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Information on EC 1.1.1.252 - tetrahydroxynaphthalene reductase
for references in articles please use BRENDA:EC1.1.1.252
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EC Tree 1 Oxidoreductases
1.1 Acting on the CH-OH group of donors
1.1.1 With NAD+ or NADP+ as acceptor
1.1.1.252 tetrahydroxynaphthalene reductase
IUBMB 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.
The expected taxonomic range for this enzyme is: Eukaryota, Bacteria
- 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
showSynonyms
thnr, trihydroxynaphthalene reductase, 1,3,8-trihydroxynaphthalene reductase, tetrahydroxynaphthalene reductase, naphthol reductase, t4hnr, hydroxynaphthalene reductase, t4hn reductase, 1,3,6,8-tetrahydroxynaphthalene reductase, more
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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
LITERATURE
COMMENTARY
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+
Substrates: -
Products: -
Products: -
?
1,3,6,8-tetrahydroxynaphthalene + NADPH + H+
(R)-scytalone + NADP+
-
Substrates: -
Products: -
Products: -
?
1,3,6-trihydroxynaphthalene + NADPH + H+
(R)-8-deoxyscytalone + NADP+
-
Substrates: -
Products: -
Products: -
?
1,3-dihydroxynaphthalene + NADPH + H+
3-hydroxy-3,4-dihydronaphthalen-1(2H)-one + NADP+
-
Substrates: very low activity
Products: -
Products: -
?
1,4-androstadiene-3,17-dione + NADPH + H+
? + NADP+
-
Substrates: poor substrate of 3HNR
Products: -
Products: -
?
1-(1,6,8-trihydroxy-3-methylnaphthalen-2-yl)ethan-1-one + NADPH + H+
? + NADP+
Substrates: -
Products: -
Products: -
?
1-(1,8-dihydroxy-3-methylnaphthalen-2-yl)ethan-1-one + NADPH + H+
? + NADP+
Substrates: -
Products: -
Products: -
?
1-(3,6,8-trihydroxy-1-methylnaphthalen-2-yl)ethan-1-one + NADPH + H+
? + NADP+
Substrates: -
Products: -
Products: -
?
2,(5alpha)-androstene-17-one + NADPH + H+
? + NADP+
-
Substrates: -
Products: -
Products: -
?
2,3-Dihydro-2,5-dihydroxy-4H-benzopyran-4-one + NAD+
?
-
Substrates: -
Products: -
Products: -
?
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+
-
Substrates: -
Products: -
Products: -
?
2,3-dihydronaphthalene-1,4-dione + NADPH + H+
(4S)-4-hydroxy-3,4-dihydronaphthalen-1(2H)-one + NADP+
-
Substrates: -
Products: 21% yield, 98% enantiomeric excess
Products: 21% yield, 98% enantiomeric excess
?
2,8-dihydroxynaphthalene-1,4-dione + NADPH + H+
(2S)-2,8-dihydroxy-2,3-dihydronaphthalene-1,4-dione + NADP+
Substrates: -
Products: -
Products: -
?
2-hydroxyjuglone + NADPH + H+
(3S,4R)-3,4,8-trihydroxy-1-tetralone + NADP+
Substrates: -
Products: -
Products: -
?
2-methylcyclohexanone + NADPH + H+
trans-2-methylcyclohexanol + NADP+
-
Substrates: -
Products: -
Products: -
?
2-tetralone + NADPH + H+
2-tetralol + NADP+
-
Substrates: high activity, almost complete conversion
Products: -
Products: -
?
3,4-dihydronaphthalen-2(1H)-one + NADPH + H+
(2S)-1,2,3,4-tetrahydronaphthalen-2-ol + NADP+
-
Substrates: -
Products: 77% yield, 61% enantiomeric excess
Products: 77% yield, 61% enantiomeric excess
?
4-androstene-3,17-dione + NADPH + H+
? + NADP+
-
Substrates: poor substrate of 3HNR
Products: -
Products: -
?
4-estrene-3,17-dione + NADPH + H+
? + NADP+
-
Substrates: poor substrate of 3HNR
Products: -
Products: -
?
5-androstene-3beta-ol-17-one + NADPH + H+
? + NADP+
-
Substrates: -
Products: -
Products: -
?
