Information on EC 1.1.3.15 - (S)-2-hydroxy-acid oxidase

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The expected taxonomic range for this enzyme is: Bacteria, Eukaryota

EC NUMBER
COMMENTARY hide
1.1.3.15
-
RECOMMENDED NAME
GeneOntology No.
(S)-2-hydroxy-acid oxidase
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
an (S)-2-hydroxy carboxylate + O2 = a 2-oxo carboxylate + H2O2
show the reaction diagram
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
oxidation
-
-
-
-
oxidative decarboxylation
-
-
-
-
redox reaction
-
-
-
-
reduction
-
-
-
-
PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
Biosynthesis of antibiotics
-
-
Biosynthesis of secondary metabolites
-
-
glycine metabolism
-
-
Glyoxylate and dicarboxylate metabolism
-
-
Metabolic pathways
-
-
Microbial metabolism in diverse environments
-
-
photorespiration
-
-
SYSTEMATIC NAME
IUBMB Comments
(S)-2-hydroxy-acid:oxygen 2-oxidoreductase
A flavoprotein (FMN). Exists as two major isoenzymes; the A form preferentially oxidizes short-chain aliphatic hydroxy acids, and was previously listed as EC 1.1.3.1, glycolate oxidase; the B form preferentially oxidizes long-chain and aromatic hydroxy acids. The rat isoenzyme B also acts as EC 1.4.3.2, L-amino-acid oxidase.
CAS REGISTRY NUMBER
COMMENTARY hide
9037-63-2
-
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
green amaranth
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
chicken
-
-
Manually annotated by BRENDA team
cv. Pripyat, various isozymes
-
-
Manually annotated by BRENDA team
IL 1403
UniProt
Manually annotated by BRENDA team
correlation of enzyme activity with content of beta-N-oxalyl-L-alpha,beta-diaminopropionic acid under high light treatment
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
gene glcD
-
-
Manually annotated by BRENDA team
-
SwissProt
Manually annotated by BRENDA team
Pediococcus sp.
plant
-
-
-
Manually annotated by BRENDA team
gene glcD
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
Roseobacter sp.
gene glcD
-
-
Manually annotated by BRENDA team
type 2 lactate oxidase isolated from Strptococcus iniae; strain QMA0177 (novel type 2 enzyme), major pathogen of farmed fish, type 2 is an isolate from diseased barramundi (Lates calcarifer) in Northern Territory, Australia
UniProt
Manually annotated by BRENDA team
activities of both lactarte oxidase and pyruvate oxidase in wild-type cultures are detectable even in the early exponential phase of growth and attain the highest levels in the early stationary phase
-
-
Manually annotated by BRENDA team
pig
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
evolution
malfunction
-
the enzyme is involved in primary hyperoxaluria, a genetic disorder where overproduction of oxalate results in the formation of kidney stones
metabolism
physiological function
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
(S)-lactate + O2
acetate + CO2 + H2O
show the reaction diagram
(S)-lactate + O2
pyruvate + H2O2
show the reaction diagram
2-hydroxy-3-methylvalerate + O2
?
show the reaction diagram
-
A95G-mutant
-
-
?
2-hydroxybutanoate + bromopyruvate + ?
bromolactate + pyruvate + ?
show the reaction diagram
-
transhydrogenation reaction
-
?
2-hydroxybutyrate + O2
?
show the reaction diagram
-
wild-type and A95G-mutant
-
-
?
2-hydroxyisovalerate + O2
?
show the reaction diagram
-
A95G-mutant
-
-
?
2-hydroxyoctanoate + 2,6-dichlorophenolindophenol
2-oxo-octanoate + reduced 2,6-dichlorophenolindophenol
show the reaction diagram
-
-
-
r
2-hydroxyoctanoate + O2
2-oxooctanoate + H2O2
show the reaction diagram
-
substrates for isoenzymes HAOX1, HAOX2, preferred substrate for isoenzyme HAOX3
-
?
2-hydroxypalmitate + O2
2-oxopalmitate + H2O2
show the reaction diagram
-
substrates for isoenzymes HAOX1, HAOX2
-
?
