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Ligand 5alpha-cholest-7-en-3beta-ol

Basic Ligand Information

Molecular Structure

Related pathways

Show all BRENDA pathways known for 5alpha-cholest-7-en-3beta-ol

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Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (7 results)

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Show Natural Substrate (7 entries)

EC NUMBER

PROVEN IN VIVO REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.14.14.23

lathosterol + NADPH + H+ = 7-oxocholestanol + cholestanol-7alpha,8alpha-epoxide + NADP+ + H2O

725442

-

1.14.19.20

5alpha-cholest-7-en-3beta-ol + 2 ferrocytochrome b5 + O2 + 2 H+ = cholesta-5,7-dien-3beta-ol + 2 ferricytochrome b5 + 2 H2O

390931, 390932

-

1.14.19.20

5alpha-cholest-7-en-3beta-ol + ferrocytochrome b5 + H+ + O2 = cholesta-5,7-dien-3beta-ol + ferricytochrome b5 + 2 H2O

697681

-

1.14.19.20

lathosterol + ferrocytochrome b5 + O2 + H+ = 7-dehydrocholesterol + ferricytochrome b5 + H2O

733205, 734114, 734121

-

1.14.19.20

lathosterol + O2 + ferrocytochrome b5 = 7-dehydrocholesterol + H2O + ferricytochrome b5

655698

-

1.14.19.20

4 entries

1.3.1.72

5alpha-cholest-7-en-3beta-ol + NADP+ = 5alpha-cholesta-7,24-dien-3beta-ol + NADPH + H+

711128, 711130, 763004

-

5.3.3.5

5alpha-cholest-7-en-3beta-ol = ?

649702

-

In Vivo Product in Enzyme-catalyzed Reactions (6 results)

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Show Natural Product (6 entries)

EC NUMBER

PROVEN IN VIVO REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.14.19.21

5alpha-cholestan-3beta-ol + O2 + NADH + H+ = 5alpha-cholest-7-en-3beta-ol + NAD+ + H2O

0

-

1.14.19.21

5alpha-cholestan-3beta-ol + O2 + NADPH + H+ = 5alpha-cholest-7-en-3beta-ol + NADP+ + H2O

0

-

1.3.1.72

5alpha-cholesta-7,24-dien-3beta-ol + NADPH = 5alpha-cholest-7-en-3beta-ol + NADP+

0

-

1.3.1.72

5alpha-cholesta-7,24-dien-3beta-ol + NADPH = 5alpha-cholesta-7-en-3beta-ol + NADP+

0

-

1.3.1.72

cholesta-7,24-dien-3beta-ol + NADPH + H+ = lathosterol + NADP+

0

-

1.14.19.21

2 entries

1.3.1.72

3 entries

5.3.3.5

zymostenol = lathosterol

0

-

Substrate in Enzyme-catalyzed Reactions (14 results)

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Show Substrate (14 entries)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.14.14.23

lathosterol + NADPH + H+ = 7-oxocholestanol + cholestanol-7alpha,8alpha-epoxide + NADP+ + H2O

725442

-

1.14.19.20

5alpha-cholest-7-en-3beta-ol + 2 ferrocytochrome b5 + O2 + 2 H+ = cholesta-5,7-dien-3beta-ol + 2 ferricytochrome b5 + 2 H2O

390940, 390931, 390932, 390933

-

1.14.19.20

5alpha-cholest-7-en-3beta-ol + ferrocytochrmoe b5 + H+ + O2 = cholesta-5,7-dien-3beta-ol + ferricytochrome b5 + H2O

390939

-

1.14.19.20

5alpha-cholest-7-en-3beta-ol + ferrocytochrome b5 + H+ + O2 = cholesta-5,7-dien-3beta-ol + ferricytochrome b5 + 2 H2O

697681, 390939

-

1.14.19.20

5alpha-cholest-7-en-3beta-ol + ferrocytochrome b5 + O2 + H+ = ? + ferricytochrome b5 + H2O

734114

-

1.14.19.20

lathosterol + 2 ferrocytochrome b5 + O2 + 2 H+ = 7-dehydrocholesterol + 2 ferricytochrome b5 + 2 H2O

745646

-

1.14.19.20

lathosterol + ferrocytochrome b5 + O2 + H+ = 7-dehydrocholesterol + ferricytochrome b5 + H2O

733205, 734114, 734121

-

1.14.19.20

lathosterol + ferrocytochrome b5 + O2 + H+ = ?

