1.14.13.128: 7-methylxanthine demethylase
This is an abbreviated version!
For detailed information about 7-methylxanthine demethylase, go to the full flat file.
Word Map on EC 1.14.13.128
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1.14.13.128
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putida
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demethylation
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theophylline
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bioreactors
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uric
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coffee
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trimethyl
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costly
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1,3,7-trimethylxanthine
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rhodococcus
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paraxanthine
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3,7-dimethylxanthine
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formaldehyde
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aminopyrine
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alcaligenes
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rieske
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broad-specificity
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non-heme
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3-methylxanthine
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oxygen-dependent
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methylxanthines
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commences
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bioprocess
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klebsiella
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pharmacology
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medicine
- 1.14.13.128
- putida
-
demethylation
- theophylline
-
bioreactors
-
uric
- coffee
-
trimethyl
-
costly
- 1,3,7-trimethylxanthine
- rhodococcus
- paraxanthine
- 3,7-dimethylxanthine
- formaldehyde
- aminopyrine
- alcaligenes
-
rieske
-
broad-specificity
-
non-heme
- 3-methylxanthine
-
oxygen-dependent
- methylxanthines
-
commences
-
bioprocess
- klebsiella
- pharmacology
- medicine
Reaction
Synonyms
7-methylxanthine-specific N-demethylase, bacterial N-demethylase, caffeine demethylase, heteroxanthine demethylase, methylxanthine N-demethylase, N-demethylase, ndmA, NdmC, theobromine demethylase
ECTree
1.14.13.128 7-methylxanthine demethylaseAdvanced search results
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results (Substrates Products
Substrates Products on EC 1.14.13.128 - 7-methylxanthine demethylase
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SUBSTRATE 
PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
1,3,7-trimethylxanthine + O2 + NAD(P)H + H+
3,7-dimethylxanthine + formaldehyde + NAD(P)+
-
i.e. caffeine
i.e. theobromine
-
?
1,3,7-trimethylxanthine + O2 + NADPH + H+
1,3-dimethylxanthine + formaldehyde + NADP+ + H2O
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i.e. caffeine
i.e. theophylline
-
?
1,3,7-trimethylxanthine + O2 + NADPH + H+
1,7-dimethylxanthine + formaldehyde + NADP+ + H2O
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i.e. caffeine
i.e. paraxanthine
-
?
1,7-dimethylxanthine + O2 + NADPH + H+
7-methylxanthine + NADP+ + H2O + formaldehyde
-
i.e. paraxanthine, activity of the reductase component of the N-demethylase holoenzyme (Ccr) with NADPH is 22% of that with NADH. The enzyme also catalyzes the further demethylation of the product 7-methylxanthine to xanthine. Activity is absolutely dependent of oxygen as a cosubstrate
-
-
?
3,7-dimethylxanthine + O2 + NAD(P)H + H+
monomethylxanthine + formaldehyde + NADP+
-
theobromine demethylase
-
-
?
3-methylxanthine + O2 + NADH + H+
xanthine + NAD+ + H2O + formaldehyde
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3-methylxanthine demethylation is 12% of the activity compared to demethylation of 7-methylxanthine. Activity is absolutely dependent of oxygen as a cosubstrate
-
-
?
7-methylxanthine + O2 + NAD(P)H + H+
xanthine + formaldehyde + NADP+
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heteroxanthine demethylase, substrate-selective
-
-
?
7-methylxanthine + O2 + NADPH + H+
xanthine + NADP+ + H2O + formaldehyde
-
-
-
-
?
caffeine + 2 O2 + 2 NADH + 2 H+
7-methylxanthine + 2 NAD+ + 2 H2O + 2 formaldehyde
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i.e. 1,3,7-trimethylxanthine. Caffeine demethylation is 7% of the activity compared to demethylation of 7-methylxanthine. Activity is absolutely dependent of oxygen as a cosubstrate
-
-
?
caffeine + 3 O2 + 3 NADH + 3 H+
xanthine + 3 NAD+ + 3 H2O + 3 formaldehyde
-
i.e. 1,3,7-trimethylxanthine. Caffeine demethylation is 7% of the activity compared to demethylation of 7-methylxanthine. Activity is absolutely dependent of oxygen as a cosubstrate
-
-
?
