IntEnz - EC 1.14.13.178

EC 1 - Oxidoreductases

EC 1.14 - Acting on paired donors, with incorporation or reduction of molecular oxygen. The oxygen incorporated need not be derived from O₂

EC 1.14.13 - With NADH or NADPH as one donor, and incorporation of one atom of oxygen

EC 1.14.13.178 - Methylxanthine N¹-demethylase

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IntEnz Enzyme Nomenclature
EC 1.14.13.178

Names

Accepted name:

methylxanthine N¹-demethylase

Other name:

ndmA (gene name)

Systematic name:

caffeine:oxygen oxidoreductase (N¹-demethylating)

Reactions

30315 [IUBMB]

1,7-dimethylxanthine

1,7-dimethylxanthine

Name origin: UniProt - CHECKED (C)

CHEBI:25858

Formula: C7H8N4O2
Charge: 0

ChEBI compound status: CHECKED (C)

+

H⁺

H(+)

Name origin: UniProt - CHECKED (C)

CHEBI:15378

Formula: H
Charge: 1

ChEBI compound status: CHECKED (C)

+

NADH

NADH

Name origin: UniProt - CHECKED (C)

CHEBI:57945

Formula: C21H27N7O14P2
Charge: -2

ChEBI compound status: CHECKED (C)

+

O₂

O2

Name origin: UniProt - CHECKED (C)

CHEBI:15379

Formula: O2
Charge: 0

ChEBI compound status: CHECKED (C)

=

7-methylxanthine

7-methylxanthine

Name origin: UniProt - CHECKED (C)

CHEBI:48991

Formula: C6H6N4O2
Charge: 0

ChEBI compound status: CHECKED (C)

+

formaldehyde

formaldehyde

Name origin: UniProt - CHECKED (C)

CHEBI:16842

Formula: CH2O
Charge: 0

ChEBI compound status: CHECKED (C)

+

H₂O

H2O

Name origin: UniProt - CHECKED (C)

CHEBI:15377

Formula: H2O
Charge: 0

ChEBI compound status: CHECKED (C)

+

NAD⁺

NAD(+)

Name origin: UniProt - CHECKED (C)

CHEBI:57540

Formula: C21H26N7O14P2
Charge: -1

ChEBI compound status: CHECKED (C)
36267 [IUBMB]

caffeine

caffeine

Name origin: UniProt - CHECKED (C)

CHEBI:27732

Formula: C8H10N4O2
Charge: 0

ChEBI compound status: CHECKED (C)

+

H⁺

H(+)

Name origin: UniProt - CHECKED (C)

CHEBI:15378

Formula: H
Charge: 1

ChEBI compound status: CHECKED (C)

+

NADH

NADH

Name origin: UniProt - CHECKED (C)

CHEBI:57945

Formula: C21H27N7O14P2
Charge: -2

ChEBI compound status: CHECKED (C)

+

O₂

O2

Name origin: UniProt - CHECKED (C)

CHEBI:15379

Formula: O2
Charge: 0

ChEBI compound status: CHECKED (C)

=

formaldehyde

formaldehyde

Name origin: UniProt - CHECKED (C)

CHEBI:16842

Formula: CH2O
Charge: 0

ChEBI compound status: CHECKED (C)

+

H₂O

H2O

Name origin: UniProt - CHECKED (C)

CHEBI:15377

Formula: H2O
Charge: 0

ChEBI compound status: CHECKED (C)

+

NAD⁺

NAD(+)

Name origin: UniProt - CHECKED (C)

CHEBI:57540

Formula: C21H26N7O14P2
Charge: -1

ChEBI compound status: CHECKED (C)

+

theobromine

theobromine

Name origin: UniProt - CHECKED (C)

CHEBI:28946

Formula: C7H8N4O2
Charge: 0

ChEBI compound status: CHECKED (C)
36271 [IUBMB]

caffeine

caffeine

Name origin: UniProt - CHECKED (C)

CHEBI:27732

Formula: C8H10N4O2
Charge: 0

ChEBI compound status: CHECKED (C)

+

H⁺

H(+)

Name origin: UniProt - CHECKED (C)

CHEBI:15378

Formula: H
Charge: 1

ChEBI compound status: CHECKED (C)

+

NADPH

NADPH

Name origin: UniProt - CHECKED (C)

CHEBI:57783

Formula: C21H26N7O17P3
Charge: -4

ChEBI compound status: CHECKED (C)

+

O₂

O2

Name origin: UniProt - CHECKED (C)

CHEBI:15379

Formula: O2
Charge: 0

ChEBI compound status: CHECKED (C)

=

formaldehyde

formaldehyde

Name origin: UniProt - CHECKED (C)

CHEBI:16842

Formula: CH2O
Charge: 0

ChEBI compound status: CHECKED (C)

+

H₂O

H2O

Name origin: UniProt - CHECKED (C)

CHEBI:15377

Formula: H2O
Charge: 0

ChEBI compound status: CHECKED (C)

+

NADP⁺

NADP(+)

Name origin: UniProt - CHECKED (C)

CHEBI:58349

Formula: C21H25N7O17P3
Charge: -3

ChEBI compound status: CHECKED (C)

+

theobromine

theobromine

Name origin: UniProt - CHECKED (C)

CHEBI:28946

Formula: C7H8N4O2
Charge: 0

ChEBI compound status: CHECKED (C)
36275 [IUBMB]

H⁺

H(+)

Name origin: UniProt - CHECKED (C)

CHEBI:15378

Formula: H
Charge: 1

ChEBI compound status: CHECKED (C)

