Information on EC 1.1.1.252 - tetrahydroxynaphthalene reductase

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The enzyme appears in viruses and cellular organisms

EC NUMBER
COMMENTARY hide
1.1.1.252
-
RECOMMENDED NAME
GeneOntology No.
tetrahydroxynaphthalene reductase
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
scytalone + NADP+ = 1,3,6,8-tetrahydroxynaphthalene + NADPH + H+
show the reaction diagram
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
oxidation
-
-
-
-
reduction
-
-
-
-
SYSTEMATIC NAME
IUBMB Comments
scytalone:NADP+ DELTA5-oxidoreductase
Reduces 1,3,6,8-tetrahydroxynaphthalene to scytalone and also reduces 1,3,8-trihydroxynaphthalene to vermelone. Involved with EC 4.2.1.94 scytalone dehydratase in the biosynthesis of melanin in pathogenic fungi.
CAS REGISTRY NUMBER
COMMENTARY hide
141350-13-2
-
153702-05-7
reductase, naphthol (Magnaporthe grisea clone pAV501 precursor reduced) /tetrahydroxynaphthalene reductase (Magnaporthe grisea clone pAV501)
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
-
-
-
Manually annotated by BRENDA team
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
evolution
-
the enzyme is a member of the short-chain dehydrogenase/reductase (SDR) family of enzymes
metabolism
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the enzyme catalyzes a step in 1,8-dihydroxynaphthalene-melanin biosynthesis, overview
additional information
-
structure-activity relationship of T4HNR and dynamics of its catalytic cycle, substrate docking study, the carboxylate of Ile274 might have an impact on substrate orientation, overview. Two orientations of tetralones in the active site of T4HNR revealed by docking studies: 1. si-face orientation (representing the preferential hydrophobic interaction of the methoxy group of substrate 5-methoxy-2-tetralone) and 2. the re-face orientation
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
1,3,6,8-Tetrahydroxynaphthalene + NADPH
Scytalone + NADP+
show the reaction diagram
1,3,6,8-tetrahydroxynaphthalene + NADPH + H+
scytalone + NADP+
show the reaction diagram
1,3,6-trihydroxynaphthalene + NADPH + H+
(R)-8-deoxyscytalone + NADP+
show the reaction diagram
-
-
-
-
?
1,3,8-trihydroxynaphthalene + NADPH + H+
vermelone + NADP+
show the reaction diagram
1,3-dihydroxynaphthalene + NADPH + H+
3-hydroxy-3,4-dihydronaphthalen-1(2H)-one + NADP+
show the reaction diagram
-
very low activity
-
-
?
1,4-androstadiene-3,17-dione + NADPH + H+
? + NADP+
show the reaction diagram
-
poor substrate of 3HNR
-
-
?
2,(5alpha)-androstene-17-one + NADPH + H+
? + NADP+
show the reaction diagram
-
-
-
-
?
2,3-Dihydro-2,5-dihydroxy-4H-benzopyran-4-one + NAD+
?
show the reaction diagram
-
-
-
-
-
2,3-Dihydro-2,5-dihydroxy-4H-benzopyran-4-one + NADP+
4,5-Dihydroxy-2H-benzopyran-2-one + NADPH
show the reaction diagram
2,3-dihydro-2,5-dihydroxy-4H-benzopyran-4-one + NADP+
4,5-dihydroxy-2H-benzopyran-2-one + NADPH + H+
show the reaction diagram
-
-
-
-
?
2-methylcyclohexanone + NADPH + H+
trans-2-methylcyclohexanol + NADP+
show the reaction diagram
-
-
-
-
?
2-tetralone + NADPH + H+
2-tetralol + NADP+
show the reaction diagram
-
high activity, almost complete conversion
-
-
?
4-androstene-3,17-dione + NADPH + H+
? + NADP+
show the reaction diagram
-
poor substrate of 3HNR
-
-
?
4-estrene-3,17-dione + NADPH + H+
? + NADP+
show the reaction diagram
-
poor substrate of 3HNR
-
-
?
5-androstene-3beta-ol-17-one + NADPH + H+
? + NADP+
show the reaction diagram
-
-
-
-
?
5-hydroxy-2-tetralone + NADPH + H+
5-hydroxy-2-tetralol + NADP+
show the reaction diagram
-
-
-
-
?
5-methoxy-2-tetralone + NADPH + H+
5-methoxy-2-tetralol + NADP+
show the reaction diagram
-
high activity, almost complete conversion
-
-
?
5alpha-androstane-3,17-dione + NADPH + H+
? + NADP+
show the reaction diagram
-
best steroid substrate for 3HNR
-
-
?
5alpha-androstane-3-one + NADPH + H+
? + NADP+
show the reaction diagram
-
-
-
-
?
5alpha-androstane-3alpha-ol-17-one + NADPH + H+
? + NADP+
show the reaction diagram
-
-
-
-
?
5alpha-androstane-3beta-ol-17-one + NADPH + H+
? + NADP+
show the reaction diagram
-
-
-
-
?