2-hydroxyvalerate + O2
?
show the reaction diagram
-
wild-type and A95G-mutant
-
-
?
D-2 -hydroxyisocaproate + O2
2-oxoisocaproate + H2O2
show the reaction diagram
D-lactate + O2
pyruvate + H2O2
show the reaction diagram
DL-2-hydroxy-3-butynoate + O2
2-oxo-3-butynoate + H2O2
show the reaction diagram
-
good substrate, but inactivation after 25 turnovers
-
?
DL-2-hydroxy-3-heptynoate + O2
2-oxo-3-heptynoate + H2O2
show the reaction diagram
-
86% of the activity compared to DL-2-hydroxybutyrate
-
?
DL-2-hydroxy-3-hexynoate + O2
2-oxo-3-hexynoate + H2O2
show the reaction diagram
-
65% of the activity compared to DL-2-hydroxybutyrate
-
?
DL-2-hydroxy-3-octynoate + O2
2-oxo-3-octynoate + H2O2
show the reaction diagram
-
70% of the activity compared to DL-2-hydroxybutyrate
-
?
DL-2-hydroxy-3-pentynoate + O2
2-oxo-3-pentynoate + H2O2
show the reaction diagram
-
2fold higher activity compared to DL-2-hydroxybutyrate
-
?
DL-2-hydroxy-4-methylmercaptobutyrate + 2,6-dichlorophenolindophenol
2-oxo-4-methylmercaptobutyrate + reduced 2,6-dichlorophenolindophenol
show the reaction diagram
-
good substrate for long chain oxidase, low activity for short chain oxidase
-
?
DL-2-hydroxy-4-methylthiobutanoic acid + 2,6-dichlorophenolindophenol
2-oxo-4-methylthiobutanoic acid + reduced 2,6-dichlorophenolindophenol
show the reaction diagram
-
-
-
?
DL-2-hydroxybutyrate + 2,4-dinitrophenyl hydrazone
2-oxobutyrate + ?
show the reaction diagram
-
low activity
-
?
DL-2-hydroxybutyrate + 2,6-dichlorophenolindophenol
2-oxobutyrate + reduced 2,6-dichlorophenolindophenol
show the reaction diagram
DL-2-hydroxybutyrate + O2
2-oxobutyrate + H2O2
show the reaction diagram
DL-2-hydroxycaproate + 2,6-dichlorophenolindophenol
2-oxocaproate + reduced 2,6-dichlorophenolindophenol
show the reaction diagram
-
low activity for short chain oxidase, moderate activity for long chain oxidase
-
?
DL-2-hydroxycaproate + O2
2-oxocaproate + H2O2
show the reaction diagram
DL-2-hydroxydecanoate + 2,6-dichlorophenolindophenol
2-oxodecanoate + reduced 2,6-dichlorophenolindophenol
show the reaction diagram
-
good substrate for long chain oxidase, traces of activity for short chain oxidase
-
?
DL-2-hydroxyisocaproate + O2
2-oxoisocaproate + H2O2
show the reaction diagram
DL-2-hydroxyisovalerate + 2,4-dinitrophenyl hydrazone
2-oxoisovalerate + ?
show the reaction diagram
-
very low activity
-
?
DL-2-hydroxyisovalerate + 2,6-dichlorophenolindophenol
2-oxoisovalerate + reduced 2,6-dichlorophenolindophenol
show the reaction diagram
-
no activity for short chain oxidase, moderate activity for long chain oxidase
-
?
DL-2-hydroxyisovalerate + O2
2-oxoisovalerate + H2O2
show the reaction diagram
DL-2-hydroxyoctanoate + 2,6-dichlorophenolindophenol
2-oxooctanoate + reduced 2,6-dichlorophenolindophenol
show the reaction diagram
-
good substrate for long chain oxidase, no activity for short chain oxidase
-
?
DL-2-hydroxyvalerate + 2,6-dichlorophenolindophenol
2-oxovalerate + reduced 2,6-dichlorophenolindophenol
show the reaction diagram
-
low activity for short chain oxidase, moderate activity for long chain oxidase
-
?