5-hydroxy-2,3-dihydronaphthalene-1,4-dione + NADPH + H+
(4S)-4,8-dihydroxy-3,4-dihydronaphthalen-1(2H)-one + NADP+
-
Substrates: -
Products: 9% yield, 95% enantiomeric excess
Products: 9% yield, 95% enantiomeric excess
?
5-hydroxy-2-tetralone + NADPH + H+
5-hydroxy-2-tetralol + NADP+
-
Substrates: -
Products: -
Products: -
?
5-methoxy-2-tetralone + NADPH + H+
5-methoxy-2-tetralol + NADP+
-
Substrates: high activity, almost complete conversion
Products: -
Products: -
?
5alpha-androstane-3,17-dione + NADPH + H+
? + NADP+
-
Substrates: best steroid substrate for 3HNR
Products: -
Products: -
?
5alpha-androstane-3-one + NADPH + H+
? + NADP+
-
Substrates: -
Products: -
Products: -
?
5alpha-androstane-3alpha-ol-17-one + NADPH + H+
? + NADP+
-
Substrates: -
Products: -
Products: -
?
5alpha-androstane-3beta-ol-17-one + NADPH + H+
? + NADP+
-
Substrates: -
Products: -
Products: -
?
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+
Substrates: -
Products: -
Products: -
?
6-acetyl-2-hydroxy-5,7-dimethyl-4a,8a-dihydronaphthalene-1,4-dione + NADPH + H+
? + NADP+
Substrates: -
Products: -
Products: -
?
6-hydroxy-2-tetralone + NADPH + H+
6-hydroxy-2-tetralol + NADP+
-
Substrates: -
Products: -
Products: -
?
6-methoxy-2-tetralone + NADPH + H+
6-methoxy-2-tetralol + NADP+
-
Substrates: -
Products: -
Products: -
?
6-methoxy-3,4-dihydronaphthalen-2(1H)-one + NADPH + H+
(2S)-6-methoxy-1,2,3,4-tetrahydronaphthalen-2-ol + NADP+
-
Substrates: -
Products: 71% yield, 99% enantiomeric excess
Products: 71% yield, 99% enantiomeric excess
?
7-hydroxy-2-tetralone + NADPH + H+
7-hydroxy-2-tetralol + NADP+
-
Substrates: high activity, almost complete conversion
Products: -
Products: -
?
7-methoxy-2-tetralone + NADPH + H+
7-methoxy-2-tetralol + NADP+
-
Substrates: high activity, almost complete conversion
Products: -
Products: -
?
8-hydroxy-2-tetralone + NADPH + H+
8-hydroxy-2-tetralol + NADP+
-
Substrates: high activity, almost complete conversion
Products: -
Products: -
?
8-methoxy-2-tetralone + NADPH + H+
8-methoxy-2-tetralol + NADP+
-
Substrates: high activity, almost complete conversion
Products: -
Products: -
?
8-methoxy-3,4-dihydronaphthalen-2(1H)-one + NADPH + H+
(2R)-8-methoxy-1,2,3,4-tetrahydronaphthalen-2-ol + NADP+
-
Substrates: -
Products: 75% yield, 99% enantiomeric excess
Products: 75% yield, 99% enantiomeric excess
?
lawsone + 2 NADPH + 2 H+
(3S,4R)-3,4-dihydroxy-1-tetralone + 2 NADP+
Substrates: -
Products: -
Products: -
?
1,3,6,8-Tetrahydroxynaphthalene + NADPH
Scytalone + NADP+
-
Substrates: the enzyme is involved in melanin biosynthesis and pathogenicity
Products: -
Products: -
?
1,3,6,8-Tetrahydroxynaphthalene + NADPH
Scytalone + NADP+
-
Substrates: involved in the biosynthesis of melanin
Products: -
Products: -
?
1,3,6,8-Tetrahydroxynaphthalene + NADPH
Scytalone + NADP+
-
Substrates: -
Products: -
Products: -
?
1,3,6,8-Tetrahydroxynaphthalene + NADPH
Scytalone + NADP+
-
Substrates: the enzyme is an essential enzyme in the biosynthesis of fungal melanin, DHN type melanin biosynthetic pathway
Products: -
Products: -
?
1,3,6,8-Tetrahydroxynaphthalene + NADPH
Scytalone + NADP+
-
Substrates: -
Products: -
Products: -
?
