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Information on EC 1.5.99.4 - nicotine dehydrogenase
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1.5.99.4 nicotine dehydrogenaseIUBMB Comments
A metalloprotein (FMN). The enzyme can act on both the naturally found (S)-enantiomer and the synthetic (R)-enantiomer of nicotine, with retention of configuration in both cases .
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Word Map
- 1.5.99.4
- arthrobacter
- molybdopterins
- barkeri
- nicotinovorans
- molybdenum
- xanthine
- 6-hydroxynicotine
-
selenium-containing
- selenocysteine
-
molybdenum-containing
-
selenoproteins
- selenide
-
nicotine-degrading
- 6-hydroxy-l-nicotine
The expected taxonomic range for this enzyme is: Bacteria, Eukaryota
Synonyms
nicotinic acid hydroxylase, nicotine dehydrogenase, ndhab, 
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SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
D-nicotine oxidase
-
-
-
-
NDH
NdhAB
nicotine dehydrogenase
-
-
-
-
nicotine oxidase
-
-
-
-
nicotinic acid hydroxylase
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
(S)-nicotine + acceptor + H2O = (S)-6-hydroxynicotine + reduced acceptor
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-
-
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(S)-nicotine + acceptor + H2O = (S)-6-hydroxynicotine + reduced acceptor
A metalloprotein (FMN). Acts on both (R)- and (S)-isomers
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-
-
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
oxidation
-
-
-
-
redox reaction
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-
-
-
reduction
-
-
-
-
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PATHWAY SOURCE
PATHWAYS
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SYSTEMATIC NAME
IUBMB Comments
nicotine:acceptor 6-oxidoreductase (hydroxylating)
A metalloprotein (FMN). The enzyme can act on both the naturally found (S)-enantiomer and the synthetic (R)-enantiomer of nicotine, with retention of configuration in both cases [4].
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CAS REGISTRY NUMBER
COMMENTARY
37256-31-8
-
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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
(R)-nicotine + acceptor + H2O
(R)-6-hydroxynicotine + reduced acceptor
-
-
-
?
(S)-nicotine + 2,6-dichlorophenolindophenol + H2O
(S)-6-hydroxynicotine + reduced 2,6-dichlorophenolindophenol
(S)-nicotine + acceptor
(S)-nicotine delta1',5'-iminium ion + reduced acceptor
-
-
-
?
(S)-nicotine + acceptor + H2O
nicotine-N-oxide + reduced acceptor
-
-
-
?
(S)-nicotine + acceptor + H2O
nornicotine + reduced acceptor + ?
-
-
-
?
(S)-nicotine + brilliant cresyl blue + H2O
(S)-6-hydroxynicotine + reduced brilliant cresyl blue
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-
-
-
r
(S)-nicotine + menadione + H2O
(S)-6-hydroxynicotine + menadiol
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-
-
-
r
(S)-nicotine + methylene blue + H2O
(S)-6-hydroxynicotine + reduced methylene blue
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-
-
-
r
(S)-nicotine + vitamin K5 + H2O
(S)-6-hydroxynicotine + reduced vitamin K5
-
-
-
-
r
anabasine + acceptor + H2O
6-hydroxyanabasine + reduced acceptor
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-
-
?
D-nicotine + acceptor + H2O
(R)-6-hydroxynicotine + reduced acceptor
isozyme specific for the D-isomer
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-
?
DL-nicotine + ?
6-hydroxynicotine + ?
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first enzyme in nicotine pathway
-
?
nicotine-N-oxide + acceptor + H2O
6-hydroxynicotine-N-oxide + reduced acceptor
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-
-
?
(RS)-nicotine + acceptor + H2O
pseudooxynicotine + reduced acceptor
via N-methylmyosmine, which then spontaneously hydrolyzes to pseudooxynicotine. The two enantiomers are degraded at approximately the same rate, indicating that NOX does not show chiral selectivity
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-
?