DL-2-hydroxyvalerate + O2
2-oxovalerate + H2O2
show the reaction diagram
DL-3-chlorolactate + O2
3-chloropyruvate + H2O2
show the reaction diagram
DL-3-indolelactate + 2,6-dichlorophenolindophenol
3-indolepyruvate + reduced 2,6-dichlorophenolindophenol
show the reaction diagram
-
good substrate for long chain oxidase, no activity for short chain oxidase
-
?
DL-3-indolelactate + O2
3-indolepyruvate + H2O2
show the reaction diagram
-
-
-
?
DL-3-methoxy-4-hydroxymandelate + 2,6-dichlorophenolindophenol
(3-methoxy-4-hydroxyphenyl)pyruvate + reduced 2,6-dichlorophenolindophenol
show the reaction diagram
-
-
-
?
DL-beta-phenyllactate + 2,6-dichlorophenolindophenol
phenylpyruvate + reduced 2,6-dichlorophenolindophenol
show the reaction diagram
-
no activity for short chain oxidase
-
?
DL-glycerate + O2
? + H2O2
show the reaction diagram
-
-
-
?
DL-lactate + O2
pyruvate + H2O2
show the reaction diagram
-
-
-
?
DL-mandelate + 2,6-dichlorophenolindophenol
oxo(phenyl)acetic acid + reduced 2,6-dichlorophenolindophenol
show the reaction diagram
-
low activity
-
?
DL-mandelate + O2
phenylglyoxylic acid + H2O2
show the reaction diagram
-
the step involving the removal of the alpha-hydrogen is rate-limiting, A95G-mutant is also reactive
-
-
?
DL-methionine + O2
? + H2O2
show the reaction diagram
-
-
-
?
DL-p-hydroxy-beta-phenyllactate + 2,6-dichlorophenolindophenol
(4-hydroxyphenyl)pyruvate + reduced 2,6-dichlorophenolindophenol
show the reaction diagram
-
no activity for short chain oxidase
-
?
DL-p-hydroxymandelate + O2
?
show the reaction diagram
-
the step involving the removal of the alpha-hydrogen is rate-limiting, A95G-mutant is also reactive
-
-
?
DL-phenyllactate + O2
phenylpyruvate + H2O2
show the reaction diagram
DL-vinylglycolate + O2
2-oxo-3-butenoic acid + H2O2
show the reaction diagram
-
90% of the activity compared to DL-2-hydroxybutyrate
-
?
glycerate + O2
? + H2O2
show the reaction diagram
-
-
-
-
?
glycolate + 2,4-dinitrophenyl hydrazone
glyoxylate + ?
show the reaction diagram
-
best substrate tested
-
?
glycolate + 2,6-dichlorophenolindophenol
glyoxylate + reduced 2,6-dichlorophenolindophenol
show the reaction diagram
glycolate + ferricyanide
glyoxylate + ferrocyanide
show the reaction diagram
glycolate + O2
glyoxylate + H2O2
show the reaction diagram
glyoxalate + O2
oxalate + H2O2
show the reaction diagram
-
-
-
-
?
glyoxylate + 2,4-dinitrophenyl hydrazone
oxalate + ?
show the reaction diagram
-
25% of the activity compared to glycolate
-
?
glyoxylate + 2,6-dichlorophenolindophenol
?
show the reaction diagram
-
-
-
-
?
glyoxylate + 2,6-dichlorophenolindophenol
? + reduced 2,6-dichlorophenolindophenol
show the reaction diagram
glyoxylate + ferricyanide
? + ferrocyanide
show the reaction diagram
-
-
-
?
glyoxylate + O2
? + H2O2
show the reaction diagram
glyoxylate thiohemiacetals + O2
? + H2O2
show the reaction diagram
-
possible natural substrates, i.e. glyoxylate thiohemiacetals of coemzyme A, D-phosphopantetheine, D-pantetheine, N-acetylcysteamine, 2-mercaptoethanol, DL-dihydrolipoate, propane-1,3-dithiol
-
?
homoserine + O2
? + H2O2
show the reaction diagram
-
traces of activity
-
?
L-2-hydroxy octanoate + O2
2-oxo-octanoate + H2O2
show the reaction diagram
-
-
-
?