1,3,6,8-Tetrahydroxynaphthalene + NADPH
Scytalone + NADP+
-
Substrates: -
Products: -
Products: -
?
1,3,6,8-Tetrahydroxynaphthalene + NADPH
Scytalone + NADP+
-
Substrates: the enzyme is involved in the post-aromatic deoxygenation process of fungal melanin and pigments
Products: -
Products: -
?
1,3,6,8-Tetrahydroxynaphthalene + NADPH
Scytalone + NADP+
-
Substrates: -
Products: -
Products: -
?
1,3,6,8-Tetrahydroxynaphthalene + NADPH
Scytalone + NADP+
-
Substrates: -
Products: r
Products: r
?
1,3,6,8-Tetrahydroxynaphthalene + NADPH
Scytalone + NADP+
-
Substrates: -
Products: -
Products: -
?
1,3,6,8-Tetrahydroxynaphthalene + NADPH
Scytalone + NADP+
-
Substrates: essential reaction in the biosynthesis of melanin
Products: -
Products: -
?
1,3,6,8-Tetrahydroxynaphthalene + NADPH
Scytalone + NADP+
-
Substrates: the enzyme is involved in the biosynthesis of melanin
Products: -
Products: -
?
1,3,6,8-Tetrahydroxynaphthalene + NADPH
Scytalone + NADP+
-
Substrates: -
Products: -
Products: -
?
1,3,6,8-Tetrahydroxynaphthalene + NADPH
Scytalone + NADP+
-
Substrates: r
Products: -
Products: -
?
1,3,6,8-Tetrahydroxynaphthalene + NADPH
Scytalone + NADP+
-
Substrates: spefific for NADPH
Products: -
Products: -
?
1,3,6,8-Tetrahydroxynaphthalene + NADPH
Scytalone + NADP+
-
Substrates: the enzyme is involved in the pentaketide pathway of melanin and flaviolin and 2-HJ
Products: -
Products: -
?
1,3,6,8-tetrahydroxynaphthalene + NADPH + H+
scytalone + NADP+
-
Substrates: reduction reaction via the via the 3-keto tautomer of 1,3,6,8-tetrahydroxynaphthalene
Products: -
Products: -
?
1,3,6,8-tetrahydroxynaphthalene + NADPH + H+
scytalone + NADP+
-
Substrates: with enatiomeric excess of over 95%, reduction reaction via the via the 3-oxo tautomer of 1,3,6,8-tetrahydroxynaphthalene
Products: -
Products: -
?
1,3,8-trihydroxynaphthalene + NADPH + H+
vermelone + NADP+
-
Substrates: -
Products: -
Products: -
?
1,3,8-trihydroxynaphthalene + NADPH + H+
vermelone + NADP+
-
Substrates: the enzyme is an essential enzyme in the biosynthesis of fungal melanin
Products: -
Products: -
?
1,3,8-trihydroxynaphthalene + NADPH + H+
vermelone + NADP+
-
Substrates: -
Products: -
Products: -
?
1,3,8-trihydroxynaphthalene + NADPH + H+
vermelone + NADP+
-
Substrates: the enzyme is an essential enzyme in the biosynthesis of fungal melanin, DHN type melanin biosynthetic pathway
Products: -
Products: -
?
1,3,8-trihydroxynaphthalene + NADPH + H+
vermelone + NADP+
-
Substrates: theoretical studies on energies of 1,3,6,8-trihydroxynaphthalene conformer stability, its tautomeric forms and their rotamers, by different methods, overview
Products: -
Products: -
?
1,3,8-trihydroxynaphthalene + NADPH + H+
vermelone + NADP+
-
Substrates: -
Products: -
Products: -
?
1,3,8-trihydroxynaphthalene + NADPH + H+
vermelone + NADP+
-
Substrates: -
Products: -
Products: -
?
1,3,8-trihydroxynaphthalene + NADPH + H+
vermelone + NADP+
-
Substrates: r
Products: -
Products: -
?
1,3,8-trihydroxynaphthalene + NADPH + H+
vermelone + NADP+
-
Substrates: 1,3,8-trihydroxynaphthalene rapidly autooxidizes
Products: -
Products: -
?
1,3,8-trihydroxynaphthalene + NADPH + H+
vermelone + NADP+
-
Substrates: ordered sequential mechanism with nucleotide binding first and leaving last
Products: -
Products: -
?