caffeine + O2 + NADH + H+
1,7-dimethylxanthine + NAD+ + H2O + formaldehyde
-
i.e. 1,3,7-trimethylxanthine. Caffeine demethylation is 7% of the activity compared to demethylation of 7-methylxanthine. Activity is absolutely dependent of oxygen as a cosubstrate
-
-
?
theobromine + 2 O2 + 2 NADH + 2 H+
xanthine + 2 NAD+ + 2 H2O + 2 formaldehyde
-
i.e. 3,7-dimethylxanthine. Theobromine demethylation is 13% of the activity compared to demethylation of 7-methylxanthine. Activity is absolutely dependent of oxygen as a cosubstrate
-
-
?
theobromine + O2 + NADH + H+
3-methylxanthine + NAD+ + H2O + formaldehyde
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i.e. 3,7-dimethylxanthine. Theobromine demethylation is 13% of the activity compared to demethylation of 7-methylxanthine. Activity is absolutely dependent of oxygen as a cosubstrate
-
-
?
theobromine + O2 + NADH + H+
7-methylxanthine + NAD+ + H2O + formaldehyde
-
i.e. 3,7-dimethylxanthine. Theobromine demethylation is 13% of the activity compared to demethylation of 7-methylxanthine. Activity is absolutely dependent of oxygen as a cosubstrate
-
-
?
theophylline + 2 O2 + 2 NADH + 2 H+
xanthine + 2 NAD+ + 2 H2O + 2 formaldehyde
-
1,3-dimethylxanthine. Theophylline demethylation is 3% of the activity compared to demethylation of 7-methylxanthine. Activity is absolutely dependent of oxygen as a cosubstrate
-
-
?
theophylline + O2 + NADH + H+
1-methylxanthine + NAD+ + H2O + formaldehyde
-
1,3-dimethylxanthine. Theophylline demethylation is 3% of the activity compared to demethylation of 7-methylxanthine. Activity is absolutely dependent of oxygen as a cosubstrate
-
-
?
1,7-dimethylxanthine + 2 O2 + 2 NADH + 2 H+
xanthine + 2 NAD+ + 2 H2O + 2 formaldehyde
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i.e. paraxanthine, NADH is the preferred cofactor of reductase component of the N-demethylase holoenzyme (Ccr). The product 7-methylxanthine is further demethylated to xanthine. 1,7-Dimethylxanthine (paraxanthine) demethylation is 22% of the activity compared to demethylation of 7-methylxanthine. Activity is absolutely dependent of oxygen as a cosubstrate
-
-
?
1,7-dimethylxanthine + 2 O2 + 2 NADH + 2 H+
xanthine + 2 NAD+ + 2 H2O + 2 formaldehyde
-
i.e. paraxanthine, NADH is the preferred cofactor of reductase component of the N-demethylase holoenzyme (Ccr). The product 7-methylxanthine is further demethylated to xanthine. 1,7-Dimethylxanthine (paraxanthine) demethylation is 22% of the activity compared to demethylation of 7-methylxanthine. Activity is absolutely dependent of oxygen as a cosubstrate
-
-
?
1,7-dimethylxanthine + 2 O2 + 2 NADPH + 2 H+
xanthine + 2 NADP+ + 2 H2O + 2 formaldehyde
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i.e. paraxanthine, activity of the reductase component of the N-demethylase holoenzyme (Ccr) with NADPH is 22% of that with NADH. The enzyme also catalyzes the further demethylation of the product 7-methylxanthine to xanthine. Activity is absolutely dependent of oxygen as a cosubstrate
-
-
?
1,7-dimethylxanthine + 2 O2 + 2 NADPH + 2 H+
xanthine + 2 NADP+ + 2 H2O + 2 formaldehyde
-
i.e. paraxanthine, activity of the reductase component of the N-demethylase holoenzyme (Ccr) with NADPH is 22% of that with NADH. The enzyme also catalyzes the further demethylation of the product 7-methylxanthine to xanthine. Activity is absolutely dependent of oxygen as a cosubstrate
-
-
?
