KEGG   ORTHOLOGY: K21722
Entry
K21722                      KO                                     
Symbol
ndmA
Name
methylxanthine N1-demethylase [EC:1.14.13.178]
Pathway
map00232  Caffeine metabolism
map01100  Metabolic pathways
map01110  Biosynthesis of secondary metabolites
map01120  Microbial metabolism in diverse environments
Module
M00915  Caffeine degradation, caffeine => xanthine
Reaction
R07955  caffeine:oxygen oxidoreductase (N1-demethylating)
R07956  caffeine:oxygen oxidoreductase (N1-demethylating)
R07957  paraxanthine:oxygen oxidoreductase (N1-demethylating)
R07958  paraxanthine:oxygen oxidoreductase (N1-demethylating)
R07969  1-methylxanthine:oxygen oxidoreductase (N1-demethylating)
R07970  1-methylxanthine:oxygen oxidoreductase (N1-demethylating)
R07973  theophylline:oxygen oxidoreductase (N1-demethylating)
R07974  theophylline:oxygen oxidoreductase (N1-demethylating)
Brite
KEGG Orthology (KO) [BR:ko00001]
 09100 Metabolism
  09110 Biosynthesis of other secondary metabolites
   00232 Caffeine metabolism
    K21722  ndmA; methylxanthine N1-demethylase
Enzymes [BR:ko01000]
 1. Oxidoreductases
  1.14  Acting on paired donors, with incorporation or reduction of molecular oxygen
   1.14.13  With NADH or NADPH as one donor, and incorporation of one atom of oxygen into the other donor
    1.14.13.178  methylxanthine N1-demethylase
     K21722  ndmA; methylxanthine N1-demethylase
Other DBs
COG: COG4638
Genes
PCAF: DSC91_007649
PYE: A6J80_10900
PZH: CX676_16200
ASZ: ASN_2329
PARH: I5S86_05095
IAM: HC251_12390
AG: AFD03116(ndmA)
Reference
PMID:22328667
  Authors
Summers RM, Louie TM, Yu CL, Gakhar L, Louie KC, Subramanian M
  Title
Novel, highly specific N-demethylases enable bacteria to live on caffeine and related purine alkaloids.
  Journal
J Bacteriol 194:2041-9 (2012)
DOI:10.1128/JB.06637-11
  Sequence
[ag:AFD03116]
LinkDB

KEGG   ENZYME: 1.14.13.178
Entry
EC 1.14.13.178              Enzyme                                 
Name
methylxanthine N1-demethylase;
ndmA (gene name)
Class
Oxidoreductases;
Acting on paired donors, with incorporation or reduction of molecular oxygen;
With NADH or NADPH as one donor, and incorporation of one atom of oxygen into the other donor
Sysname
caffeine:oxygen oxidoreductase (N1-demethylating)
Reaction(IUBMB)
(1) caffeine + O2 + NAD(P)H + H+ = theobromine + NAD(P)+ + H2O + formaldehyde [RN:R07955 R07956];
(2) theophylline + O2 + NAD(P)H + H+ = 3-methylxanthine + NAD(P)+ + H2O + formaldehyde [RN:R07973 R07974];
(3) paraxanthine + O2 + NAD(P)H + H+ = 7-methylxanthine + NAD(P)+ + H2O + formaldehyde [RN:R07957 R07958]
Reaction(KEGG)
R07955 R07956 R07957 R07958 R07973 R07974;
(other) R07969 R07970
Substrate
caffeine [CPD:C07481];
O2 [CPD:C00007];
NADH [CPD:C00004];
NADPH [CPD:C00005];
H+ [CPD:C00080];
theophylline [CPD:C07130];
paraxanthine [CPD:C13747]
Product
theobromine [CPD:C07480];
NAD+ [CPD:C00003];
NADP+ [CPD:C00006];
H2O [CPD:C00001];
formaldehyde [CPD:C00067];
3-methylxanthine [CPD:C16357];
7-methylxanthine [CPD:C16353]
Comment
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.
History
EC 1.14.13.178 created 2013
Pathway
ec00232  Caffeine metabolism
ec01100  Metabolic pathways
ec01110  Biosynthesis of secondary metabolites
ec01120  Microbial metabolism in diverse environments
Orthology
K21722  methylxanthine N1-demethylase
Genes
PCAF: DSC91_007649
PYE: A6J80_10900
PZH: CX676_16200
ASZ: ASN_2329
PARH: I5S86_05095
IAM: HC251_12390
Reference
1  [PMID:20966097]
  Authors
Summers RM, Louie TM, Yu CL, Subramanian M
  Title
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.
  Journal
Microbiology 157:583-92 (2011)
DOI:10.1099/mic.0.043612-0
  Sequence
[ag:AFD03116]
Reference
2  [PMID:22328667]
  Authors
Summers RM, Louie TM, Yu CL, Gakhar L, Louie KC, Subramanian M
  Title
Novel, highly specific N-demethylases enable bacteria to live on caffeine and related purine alkaloids.
  Journal
J Bacteriol 194:2041-9 (2012)
DOI:10.1128/JB.06637-11
  Sequence
[ag:AFD03116]
Other DBs
ExplorEnz - The Enzyme Database: 1.14.13.178
IUBMB Enzyme Nomenclature: 1.14.13.178
ExPASy - ENZYME nomenclature database: 1.14.13.178
BRENDA, the Enzyme Database: 1.14.13.178
LinkDB