6-hydroxy-2-tetralone + NADPH + H+
6-hydroxy-2-tetralol + NADP+
show the reaction diagram
-
-
-
-
?
6-methoxy-2-tetralone + NADPH + H+
6-methoxy-2-tetralol + NADP+
show the reaction diagram
-
-
-
-
?
7-hydroxy-2-tetralone + NADPH + H+
7-hydroxy-2-tetralol + NADP+
show the reaction diagram
-
high activity, almost complete conversion
-
-
?
7-methoxy-2-tetralone + NADPH + H+
7-methoxy-2-tetralol + NADP+
show the reaction diagram
-
high activity, almost complete conversion
-
-
?
8-hydroxy-2-tetralone + NADPH + H+
8-hydroxy-2-tetralol + NADP+
show the reaction diagram
-
high activity, almost complete conversion
-
-
?
8-methoxy-2-tetralone + NADPH + H+
8-methoxy-2-tetralol + NADP+
show the reaction diagram
-
high activity, almost complete conversion
-
-
?
Phenanthrenequinone + NADPH
?
show the reaction diagram
-
-
-
-
-
additional information
?
-
-
no activity with estrone
-
-
-
NATURAL SUBSTRATES
NATURAL PRODUCTS
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
1,3,6,8-Tetrahydroxynaphthalene + NADPH
Scytalone + NADP+
show the reaction diagram
1,3,6,8-tetrahydroxynaphthalene + NADPH + H+
scytalone + NADP+
show the reaction diagram
-
reduction reaction via the via the 3-keto tautomer of 1,3,6,8-tetrahydroxynaphthalene
-
-
?
1,3,8-trihydroxynaphthalene + NADPH + H+
vermelone + NADP+
show the reaction diagram
COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
NADP+
NADPH
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
1,3,8-Trihydroxynaphthalene
-
competitive to 1,3,6,8-tetrahydroxynaphthalene
1H-indene-1,3(2H)-dione
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-
2,3,4,5,6-Pentachlorobenzyl alcohol
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-
2,3-Dihydro-2,5-dihydroxy-4H-benzopyran-4-one
3,7-dihydroxyflavone
3-hydroxyflavone
5,7-dihydroxyflavone
5-hydroxyflavone
5-methoxyflavone
5-methyl-(1,2,4)-triazolo[3,4-b]benzothiazole
-
tricyclazole, specific inhibitor of 3HNR
6-hydroxyflavone
-
inhibits by 15%
7,4'-Dihydroxyflavone
-
inhibits by 51%
7-hydroxyflavone
-
inhibits by 9%
acacetin
-
inhibits by 90%
apigenin
baicalein
-
affects fungal pigmentation and growth, inhibits by 75%
Biochanin A
Chlobenthiazone
-
-
chrysoeriol
-
inhibits by 55%
diclofenac
-
-
diosmetin
-
inhibits by 83%
ethyl 6-methyl-4-oxo-4H-chromene-2-carboxylate
-
-
ethyl 6-methyl-8-nitro-4-oxo-4H-chromene-2-carboxylate
-
-
etodolac
-
-
fisetin
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inhibits by 12%
flavanone
-
inhibits by 9%
flavone
-
inhibits by 38%
Fthalide
-
-
genistein
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inhibits by 19%
genkwanin
-
inhibits by 28%
kaempferol
luteolin
myricetin
-
inhibits by 13%
N-Methyl-2-quinolone
-
weak
nabumetone
-
-
naringenin
pinostrobin
-
inhibits by 38%
Pyroquilon
-
-
quercetin
-
inhibits by 52%
s-Triazolo[4,3-a]-quinoline
-
weak
scutellarein
-
inhibits by 67%
Tricyclazole
additional information
-
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.079
1,3,6,8-Tetrahydroxynaphthalene
-
-
0.005 - 0.033
2,3-Dihydro-2,5-dihydroxy-4H-benzopyran-4-one
3
NAD+
-
with 2,3-dihydro-2,5-dihydroxy-4H-benzopyran-4-one as cosubstrate
0.025 - 0.033
NADP+
-
with 2,3-dihydro-2,5-dihydroxy-4H-benzopyran-4-one as cosubstrate
0.0087 - 0.021
NADPH
0.003
Phenanthrenequinone
-
-
0.006 - 0.22
Scytalone
TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
14
2,3-Dihydro-2,5-dihydroxy-4H-benzopyran-4-one
Magnaporthe grisea
-
-
13
Phenanthrenequinone
Magnaporthe grisea
-
-
0.38
Scytalone
Magnaporthe grisea
-
-
Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.017
1H-indene-1,3(2H)-dione
-
pH 7.0
0.0026
5,7-dihydroxyflavone
-
-
0.01
7,4'-Dihydroxyflavone
-
at 0.04 mM 2,3-dihydro-2,5-dihydroxy-4H-benzopyran-4-one, at pH 7.0 and 25C
0.0022
acacetin
-
-
0.0012
apigenin
-
-
0.0054
baicalein
0.0081
chrysoeriol
-
at 0.04 mM 2,3-dihydro-2,5-dihydroxy-4H-benzopyran-4-one, at pH 7.0 and 25C
0.108
diclofenac
-
pH 7.0