+

NADPH

NADPH

Name origin: UniProt - CHECKED (C)

CHEBI:57783

Formula: C21H26N7O17P3
Charge: -4

ChEBI compound status: CHECKED (C)

+

O₂

O2

Name origin: UniProt - CHECKED (C)

CHEBI:15379

Formula: O2
Charge: 0

ChEBI compound status: CHECKED (C)

+

theophylline

theophylline

Name origin: UniProt - CHECKED (C)

CHEBI:28177

Formula: C7H8N4O2
Charge: 0

ChEBI compound status: CHECKED (C)

=

3-methylxanthine

3-methylxanthine

Name origin: UniProt - CHECKED (C)

CHEBI:62208

Formula: C6H6N4O2
Charge: 0

ChEBI compound status: CHECKED (C)

+

formaldehyde

formaldehyde

Name origin: UniProt - CHECKED (C)

CHEBI:16842

Formula: CH2O
Charge: 0

ChEBI compound status: CHECKED (C)

+

H₂O

H2O

Name origin: UniProt - CHECKED (C)

CHEBI:15377

Formula: H2O
Charge: 0

ChEBI compound status: CHECKED (C)

+

NADP⁺

NADP(+)

Name origin: UniProt - CHECKED (C)

CHEBI:58349

Formula: C21H25N7O17P3
Charge: -3

ChEBI compound status: CHECKED (C)
36279 [IUBMB]

H⁺

H(+)

Name origin: UniProt - CHECKED (C)

CHEBI:15378

Formula: H
Charge: 1

ChEBI compound status: CHECKED (C)

+

NADH

NADH

Name origin: UniProt - CHECKED (C)

CHEBI:57945

Formula: C21H27N7O14P2
Charge: -2

ChEBI compound status: CHECKED (C)

+

O₂

O2

Name origin: UniProt - CHECKED (C)

CHEBI:15379

Formula: O2
Charge: 0

ChEBI compound status: CHECKED (C)

+

theophylline

theophylline

Name origin: UniProt - CHECKED (C)

CHEBI:28177

Formula: C7H8N4O2
Charge: 0

ChEBI compound status: CHECKED (C)

=

3-methylxanthine

3-methylxanthine

Name origin: UniProt - CHECKED (C)

CHEBI:62208

Formula: C6H6N4O2
Charge: 0

ChEBI compound status: CHECKED (C)

+

formaldehyde

formaldehyde

Name origin: UniProt - CHECKED (C)

CHEBI:16842

Formula: CH2O
Charge: 0

ChEBI compound status: CHECKED (C)

+

H₂O

H2O

Name origin: UniProt - CHECKED (C)

CHEBI:15377

Formula: H2O
Charge: 0

ChEBI compound status: CHECKED (C)

+

NAD⁺

NAD(+)

Name origin: UniProt - CHECKED (C)

CHEBI:57540

Formula: C21H26N7O14P2
Charge: -1

ChEBI compound status: CHECKED (C)
36283 [IUBMB]

1,7-dimethylxanthine

1,7-dimethylxanthine

Name origin: UniProt - CHECKED (C)

CHEBI:25858

Formula: C7H8N4O2
Charge: 0

ChEBI compound status: CHECKED (C)

+

H⁺

H(+)

Name origin: UniProt - CHECKED (C)

CHEBI:15378

Formula: H
Charge: 1

ChEBI compound status: CHECKED (C)

+

NADPH

NADPH

Name origin: UniProt - CHECKED (C)

CHEBI:57783

Formula: C21H26N7O17P3
Charge: -4

ChEBI compound status: CHECKED (C)

+

O₂

O2

Name origin: UniProt - CHECKED (C)

CHEBI:15379

Formula: O2
Charge: 0

ChEBI compound status: CHECKED (C)

=

7-methylxanthine

7-methylxanthine

Name origin: UniProt - CHECKED (C)

CHEBI:48991

Formula: C6H6N4O2
Charge: 0

ChEBI compound status: CHECKED (C)

+

formaldehyde

formaldehyde

Name origin: UniProt - CHECKED (C)

CHEBI:16842

Formula: CH2O
Charge: 0

ChEBI compound status: CHECKED (C)

+

H₂O

H2O

Name origin: UniProt - CHECKED (C)

CHEBI:15377

Formula: H2O
Charge: 0

ChEBI compound status: CHECKED (C)

+

NADP⁺

NADP(+)

Name origin: UniProt - CHECKED (C)

CHEBI:58349

Formula: C21H25N7O17P3
Charge: -3

ChEBI compound status: CHECKED (C)

Cofactor

Fe cation

Comments:

A non-heme iron oxygenase. The enzyme from the bacterium Pseudomonas putida shares an NAD(P)H-FMN reductase subunit with EC 1.14.13.179, methylxanthine N3-demethylase, and has a 5-fold higher activity with NADH than with NADPH [2]. Also demethylate 1-methylxantine with lower efficiency. Forms part of the degradation pathway of methylxanthines.

Links to other databases

Enzymes and pathways: NC-IUBMB , BRENDA , ExplorEnz , ENZYME@ExPASy , KEGG , MetaCyc , UniPathway

Structural data: CSA , EC2PDB

UniProtKB/Swiss-Prot:

H9N289

NDMA_PSEPU

References

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

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.

Microbiology (Reading, Engl.) 157 : 583-592 (2011). [PMID: 20966097]
Summers, R. M., Louie, T. M., Yu, C. L., Gakhar, L., Louie, K. C., Subramanian, M.

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

J. Bacteriol. 194 : 2041-2049 (2012). [PMID: 22328667]

[EC 1.14.13.178 created 2013]