KEGG   REACTION: R07973
Entry
R07973                      Reaction                               
Name
theophylline:oxygen oxidoreductase (N1-demethylating)
Definition
Theophylline + NADH + H+ + Oxygen <=> 3-Methylxanthine + NAD+ + Formaldehyde + H2O
Equation
C07130 + C00004 + C00080 + C00007 <=> C16357 + C00003 + C00067 + C00001
Reaction class
RC00001  C00003_C00004
RC00334  C07130_C16357
RC01797  C00067_C07130
Enzyme
1.14.13.178
Pathway
rn00232  Caffeine metabolism
rn01100  Metabolic pathways
rn01110  Biosynthesis of secondary metabolites
rn01120  Microbial metabolism in diverse environments
Brite
Enzymatic reactions [BR:br08201]
 1. Oxidoreductase reactions
  1.14  Acting on paired donors, with incorporation or reduction of molecular oxygen
   1.14.13  With NADH or NADPH as one donor, and incorporation of one atom of oxygen into the other donor
    1.14.13.178
     R07973  Theophylline + NADH + H+ + Oxygen <=> 3-Methylxanthine + NAD+ + Formaldehyde + H2O
Orthology
K21722  methylxanthine N1-demethylase [EC:1.14.13.178]
Other DBs
RHEA: 36282
LinkDB

KEGG   REACTION: R07974
Entry
R07974                      Reaction                               
Name
theophylline:oxygen oxidoreductase (N1-demethylating)
Definition
Theophylline + NADPH + H+ + Oxygen <=> 3-Methylxanthine + NADP+ + Formaldehyde + H2O
Equation
C07130 + C00005 + C00080 + C00007 <=> C16357 + C00006 + C00067 + C00001
Reaction class
RC00001  C00005_C00006
RC00334  C07130_C16357
RC01797  C00067_C07130
Enzyme
1.14.13.178
Pathway
rn00232  Caffeine metabolism
rn01100  Metabolic pathways
rn01110  Biosynthesis of secondary metabolites
rn01120  Microbial metabolism in diverse environments
Brite
Enzymatic reactions [BR:br08201]
 1. Oxidoreductase reactions
  1.14  Acting on paired donors, with incorporation or reduction of molecular oxygen
   1.14.13  With NADH or NADPH as one donor, and incorporation of one atom of oxygen into the other donor
    1.14.13.178
     R07974  Theophylline + NADPH + H+ + Oxygen <=> 3-Methylxanthine + NADP+ + Formaldehyde + H2O
Orthology
K21722  methylxanthine N1-demethylase [EC:1.14.13.178]
Other DBs
RHEA: 36278
LinkDB

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