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Information on EC 1.1.1.252 - tetrahydroxynaphthalene reductase
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1.1.1.252 tetrahydroxynaphthalene reductaseIUBMB Comments
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.
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Word Map
- 1.1.1.252
- melanin
- lunata
- curvularia
- tetralin
- cochliobolus
- tricyclazole
- 1,8-dihydroxynaphthalene
-
lysr-type
-
teleomorph
-
homology-built
-
17beta-hydroxysteroid
- 17beta-hsdcl
- drug development
- lagenarium
- flaviolin
-
pentaketide
- agriculture
- medicine
The expected taxonomic range for this enzyme is: Eukaryota, Bacteria
Synonyms
thnr, trihydroxynaphthalene reductase, 1,3,8-trihydroxynaphthalene reductase, tetrahydroxynaphthalene reductase, naphthol reductase, t4hnr, hydroxynaphthalene reductase, t4hn reductase, 1,3,6,8-tetrahydroxynaphthalene reductase, 
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SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
1,3,6,8-tetrahydroxynaphthalene reductase
-
-
-
-
1,3,8-trihydroxynaphthalene reductase
-
-
-
-
3HNR
EC 1.3.1.50
-
-
formerly
-
hydroxynaphthalene reductase
-
-
-
-
MGG_02252
NADPH-dependent naphthol reductase
-
-
-
-
naphthol reductase
-
-
-
-
reductase, naphthol
-
-
-
-
reductase, naphthol (Magnaporthe grisea clone pAV501 precursor reduced)
-
-
-
-
T4HN reductase
-
-
-
-
tetrahydroxynaphthalene reductase (Magnaporthe grisea clone pAV501)
-
-
-
-
THNR
-
-
-
-
trihydroxynaphthalene reductase
3HNR
-
-
-
-
trihydroxynaphthalene reductase
-
-
-
-
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
scytalone + NADP+ = 1,3,6,8-tetrahydroxynaphthalene + NADPH + H+
-
-
-
-
scytalone + NADP+ = 1,3,6,8-tetrahydroxynaphthalene + NADPH + H+
the catalytic triad is formed by residues S149, Y163, and K167
-
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
oxidation
-
-
-
-
reduction
-
-
-
-
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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.
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CAS REGISTRY NUMBER
COMMENTARY
141350-13-2
-
153702-05-7
reductase, naphthol (Magnaporthe grisea clone pAV501 precursor reduced) /tetrahydroxynaphthalene reductase (Magnaporthe grisea clone pAV501)
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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
(2S)-2,8-dihydroxy-2,3-dihydronaphthalene-1,4-dione + NADPH + H+
(2S,4R)-2,4,8-trihydroxy-3,4-dihydronaphthalen-1(2H)-one + NADP+
-
-
-
?
1,3,6,8-tetrahydroxynaphthalene + NADPH + H+
(R)-scytalone + NADP+
-
-
-
-
?
1,3,6-trihydroxynaphthalene + NADPH + H+
(R)-8-deoxyscytalone + NADP+
-
-
-
-
?
1,3-dihydroxynaphthalene + NADPH + H+
3-hydroxy-3,4-dihydronaphthalen-1(2H)-one + NADP+
-
very low activity
-
-
?
1,4-androstadiene-3,17-dione + NADPH + H+
? + NADP+
-
poor substrate of 3HNR
-
-
?
1-(1,6,8-trihydroxy-3-methylnaphthalen-2-yl)ethan-1-one + NADPH + H+
? + NADP+
-
-
-
?
1-(1,8-dihydroxy-3-methylnaphthalen-2-yl)ethan-1-one + NADPH + H+
? + NADP+
-
-
-
?
1-(3,6,8-trihydroxy-1-methylnaphthalen-2-yl)ethan-1-one + NADPH + H+
? + NADP+
-
-
-
?
2,3-Dihydro-2,5-dihydroxy-4H-benzopyran-4-one + NADP+
4,5-Dihydroxy-2H-benzopyran-2-one + NADPH
2,3-dihydro-2,5-dihydroxy-4H-benzopyran-4-one + NADP+
4,5-dihydroxy-2H-benzopyran-2-one + NADPH + H+
-
-
-
-
?