733204

-

1.14.19.20

lathosterol + O2 + ferrocytochrome b5 = 7-dehydrocholesterol + H2O + ferricytochrome b5

655698

-

1.14.19.20

8 entries

1.3.1.72

5alpha-cholest-7-en-3beta-ol + NADP+ = 5alpha-cholesta-7,24-dien-3beta-ol + NADPH + H+

711128, 711130, 763004

-

2.3.1.26

oleoyl-CoA + lathosterol = CoA + lathosteryl oleate

486677, 486681

-

2.4.1.173

5alpha-cholest-7-en-3beta-ol + UDP-glucose = ?

690224

-

5.3.3.5

5alpha-Cholest-7-en-3beta-ol = 5alpha-Cholest-8-en-3beta-ol

2983, 2984, 2985

-

5.3.3.5

5alpha-cholest-7-en-3beta-ol = ?

649702

-

5.3.3.5

2 entries

Product in Enzyme-catalyzed Reactions (8 results)

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Show Product (8 entries)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.14.19.21

5alpha-cholestan-3beta-ol + O2 + NADH + H+ = 5alpha-cholest-7-en-3beta-ol + NAD+ + H2O

0

-

1.14.19.21

5alpha-cholestan-3beta-ol + O2 + NADPH + H+ = 5alpha-cholest-7-en-3beta-ol + NADP+ + H2O

0

-

1.14.19.21

2 entries

1.3.1.70

5alpha-cholesta-7,14-dien-3beta-ol + NADPH = 5alpha-cholesta-7-en-3beta-ol + NADP+

0

-

1.3.1.72

5alpha-cholesta-7,24-dien-3beta-ol + NADPH = 5alpha-cholest-7-en-3beta-ol + NADP+

0

-

1.3.1.72

5alpha-cholesta-7,24-dien-3beta-ol + NADPH = 5alpha-cholesta-7-en-3beta-ol + NADP+

288498, 288496, 0

-

1.3.1.72

cholesta-7,24-dien-3beta-ol + NADPH + H+ = lathosterol + NADP+

0

-

5.3.3.5

dihydrozymosterol = lathosterol

0

-

5.3.3.5

zymostenol = lathosterol

0

-

1.3.1.72

3 entries

5.3.3.5

2 entries

Inhibitor in Enzyme-catalyzed Reactions (1 result)

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Show Inhibitors (1 entry)

EC NUMBER

COMMENTARY

LITERATURE

ENZYME 3D STRUCTURE

1.1.1.170

15.5-65% inhibition between 30 and 260 nmol

286111

-

Enzyme Kinetic Parameters

k_cat Value (Turnover Number) (2 results)

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Show Turnover Number (2 entries)

EC NUMBER

TURNOVER NUMBER [1/S]

TURNOVER NUMBER MAXIMUM [1/S]

COMMENTARY

LITERATURE

1.14.14.23

0.06

-

7-oxocholestanol formation, pH 7.4, 30°C

725442

1.14.14.23

0.12

-

epoxide formation, pH 7.4, 30°C

725442

1.14.14.23

2 entries

K_M Value (16 results)

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Show KM Value (16 entries)

EC NUMBER

KM VALUE [MM]

KM VALUE MAXIMUM [MM]

COMMENTARY

LITERATURE

1.14.14.23

0.0018

-

7-oxocholestanol formation, pH 7.4, 30°C

725442

1.14.14.23

0.0021

-

epoxide formation, pH 7.4, 30°C

725442

1.14.19.20

0.032

-

-

390939

1.14.19.20

0.032

-

30°C, wild-type enzyme

390939

1.14.19.20

0.0357

-

reconstituted enzyme system consisting of: cytochrome b5, cytochrome b5 reductase and egg lecithin liposomes

