print visible entries

print all entries

Ligand 3-Methylxanthine

Basic Ligand Information

Molecular Structure

Related pathways

close all tables

open all tables

Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (3 results)

top print hide

Show Natural Substrate (3 entries)

EC NUMBER

PROVEN IN VIVO REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.14.13.179

3-methylxanthine + O2 + NAD(P)H + H+ = xanthine + NAD(P)+ + H2O + formaldehyde

722538

-

2.1.1.160

S-adenosyl-L-methionine + 3-methylxanthine = S-adenosyl-L-homocysteine + 3,7-dimethylxanthine

778518

-

2.1.1.B163

S-adenosyl-L-methionine + 3-methylxanthine = S-adenosyl-L-homocysteine + 1,3-dimethylxanthine

778518

-

In Vivo Product in Enzyme-catalyzed Reactions (3 results)

top print hide

Show Natural Product (3 entries)

EC NUMBER

PROVEN IN VIVO REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.14.13.178

theophylline + O2 + NAD(P)H + H+ = 3-methylxanthine + NAD(P)+ + H2O + formaldehyde

-

-

1.14.13.178

theophylline + O2 + NADPH + H+ = 3-methylxanthine + NADP+ + H2O + formaldehyde

-

-

1.14.13.178

2 entries

2.1.1.B163

S-adenosyl-L-methionine + xanthine = S-adenosyl-L-homocysteine + 3-methylxanthine

-

-

Substrate in Enzyme-catalyzed Reactions (9 results)

top print hide

Show Substrate (9 entries)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.14.13.128

3-methylxanthine + O2 + NADH + H+ = xanthine + NAD+ + H2O + formaldehyde

709854

-

1.14.13.179

3-methylxanthine + O2 + NAD(P)H + H+ = xanthine + NAD(P)+ + H2O + formaldehyde

722538, 709854

-

1.14.13.179

3-methylxanthine + O2 + NADH + H+ = xanthine + NAD+ + H2O + formaldehyde

722538

-

1.14.13.179

2 entries

1.17.1.4

3-methylxanthine + ferricyanide + H2O = 3-methylurate + ferrocyanide

644594

-

1.17.3.2

3-methylxanthine + H2O + O2 = 3-methylurate + H2O2

659642

-

2.1.1.159

S-adenosyl-L-methionine + 3-methylxanthine = S-adenosyl-L-homocysteine + 1,3-dimethylxanthine

670371, 670577

-

2.1.1.160

S-adenosyl-L-methionine + 3-methylxanthine = S-adenosyl-L-homocysteine + 1,3-dimethylxanthine

670371, 670577

-

2.1.1.160

S-adenosyl-L-methionine + 3-methylxanthine = S-adenosyl-L-homocysteine + 3,7-dimethylxanthine

778518

-

2.1.1.160

2 entries

2.1.1.B163

S-adenosyl-L-methionine + 3-methylxanthine = S-adenosyl-L-homocysteine + 1,3-dimethylxanthine

778518

-

Product in Enzyme-catalyzed Reactions (9 results)

top print hide

Show Product (9 entries)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.14.13.128

theobromine + O2 + NADH + H+ = 3-methylxanthine + NAD+ + H2O + formaldehyde

-

-

1.14.13.128

theophylline + O2 + NADH + H+ = 3-methylxanthine + NAD+ + H2O + formaldehyde

-

-

1.14.13.128

3,7-dimethylxanthine + O2 + NAD(P)H + H+ = monomethylxanthine + formaldehyde + NADP+

-

-

1.14.13.178

theophylline + O2 + NAD(P)H + H+ = 3-methylxanthine + NAD(P)+ + H2O + formaldehyde

-

-

1.14.13.178

theophylline + O2 + NADH + H+ = 3-methylxanthine + NAD+ + H2O + formaldehyde

-

-

1.14.13.178

theophylline + O2 + NADPH + H+ = 3-methylxanthine + NADP+ + H2O + formaldehyde

-

-

1.14.13.128

3 entries

1.14.13.178

3 entries

1.17.3.2

3-methylhypoxanthine + H2O + O2 = 3-methylxanthine + H2O2

393008

-

2.1.1.B163

S-adenosyl-L-methionine + xanthine = S-adenosyl-L-homocysteine + 3-methylxanthine