2,3-dihydronaphthalene-1,4-dione + NADPH + H+
(4S)-4-hydroxy-3,4-dihydronaphthalen-1(2H)-one + NADP+
-
-
21% yield, 98% enantiomeric excess
-
?
2,8-dihydroxynaphthalene-1,4-dione + NADPH + H+
(2S)-2,8-dihydroxy-2,3-dihydronaphthalene-1,4-dione + NADP+
-
-
-
?
2-hydroxyjuglone + NADPH + H+
(3S,4R)-3,4,8-trihydroxy-1-tetralone + NADP+
-
-
-
?
2-methylcyclohexanone + NADPH + H+
trans-2-methylcyclohexanol + NADP+
-
-
-
-
?
2-tetralone + NADPH + H+
2-tetralol + NADP+
-
high activity, almost complete conversion
-
-
?
3,4-dihydronaphthalen-2(1H)-one + NADPH + H+
(2S)-1,2,3,4-tetrahydronaphthalen-2-ol + NADP+
-
-
77% yield, 61% enantiomeric excess
-
?
4-androstene-3,17-dione + NADPH + H+
? + NADP+
-
poor substrate of 3HNR
-
-
?
5-hydroxy-2,3-dihydronaphthalene-1,4-dione + NADPH + H+
(4S)-4,8-dihydroxy-3,4-dihydronaphthalen-1(2H)-one + NADP+
-
-
9% yield, 95% enantiomeric excess
-
?
5-methoxy-2-tetralone + NADPH + H+
5-methoxy-2-tetralol + NADP+
-
high activity, almost complete conversion
-
-
?
5alpha-androstane-3,17-dione + NADPH + H+
? + NADP+
-
best steroid substrate for 3HNR
-
-
?
6-acetyl-2,5-dihydroxy-7-methylnaphthalene-1,4-dione + 2 NADPH + 2 H+
(3S,4R)-7-acetyl-3,4,8-trihydroxy-6-methyl-3,4-dihydronaphthalen-1(2H)-one + 2 NADP+
-
-
-
?
6-acetyl-2-hydroxy-5,7-dimethyl-4a,8a-dihydronaphthalene-1,4-dione + NADPH + H+
? + NADP+
-
-
-
?
6-methoxy-3,4-dihydronaphthalen-2(1H)-one + NADPH + H+
(2S)-6-methoxy-1,2,3,4-tetrahydronaphthalen-2-ol + NADP+
-
-
71% yield, 99% enantiomeric excess
-
?
7-hydroxy-2-tetralone + NADPH + H+
7-hydroxy-2-tetralol + NADP+
-
high activity, almost complete conversion
-
-
?
7-methoxy-2-tetralone + NADPH + H+
7-methoxy-2-tetralol + NADP+
-
high activity, almost complete conversion
-
-
?
8-hydroxy-2-tetralone + NADPH + H+
8-hydroxy-2-tetralol + NADP+
-
high activity, almost complete conversion
-
-
?
8-methoxy-2-tetralone + NADPH + H+
8-methoxy-2-tetralol + NADP+
-
high activity, almost complete conversion
-
-
?
8-methoxy-3,4-dihydronaphthalen-2(1H)-one + NADPH + H+
(2R)-8-methoxy-1,2,3,4-tetrahydronaphthalen-2-ol + NADP+
-
-
75% yield, 99% enantiomeric excess
-
?
lawsone + 2 NADPH + 2 H+
(3S,4R)-3,4-dihydroxy-1-tetralone + 2 NADP+
-
-
-
?
1,3,6,8-Tetrahydroxynaphthalene + NADPH
Scytalone + NADP+
-
the enzyme is involved in melanin biosynthesis and pathogenicity
-
-
?
1,3,6,8-Tetrahydroxynaphthalene + NADPH
Scytalone + NADP+
-
involved in the biosynthesis of melanin
-
-
?
1,3,6,8-Tetrahydroxynaphthalene + NADPH
Scytalone + NADP+
-
the enzyme is an essential enzyme in the biosynthesis of fungal melanin, DHN type melanin biosynthetic pathway
-
-
?
