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Ligand 3-hydroxy-3-methylglutarate

Basic Ligand Information

Molecular Structure

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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

2.8.3.13

succinyl-CoA + 3-hydroxy-3-methylglutarate = succinate + 3-hydroxy-3-methylglutaryl-CoA

643832, 643833, 643834

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

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Show Natural Product (1 entry)

EC NUMBER

PROVEN IN VIVO REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

3.1.2.27

hydroxymethylglutaryl-CoA + H2O = hydroxymethylglutarate + CoA

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Substrate in Enzyme-catalyzed Reactions (6 results)

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Show Substrate (6 entries)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

2.8.3.13

adipyl-CoA + 3-hydroxy-3-methylglutarate = adipate + 3-hydroxy-3-methylglutaryl-CoA

643834

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2.8.3.13

butyryl-CoA + 3-hydroxy-3-methylglutarate = butyrate + 3-hydroxy-3-methylglutaryl-CoA

643832

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2.8.3.13

glutaryl-CoA + 3-hydroxy-3-methylglutarate = glutarate + 3-hydroxy-3-methylglutaryl-CoA

643834

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2.8.3.13

malonyl-CoA + 3-hydroxy-3-methylglutarate = malonate + 3-hydroxy-3-methylglutaryl-CoA

643832, 643834

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2.8.3.13

methylmalonyl-CoA + 3-hydroxy-3-methylglutarate = methylmalonate + 3-hydroxy-3-methylglutaryl-CoA

643834

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2.8.3.13

succinyl-CoA + 3-hydroxy-3-methylglutarate = succinate + 3-hydroxy-3-methylglutaryl-CoA

643832, 643833, 643834

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2.8.3.13

6 entries

Product in Enzyme-catalyzed Reactions (12 results)

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Show Product (12 entries)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

2.8.3.13

3-hydroxy-3-methylglutaryl-CoA + adipate = 3-hydroxy-3-methylglutarate + adipyl-CoA

643834

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2.8.3.13

3-hydroxy-3-methylglutaryl-CoA + glutarate = 3-hydroxy-3-methylglutarate + glutaryl-CoA

643834,

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2.8.3.13

3-hydroxy-3-methylglutaryl-CoA + malonate = 3-hydroxy-3-methylglutarate + malonyl-CoA

643834

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2.8.3.13

3-hydroxy-3-methylglutaryl-CoA + methylmalonate = 3-hydroxy-3-methylglutarate + methylmalonyl-CoA

643834

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2.8.3.13

3-hydroxy-3-methylglutaryl-CoA + succinate = 3-hydroxy-3-methylglutarate + succinyl-CoA

643834,

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3.1.2.2

3-hydroxy-3-methyl glutaryl-CoA + H2O = CoA + 3-hydroxy-3-methyl glutarate

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-

3.1.2.2

3-hydroxy-3-methylglutaryl-CoA + H2O = CoA + 3-hydroxy-3-methylglutarate

646200

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3.1.2.20

3-hydroxy-3-methyl glutaryl-CoA + H2O = CoA + 3-hydroxy-3-methyl glutarate

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3.1.2.20

3-hydroxy-3-methylglutaryl-CoA + H2O = CoA + 3-hydroxy-3-methylglutarate

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3.1.2.20

DL-3-hydroxy-3-methylglutaryl-CoA + H2O = CoA + 3-hydroxy-3-methylglutarate

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2.8.3.13

5 entries

3.1.2.2

2 entries

3.1.2.20

3 entries

3.1.2.27

hydroxymethylglutaryl-CoA + H2O = hydroxymethylglutarate + CoA

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3.1.2.5

(S)-3-hydroxy-3-methylglutaryl-CoA + H2O = CoA + 3-hydroxy-3-methylglutarate

, 81014

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Inhibitor in Enzyme-catalyzed Reactions (7 results)

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Show Inhibitors (7 entries)

EC NUMBER

COMMENTARY

LITERATURE

ENZYME 3D STRUCTURE

1.1.1.34

-

286568

1dq8, 3D-view

1.1.1.34

-

286568

1dqa, 3D-view

1.1.1.34

2 mM, slightly inhibitory

286568

1dq8, 3D-view

1.1.1.34

2 mM, slightly inhibitory

286568

1dqa, 3D-view

1.1.1.88

-

287495, 657303

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1.1.1.88

competitive inhibitor

287496, 287497

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1.1.1.34

4 entries

1.1.1.88

2 entries

3.1.3.47

-

94957

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3D Structure of Enzyme-Ligand-Complex (PDB) (12 results)

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Show 3D Structure of Enzyme-Ligand-Complex (PDB) (12 entries)