1,3,8-trihydroxynaphthalene + NADPH + H+
vermelone + NADP+
-
Substrates: -
Products: -
Products: -
?
1,3,8-trihydroxynaphthalene + NADPH + H+
vermelone + NADP+
-
Substrates: specific for NADPH
Products: -
Products: -
?
1,3,8-trihydroxynaphthalene + NADPH + H+
vermelone + NADP+
-
Substrates: -
Products: -
Products: -
?
2,3-Dihydro-2,5-dihydroxy-4H-benzopyran-4-one + NADP+
4,5-Dihydroxy-2H-benzopyran-2-one + NADPH
-
Substrates: ir
Products: -
Products: -
?
2,3-Dihydro-2,5-dihydroxy-4H-benzopyran-4-one + NADP+
4,5-Dihydroxy-2H-benzopyran-2-one + NADPH
-
Substrates: substrate and product are stable in aerated aqueous solution
Products: -
Products: -
?
2,3-Dihydro-2,5-dihydroxy-4H-benzopyran-4-one + NADP+
4,5-Dihydroxy-2H-benzopyran-2-one + NADPH
-
Substrates: -
Products: -
Products: -
?
additional information
?
-
-
Substrates: no activity with estrone
Products: -
Products: -
?
additional information
?
-
Substrates: no substrates: menadione, plumbagin, 2-methoxy-1,4-naphthoquinone, 2-methoxyjuglone, 2-hydroxy-3-methyl-1,4-naphthoquinone
Products: -
Products: -
?
additional information
?
-
-
Substrates: no substrates: menadione, plumbagin, 2-methoxy-1,4-naphthoquinone, 2-methoxyjuglone, 2-hydroxy-3-methyl-1,4-naphthoquinone
Products: -
Products: -
?
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NATURAL SUBSTRATE
NATURAL PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
LITERATURE
COMMENTARY
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
1,3,6,8-tetrahydroxynaphthalene + NADPH + H+
scytalone + NADP+
-
Substrates: reduction reaction via the via the 3-keto tautomer of 1,3,6,8-tetrahydroxynaphthalene
Products: -
Products: -
?
1,3,6,8-Tetrahydroxynaphthalene + NADPH
Scytalone + NADP+
-
Substrates: the enzyme is involved in melanin biosynthesis and pathogenicity
Products: -
Products: -
?
1,3,6,8-Tetrahydroxynaphthalene + NADPH
Scytalone + NADP+
-
Substrates: involved in the biosynthesis of melanin
Products: -
Products: -
?
1,3,6,8-Tetrahydroxynaphthalene + NADPH
Scytalone + NADP+
-
Substrates: the enzyme is an essential enzyme in the biosynthesis of fungal melanin, DHN type melanin biosynthetic pathway
Products: -
Products: -
?
1,3,6,8-Tetrahydroxynaphthalene + NADPH
Scytalone + NADP+
-
Substrates: the enzyme is involved in the post-aromatic deoxygenation process of fungal melanin and pigments
Products: -
Products: -
?
1,3,6,8-Tetrahydroxynaphthalene + NADPH
Scytalone + NADP+
-
Substrates: essential reaction in the biosynthesis of melanin
Products: -
Products: -
?
1,3,6,8-Tetrahydroxynaphthalene + NADPH
Scytalone + NADP+
-
Substrates: the enzyme is involved in the biosynthesis of melanin
Products: -
Products: -
?
1,3,6,8-Tetrahydroxynaphthalene + NADPH
Scytalone + NADP+
-
Substrates: the enzyme is involved in the pentaketide pathway of melanin and flaviolin and 2-HJ
Products: -
Products: -
?
1,3,8-trihydroxynaphthalene + NADPH + H+
vermelone + NADP+
-
Substrates: the enzyme is an essential enzyme in the biosynthesis of fungal melanin
Products: -
Products: -
?
1,3,8-trihydroxynaphthalene + NADPH + H+
vermelone + NADP+
-
Substrates: -
Products: -
Products: -
?