1,3,6,8-Tetrahydroxynaphthalene + NADPH
Scytalone + NADP+
-
the enzyme is involved in the post-aromatic deoxygenation process of fungal melanin and pigments
-
-
?
1,3,6,8-Tetrahydroxynaphthalene + NADPH
Scytalone + NADP+
-
essential reaction in the biosynthesis of melanin
-
-
?
1,3,6,8-Tetrahydroxynaphthalene + NADPH
Scytalone + NADP+
-
the enzyme is involved in the biosynthesis of melanin
-
-
?
1,3,6,8-Tetrahydroxynaphthalene + NADPH
Scytalone + NADP+
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spefific for NADPH
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-
?
1,3,6,8-Tetrahydroxynaphthalene + NADPH
Scytalone + NADP+
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the enzyme is involved in the pentaketide pathway of melanin and flaviolin and 2-HJ
-
-
?
1,3,6,8-tetrahydroxynaphthalene + NADPH + H+
scytalone + NADP+
-
reduction reaction via the via the 3-keto tautomer of 1,3,6,8-tetrahydroxynaphthalene
-
-
?
1,3,6,8-tetrahydroxynaphthalene + NADPH + H+
scytalone + NADP+
-
with enatiomeric excess of over 95%, reduction reaction via the via the 3-oxo tautomer of 1,3,6,8-tetrahydroxynaphthalene
-
-
?
1,3,8-trihydroxynaphthalene + NADPH + H+
vermelone + NADP+
-
-
-
?
1,3,8-trihydroxynaphthalene + NADPH + H+
vermelone + NADP+
-
-
-
-
?
1,3,8-trihydroxynaphthalene + NADPH + H+
vermelone + NADP+
-
-
-
-
?
1,3,8-trihydroxynaphthalene + NADPH + H+
vermelone + NADP+
-
the enzyme is an essential enzyme in the biosynthesis of fungal melanin
-
-
?
1,3,8-trihydroxynaphthalene + NADPH + H+
vermelone + NADP+
-
the enzyme is an essential enzyme in the biosynthesis of fungal melanin, DHN type melanin biosynthetic pathway
-
-
?
1,3,8-trihydroxynaphthalene + NADPH + H+
vermelone + NADP+
-
theoretical studies on energies of 1,3,6,8-trihydroxynaphthalene conformer stability, its tautomeric forms and their rotamers, by different methods, overview
-
-
?
1,3,8-trihydroxynaphthalene + NADPH + H+
vermelone + NADP+
-
1,3,8-trihydroxynaphthalene rapidly autooxidizes
-
-
?
1,3,8-trihydroxynaphthalene + NADPH + H+
vermelone + NADP+
-
ordered sequential mechanism with nucleotide binding first and leaving last
-
-
?
1,3,8-trihydroxynaphthalene + NADPH + H+
vermelone + NADP+
-
specific for NADPH
-
-
?
2,3-Dihydro-2,5-dihydroxy-4H-benzopyran-4-one + NADP+
4,5-Dihydroxy-2H-benzopyran-2-one + NADPH
-
-
-
-
?
2,3-Dihydro-2,5-dihydroxy-4H-benzopyran-4-one + NADP+
4,5-Dihydroxy-2H-benzopyran-2-one + NADPH
-
ir
-
?
2,3-Dihydro-2,5-dihydroxy-4H-benzopyran-4-one + NADP+
4,5-Dihydroxy-2H-benzopyran-2-one + NADPH
-
substrate and product are stable in aerated aqueous solution
-
?
additional information
?
-
no substrates: menadione, plumbagin, 2-methoxy-1,4-naphthoquinone, 2-methoxyjuglone, 2-hydroxy-3-methyl-1,4-naphthoquinone
-
-
-
additional information
?
-
-
no substrates: menadione, plumbagin, 2-methoxy-1,4-naphthoquinone, 2-methoxyjuglone, 2-hydroxy-3-methyl-1,4-naphthoquinone
-
-
-
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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
1,3,6,8-tetrahydroxynaphthalene + NADPH + H+
scytalone + NADP+
-
reduction reaction via the via the 3-keto tautomer of 1,3,6,8-tetrahydroxynaphthalene
-
-
?
1,3,6,8-Tetrahydroxynaphthalene + NADPH
Scytalone + NADP+
-
the enzyme is involved in melanin biosynthesis and pathogenicity
-
-
?
