo Product in Enzyme-catalyzed Reactions (4 results)

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EC NUMBER

PROVEN IN VIVO REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.14.14.25

cholesterol + [reduced NADPH-hemoprotein reductase] + H+ + O2 = (24S)-24-hydroxycholesterol + [oxidized NADPH-hemoprotein reductase] + H2O

1.14.14.25

cholesterol + [reduced NADPH-hemoprotein reductase] + O2 = (24S)-cholest-5-ene-3beta,24-diol + [oxidized NADPH-hemoprotein reductase] + H2O

1.14.14.25

cholesterol + NADPH + O2 = (24S)-hydroxycholesterol + NADP+ + H2O

1.14.14.25

cholesterol + reduced adrenodoxin + O2 = 24-hydroxycholesterol + oxidized adrenodoxin + H2O

1.14.14.25

4 entries

Substrate in Enzyme-catalyzed Reactions (9 results)

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EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.1.3.6

24-hydroxycholesterol + O2 = 24-hydroxycholest-5-en-3-one + H2O2

287664

1.14.14.25

(24S)-24-hydroxycholesterol + [reduced NADPH-hemoprotein reductase] + O2 = 24,25-dihydroxycholesterol + [oxidized NADPH-hemoprotein reductase] + H2O

657671, 657971

1.14.14.25

(24S)-24-hydroxycholesterol + [reduced NADPH-hemoprotein reductase] + O2 = 24,27-dihydroxycholesterol + [oxidized NADPH-hemoprotein reductase] + H2O

657671, 657971

1.14.14.25

(24S)-hydroxycholesterol + [reduced NADPH-hemoprotein reductase] + O2 = 24,25-dihydroxycholesterol + 24,27-dihydroxycholesterol + [oxidized NADPH-hemoprotein reductase] + H2O

24-hydroxycholesterol + NADPH + H+ + O2 = 7alpha,24-dihydroxycholesterol + NADP+ + H2O

659143

2.3.1.26

acyl-CoA + 24(S)-hydroxycholesterol = CoA + acyl (24S)-24-hydroxycholesterol

736702

2.3.1.43

phosphatidylcholine + 24-hydroxycholesterol = 1-acylglycerophosphocholine + a 24-hydroxycholesterol 3-O-acyl ester

736889

2.3.1.43

1-palmitoyl-2-(6-[(7-nitro-2-1,3-benzoxadiazol-4-yl)amino]hexanoyl)-sn-glycero-3-phosphocholine + cerebrosterol = 1-palmitoyl-sn-glycero-3-phosphocholine + cerebrosteryl-(6-[(7-nitro-2-1,3-benzoxadiazol-4-yl)amino]hexanoyl)-ester

736674

2.3.1.43

phosphatidylcholine + cerebrosterol = 1-acylglycerophosphocholine + cerebrosteryl ester

755762, 757930, 736674

2.3.1.43

3 entries

Product in Enzyme-catalyzed Reactions (5 results)

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EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.14.14.25

cholesterol + [reduced NADPH-hemoprotein reductase] + H+ + O2 = (24S)-24-hydroxycholesterol + [oxidized NADPH-hemoprotein reductase] + H2O

1.14.14.25

cholesterol + [reduced NADPH-hemoprotein reductase] + O2 = (24S)-cholest-5-ene-3beta,24-diol + [oxidized NADPH-hemoprotein reductase] + H2O

1.14.14.25

cholesterol + NADPH + O2 = (24S)-hydroxycholesterol + NADP+ + H2O

1.14.14.25

cholesterol + reduced adrenodoxin + O2 = 24-hydroxycholesterol + oxidized adrenodoxin + H2O

1.14.14.25

4 entries

1.14.15.15

cholesterol + reduced adrenodoxin + O2 = 24-hydroxycholesterol + oxidized adrenodoxin + H2O

Inhibitor in Enzyme-catalyzed Reactions (2 results)

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EC NUMBER

COMMENTARY

LITERATURE

ENZYME 3D STRUCTURE

3.1.1.1

slight inhibition of CES1, not CES2

707570

4.1.1.33

down-regulates the expression

688660

Enzyme Kinetic Parameters

k_cat Value (Turnover Number) (3 results)

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EC NUMBER

TURNOVER NUMBER [1/S]

TURNOVER NUMBER MAXIMUM [1/S]

COMMENTARY

LITERATURE

1.14.14.25

0.00117

full length enzyme

657671

1.14.14.25

0.0142

recombinant truncation mutant enzyme

689814

1.14.14.25

0.0153

recombinant wild-type enzyme

689814

1.14.14.25

3 entries

K_M Value (4 results)

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EC NUMBER

KM VALUE [MM]

KM VALUE MAXIMUM [MM]

COMMENTARY

LITERATURE

1.1.3.6

0.0043

287664

1.14.14.25

0.0015

recombinant truncation mutant enzyme

689814

1.14.14.25

0.0022

full length enzyme

657671

1.14.14.25

0.0039

recombinant wild-type enzyme

689814

1.14.14.25

3 entries

References & Links

Literature References (13)

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BRENDA REFERENCE ID

PUBMED ID

TITLE

YEAR

AUTHORS

JOURNAL

VOLUME

PAGES

287664

1184684

Cholesterol oxidase. Further studies of substrate specificity in relation to the analytical characterisation of steroids

1975

Brooks, C.J.W.; Smith, A.G.

