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Information on EC 1.14.13.64 - 4-hydroxybenzoate 1-hydroxylase
for references in articles please use BRENDA:EC1.14.13.64
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EC Tree 1 Oxidoreductases
1.14 Acting on paired donors, with incorporation or reduction of molecular oxygen
1.14.13 With NADH or NADPH as one donor, and incorporation of one atom of oxygen into the other donor
1.14.13.64 4-hydroxybenzoate 1-hydroxylase
IUBMB Comments
Requires FAD. The enzyme from Candida parapsilosis is specific for 4-hydroxybenzoate derivatives and prefers NADH to NADPH as electron donor.
The expected taxonomic range for this enzyme is: Saccharomycetales
- 1.14.13.64
- parapsilosis
- hydroquinone
- phenol
- flavoprotein
-
fad-dependent
-
glucosyltransferase
- shikimate
- arbutin
- 3-hydroxybenzoate
-
6-hydroxylase
- 1,4-dihydroxybenzene
- synthesis
- gentisate
- pharmacology
showSynonyms
4-hydroxybenzoate 1-hydroxylase, mnx1p, 4hb1h, 4-hydroxybenzoate 1-hydroxylase (decarboxylating), more
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SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
4-hydroxybenzoate 1-hydroxylase
4-hydroxybenzoate 1-hydroxylase (decarboxylating)
4-hydroxybenzoate 1-monooxygenase
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-
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4HB1H
Cp_4HB1H
FAD-dependent 4-hydroxybenzoate hydroxylase
MNX1
Mnx1p
Oxygenase, 4-hydroxybenzoate 1-mono
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-
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PHBH
4-hydroxybenzoate 1-hydroxylase (decarboxylating)
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-
-
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
4-hydroxybenzoate + NAD(P)H + H+ + O2 = hydroquinone + NAD(P)+ + H2O + CO2
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4-hydroxybenzoate + NAD(P)H + H+ + O2 = hydroquinone + NAD(P)+ + H2O + CO2
the conversion of 4-HB involves an ipso-attack of the electrophilic flavin C4a-hydroperoxide at the C1-atom of the activated substrate, resulting in a tetrahedral benzoquinone species and subsequent release of the carboxyl side chain. It cannot be excluded that His230 activates 4-HB in 4HB1H for ipso-attack by the flavin C4a-hydroperoxide. Furthermore, it can also not be ruled out that the substrate of 4HB1H binds in a flipped orientation with the 4-hydroxyl moiety pointing towards the side chains of Tyr116 and His118
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4-hydroxybenzoate + NAD(P)H + H+ + O2 = hydroquinone + NAD(P)+ + H2O + CO2
the conversion of 4-HB involves an ipso-attack of the electrophilic flavin C4a-hydroperoxide at the C1-atom of the activated substrate, resulting in a tetrahedral benzoquinone species and subsequent release of the carboxyl side chain. It cannot be excluded that His230 activates 4-HB in 4HB1H for ipso-attack by the flavin C4a-hydroperoxide. Furthermore, it can also not be ruled out that the substrate of 4HB1H binds in a flipped orientation with the 4-hydroxyl moiety pointing towards the side chains of Tyr116 and His118
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
oxidation
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reduction
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PATHWAY SOURCE
PATHWAYS
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SYSTEMATIC NAME
IUBMB Comments
4-hydroxybenzoate,NAD(P)H:oxygen oxidoreductase (1-hydroxylating, decarboxylating)
Requires FAD. The enzyme from Candida parapsilosis is specific for 4-hydroxybenzoate derivatives and prefers NADH to NADPH as electron donor.
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CAS REGISTRY NUMBER
COMMENTARY
134214-78-1
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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
2,3,5,6-Tetrafluoro-4-hydroxybenzoate + NADH + O2
?
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Substrates: -
Products: -
Products: -
?
2,3,5,6-Tetrafluoro-4-hydroxybenzoate + NADPH + O2
?
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Substrates: -
Products: -
Products: -
?
2,4-dihydroxybenzoate + NADPH + O2
1,2,4-trihydroxybenzene + NADP+ + CO2
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Substrates: -
Products: -
Products: -
?
2,5-Difluoro-4-hydroxybenzoate + NADH + O2
?
