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Ligand melilotate

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

1.14.13.4

3-(2-hydroxyphenyl)propanoate + NADH + O2 = 3-(2,3-dihydroxyphenyl)propanoate + NAD+ + H2O

396422

-

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

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Show Natural Product (4 entries)

EC NUMBER

PROVEN IN VIVO REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.3.1.11

2-coumarate + NADH = melilotate + NAD+

390510

-

3.1.1.35

dihydrocoumarin + H2O = 3-(2-hydroxyphenyl)propionic acid

651069, 652955

-

3.1.1.35

3,4-dihydrocoumarin + H2O = melilotate

-

-

3.1.1.35

dihydrocoumarin + H2O = melilotate

649404, 651167

-

3.1.1.35

3 entries

Substrate in Enzyme-catalyzed Reactions (1 result)

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Show Substrate (1 entry)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.14.13.4

3-(2-hydroxyphenyl)propanoate + NADH + O2 = 3-(2,3-dihydroxyphenyl)propanoate + NAD+ + H2O

390102, 396421, 396423, 396424, 396425, 396426, 396427, 396420, 396422

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Product in Enzyme-catalyzed Reactions (8 results)

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Show Product (8 entries)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.3.1.11

2-coumarate + NADH = melilotate + NAD+

390510

-

1.3.1.31

(E)-o-hydroxycinnamate + NADH = 3-(2-hydroxyphenyl)propionate + NAD+

-

-

3.1.1.25

dihydrocoumarin + H2O = 3-(2-hydroxyphenyl)-propionic acid

-

-

3.1.1.25

dihydrocoumarin + H2O = 3-(2-hydroxyphenyl)propanoic acid

-

-

3.1.1.35

3,4-dihydrocoumarin + H2O = 3-(2-hydroxyphenyl)propionic acid

651069, 652955, , 651167, 649404

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3.1.1.35

dihydrocoumarin + H2O = 3-(2-hydroxyphenyl)propionic acid

651069, 652955

-

3.1.1.35

3,4-dihydrocoumarin + H2O = melilotate

-

-

3.1.1.35

dihydrocoumarin + H2O = melilotate

649404, 651167

-

3.1.1.25

2 entries

3.1.1.35

4 entries

Inhibitor in Enzyme-catalyzed Reactions (2 results)

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Show Inhibitors (2 entries)

EC NUMBER

COMMENTARY

LITERATURE

ENZYME 3D STRUCTURE

1.13.11.27

50% inhibition above 10 mM, competitive

395375

-

2.6.1.57

-

636671

-

Enzyme Kinetic Parameters

k_cat Value (Turnover Number) (1 result)

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Show Turnover Number (1 entry)

EC NUMBER

TURNOVER NUMBER [1/S]

TURNOVER NUMBER MAXIMUM [1/S]

COMMENTARY

LITERATURE

1.14.13.4

3.87

4.48

-

396425

K_M Value (4 results)

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Show KM Value (4 entries)

EC NUMBER

KM VALUE [MM]

KM VALUE MAXIMUM [MM]

COMMENTARY

LITERATURE

1.14.13.4

0.0013

-

-

396423

1.14.13.4

0.0013

-

overview

390102

1.14.13.4

0.0027

-

-

396425

1.14.13.4

0.086

-

-

396422

1.14.13.4

4 entries

References & Links

Literature References (16)

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Show Reference (16 entries)

BRENDA REFERENCE ID

PUBMED ID

TITLE

YEAR

AUTHORS

JOURNAL

VOLUME

PAGES

390102

-

Flavoprotein oxygenases

1974

Flashner, M.S.; Massey, V.

Mol. Mech. Oxygen Activ. (Hayaishi, O., ed.) Academic Press, New York

-

245-283

390510

14269315

The metabolism of coumarin by a microorganism. II. The reduction of o-coumaric acid to melilotic acid

1964

Levy, C.C.; Weinstein, G.D.

Biochemistry

3

1944-1947

395375

7118918

Blue color, metal content, and substrate binding in 4-hydroxyphenylpyruvate dioxygenase from Pseudomonas sp. strain P. J. 874

1982

Lindstedt, S.; Rundgren, M.

J. Biol. Chem.

257

11922-11931

396420

6017743

Melilotate hydroxylase. Purification of the enzyme and the nature of the prosthetic group

1967

Levy, C.C.

J. Biol. Chem.

242

747-753

396421

4348920

The purification and properties of the flavoprotein melilotate hydroxylase

1973

Strickland, S.; Massey, V.

J. Biol. Chem.

248

2944-2952

396422

4285850

The metabolism of coumarin by a microorganism. V. Melilotate hydroxylase

1966

Levy, C.C.; Frost, P.

J. Biol. Chem.

241

997-1003

396423

4348921

The mechanism of action of the flavoprotein melilotate hydroxylase

1973

Strickland, S.; Massey, V.

J. Biol. Chem.

248

2953-2962

396424

1148167

Kinetic and mechanistic studies on the reaction of melilotate hydroxylase with deuterated melilotate

1975

Strickland, S.; Schopfer, L.M.; Massey, V.

Biochemistry

14

2230-2235

396425

227848

Kinetic and mechanistic studies on the reduction of melilotate hydroxylase by reduced pyridine nucleotides

1979

Schopfer, L.M.; Massey, V.

J. Biol. Chem.

254

10634-10643

396426

3801393

Absolute stereochemistry of flavins in enzyme-catalyzed reactions

1986

Manstein, D.J.; Pai, E.F.

Biochemistry

25

6807-6816

396427

195526

The stereospecificity of bacterial external flavoprotein monooxygenases for nicotinamide adenine dinucleotide

1977

You, K.S.; Arnold, L.J.; Kaplan, N.O.

Arch. Biochem. Biophys.

180

550-554

636671

9930977

The active site of Paracoccus denitrificans aromatic amino acid aminotransferase has contrary properties: flexibility and rigidity

1999

Okamoto, A.; Ishii, S.; Hirotsu, K.; Kagamiyama, H.

Biochemistry

38

1176-1184

649404

12436309

Enzymatic preparation of D-beta-acetylthioisobutyric acid and cetraxate hydrochloride using a stereo-and/or regioselective hydrolase, 3,4-dihydrocoumarin hydrolase from Acinetobacter calcoaceticus

2002

Honda, K.; Kataoka, M.; Shimizu, S.

Appl. Microbiol. Biotechnol.

60

288-292

651069

10601844

3,4-Dihydrocoumarin hydrolase with haloperoxidase activity from Acinetobacter calcoaceticus F46

2000

Kataoka, M.; Honda, K.; Shimizu, S.

Eur. J. Biochem.

267

3-10

651167

12542698

Role of Acinetobacter calcoaceticus 3,4-dihydrocoumarin hydrolase in oxidative stress defence against peroxoacids

2003

Honda, K.; Kataoka, M.; Sakuradani, E.; Shimizu, S.

Eur. J. Biochem.

270

486-494

652955

-

A novel dihydrocoumarin hydrolase from Acinetobacter calcoaceticus: application to the production of useful compounds

2002

Kataoka, M.; Honda, K.; Shimizu, S.

J. Mol. Catal. B

19-20

231-235

Links to other databases for melilotate

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Show Links (1 entry)

ChEBI

PubChem

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