(RS)-nicotine + acceptor + H2O
pseudooxynicotine + reduced acceptor
via N-methylmyosmine, which then spontaneously hydrolyzes to pseudooxynicotine. The two enantiomers are degraded at approximately the same rate, indicating that NOX does not show chiral selectivity
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-
?
(S)-nicotine + 2,6-dichlorophenolindophenol + H2O
(S)-6-hydroxynicotine + reduced 2,6-dichlorophenolindophenol
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-
-
-
?
(S)-nicotine + 2,6-dichlorophenolindophenol + H2O
(S)-6-hydroxynicotine + reduced 2,6-dichlorophenolindophenol
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-
-
-
?
(S)-nicotine + 2,6-dichlorophenolindophenol + H2O
(S)-6-hydroxynicotine + reduced 2,6-dichlorophenolindophenol
-
-
-
-
r
(S)-nicotine + acceptor + H2O
pseudooxynicotine + reduced acceptor
via N-methylmyosmine, which then spontaneously hydrolyzes to pseudooxynicotine. The two enantiomers are degraded at approximately the same rate, indicating that NOX does not show chiral selectivity
-
-
?
(S)-nicotine + acceptor + H2O
pseudooxynicotine + reduced acceptor
via N-methylmyosmine, which then spontaneously hydrolyzes to pseudooxynicotine. The two enantiomers are degraded at approximately the same rate, indicating that NOX does not show chiral selectivity
-
-
?
(S)-nicotine + pseudoazurin + H2O
(S)-6-hydroxynicotine + reduced pseudoazurin
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acceptor pseudoazurin is a single-electron carrier and is able to bind a single copper atom while accepting or discharging one electron
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-
?
(S)-nicotine + pseudoazurin + H2O
(S)-6-hydroxynicotine + reduced pseudoazurin
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acceptor pseudoazurin is a single-electron carrier and is able to bind a single copper atom while accepting or discharging one electron
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-
?
L-nicotine + acceptor + H2O
(S)-6-hydroxynicotine + reduced acceptor
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-
-
-
?
L-nicotine + acceptor + H2O
(S)-6-hydroxynicotine + reduced acceptor
Nocardioides sp. JS614 / ATCC BAA-499
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-
-
-
?
L-nicotine + acceptor + H2O
(S)-6-hydroxynicotine + reduced acceptor
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-
-
-
?
L-nicotine + acceptor + H2O
(S)-6-hydroxynicotine + reduced acceptor
isozyme strictly specific for the L-isomer
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-
?
nicotine + acceptor + H2O
6-hydroxynicotine + reduced acceptor
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non-stereospecific enzyme if grown on L-nicotine, assayed with 2,6-dichlorophenolindophenol
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?
nicotine + acceptor + H2O
6-hydroxynicotine + reduced acceptor
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brilliant cresyl blue, methylene blue, 5-hydroxy-1,4-naphthoquinone, 2,6-dichlorophenolindophenol, menadione and vitamin K5 used as electron acceptors
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?
nicotine + acceptor + H2O
6-hydroxynicotine + reduced acceptor
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preferentially 2,6-dichlorophenolindophenol used as electron acceptor
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?
nicotine + acceptor + H2O
6-hydroxynicotine + reduced acceptor
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molybdate is required
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?
nicotine + acceptor + H2O
6-hydroxynicotine + reduced acceptor
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molybdate is required
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?
nicotine + acceptor + H2O
6-hydroxynicotine + reduced acceptor
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first enzyme in the nicotine degradation pathway
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?
nicotine + acceptor + H2O
6-hydroxynicotine + reduced acceptor
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first enzyme in the nicotine degradation pathway
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?
nicotine + acceptor + H2O
6-hydroxynicotine + reduced acceptor
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-
-
?
nicotine + acceptor + H2O
6-hydroxynicotine + reduced acceptor
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-
-
?
nicotinic acid + acceptor + H2O
6-hydroxynicotinic acid + reduced acceptor
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-
-
?