1,3,6,8-Tetrahydroxynaphthalene + NADPH
Scytalone + NADP+
-
involved in the biosynthesis of melanin
-
-
?
1,3,6,8-Tetrahydroxynaphthalene + NADPH
Scytalone + NADP+
-
the enzyme is an essential enzyme in the biosynthesis of fungal melanin, DHN type melanin biosynthetic pathway
-
-
?
1,3,6,8-Tetrahydroxynaphthalene + NADPH
Scytalone + NADP+
-
the enzyme is involved in the post-aromatic deoxygenation process of fungal melanin and pigments
-
-
?
1,3,6,8-Tetrahydroxynaphthalene + NADPH
Scytalone + NADP+
-
essential reaction in the biosynthesis of melanin
-
-
?
1,3,6,8-Tetrahydroxynaphthalene + NADPH
Scytalone + NADP+
-
the enzyme is involved in the biosynthesis of melanin
-
-
?
1,3,6,8-Tetrahydroxynaphthalene + NADPH
Scytalone + NADP+
-
the enzyme is involved in the pentaketide pathway of melanin and flaviolin and 2-HJ
-
-
?
1,3,8-trihydroxynaphthalene + NADPH + H+
vermelone + NADP+
-
the enzyme is an essential enzyme in the biosynthesis of fungal melanin
-
-
?
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COFACTOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
NADPH
-
coenzyme specificity is partly conferred by the interaction of a single basic residue, Arg39, with the 2' phosphate group of NADPH
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INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
1,3,8-Trihydroxynaphthalene
-
competitive to 1,3,6,8-tetrahydroxynaphthalene
1-[(Z)-2-bromo-2-nitroethenyl]-3-fluorobenzene
high in vivo activities against Magnaporthe oryzae, EC50 9.5 ppm
1-[(Z)-2-bromo-2-nitroethenyl]-4-ethylbenzene
beta-nitrostyrene compound highest inhibitory activity among compounds analyzed
5-methyl-(1,2,4)-triazolo[3,4-b]benzothiazole
-
tricyclazole, specific inhibitor of 3HNR
2,3-Dihydro-2,5-dihydroxy-4H-benzopyran-4-one
-
DDBO, an artificial substrate, chemical synthesis method development, overview
2,3-Dihydro-2,5-dihydroxy-4H-benzopyran-4-one
-
activity of the holoenzyme is inhibited by high substrate concentrations. Apigenin prevents the substrate inhibition at high substrate concentrations
apigenin
-
acts as competititive inhibitor of 3HNR, inhibits by 90%. The inhibitor is stacked between the phenol ring of Tyr208 and the coenzyme nicotinamide moiety, forming two Hbonds with Ser149 and Ser228, and Ser149 and Tyr163, respectively. It affects fungal pigmentation and growth
apigenin
-
strong inhibition of 3HNR by apigenin at low 2,3-dihydro-2,5-dihydroxy-4H-benzopyran-4-one concentrations and a steep increase of the activity at higher 2,3-dihydro-2,5-dihydroxy-4H-benzopyran-4-one concentrations
Biochanin A
-
acts as competititive inhibitor of 3HNR. The inhibitor is stacked between the phenol ring of Tyr208 and the coenzyme nicotinamide moiety, forming two Hbonds with Ser149 and Ser228, and Ser149 and Tyr163, respectively
Tricyclazole
determination of sensitivity to tricyclazole of 129 single-conidial isolates of rice blast fungus Magnaporthe grisea. Sensitivities of GY-6 and DY-2, the most sensitive isolates, to tricyclazole are both unstable in sub-cultured single-conidial offspring isolates, with respective mean EC50 values of 5.40 and 4.50 mg/l calculated from seedling tests. There is no amino acid difference between them in the coding sequences of 1,3,6,8-tetrahydroxynaphthalene reductase and 1,3,8-trihydroxynaphthalene reductase among the isolates
Tricyclazole
-
binds at the active site in the vicinity of the NADPH nicotinamide ring
Tricyclazole
-
noncompetitive with respect to 1,3,6,8-tetrahydroxynaphthalene, uncompetitive with respect to 1,3,8-trihydroxynaphthalene
additional information
-
the effect of melanin inhibitors on the enzyme activity can be used to predict their effect in preventing rice blast disease
-
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DISEASE
TITLE OF PUBLICATION
LINK TO PUBMED
tetrahydroxynaphthalene reductase deficiency
Isolation and characterisation of Gaeumannomyces graminis var. graminis melanin mutants.