1,7-dimethylxanthine + O2 + NADH + H+
7-methylxanthine + NAD+ + H2O + formaldehyde
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i.e. paraxanthine, NADH is the preferred cofactor of reductase component of the N-demethylase holoenzyme (Ccr). The product 7-methylxanthine is further demethylated to xanthine. 1,7-Dimethylxanthine (paraxanthine) demethylation is 22% of the activity compared to demethylation of 7-methylxanthine. Activity is absolutely dependent of oxygen as a cosubstrate
-
-
?
1,7-dimethylxanthine + O2 + NADH + H+
7-methylxanthine + NAD+ + H2O + formaldehyde
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i.e. paraxanthine, NADH is the preferred cofactor of reductase component of the N-demethylase holoenzyme (Ccr). The product 7-methylxanthine is further demethylated to xanthine. 1,7-Dimethylxanthine (paraxanthine) demethylation is 22% of the activity compared to demethylation of 7-methylxanthine. Activity is absolutely dependent of oxygen as a cosubstrate
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-
?
7-methylxanthine + O2 + NAD(P)H + H+
xanthine + NAD(P)+ + H2O + formaldehyde
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part of the caffeine degradation pathway in Pseudomonas putida
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-
?
7-methylxanthine + O2 + NAD(P)H + H+
xanthine + NAD(P)+ + H2O + formaldehyde
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part of the caffeine degradation pathway in Pseudomonas putida
-
-
?
7-methylxanthine + O2 + NAD(P)H + H+
xanthine + NAD(P)+ + H2O + formaldehyde
-
-
-
?
7-methylxanthine + O2 + NADH + H+
xanthine + NAD+ + H2O + formaldehyde
-
-
-
-
?
7-methylxanthine + O2 + NADH + H+
xanthine + NAD+ + H2O + formaldehyde
-
-
-
?
7-methylxanthine + O2 + NADH + H+
xanthine + NAD+ + H2O + formaldehyde
specific substrate
-
-
?
7-methylxanthine + O2 + NADH + H+
xanthine + NAD+ + H2O + formaldehyde
-
the enzyme most actively demethylates 7-methylxanthine. Activity is absolutely dependent of oxygen as a cosubstrate
-
-
?
7-methylxanthine + O2 + NADH + H+
xanthine + NAD+ + H2O + formaldehyde
the N7-demethylation reaction absolutely requires a unique, tightly bound protein complex composed of NdmC, NdmD, and NdmE. NdmE functions as a noncatalytic subunit that serves a structural role in the complexation of the oxygenase (NdmC) and Rieske domains (NdmD)
-
-
?
7-methylxanthine + O2 + NADH + H+
xanthine + NAD+ + H2O + formaldehyde
immediate degradation via the NdmCDE complex
-
-
?
7-methylxanthine + O2 + NADH + H+
xanthine + NAD+ + H2O + formaldehyde
NdmC specifically detaches methyl groups from the N-7 position of methylxanthine derivatives
-
-
?
7-methylxanthine + O2 + NADH + H+
xanthine + NAD+ + H2O + formaldehyde
-
-
-
?
7-methylxanthine + O2 + NADH + H+
xanthine + NAD+ + H2O + formaldehyde
specific substrate
-
-
?
7-methylxanthine + O2 + NADH + H+
xanthine + NAD+ + H2O + formaldehyde
the N7-demethylation reaction absolutely requires a unique, tightly bound protein complex composed of NdmC, NdmD, and NdmE. NdmE functions as a noncatalytic subunit that serves a structural role in the complexation of the oxygenase (NdmC) and Rieske domains (NdmD)
-
-
?
7-methylxanthine + O2 + NADH + H+
xanthine + NAD+ + H2O + formaldehyde
immediate degradation via the NdmCDE complex
-
-
?