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Substrates: -
Products: -
Products: -
?
2,5-Difluoro-4-hydroxybenzoate + NADPH + O2
?
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Substrates: -
Products: -
Products: -
?
2,6-Difluoro-4-hydroxybenzoate + NADH + O2
?
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Substrates: -
Products: -
Products: -
?
2,6-Difluoro-4-hydroxybenzoate + NADPH + O2
?
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Substrates: -
Products: -
Products: -
?
2-fluoro-4-hydroxybenzoate + NADPH + O2
2-fluoro-1,4-dihydroxybenzene + NADP+ + CO2
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Substrates: -
Products: -
Products: -
?
3,4-Dihydroxybenzoate + NADH + O2
1,2,4-Trihydroxybenzene + NAD+ + CO2
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Substrates: -
Products: -
Products: -
?
3,4-Dihydroxybenzoate + NADPH + O2
1,2,4-Trihydroxybenzene + NADP+ + CO2
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Substrates: -
Products: -
Products: -
?
3,5-Difluoro-4-hydroxybenzoate + NADH + O2
?
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Substrates: -
Products: -
Products: -
?
3,5-Difluoro-4-hydroxybenzoate + NADPH + O2
?
-
Substrates: -
Products: -
Products: -
?
4-hydroxybenzoate + NAD(P)H + 2 H+ + O2
hydroquinone + NAD(P)+ + H2O + CO2
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Substrates: -
Products: -
Products: -
?
tetrafluoro-4-hydroxybenzoate + NAD(P)H + O2
2,3,5,6-tetrafluorohydroquinone + NAD(P)+ + CO2
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Substrates: -
Products: -
Products: -
?
2,4-dihydroxybenzoate + NAD(P)H + H+ + O2
benzene-1,2,4-triol + NAD(P)+ + H2O + CO2
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Substrates: -
Products: -
Products: -
?
2,4-dihydroxybenzoate + NAD(P)H + H+ + O2
benzene-1,2,4-triol + NAD(P)+ + H2O + CO2
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Substrates: -
Products: -
Products: -
?
2,4-Dihydroxybenzoate + NADH + O2
1,2,4-Trihydroxybenzene + NAD+ + CO2
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Substrates: -
Products: -
Products: -
?
2,4-Dihydroxybenzoate + NADH + O2
1,2,4-Trihydroxybenzene + NAD+ + CO2
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Substrates: -
Products: -
Products: -
?
2-chloro-4-hydroxybenzoate + NADH + O2
?
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Substrates: -
Products: -
Products: -
?
2-fluoro-4-hydroxybenzoate + NADH + O2
2-fluoro-1,4-dihydroxybenzene + NAD+ + CO2
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Substrates: -
Products: -
Products: -
?
2-fluoro-4-hydroxybenzoate + NADH + O2
2-fluoro-1,4-dihydroxybenzene + NAD+ + CO2
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Substrates: -
Products: -
Products: -
?
3,4-dihydroxybenzoate + NAD(P)H + H+ + O2
benzene-1,2,4-triol + NAD(P)+ + H2O + CO2
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Substrates: -
Products: -
Products: -
?
3,4-dihydroxybenzoate + NAD(P)H + H+ + O2
benzene-1,2,4-triol + NAD(P)+ + H2O + CO2
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Substrates: -
Products: -
Products: -
?
4-hydroxy-3-nitrobenzoate + NAD(P)H + O2
2-nitrobenzene-1,4-diol + NAD(P)+ + CO2
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Substrates: -
Products: -
Products: -
?
4-hydroxy-3-nitrobenzoate + NAD(P)H + O2
2-nitrobenzene-1,4-diol + NAD(P)+ + CO2
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Substrates: -
Products: -
Products: -
?
4-hydroxybenzoate + NAD(P)H + H+ + O2
hydroquinone + NAD(P)+ + H2O + CO2
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Substrates: -
Products: -
Products: -
?
4-hydroxybenzoate + NAD(P)H + H+ + O2
hydroquinone + NAD(P)+ + H2O + CO2
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Substrates: -
Products: -
Products: -
?
4-Hydroxybenzoate + NAD(P)H + O2
?
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Substrates: initial reaction of the catabolism of 4-hydroxybenzoate
Products: -
Products: -
?