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.025 - 0.033
NADP+
-
with 2,3-dihydro-2,5-dihydroxy-4H-benzopyran-4-one as cosubstrate
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TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.01
7,4'-Dihydroxyflavone
-
at 0.04 mM 2,3-dihydro-2,5-dihydroxy-4H-benzopyran-4-one, at pH 7.0 and 25°C
0.0054
baicalein
-
at 0.04 mM 2,3-dihydro-2,5-dihydroxy-4H-benzopyran-4-one, at pH 7.0 and 25°C
0.0054
Biochanin A
-
at 0.04 mM 2,3-dihydro-2,5-dihydroxy-4H-benzopyran-4-one, at pH 7.0 and 25°C
0.0081
chrysoeriol
-
at 0.04 mM 2,3-dihydro-2,5-dihydroxy-4H-benzopyran-4-one, at pH 7.0 and 25°C
0.025
flavone
-
at 0.04 mM 2,3-dihydro-2,5-dihydroxy-4H-benzopyran-4-one, at pH 7.0 and 25°C
0.012
naringenin
-
at 0.04 mM 2,3-dihydro-2,5-dihydroxy-4H-benzopyran-4-one, at pH 7.0 and 25°C
0.012
quercetin
-
at 0.04 mM 2,3-dihydro-2,5-dihydroxy-4H-benzopyran-4-one, at pH 7.0 and 25°C
0.0068
scutellarein
-
at 0.04 mM 2,3-dihydro-2,5-dihydroxy-4H-benzopyran-4-one, at pH 7.0 and 25°C
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IC50 VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.00058
1-[(Z)-2-bromo-2-nitroethenyl]-3-fluorobenzene
Pyricularia oryzae
pH 7.0, 30°C
0.025
3,7-dihydroxyflavone
Curvularia lunata
-
at 0.04 mM 2,3-dihydro-2,5-dihydroxy-4H-benzopyran-4-one
0.025
3-hydroxyflavone
Curvularia lunata
-
at 0.04 mM 2,3-dihydro-2,5-dihydroxy-4H-benzopyran-4-one
0.025
5-hydroxyflavone
Curvularia lunata
-
at 0.04 mM 2,3-dihydro-2,5-dihydroxy-4H-benzopyran-4-one
0.025
5-methoxyflavone
Curvularia lunata
-
at 0.04 mM 2,3-dihydro-2,5-dihydroxy-4H-benzopyran-4-one
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 25°C
0.0049
acacetin
Curvularia lunata
-
at 0.04 mM 2,3-dihydro-2,5-dihydroxy-4H-benzopyran-4-one, at pH 7.0 and 25°C
0.012
baicalein
Curvularia lunata
-
at 0.04 mM 2,3-dihydro-2,5-dihydroxy-4H-benzopyran-4-one, at pH 7.0 and 25°C
0.018
chrysoeriol
Curvularia lunata
-
at 0.04 mM 2,3-dihydro-2,5-dihydroxy-4H-benzopyran-4-one, at pH 7.0 and 25°C
0.0057
diosmetin
Curvularia lunata
-
at 0.04 mM 2,3-dihydro-2,5-dihydroxy-4H-benzopyran-4-one, at pH 7.0 and 25°C
0.055
flavone
Curvularia lunata
-
at 0.04 mM 2,3-dihydro-2,5-dihydroxy-4H-benzopyran-4-one, at pH 7.0 and 25°C
0.026
quercetin
Curvularia lunata
-
at 0.04 mM 2,3-dihydro-2,5-dihydroxy-4H-benzopyran-4-one, at pH 7.0 and 25°C
0.015
scutellarein
Curvularia lunata
-
at 0.04 mM 2,3-dihydro-2,5-dihydroxy-4H-benzopyran-4-one, at pH 7.0 and 25°C
0.0058