7-methylxanthine + O2 + NADH + H+
xanthine + NAD+ + H2O + formaldehyde
NdmC specifically detaches methyl groups from the N-7 position of methylxanthine derivatives
-
-
?
caffeine + O2 + NADH + H+
theobromine + NAD+ + H2O + formaldehyde
-
-
-
?
caffeine + O2 + NADH + H+
theobromine + NAD+ + H2O + formaldehyde
-
i.e. 1,3,7-trimethylxanthine. Caffeine demethylation is 7% of the activity compared to demethylation of 7-methylxanthine. Activity is absolutely dependent of oxygen as a cosubstrate
-
-
?
caffeine + O2 + NADH + H+
theobromine + NAD+ + H2O + formaldehyde
-
-
-
?
theophylline + O2 + NADH + H+
3-methylxanthine + NAD+ + H2O + formaldehyde
-
-
-
?
theophylline + O2 + NADH + H+
3-methylxanthine + NAD+ + H2O + formaldehyde
-
1,3-dimethylxanthine. Theophylline demethylation is 3% of the activity compared to demethylation of 7-methylxanthine. Activity is absolutely dependent of oxygen as a cosubstrate
-
-
?
theophylline + O2 + NADH + H+
3-methylxanthine + NAD+ + H2O + formaldehyde
-
-
-
?
additional information
?
-
-
Ndm exhibits broad-based activity towards caffeine, theophylline, theobromine, 7-methylxanthine and 3-methylxanthine, all of which are growth substrates for Pseudomonas putida CBB5. Production of xanthine from all of these methylxanthines is confirmed. Ndm is most active on 7-methylxanthine, followed by 1,7-dimethylxanthine (paraxanthine), theobromine, 3-methylxanthine, caffeine and theophylline. Ndm does not catalyse O-demethylation of vanillate or vanillin, even after prolonged incubation
-
-
?
additional information
?
-
-
the metabolite is 1,3-dimethylxanthine, i.e. theophylline, is produced by the demethylation in the 7th position of the purine ring, mainly in fungi, overview
-
-
?
additional information
?
-
-
no activity of the heteroxanthine demethylase, when either caffeine or dimethylxanthines are used as substrates
-
-
?
additional information
?
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caffeine, paraxanthine, and theobromine are not demethylated by the enzyme
-
-
?
additional information
?
-
no activity toward caffeine or theobromine
-
-
?
additional information
?
-
enzyme NdmA catalyzes NADH-dependent N1-demethylation of caffeine to theobromine and theophylline to 3-methylxanthine, and subsequently to 7-methylxanthine, and xanthine. Theobromine is the major product due to highly selective N1-demethylation caffeine by NdmA. But the minor production of paraxanthine from caffeine is due to slight promiscuity of the NdmA towards the N3-position on the caffeine molecule. Direct N-demethylation of caffeine at the N3 position does not occur appreciably with the three N-demethylases involved in caffeine degradation in CBB5
-
-
?
additional information
?
-
-
Ndm exhibits broad-based activity towards caffeine, theophylline, theobromine, 7-methylxanthine and 3-methylxanthine, all of which are growth substrates for Pseudomonas putida CBB5. Production of xanthine from all of these methylxanthines is confirmed. Ndm is most active on 7-methylxanthine, followed by 1,7-dimethylxanthine (paraxanthine), theobromine, 3-methylxanthine, caffeine and theophylline. Ndm does not catalyse O-demethylation of vanillate or vanillin, even after prolonged incubation
-
-
?
additional information
?
-
enzyme NdmA catalyzes NADH-dependent N1-demethylation of caffeine to theobromine and theophylline to 3-methylxanthine, and subsequently to 7-methylxanthine, and xanthine. Theobromine is the major product due to highly selective N1-demethylation caffeine by NdmA. But the minor production of paraxanthine from caffeine is due to slight promiscuity of the NdmA towards the N3-position on the caffeine molecule. Direct N-demethylation of caffeine at the N3 position does not occur appreciably with the three N-demethylases involved in caffeine degradation in CBB5
-
-
?
additional information
?
-
caffeine, paraxanthine, and theobromine are not demethylated by the enzyme
-
-
?
additional information
?
-
-
caffeine, paraxanthine, and theobromine are not demethylated by the enzyme
-
-
?
additional information
?
-
no activity toward caffeine or theobromine
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-
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