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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
5,7-dihydroxyflavone
Curvularia lunata
-
at 0.04 mM 2,3-dihydro-2,5-dihydroxy-4H-benzopyran-4-one
0.0058
5,7-dihydroxyflavone
Curvularia lunata
-
at 0.04 mM 2,3-dihydro-2,5-dihydroxy-4H-benzopyran-4-one, at pH 7.0 and 25°C
0.0031
apigenin
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
Biochanin A
Curvularia lunata
-
at 0.04 mM 2,3-dihydro-2,5-dihydroxy-4H-benzopyran-4-one
0.012
Biochanin A
Curvularia lunata
-
at 0.04 mM 2,3-dihydro-2,5-dihydroxy-4H-benzopyran-4-one, at pH 7.0 and 25°C
0.0079
kaempferol
Curvularia lunata
-
at 0.04 mM 2,3-dihydro-2,5-dihydroxy-4H-benzopyran-4-one
0.0079
kaempferol
Curvularia lunata
-
at 0.04 mM 2,3-dihydro-2,5-dihydroxy-4H-benzopyran-4-one, at pH 7.0 and 25°C
0.0068
luteolin
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
naringenin
Curvularia lunata
-
at 0.04 mM 2,3-dihydro-2,5-dihydroxy-4H-benzopyran-4-one
0.026
naringenin
Curvularia lunata
-
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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SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
11
-
2,3-dihydro-2,5-dihydroxy-4H-benzopyran-4-one converted by the recombinant protein
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pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
8 - 9
-
optimal pH for oxidation of 2,3-dihydro-2,5-dihydroxy-4H-benzopyran-4-one
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pH RANGE
ORGANISM
UNIPROT
COMMENTARY
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
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TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
25 - 30
-
optimal temperature for oxidation of 2,3-dihydro-2,5-dihydroxy-4H-benzopyran-4-one
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ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
Highest Expressing Human Cell Lines
Cell Line LinksPlease wait a moment until the data is sorted. This message will disappear when the data is sorted.
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
evolution
-
the enzyme is a member of the short-chain dehydrogenase/reductase (SDR) family of enzymes
metabolism
-
the enzyme catalyzes a step in 1,8-dihydroxynaphthalene-melanin biosynthesis, overview
physiological function
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
physiological function
-
enzyme-deficient mutants produce orange-brown or green-brown spore suspensions compared with the black spore suspension of the wild-type strain
physiological function
-
expression of genes CHS1, BdsA, and BdsB is necessary and sufficient for the production of 1,8-dihydroxynaphthalene in a heterologous host. Polyketide synthase CHS1 catalyzes the synthesis of 1,3,6,8-tetrahydroxynaphthalene (T4HN) in vitro. T4HN is converted to 1,8-dihydroxynaphthalene by successive steps of reduction and dehydration, which are catalyzed by BdsA and BdsB. BdsA catalyzes the reduction of T4HN and 1,3,8-trihydroxynaphthalene (T3HN) to scytalone and vermelone, respectively. T4HN reduction by BdsA occurs on the si-face to give (R)-scytalone with more than 99% optical purity
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UNIPROT
ENTRY NAME
ORGANISM
NO. OF AA
NO. OF TRANSM. HELICES
MOLECULAR WEIGHT[Da]
SOURCE
SEQUENCE
LOCALIZATION PREDICTION
The reliability class of the localization prediction ranges from 1 (very reliable) to 5 (not reliable).
The reliability class of the localization prediction ranges from 1 (very reliable) to 5 (not reliable). T4HR_ZYMTI
Zymoseptoria tritici (strain CBS 115943 / IPO323)
267
0
28465
Swiss-Prot
-
T4HR_PYRO7
Pyricularia oryzae (strain 70-15 / ATCC MYA-4617 / FGSC 8958)
283
0
30054
Swiss-Prot
-
PFMAG_PESFW
Pestalotiopsis fici (strain W106-1 / CGMCC3.15140)
277
0
29271
Swiss-Prot
other Location (Reliability: 2)
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PDB
SCOP
CATH
UNIPROT
ORGANISM
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MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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SUBUNIT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
tetramer
additional information
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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
-
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PROTEIN VARIANTS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
additional information
-
generation of the C-terminally Ile274-truncated variant T4HNR(1-273)
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STORAGE STABILITY
ORGANISM
UNIPROT
LITERATURE
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PURIFICATION (Commentary)
ORGANISM
UNIPROT
LITERATURE
recombinant GST-tagged enzyme from Escherichia coli by glutathione affinity chromatography
-
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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
-
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APPLICATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
agriculture
drug development
medicine
-
development of a monoclonal antibody to be used in combination with a semiselective isolation procedure in order to track the opportunistic pathogen Scedosporium apiospermum in environmental samples containing mixed populations of human pathogenic fungi
agriculture
-
the effect of melanin inhibitors on the enzyme activity can be used to predict their effect in preventing rice blast disease
agriculture
loss of efficacy of tricyclazole for the control of rice blast disease in the field is not due to resistance to tricyclazole
drug development
-
the enzyme represents a target for the development of fungicides and antimicotics
drug development
-
flavonoids inhibit 3HNR, which can thus be considered a potential target for flavonoid action. In addition to being a known target for different fungicides, 3HNR can also serve as an interesting and novel target for the development of antimycotics
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REF.