0.0026
diosmetin
-
-
0.108
ethyl 6-methyl-4-oxo-4H-chromene-2-carboxylate
-
pH 7.0
0.111
ethyl 6-methyl-8-nitro-4-oxo-4H-chromene-2-carboxylate
-
pH 7.0
0.017
etodolac
-
pH 7.0
0.025
flavone
-
at 0.04 mM 2,3-dihydro-2,5-dihydroxy-4H-benzopyran-4-one, at pH 7.0 and 25C
0.0036
kaempferol
-
-
0.0031
luteolin
-
-
0.111
nabumetone
-
pH 7.0
0.012
naringenin
0.0068
scutellarein
-
at 0.04 mM 2,3-dihydro-2,5-dihydroxy-4H-benzopyran-4-one, at pH 7.0 and 25C
IC50 VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.025
3,7-dihydroxyflavone
0.0058
5,7-dihydroxyflavone
0.025
5-hydroxyflavone
0.023
7,4'-Dihydroxyflavone
Curvularia lunata
-
at 0.04 mM 2,3-dihydro-2,5-dihydroxy-4H-benzopyran-4-one, at pH 7.0 and 25C
0.0049
acacetin
Curvularia lunata
-
at 0.04 mM 2,3-dihydro-2,5-dihydroxy-4H-benzopyran-4-one, at pH 7.0 and 25C
0.0031
apigenin
0.012
baicalein
0.018
chrysoeriol
Curvularia lunata
-
at 0.04 mM 2,3-dihydro-2,5-dihydroxy-4H-benzopyran-4-one, at pH 7.0 and 25C
0.0057
diosmetin
Curvularia lunata
-
at 0.04 mM 2,3-dihydro-2,5-dihydroxy-4H-benzopyran-4-one, at pH 7.0 and 25C
0.055
flavone
Curvularia lunata
-
at 0.04 mM 2,3-dihydro-2,5-dihydroxy-4H-benzopyran-4-one, at pH 7.0 and 25C
0.0079
kaempferol
0.0068
luteolin
0.026
naringenin
0.015
scutellarein
Curvularia lunata
-
at 0.04 mM 2,3-dihydro-2,5-dihydroxy-4H-benzopyran-4-one, at pH 7.0 and 25C
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
11
-
2,3-dihydro-2,5-dihydroxy-4H-benzopyran-4-one converted by the recombinant protein
additional information
-
-
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
5.5
-
reduction of 1,3,6,8-tetrahydroxynaphthalene
7
-
assay at
7.5
-
oxidation of scytalone
8 - 9
-
optimal pH for oxidation of 2,3-dihydro-2,5-dihydroxy-4H-benzopyran-4-one
pH RANGE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
4.2 - 6.5
-
pH 4.2: about 40% of maximal activity, pH 6.5: about 30% of maximal activity
7 - 8
-
pH 7.0: about 95% of maximal activity, pH 8.0: about 80% of maximal activity
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
25 - 30
-
optimal temperature for oxidation of 2,3-dihydro-2,5-dihydroxy-4H-benzopyran-4-one
PDB
SCOP
CATH
ORGANISM
UNIPROT
Magnaporthe oryzae (strain 70-15 / ATCC MYA-4617 / FGSC 8958)
Magnaporthe oryzae (strain 70-15 / ATCC MYA-4617 / FGSC 8958)
Magnaporthe oryzae (strain 70-15 / ATCC MYA-4617 / FGSC 8958)
Magnaporthe oryzae (strain 70-15 / ATCC MYA-4617 / FGSC 8958)
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
120400
-
gel filtration
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
tetramer
-
4 * 29900, calculation from nucleotide sequence; 4 * 30000, SDS-PAGE
additional information
Crystallization/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
crystal structure of the apoenzyme. The crystallographic study identifies one protein region close to the active site as flexible and suggests that this helix-loop-helix motif might act as a lid which covers the active site upon binding of the substrate
-
STORAGE STABILITY
ORGANISM
UNIPROT
LITERATURE
-20C, with glycerol, stable over several months
-
Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
by affinity binding followed by cleavage with thrombin
-
recombinant GST-tagged enzyme from Escherichia coli by glutathione affinity chromatography
-
Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
complementation of a tetrahydroxynaphthalene reductase deficiency mutant
-
expressed as a glutathione S-transferase (GST)-fusion protein in Escherichia coli BL21 cells
-
expressed as a glutathione S-transferase (GST)-fusion protein in Escherichia coli BL21-AI cells
-
GST-tagged enzyme expression in Escherichia coli
-
ENGINEERING
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
additional information
-
generation of the C-terminally Ile274-truncated variant T4HNR(1-273)
APPLICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
agriculture
drug development