EC NUMBER

ENZYME 3D STRUCTURE

1.1.1.34

1dq8, 3D-view

1.1.1.34

1dqa, 3D-view

1.1.1.34

1dq8, 3D-view

1.1.1.34

1dqa, 3D-view

1.1.1.34

1dq8, 3D-view

1.1.1.34

1dqa, 3D-view

1.1.1.34

1dq8, 3D-view

1.1.1.34

1dqa, 3D-view

1.1.1.34

1dq8, 3D-view

1.1.1.34

1dqa, 3D-view

1.1.1.34

1dq8, 3D-view

1.1.1.34

1dqa, 3D-view

1.1.1.34

12 entries

Enzyme Kinetic Parameters

K_M Value (7 results)

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Show KM Value (7 entries)

EC NUMBER

KM VALUE [MM]

KM VALUE MAXIMUM [MM]

COMMENTARY

LITERATURE

2.8.3.13

0.76

-

pH 7.8, 30°C, cosubstrate adipyl-CoA

643834

2.8.3.13

1.25

-

pH 7.8, 30°C, cosubstrate glutaryl-CoA

643834

2.8.3.13

1.42

-

pH 7.8, 30°C, cosubstrate succinyl-CoA

643834

2.8.3.13

1.7

-

pH 8.5, 30°C

643832

2.8.3.13

1.78

-

pH 7.8, 30°C

643833

2.8.3.13

1.8

-

pH 7.8, 30°C, cosubstrate malonyl-CoA

643834

2.8.3.13

2.33

-

pH 7.8, 30°C, cosubstrate methylmalonyl-CoA

643834

2.8.3.13

7 entries

K_i Value (1 result)

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Show KI Value (1 entry)

EC NUMBER

KI VALUE [MM]

KI VALUE MAXIMUM [MM]

COMMENTARY

LITERATURE

1.1.1.88

4.5

-

standard conditions, inhibition by substrate analog

657303

References & Links

Literature References (11)

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Show Reference (11 entries)

BRENDA REFERENCE ID

PUBMED ID

TITLE

YEAR

AUTHORS

JOURNAL

VOLUME

PAGES

81014

6170340

beta-hydroxy-beta-methylglutaryl coenzyme A hydrolase of rat liver

1981

Sipat, A.B.; Sabine, J.R.

Biochim. Biophys. Acta

666

181-190

94957

6631216

Inactivation of rat liver HMG-CoA reductase phosphatases by polycarboxylic acids

1983

Hegardt G.; Gil G.; Calvet E.

J. Lipid Res.

24

821-830

286568

-

Hydroxymethylglutaryl CoA reductase (NADPH) in the latex of Hevea brasiliensis

1982

Sipat, A.P.

Phytochemistry

21

2613-2618

287495

-

Substrate-competitive inhibition of bacterial mevalonate:nicotinamide-adenine dinucleotide oxidoreductase (acylating CoA)

1965

Fimognari, G.M.; Rodwell, V.W.

Biochemistry

4

2086-2090

287496

4321764

Purification and properties of 3-hydroxy-3-methylglutaryl coenzyme A reductase from Pseudomonas

1970

Bensch, W.R.; Rodwell, V.W.

J. Biol. Chem.

245

3755-3762

287497

7278665

S-3-Hydroxy-3-methylglutaryl-CoA reductase from Pseudomonas

1981

Rodwell, V.W.; Bensch, W.R.

Methods Enzymol.

71

480-486

643832

6946836

Submitochondrial localization and partial purification of the succinylCoA: 3-hydroxy-3-methylglutarate coenzyme A transferase from rat liver

1981

Deana, R.; Rigoni, F.; Donella Deana, A.; Galzigna, L.

Biochim. Biophys. Acta

662

119-124

643833

2597704

Further purification and characterization of the succinyl-CoA:3-hydroxy-3-methylglutarate coenzyme A transferase from rat-liver mitochondria

1989

Francesconi, M.A.; Donella-Deana, A.; Furlanetto, V.; Cavallini, L.; Palatini, P.; Deana, R.

Biochim. Biophys. Acta

999

163-170

643834

1610380

Substrate specificity of a dicarboxyl-CoA: dicarboxylic acid coenzyme A transferase from rat liver mitochondria

1992

Deana, R.

Biochem. Int.

26

767-773

646200

11673457

Characterization of an acyl-coA thioesterase that functions as a major regulator of peroxisomal lipid metabolism

2002

Hunt, M.C.; Solaas, K.; Kase, B.F.; Alexson, S.E.

J. Biol. Chem.

277

1128-1138

657303

15152097

Inhibition of the Class II HMG-CoA reductase of Pseudomonas mevalonii

2004

Hedl, M.; Rodwell, V.W.

Protein Sci.

13

1693-1697

Links to other databases for 3-hydroxy-3-methylglutarate

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Show Links (1 entry)

ChEBI

PubChem

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