4-Hydroxybenzoate + NAD(P)H + O2
?
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Substrates: the enzyme is induced when the yeast is grown on either 4-hydroxybenzoate, 2,3-dihydroxybenzoate, or 3,4-dihydroxybenzoate as the sole carbon source
Products: -
Products: -
?
4-Hydroxybenzoate + NAD(P)H + O2
?
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Substrates: initial reaction of the catabolism of 4-hydroxybenzoate
Products: -
Products: -
?
4-hydroxybenzoate + NADH + 2 H+ + O2
hydroquinone + NAD+ + H2O + CO2
Substrates: -
Products: -
Products: -
?
4-hydroxybenzoate + NADH + 2 H+ + O2
hydroquinone + NAD+ + H2O + CO2
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Substrates: -
Products: -
Products: -
?
4-hydroxybenzoate + NADH + 2 H+ + O2
hydroquinone + NAD+ + H2O + CO2
Substrates: -
Products: -
Products: -
?
4-hydroxybenzoate + NADH + 2 H+ + O2
hydroquinone + NAD+ + H2O + CO2
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Substrates: -
Products: -
Products: -
?
4-Hydroxybenzoate + NADH + O2
1,4-Dihydroxybenzene + NAD+ + CO2
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Substrates: -
Products: -
Products: -
?
4-Hydroxybenzoate + NADH + O2
1,4-Dihydroxybenzene + NAD+ + CO2
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Substrates: NADH is the preferred electron donor
Products: -
Products: -
?
4-Hydroxybenzoate + NADH + O2
1,4-Dihydroxybenzene + NAD+ + CO2
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Substrates: -
Products: -
Products: -
?
4-Hydroxybenzoate + NADH + O2
1,4-Dihydroxybenzene + NAD+ + CO2
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Substrates: NADH is the preferred electron donor
Products: -
Products: -
?
4-hydroxybenzoate + NADH + O2
hydroquinone + NAD+ + CO2
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Substrates: the enzyme prefers NADH over NADPH as electron donor
Products: -
Products: -
?
4-hydroxybenzoate + NADH + O2
hydroquinone + NAD+ + CO2
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Substrates: the enzyme prefers NADH over NADPH as electron donor
Products: -
Products: -
?
4-Hydroxybenzoate + NADPH + O2
1,4-Dihydroxybenzene + NADP+ + CO2
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Substrates: -
Products: -
Products: -
?
4-Hydroxybenzoate + NADPH + O2
1,4-Dihydroxybenzene + NADP+ + CO2
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Substrates: NADH is the preferred electron donor
Products: -
Products: -
?
4-Hydroxybenzoate + NADPH + O2
1,4-Dihydroxybenzene + NADP+ + CO2
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Substrates: -
Products: -
Products: -
?
4-Hydroxybenzoate + NADPH + O2
1,4-Dihydroxybenzene + NADP+ + CO2
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Substrates: NADH is the preferred electron donor
Products: -
Products: -
?
4-hydroxybenzoate + NADPH + O2
hydroquinone + NADP+ + CO2
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Substrates: the enzyme prefers NADH over NADPH as electron donor
Products: -
Products: -
?
4-hydroxybenzoate + NADPH + O2
hydroquinone + NADP+ + CO2
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Substrates: the enzyme prefers NADH over NADPH as electron donor
Products: -
Products: -
?
protocatechuate + NAD(P)H + H+ + O2
?
-
Substrates: -
Products: -
Products: -
?
protocatechuate + NADH + 2 H+ + O2
hydroquinone + NAD+ + H2O + CO2
-
Substrates: -
Products: -
Products: -
?
protocatechuate + NADH + 2 H+ + O2
hydroquinone + NAD+ + H2O + CO2
-
Substrates: -
Products: -
Products: -
?
vanillate + NADH + 2 H+ + O2
3-methoxy-1,4-dihydroxybenzene + NAD+ + H2O + CO2
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Substrates: -
Products: -
Products: -
?
vanillate + NADH + 2 H+ + O2
3-methoxy-1,4-dihydroxybenzene + NAD+ + H2O + CO2
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Substrates: -
Products: -
Products: -
?
additional information
?