nicotinic acid + acceptor + H2O
6-hydroxynicotinic acid + reduced acceptor
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cytochrome-linked oxidation, hydroxylation
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?
nicotinic acid + acceptor + H2O
6-hydroxynicotinic acid + reduced acceptor
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cytochrome-linked oxidation, hydroxylation
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?
nicotinic acid + acceptor + H2O
6-hydroxynicotinic acid + reduced acceptor
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2,6-dichlorophenolindophenol used as electron acceptor
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?
nicotinic acid + acceptor + H2O
6-hydroxynicotinic acid + reduced acceptor
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2,6-dichlorophenolindophenol used as electron acceptor
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?
nornicotine + acceptor + H2O
6-hydroxynornicotine + reduced acceptor
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-
-
?
nornicotine + acceptor + H2O
6-hydroxynornicotine + reduced acceptor
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-
-
?
additional information
?
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NAD(P)+, O2, and ferredoxin cannot serve as electron acceptors
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-
-
additional information
?
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NAD(P)+, O2, and ferredoxin cannot serve as electron acceptors
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-
-
additional information
?
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enzyme expression and activity is regulated by substrate and product level via transcription repressor HdnoR
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-
?
additional information
?
-
enzyme expression and activity is regulated by substrate and product level via transcription repressor HdnoR
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-
?
additional information
?
-
enzyme expression and activity is regulated by substrate and product level via transcription repressor HdnoR
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-
?
additional information
?
-
organism can grow on L-nicotine since it is converted to D-nicotine by a racemase
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-
?
additional information
?
-
organism can grow on L-nicotine since it is converted to D-nicotine by a racemase
-
-
?
additional information
?
-
organism can grow on L-nicotine since it is converted to D-nicotine by a racemase
-
-
?
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NATURAL SUBSTRATE
NATURAL 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
(R)-nicotine + acceptor + H2O
(R)-6-hydroxynicotine + reduced acceptor
-
-
-
?
D-nicotine + acceptor + H2O
(R)-6-hydroxynicotine + reduced acceptor
isozyme specific for the D-isomer
-
-
?
DL-nicotine + ?
6-hydroxynicotine + ?
-
first enzyme in nicotine pathway
-
?
L-nicotine + acceptor + H2O
(S)-6-hydroxynicotine + reduced acceptor
isozyme strictly specific for the L-isomer
-
-
?
nornicotine + acceptor + H2O
6-hydroxynornicotine + reduced acceptor
-
-
-
?
(S)-nicotine + acceptor + H2O
pseudooxynicotine + reduced acceptor
via N-methylmyosmine, which then spontaneously hydrolyzes to pseudooxynicotine. The two enantiomers are degraded at approximately the same rate, indicating that NOX does not show chiral selectivity
-
-
?
(S)-nicotine + acceptor + H2O
pseudooxynicotine + reduced acceptor
via N-methylmyosmine, which then spontaneously hydrolyzes to pseudooxynicotine. The two enantiomers are degraded at approximately the same rate, indicating that NOX does not show chiral selectivity
-
-
?
nicotine + acceptor + H2O
6-hydroxynicotine + reduced acceptor
-
first enzyme in the nicotine degradation pathway
-
?
nicotine + acceptor + H2O
6-hydroxynicotine + reduced acceptor
-
first enzyme in the nicotine degradation pathway
-
?
nicotine + acceptor + H2O
6-hydroxynicotine + reduced acceptor
-
-
-
?
additional information
?
-
enzyme expression and activity is regulated by substrate and product level via transcription repressor HdnoR
-
-
?
additional information
?
-
enzyme expression and activity is regulated by substrate and product level via transcription repressor HdnoR
-
-
?
additional information
?
-
enzyme expression and activity is regulated by substrate and product level via transcription repressor HdnoR
-
-
?
additional information
?
-
organism can grow on L-nicotine since it is converted to D-nicotine by a racemase
-
-
?
additional information
?
-
organism can grow on L-nicotine since it is converted to D-nicotine by a racemase
-
-
?
additional information
?