J. Chromatogr.

112

499-511

657671

15234274

Expression of human cytochrome P450 46A1 in Escherichia coli: effects of N- and C-terminal modifications

2004

Mast, N.; Andersson, U.; Nakayama, K.; Bjorkhem, I.; Pikuleva, I.A.

Arch. Biochem. Biophys.

428

99-108

657971

14640697

Broad substrate specificity of human cytochrome P450 46A1 which initiates cholesterol degradation in the brain

2003

Mast, N.; Norcross, R.; Andersson, U.; Shou, M.; Nakayama, K.; Bjorkhem, I.; Pikuleva, I.A.

Biochemistry

14284-14292

659143

10748047

Expression cloning of an oxysterol 7alpha-hydroxylase selective for 24-hydroxycholesterol

2000

Li-Hawkins, J.; Lund, E.G.; Bronson, A.D.; Russell, D.W.

J. Biol. Chem.

275

16543-16549

673298

16434543

Cholesterol-metabolizing cytochromes P450

2006

Pikuleva, I.A.

Drug Metab. Dispos.

513-520

688660

18303831

The effect of 24S-hydroxycholesterol on cholesterol homeostasis in neurons: quantitative changes to the cortical neuron proteome

2008

Wang, Y.; Muneton, S.; Sjoevall, J.; Jovanovic, J.N.; Griffiths, W.J.

J. Proteome Res.

1606-1614

689814

18621681

Crystal structures of substrate-bound and substrate-free cytochrome P450 46A1, the principal cholesterol hydroxylase in the brain

2008

Mast, N.; White, M.A.; Bjorkhem, I.; Johnson, E.F.; Stout, C.D.; Pikuleva, I.A.

Proc. Natl. Acad. Sci. USA

105

9546-9551

707570

19761868

Inhibition of carboxylesterase activity of THP1 monocytes/macrophages and recombinant human carboxylesterase 1 by oxysterols and fatty acids

2010

Crow, J.A.; Herring, K.L.; Xie, S.; Borazjani, A.; Potter, P.M.; Ross, M.K.

Biochim. Biophys. Acta

1801

31-41

736674

24620755

The enzyme lecithin-cholesterol acyltransferase esterifies cerebrosterol and limits the toxic effect of this oxysterol on SH-SY5Y cells

2014

La Marca, V.; Spagnuolo, M.S.; Cigliano, L.; Marasco, D.; Abrescia, P.

J. Neurochem.

130

97-108

736702

25218443

Acyl-CoA:cholesterol acyltransferases (ACATs/SOATs): enzymes with multiple sterols as substrates and as activators

2015

Rogers, M.A.; Liu, J.; Song, B.L.; Li, B.L.; Chang, C.C.; Chang, T.Y.

J. Steroid Biochem. Mol. Biol.

151

102-107

736889

26454063

Lecithin-cholesterol acyltransferase in brain: does oxidative stress influence the 24-hydroxycholesterol esterification?

2016

La Marca, V.; Maresca, B.; Spagnuolo, M.S.; Cigliano, L.; Dal Piaz, F.; Di Iorio, G.; Abrescia, P.

Neurosci. Res.

105

19-27

755762

31103331

The P274S mutation of lecithin-cholesterol acyltransferase (LCAT) and its clinical manifestations in a large kindred

2019

Fountoulakis, N.; Lioudaki, E.; Lygerou, D.; Dermitzaki, E.K.; Papakitsou, I.; Kounali, V.; Holleboom, A.G.; Stratigis, S.; Belogianni, C.; Syngelaki, P.; Stratakis, S.; Evangeliou, A.; Gakiopoulou, H.; Kuivenhoven, J.A.; Wevers, R.; Dafnis, E.; Stylianou, K.

Am. J. Kidney Dis.

510-522

757930

28471688

Atherogenic impact of lecithin-cholesterol acyltransferase and its relation to cholesterol esterification rate in HDL (FER(HDL)) and AIP [log(TG/HDL-C)] biomarkers the butterfly effect?

2017

Dobiasova, M.

Physiol. Res.

193-203

Links to other databases for (24S)-24-hydroxycholesterol

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Show Links (1 entry)

ChEBI

PubChem

Ligand (24S)-24-hydroxycholesterol

Basic Ligand Information

Roles as Enzyme Ligand

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

In Vivo Product in Enzyme-catalyzed Reactions (4 results)

Substrate in Enzyme-catalyzed Reactions (9 results)

Product in Enzyme-catalyzed Reactions (5 results)

Inhibitor in Enzyme-catalyzed Reactions (2 results)

Enzyme Kinetic Parameters

kcat Value (Turnover Number) (3 results)

KM Value (4 results)

References & Links

Literature References (13)

Links to other databases for (24S)-24-hydroxycholesterol

k_cat Value (Turnover Number) (3 results)

K_M Value (4 results)