390931

1.14.19.20

0.07

-

30°C, mutant enzyme P175A

390939

1.14.19.20

0.07

-

P175a mutant enzyme

390939

1.14.19.20

0.086

-

30°C, mutant enzyme P175V

390939

1.14.19.20

0.086

-

P175V mutant enzyme

390939

1.14.19.20

0.09

-

30°C, mutant enzyme K115L

390939

1.14.19.20

0.09

-

K115L mutant enzyme

390939

1.14.19.20

0.115

-

at pH 7.6 and 30°C

733204

1.14.19.20

0.24

-

30°C, mutant enzyme T114I

390939

1.14.19.20

0.24

-

T114I mutant enzyme

390939

1.14.19.20

0.244

-

30°C, mutant enzyme T114S

390939

1.14.19.20

0.244

-

T114S mutant enzyme

390939

1.14.14.23

2 entries

1.14.19.20

14 entries

References & Links

Literature References (26)

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Show Reference (26 entries)

BRENDA REFERENCE ID

PUBMED ID

TITLE

YEAR

AUTHORS

JOURNAL

VOLUME

PAGES

2983

5781997

Studies on the mechanism of the enzymatic conversion of DELTA8-cholesten-3beta-ol to DELTA7-cholesten-3beta-ol

1969

Lee, W.H.; Kammereck, R.; Lutsky, B.N.; McCloskey, J.A.; Schroepfer, G.J.Jr.

J. Biol. Chem.

244

2033-2040

2984

5810070

The reversibility of the DELTA8-cholestenol-DELTA7-cholestenol isomerase reaction in cholesterol biosynthesis

1969

Wilton, D.C.; Rahimtula, A.D.; Akhtar, M.

Biochem. J.

114

71-73

2985

4475632

The reversibility of the isomerization of the DELTA8 to DELTA7 bond in cholesterol biosynthesis

1974

Scala, A.; Galli-Kienle, M.; Anastasia, M.; Galli, G.

Eur. J. Biochem.

48

263-269

286111

4401584

Investigation of the component reactions of oxidative sterol demethylation. Partial purification of a microsomal sterol 4alpha-carboxylic acid decarboxylase

1972

Rahimtula, A.D.; Gaylor, J.L.

J. Biol. Chem.

247

9-15

288496

9291139

Cholesterol biosynthesis from lanosterol: development of a novel assay method and characterization of rat liver microsomal lanosterol DELTA24-reductase

1997

Bae, S.H.; Paik, Y.K.

Biochem. J.

326

609-616

288498

-

Mechanistic and metabolic studies of sterol 24,25-double bond reduction in Manduca sexta

1996

Short, J.D.; Guo, D.A.; Svoboda, J.A.; Nes, W.D.

Arch. Insect Biochem. Physiol.

31

1-22

390931

3997841

Microsomal enzymes of cholesterol biosynthesis from lanosterol. Purification and characterization of DELTA 7-sterol 5-desaturase of rat liver microsomes

1985

Kawata, S.; Traskos, J.M.; Gaylor, J.L.

J. Biol. Chem.

260

6609-6617

390932

6815183

Total enzymic synthesis of cholesterol from 4,4,14alpha-trimethyl-5alpha-cholesta-8,24-dien-3beta-ol. Solubilization, resolution, and reconstitution of DELTA 7-sterol 5-desaturase

1982

Grinstead, G.F.; Gaylor, J.L.

J. Biol. Chem.

257

13937-13944

390933

7309744

Intermembrane transfer of 5alpha-cholest-7-en-3beta-ol. Facilitation by supernatant protein (SCP)

1981

Ishibashi, T.; Bloch, K.

J. Biol. Chem.

256

12962-12967

390939

10651635

Role of highly conserved residues in the reaction catalyzed by recombinant DELTA7-sterol-C5(6)-desaturase studied by site-directed mutagenesis

2000

Taton, M.; Husselstein, T.; Benveniste, P.; Rahier, A.

Biochemistry

39

701-711

390940

11171213

Biochemistry and site-directed mutational analysis of DELTA7-sterol-C5(6)-desaturase

2000

Rahier, A.; Benveniste, P.; Husselstein, T.; Taton, M.

Biochem. Soc. Trans.

28

799-803

486677

-

Acyl coenzyme A:cholesterol O-acyltransferase

1983

Chang, T.Y.; Doolittle, G.M.

The Enzymes, 3rd Ed. (Boyer, P. D. , ed. )

16

523-539

486681

7119575

The sterol substrate specificity of acyl CoA:cholesterol acyltransferase from rat liver

1982

Tavani, D.M.; Nes, W.R.; Billheimer, J.T.