-
organism can grow on L-nicotine since it is converted to D-nicotine by a racemase
-
-
?
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COFACTOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
FMN
-
metalloflavoprotein, protects enzyme against inhibition by acriflavine
iron-sulfur centre
subunit B carries an iron-sulfur cluster
cytochrome P450
-
small content to nicotine oxidation, cytochrome P-450-linked monooxygenase
-
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METALS and IONS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
Fe2+
Molybdenum
Tungsten
-
enzyme synthesis responds to the presence of this metal ion
additional information
Molybdenum
-
enzyme synthesis responds to the presence of this metal ion
Molybdenum
subunit C contains a molybdopterin-binding domain
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INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
Tungsten
inhibitory to enzyme activity, does not inhibit enzyme synthesis
additional information
gene repressor HdnoR binds to the 6hdno gene operator, Kd is 21 nM, and represses enzyme expression, repressor in induced by 6-hydroxy-D-nicotine and 6-hydroxy-L-nicotine in vitro and in vivo
-
additional information
gene repressor HdnoR binds to the 6hdno gene operator, Kd is 21 nM, and represses enzyme expression, repressor in induced by 6-hydroxy-D-nicotine and 6-hydroxy-L-nicotine in vitro and in vivo
-
additional information
gene repressor HdnoR binds to the 6hdno gene operator, Kd is 21 nM, and represses enzyme expression, repressor in induced by 6-hydroxy-D-nicotine and 6-hydroxy-L-nicotine in vitro and in vivo
-
additional information
-
riboflavin 5'-phosphate protects enzyme against acriflavine inhibition, FMN protects enzyme against acriflavine inhibition, FAD only partially effective, glutathione protects against p-chloromercuriphenylsulfonic inhibition
-
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ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.00087
(S)-nicotine
-
cosubstrate 2,6-dichlorophenolindophenol, pH 7, 30°C
additional information
additional information
Km of (S)-nicotine uptake is 0.0056 mM
-
additional information
additional information
Km of (S)-nicotine uptake is 0.0056 mM
-
additional information
additional information
Km of (S)-nicotine uptake is 0.0056 mM
-
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TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
0.000514 - 0.000888
-
variation caused by pre-treatment with 3-methylcholanthrene, beta-naphthoflavone or phenobarbital
additional information
-
0.119 units per mg protein, unit is defined as the amount causing a decrease in absorbancy at 578 nm of 0.001 per min
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pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
6.8
7.5
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TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
30
37
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ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
30 kDa; strain bearing the catabolic plasmid pAO1, 2 stereospecific isozymes, gene 6hdno encodes the D-nicotine inducible and specific isozyme, gene 6hlno encodes the L-nicotine inducible and specific isozyme
SwissProt
brenda
30 kDa; strain bearing the catabolic plasmid pAO1, gene 6hdno encodes the D-nicotine inducible and specific isozyme
SwissProt
brenda
87.7 kDa; strain bearing the catabolic plasmid pAO1, 2 stereospecific isozymes, gene 6hdno encodes the D-nicotine inducible and specific isozyme, gene 6hlno encodes the L-nicotine inducible and specific isozyme
SwissProt
brenda
87.7 kDa; strain bearing the catabolic plasmid pAO1, gene 6hdno encodes the D-nicotine inducible and specific isozyme
SwissProt
brenda
small 17.8 kDa subunit; strain bearing the catabolic plasmid pAO1, 2 stereospecific isozymes, gene 6hdno encodes the D-nicotine inducible and specific isozyme, gene 6hlno encodes the L-nicotine inducible and specific isozyme
SwissProt
brenda
small 17.8 kDa subunit; strain bearing the catabolic plasmid pAO1, gene 6hdno encodes the D-nicotine inducible and specific isozyme
SwissProt
brenda
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SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
SOURCE
-
brenda
-
brenda
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LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY
GeneOntology No.
LITERATURE
SOURCE
present both as soluble and membrane-associated form
brenda