-

-

3.2.2.25

3-methylxanthosine + H2O = 3-methylxanthine + D-ribose

-

-

Inhibitor in Enzyme-catalyzed Reactions (2 results)

top print hide

Show Inhibitors (2 entries)

EC NUMBER

COMMENTARY

LITERATURE

ENZYME 3D STRUCTURE

2.4.2.22

-

638008

-

2.4.2.22

-

638005

-

2.4.2.22

2 entries

Enzyme Kinetic Parameters

k_cat Value (Turnover Number) (1 result)

top print hide

Show Turnover Number (1 entry)

EC NUMBER

TURNOVER NUMBER [1/S]

TURNOVER NUMBER MAXIMUM [1/S]

COMMENTARY

LITERATURE

1.14.13.179

0.53

-

pH 7.5, 30°C

722538

K_M Value (3 results)

top print hide

Show KM Value (3 entries)

EC NUMBER

KM VALUE [MM]

KM VALUE MAXIMUM [MM]

COMMENTARY

LITERATURE

1.14.13.179

0.022

-

pH 7.5, 30°C

722538

2.1.1.160

0.0958

-

pH 7.5, 24°C

778518

2.1.1.160

0.677

-

pH 7.5, 24°C

778518

2.1.1.160

2 entries

K_i Value (1 result)

top print hide

Show KI Value (1 entry)

EC NUMBER

KI VALUE [MM]

KI VALUE MAXIMUM [MM]

COMMENTARY

LITERATURE

2.4.2.22

0.62

-

-

638005

References & Links

Literature References (10)

top print hide

Show Reference (10 entries)

BRENDA REFERENCE ID

PUBMED ID

TITLE

YEAR

AUTHORS

JOURNAL

VOLUME

PAGES

393008

-

Molybdenum iron-sulfur flavin hydroxylases and related enzymes

1975

Bray, R.C.

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

12

299-419

638005

4216296

Xanthine phosphoribosyltransferase from Streptococcus faecalis. Properties and specificity

1974

Miller, R.L.; Adamczyk, D.L.; Fyfe, J.A.; Elion, G.B.

Arch. Biochem. Biophys.

165

349-358

638008

7503772

Structure-activity relationships for the binding of ligands to xanthine or guanine phosphoribosyltransferase from Toxoplasma gondii

1995

Naguib, F.N.M.; Iltzsch, M.H.; el Kouni, M.M.; Panzica, R.P.; el Kouni, M.H.

Biochem. Pharmacol.

50

1685-1693

644594

863854

Distribution of xanthine oxidase and xanthine dehydrogenase specificity types among bacteria

1977

Woolfolk, C.A.; Downard, J.S.

J. Bacteriol.

130

1175-1191

659642

15134930

Studies on the mechanism of action of xanthine oxidase

2004

Choi, E.Y.; Stockert, A.L.; Leimkuhler, S.; Hille, R.

J. Inorg. Biochem.

98

841-848

670371

10984041

Caffeine synthase gene from tea leaves

2000

Kato, M.; Mizuno, K.; Crozier, A.; Fujimura, T.; Ashihara, H.

Nature

406

956-957

670577

10364410

Purification and characterization of caffeine synthase from tea leaves

1999

Kato, M.; Mizuno, K.; Fujimura, T.; Iwama, M.; Irie, M.; Crozier, A.; Ashihara, H.

Plant Physiol.

120

579-586

709854

20966097

Characterization of a broad-specificity non-haem iron N-demethylase from Pseudomonas putida CBB5 capable of utilizing several purine alkaloids as sole carbon and nitrogen source

2011

Summers, R.M.; Louie, T.M.; Yu, C.L.; Subramanian, M.

Microbiology

157

583-592

722538

22328667

Novel, highly specific N-demethylases enable bacteria to live on caffeine and related purine alkaloids

2012

Summers, R.M.; Louie, T.M.; Yu, C.L.; Gakhar, L.; Louie, K.C.; Subramanian, M.

J. Bacteriol.

194

2041-2049

778518

33662138

Convergent biochemical pathways for xanthine alkaloid production in plants evolved from ancestral enzymes with different catalytic properties

2021

O'Donnell, A.J.; Huang, R.; Barboline, J.J.; Barkman, T.J.

Mol. Biol. Evol.

38

2704-2714

Links to other databases for 3-Methylxanthine

top print hide

Show Links (1 entry)