-
-
Substrates: the enzyme is induced when yeast is grown on either 4-hydroxybenzoate, 2,4-dihydroxybenzoate or 3,4-dihydroxybenzoate as the sole carbon source
Products: -
Products: -
?
additional information
?
-
-
Substrates: the phenolate form of the substrates is important for catalysis and the substrate hydroxylation involvesthe electrophilic attack of the putative flavin hydroperoxide at the C1-atom of the aromatic ring
Products: -
Products: -
?
additional information
?
-
-
Substrates: 4HB1H catalyzes an oxidative decarboxylation reaction. 4HB1H is active with a wide range of 4-hydroxybenzoate (4-HB) derivatives. 4HB1H can also be induced by protocatechuate (PCA) and convert this compound directly into the central intermediate HHQ
Products: -
Products: -
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additional information
?
-
-
Substrates: 4HB1H catalyzes an oxidative decarboxylation reaction. 4HB1H is active with a wide range of 4-hydroxybenzoate (4-HB) derivatives. 4HB1H can also be induced by protocatechuate (PCA) and convert this compound directly into the central intermediate HHQ
Products: -
Products: -
-
additional information
?
-
-
Substrates: the enzyme is induced when yeast is grown on either 4-hydroxybenzoate, 2,4-dihydroxybenzoate or 3,4-dihydroxybenzoate as the sole carbon source
Products: -
Products: -
?
additional information
?
-
-
Substrates: the phenolate form of the substrates is important for catalysis and the substrate hydroxylation involvesthe electrophilic attack of the putative flavin hydroperoxide at the C1-atom of the aromatic ring
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
4-hydroxybenzoate + NAD(P)H + 2 H+ + O2
hydroquinone + NAD(P)+ + H2O + CO2
-
Substrates: -
Products: -
Products: -
?
2,4-dihydroxybenzoate + NAD(P)H + H+ + O2
benzene-1,2,4-triol + NAD(P)+ + H2O + CO2
-
Substrates: -
Products: -
Products: -
?
2,4-dihydroxybenzoate + NAD(P)H + H+ + O2
benzene-1,2,4-triol + NAD(P)+ + H2O + CO2
-
Substrates: -
Products: -
Products: -
?
3,4-dihydroxybenzoate + NAD(P)H + H+ + O2
benzene-1,2,4-triol + NAD(P)+ + H2O + CO2
-
Substrates: -
Products: -
Products: -
?
3,4-dihydroxybenzoate + NAD(P)H + H+ + O2
benzene-1,2,4-triol + NAD(P)+ + H2O + CO2
-
Substrates: -
Products: -
Products: -
?
4-hydroxybenzoate + NAD(P)H + H+ + O2
hydroquinone + NAD(P)+ + H2O + CO2
-
Substrates: -
Products: -
Products: -
?
4-hydroxybenzoate + NAD(P)H + H+ + O2
hydroquinone + NAD(P)+ + H2O + CO2
-
Substrates: -
Products: -
Products: -
?
4-Hydroxybenzoate + NAD(P)H + O2
?
-
Substrates: initial reaction of the catabolism of 4-hydroxybenzoate
Products: -
Products: -
?
4-Hydroxybenzoate + NAD(P)H + O2
?
-
Substrates: the enzyme is induced when the yeast is grown on either 4-hydroxybenzoate, 2,3-dihydroxybenzoate, or 3,4-dihydroxybenzoate as the sole carbon source
Products: -
Products: -
?
4-Hydroxybenzoate + NAD(P)H + O2
?
-
Substrates: initial reaction of the catabolism of 4-hydroxybenzoate
Products: -
Products: -
?
4-hydroxybenzoate + NADH + 2 H+ + O2
hydroquinone + NAD+ + H2O + CO2
-
Substrates: -
Products: -
Products: -
?
4-hydroxybenzoate + NADH + 2 H+ + O2
hydroquinone + NAD+ + H2O + CO2
-
Substrates: -
Products: -
Products: -
?
protocatechuate + NAD(P)H + H+ + O2
?
-
Substrates: -
Products: -
Products: -
?
additional information
?
-
-
Substrates: the enzyme is induced when yeast is grown on either 4-hydroxybenzoate, 2,4-dihydroxybenzoate or 3,4-dihydroxybenzoate as the sole carbon source
Products: -
Products: -
?
additional information
?