AUTHORS
TITLE
JOURNAL
VOL.
PAGES
YEAR
ORGANISM (UNIPROT)
PUBMED ID
SOURCE
Wheeler, M.H.; Greenblatt, G.A.
The inhibition of melanin biosynthetic reactions in Pyricularia oryzae by compounds that prevent rice blast disease
Exp. Mycol.
12
151-160
1988
Pyricularia oryzae
-
brenda
Vidal-Cros, A.; Viviani, F.; Labesse, G.; Boccara, M.; Gaudry, M.
Polyhydroxynaphthalene reductase involved in melanin biosynthesis in Magnaporthe grisea. Purification, cDNA cloning and sequencing
Eur. J. Biochem.
219
985-992
1994
Pyricularia grisea
brenda
Thompson, J.E.; Basarab, G.S.; Andersson, A.; Lindqvist, Y.; Jordan, D.B.
Trihydroxynaphthalene reductase from Magnaporthe grisea: realization of an active center inhibitor and elucidation of the kinetic mechanism
Biochemistry
36
1852-1860
1997
Pyricularia grisea
brenda
Andersson, A.; Jordan, D.; Schneider, G.; Valent, B.; Lindqvist, Y.
Crystallization and preliminary X-ray diffraction study of 1,3,8-trihydroxynaphthalene reductase from Magnaporthe grisea
Proteins Struct. Funct. Genet.
24
525-527
1996
Pyricularia grisea
brenda
Perpetua, N.S.; Kubo, Y.; Yasuda, N.; Takano, Y.; Furusawa, I.
Cloning and characterization of a melanin biosynthetic THR1 reductase gene essential for appressorial penetration of Colletotrichum lagenarium
Mol. Plant Microbe Interact.
9
323-329
1996
Colletotrichum lagenaria
brenda
Ichinose, K.; Kiyono, J.; Ebizuka, Y.; Sankawa, U.
Post-aromatic deoxygenation in polyketide biosynthesis: reduction of aromatic rings in the biosynthesis of fungal melanin and anthraquinone
Chem. Pharm. Bull.
41
2015-2021
1993
Phialocephala lagerbergii
brenda
Viviani, F.; Vors, J.P.; Gaudry, M.; Marquet, A.
Deoxygenation of polyphenols by ascomycetes: kinetic behavior of the NADPH-dependent naphthol dehydrogenase and inhibition by tricyclazole and its analogues
Bull. Soc. Chim. Fr.
130
395-404
1993
Pyricularia oryzae
-
brenda
Andersson, A.; Jordan, D.; Schneider, G.; Lindqvist, Y.
Crystal structure of the ternary complex of 1,3,8-trihydroxynaphthalene reductase from Magnaporthe grisea with NADPH and an active-site inhibitor
Structure
4
1161-1170
1996
Pyricularia grisea
brenda
Thompson, J.E.; Basarab, G.S.; Pierce, J.; Hodge, C.N.; Jordan, D.B.
2,3-Dihydro-2,5-dihydroxy-4H-benzopyran-4-one: a nonphysiological substrate for fungal melanin biosynthetic enzymes
Anal. Biochem.
256
1-6
1998
Pyricularia grisea
brenda
Andersson, A.; Jordan, D.; Schneider, G.; Lindqvist, Y.
A flexible lid controls access to the active site in 1,3,8-trihydroxynaphthalene reductase
FEBS Lett.
400
173-176
1997
Pyricularia grisea
brenda
Tsuji, G.; Sugahara, T.; Fujii, I.; Mori, Y.; Ebizuka, Y.; Shiraishi, T.; Kubo, Y.