J. Lipid Res.

23

774-781

649702

11171067

Cholesterol biosynthesis from lanosterol: molecular cloning, chromosomal localization, functional expression and liver-specific gene regulation of rat sterol DELTA8-isomerase, a cholesterogenic enzyme with multiple functions

2001

Bae, S.H.; Seong, J.; Paik, Y.K.

Biochem. J.

353

689-699

655698

12812989

Lathosterolosis: an inborn error of human and murine cholesterol synthesis due to lathosterol 5-desaturase deficiency

2003

Krakowiak, P.A.; Wassif, C.A.; Kratz, L.; Cozma, D.; Kovarova, M.; Harris, G.; Grinberg, A.; Yang, Y.; Hunter, A.G.; Tsokos, M.; Kelley, R.I.; Porter, F.D.

Hum. Mol. Genet.

12

1631-1641

690224

18196184

Metabolism of conjugated sterols in eggplant. Part 1. UDP-glucose:sterol glucosyltransferase

2008

Potocka, A.; Zimowski, J.

Acta Biochim. Pol.

55

127-134

697681

19525418

C-5(6) sterol desaturase from Tetrahymena thermophila: Gene identification and knockout, sequence analysis, and comparison to other C-5(6) sterol desaturases

2009

Nusblat, A.D.; Najle, S.R.; Tomazic, M.L.; Uttaro, A.D.; Nudel, C.B.

Eukaryot. Cell

8

1287-1297

711128

19260826

Desmosterol can replace cholesterol in sustaining cell proliferation and regulating the SREBP pathway in a sterol-DELTA24-reductase-deficient cell line

2009

Rodriguez-Acebes, S.; de la Cueva, P.; Fernandez-Hernando, C.; Ferruelo, A.J.; Lasuncion, M.A.; Rawson, R.B.; Martinez-Botas, J.; Gomez-Coronado, D.

Biochem. J.

420

305-315

711130

19426142

How essential is cholesterol?

2009

Stevenson, J.; Brown, A.J.

Biochem. J.

420

e1-e4

725442

21813643

Conversion of 7-dehydrocholesterol to 7-ketocholesterol is catalyzed by human cytochrome P450 7A1 and occurs by direct oxidation without an epoxide intermediate

2011

Shinkyo, R.; Xu, L.; Tallman, K.A.; Cheng, Q.; Porter, N.A.; Guengerich, F.P.

J. Biol. Chem.

286

33021-33028

733204

8561508

Plant sterol biosynthesis: Identification and characterization of higher plant DELTA7-sterol C5(6)-desaturase

1996

Taton, M.; Rahier, A.

Arch. Biochem. Biophys.

325

279-288

733205

9056262

Temperature-induced differential kinetic properties between an initial burst and the following steady state in membrane-bound enzymes: studies on lathosterol 5-desaturase

1997

Nishino, H.; Nakaya, J.; Nishi, S.; Kurosawa, T.; Ishibashi, T.

Arch. Biochem. Biophys.

339

298-304

734114

4019441

Partial purification and characterization of lathosterol 5-desaturase from rat liver microsomes

1985

Honjo, K.; Ishibashi, T.; Imai, Y.

J. Biochem.

97

955-959

734121

7961720

Properties and kinetics of membrane-bound enzymes when both the enzyme and substrate are components of the same microsomal membrane. Studies on lathosterol 5-desaturase

1994

Takakuwa, Y.; Nishino, H.; Ishibe, Y.; Ishibashi, T.

J. Biol. Chem.

269

27889-27893

745646

28330720

Attenuation of UVR-induced vitamin D3 synthesis in a mouse model deleted for keratinocyte lathosterol 5-desaturase

2017

Makarova, A.M.; Pasta, S.; Watson, G.; Shackleton, C.; Epstein, E.H.

J. Steroid Biochem. Mol. Biol.

171

187-194

763004

33422461

Endothelial cells control vascular smooth muscle cell cholesterol levels by regulating 24-dehydrocholesterol reductase expression

2021

Kohlhaas, J.; Jaeger, M.; Lust, L.; De La Torre, C.; Hecker, M.; Korff, T.

Exp. Cell Res.

399

112446

Links to other databases for 5alpha-cholest-7-en-3beta-ol

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ChEBI

PubChem