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Ligand 1-Methylxanthine

Basic Ligand Information

Molecular Structure

Related pathways

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Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (2 results)

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Show Natural Substrate (2 entries)

EC NUMBER

PROVEN IN VIVO REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.17.3.2

1-methylxanthine + H2O + O2 = 1-methylurate + H2O2

685496

-

2.1.1.B163

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

778518

-

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

2.1.1.B163

S-adenosyl-L-methionine + xanthine = S-adenosyl-L-homocysteine + 1-methylxanthine

-

-

Substrate in Enzyme-catalyzed Reactions (8 results)

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Show Substrate (8 entries)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.14.13.178

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

722538

-

1.17.1.4

1-methylxanthine + ferricyanide + H2O = 1-methylurate + ferrocyanide

644594, 644577

-

1.17.1.4

1-methylxanthine + NAD+ + H2O = 1-methylurate + NADH

644594, 644608

-

1.17.1.4

1-methylxanthine + NAD+ + H2O = 1-methylurate + NADH + H+

674793

-

1.17.1.4

3 entries

1.17.3.2

1-methylxanthine + H2O + O2 = 1-methylurate + H2O2

393008, 644621, 659642, 685496

-

2.1.1.159

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

670371, 670577

-

2.1.1.160

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

670371, 670577

-

2.1.1.B163

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

778518

-

Product in Enzyme-catalyzed Reactions (6 results)

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Show Product (6 entries)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.14.13.128

theophylline + O2 + NADH + H+ = 1-methylxanthine + NAD+ + H2O + formaldehyde

-

-

1.14.13.179

theophylline + O2 + NADH + H+ = 1-methylxanthine + NAD+ + H2O + formaldehyde

-

-

1.17.1.4

1-methylhypoxanthine + NAD+ + H2O = 1-methylxanthine + NADH

644608

-

2.1.1.B163

S-adenosyl-L-methionine + xanthine = S-adenosyl-L-homocysteine + 1-methylxanthine

-

-

3.2.2.25

1-methylxanthosine + H2O = 1-methylxanthine + D-ribose

-

-

3.5.4.3

1-methylguanine + H2O = 1-methylxanthine + NH3

-

-

Inhibitor in Enzyme-catalyzed Reactions (3 results)

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Show Inhibitors (3 entries)

EC NUMBER

COMMENTARY

LITERATURE

ENZYME 3D STRUCTURE

2.4.2.22

-

638005

-

2.5.1.6

10 mM, 35.9% inhibition

658351

-

3.2.2.1

weak competitive inhibitor

326384

-

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

1.14.13.178

0.27

-

pH 7.5, 30°C

722538

K_M Value (2 results)

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Show KM Value (2 entries)

EC NUMBER

KM VALUE [MM]

KM VALUE MAXIMUM [MM]

COMMENTARY

LITERATURE

1.14.13.178

0.27

-

pH 7.5, 30°C

722538

1.17.3.2

0.13

-

-

644621

References & Links

Literature References (15)

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Show Reference (15 entries)

BRENDA REFERENCE ID

PUBMED ID

TITLE

YEAR

AUTHORS

JOURNAL

VOLUME

PAGES

326384

229844

Caffeine: its action on purine metabolizing enzymes

1979

Nolan, L.L.; Kidder, G.W.

Biochem. Biophys. Res. Commun.

91

253-262

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

644577

10860985

Selenium-dependent metabolism of purines: A selenium-dependent purine hydroxylase and xanthine dehydrogenase were purified from Clostridium purinolyticum and characterized

2000

Self, W.T.; Stadtman, T.C.

Proc. Natl. Acad. Sci. USA

97

7208-7213

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

644608

-

Molecular and kinetic characterization of xanthine dehydrogenase from the phototrophic bacterium Rodopseudomonas capsulata

1981

Aretz, W.; Kaspari, H.; Klemme, J.H.

Z. Naturforsch. C

36

933-941

644621

681279

Bacterial xanthine oxidase from Arthrobacter S-2

1978

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

J. Bacteriol.

135

422-428

658351

12809568

Characterisation of methionine adenosyltransferase from Mycobacterium smegmatis and M. tuberculosis

2003

Berger, B.J.; Knodel, M.H.

BMC Microbiol.

3

12

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

674793

17327224

The role of arginine 310 in catalysis and substrate specificity in xanthine dehydrogenase from Rhodobacter capsulatus

2007

Pauff, J.M.; Hemann, C.F.; Juenemann, N.; Leimkuehler, S.; Hille, R.

J. Biol. Chem.

282

12785-12790

685496

17221922

In vivo evaluation of CYP1A2, CYP2A6, NAT-2 and xanthine oxidase activities in a Greek population sample by the RP-HPLC monitoring of caffeine metabolic ratios

2007

Begas, E.; Kouvaras, E.; Tsakalof, A.; Papakosta, S.; Asprodini, E.K.

Biomed. Chromatogr.

21

190-200

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 1-Methylxanthine

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Show Links (1 entry)