Evidence for involvement of two naphthol reductases in the first reduction step of melanin biosynthesis pathway of Colletotrichum lagenarium
Mycol. Res.
107
854-860
2003
Colletotrichum lagenaria
brenda
Brunskole, M.; Stefane, B.; Zorko, K.; Anderluh, M.; Stojan, J.; Lanisnik Rizner, T.; Gobec, S.
Towards the first inhibitors of trihydroxynaphthalene reductase from Curvularia lunata: Synthesis of artificial substrate, homology modelling and initial screening
Bioorg. Med. Chem.
16
5881-5889
2008
Curvularia lunata
brenda
Rostkowski, M.; Paneth, P.
Analysis of conformer stability for 1,3,8-trihydroxynaphthalene: natural substrate of fungal trihydroxynaphthalene reductase
J. Phys. Chem. B
111
8314-8320
2007
Fungi
brenda
Brunskole, M.; Zorko, K.; Kerbler, V.; Martens, S.; Stojan, J.; Gobec, S.; Lanisnik Rizner, T.
Trihydroxynaphthalene reductase of Curvularia lunata--a target for flavonoid action?
Chem. Biol. Interact.
178
259-267
2009
Curvularia lunata
brenda
Stojan, J.; Brunskole, M.; Rizner, T.
Simultaneous binding of coenzyme and two ligand molecules into the active site of fungal trihydroxynaphthalene reductase
Chem. Biol. Interact.
178
268-273
2009
Curvularia lunata
brenda
Kristan, K.; Brunskole, M.; Stojan, J.; Rizner, T.L.
Two homologous fungal carbonyl reductases with different substrate specificities
Chem. Biol. Interact.
178
295-302
2009
Curvularia lunata
brenda
Zhang, C.; Huang, X.; Wang, J.; Zhou, M.
Resistance development in rice blast disease caused by Magnaporthe grisea to tricyclazole
Pestic. Biochem. Physiol.
94
43-47
2009
Pyricularia grisea (Q9HFV6)
-
brenda
Schaetzle, M.A.; Flemming, S.; Husain, S.M.; Richter, M.; Guenther, S.; Mueller, M.
Tetrahydroxynaphthalene reductase: catalytic properties of an enzyme involved in reductive asymmetric naphthol dearomatization
Angew. Chem. Int. Ed. Engl.
51
2643-2646
2012
Pyricularia grisea
brenda
Chen, H.; Han, X.; Qin, N.; Wei, L.; Yang, Y.; Rao, L.; Chi, B.; Feng, L.; Ren, Y.; Wan, J.
Synthesis and biological evaluation of novel inhibitors against 1,3,8-trihydroxynaphthalene reductase from Magnaporthe grisea
Bioorg. Med. Chem.
24
1225-1230
2016
Pyricularia oryzae (Q12634), Pyricularia oryzae ATCC MYA-4617 (Q12634)
brenda
Conradt, D.; Schtzle, M.; Husain, S.; Mller, M.
Diversity in reduction with short-chain dehydrogenases: tetrahydroxynaphthalene reductase, trihydroxynaphthalene reductase, and glucose dehydrogenase
ChemCatChem
7
3116-3120
2015
Pyricularia oryzae
-
brenda
Thornton, C.R.; Ryder, L.S.; Le Cocq, K.; Soanes, D.M.
Identifying the emerging human pathogen Scedosporium prolificans by using a species-specific monoclonal antibody that binds to the melanin biosynthetic enzyme tetrahydroxynaphthalene reductase
Environ. Microbiol.
17
1023-1038
2015
Lomentospora prolificans
brenda
Sone, Y.; Nakamura, S.; Sasaki, M.; Hasebe, F.; Kim, S.; Funa, N.
Identification and characterization of bacterial enzymes catalyzing the synthesis of 1,8-dihydroxynaphthalene, a key precursor of dihydroxynaphthalene melanin, from Sorangium cellulosum
Appl. Environ. Microbiol.
84
e00258-18
2018
Sorangium cellulosum
brenda
Saha, N.; Mueller, M.; Husain, S.M.
Asymmetric synthesis of natural cis-dihydroarenediols using tetrahydroxynaphthalene reductase and its biosynthetic implications
Org. Lett.
21
2204-2208
2019
Pyricularia grisea (Q9HFV6), Pyricularia grisea
brenda
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