-
-
Substrates: the enzyme is induced when yeast is grown on either 4-hydroxybenzoate, 2,4-dihydroxybenzoate or 3,4-dihydroxybenzoate as the sole carbon source
Products: -
Products: -
?
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COFACTOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
14
-
purified recombinant enzyme, pH 7.6, 25°C, substrates 4-hydroxybenzoate and NADH
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pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
7.6
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TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
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LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY
GeneOntology No.
LITERATURE
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
metabolism
physiological function
additional information
evolution
-
phylogenetic analysis of FAD-dependent 4-hydroxybenzoate hydroxylases and 3-hydroxybenzoate 4-hydroxylase, phylogenetic analysis and tree, overview. Enzyme 4HB1H is only present in a small group of Saccharomycetes. Many FAD-binding proteins with unknown function in pezizomycetes and agaricomycetes have structural features in common with 4HB1H, but lack its C-terminal tail. 4HB1H belongs to a subgroup of structurally related group A FPMOs that catalyze para-hydroxylation reactions
evolution
-
phylogenetic analysis of FAD-dependent 4-hydroxybenzoate hydroxylases and 3-hydroxybenzoate 4-hydroxylase, phylogenetic analysis and tree, overview. Enzyme 4HB1H is only present in a small group of Saccharomycetes. Many FAD-binding proteins with unknown function in pezizomycetes and agaricomycetes have structural features in common with 4HB1H, but lack its C-terminal tail. 4HB1H belongs to a subgroup of structurally related group A FPMOs that catalyze para-hydroxylation reactions
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metabolism
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the enzyme is important in lignin degradation. The conversion of 4-hydroxybenzoate (4-HB) involves an ipso-attack of the electrophilic flavin C4a-hydroperoxide at the C1-atom of the activated substrate, resulting in a tetrahedral benzoquinone species and subsequent release of the carboxyl side chain. The second step of the catabolism of 4-HB in Candida parapsilosis catalyzed by the homodimeric hydroquinone hydroxylase, HQH
metabolism
-
the enzyme is important in lignin degradation. The conversion of 4-hydroxybenzoate (4-HB) involves an ipso-attack of the electrophilic flavin C4a-hydroperoxide at the C1-atom of the activated substrate, resulting in a tetrahedral benzoquinone species and subsequent release of the carboxyl side chain. The second step of the catabolism of 4-HB in Candida parapsilosis catalyzed by the homodimeric hydroquinone hydroxylase, HQH
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physiological function
-
overexpression of the enzyme increases the tolerance of Candida parapsilosis cells to the antifungal drug terbinafine
physiological function
-
4-hydroxybenzoate 1-hydroxylase (4HB1H) from yeast catalyzes an oxidative decarboxylation reaction and is structurally similar to 3-hydroxybenzoate 6-hydroxylase (3HB6H), salicylate hydroxylase (SALH) and 6-hydroxynicotinate 3-monooxygenase (6HNMO). Genome mining suggests that the 4HB1H activity is widespread in the fungal kingdom and might be responsible for the oxidative decarboxylation of vanillate, an import intermediate in lignin degradation
physiological function
-
overexpression of the enzyme increases the tolerance of Candida parapsilosis cells to the antifungal drug terbinafine
-
physiological function
-
4-hydroxybenzoate 1-hydroxylase (4HB1H) from yeast catalyzes an oxidative decarboxylation reaction and is structurally similar to 3-hydroxybenzoate 6-hydroxylase (3HB6H), salicylate hydroxylase (SALH) and 6-hydroxynicotinate 3-monooxygenase (6HNMO). Genome mining suggests that the 4HB1H activity is widespread in the fungal kingdom and might be responsible for the oxidative decarboxylation of vanillate, an import intermediate in lignin degradation
-
additional information
-
structure comparisons and protein homology modelling, generation of a model of Candida parapsilosis Cp_HQH and models for Cp_4HB1H, Fusarium oxysporum Fo_4HB1H-like, and Boreostereum vibrans Bv_VibMO1 using Cutaneotrichosporon cutaneum Tc_PHHY (PDB ID 1pn0), Rhodococcus jostii Rj_3HB6H (PDB ID 4bk1) and Pseudomonas putida Pp_SALH (PDB ID 5evy) as template structures, overview
additional information