L-2-hydroxy palmitate + O2
2-oxo-palmitate + H2O2
show the reaction diagram
-
-
-
?
L-2-hydroxy-4-methylthiobutanoic acid + O2
3-(methylthio)propanoate + HCO3-
show the reaction diagram
-
oxidative decarboxylation
-
?
L-2-hydroxy-beta-methylvalerate + 2,6-dichlorophenolindophenol
3-methyl-2-oxopentanoate + reduced 2,6-dichlorophenolindophenol
show the reaction diagram
L-2-hydroxyisocaproate + 2,4-dinitrophenyl hydrazone
2-oxoisocaproate + ?
show the reaction diagram
-
-
-
?
L-2-hydroxyisocaproate + 2,6-dichlorophenolindophenol
2-oxoisocaproate + reduced 2,6-dichlorophenolindophenol
show the reaction diagram
-
-
-
?
L-2-hydroxyisocaproate + O2
2-oxoisocaproate + H2O2
show the reaction diagram
L-2-hydroxyphenyllactate + O2
? + H2O2
show the reaction diagram
L-4-chloromandelate + O2
?
show the reaction diagram
-
the step involving the removal of the alpha-hydrogen is rate-limiting, A95G-mutant is also reactive
-
-
?
L-4-fluoromandelate + O2
?
show the reaction diagram
-
the step involving the removal of the alpha-hydrogen is rate-limiting, A95G-mutant is also reactive
-
-
?
L-4-methoxymandelate + O2
?
show the reaction diagram
-
the step involving the removal of the alpha-hydrogen is rate-limiting, A95G-mutant is also reactive
-
-
?
L-4-methylmandelate + O2
?
show the reaction diagram
-
the step involving the removal of the alpha-hydrogen is rate-limiting, A95G-mutant is also reactive
-
-
?
L-4-nitromandelate + O2
?
show the reaction diagram
-
the step involving the removal of the alpha-hydrogen is rate-limiting, A95G-mutant is also reactive
-
-
?
L-4-trifluoromethylmandelate + O2
?
show the reaction diagram
-
the step involving the removal of the alpha-hydrogen is rate-limiting, A95G-mutant is also reactive
-
-
?
L-alanine + O2
? + H2O2
show the reaction diagram
-
low activity
-
?
L-isoleucine + O2
? + H2O2
show the reaction diagram
-
low activity
-
?
L-lactate + 2,4-dinitrophenyl hydrazone
pyruvate + ?
show the reaction diagram
-
very low activity
-
?
L-lactate + 2,6-dichlorophenolindophenol
pyruvate + reduced 2,6-dichlorophenolindophenol
show the reaction diagram
L-lactate + O2
pyruvate + H2O2
show the reaction diagram
L-leucine + 2,6-dichlorophenolindophenol
? + reduced 2,6-dichlorophenolindophenol
show the reaction diagram
-
-
-
?
L-leucine + O2
? + H2O2
show the reaction diagram
L-lysine + O2
? + H2O2
show the reaction diagram
-
-
-
?
L-mandelate + 2,6-dichlorophenolindophenol
?
show the reaction diagram
-
-
-
-
?
L-mandelate + 2,6-dichlorophenolindophenol
oxo(phenyl)acetic acid + reduced 2,6-dichlorophenolindophenol
show the reaction diagram
L-mandelate + O2
?
show the reaction diagram
L-mandelate + O2
? + H2O2
show the reaction diagram
-
-
-
?
L-methionine + O2
? + H2O2
show the reaction diagram
L-phenylalanine + O2
? + H2O2
show the reaction diagram
-
-
-
?
L-phenyllactate + 2,6-dichlorophenolindophenol
phenylpyruvate + reduced 2,6-dichlorophenolindophenol
show the reaction diagram
L-tryptophan + O2
? + H2O2
show the reaction diagram
L-tyrosine + O2
? + H2O2
show the reaction diagram
-
-
-
?
L-valine + O2
? + H2O2
show the reaction diagram
-
low activity
-
?
lactate + O2
pyruvate + H2O2
show the reaction diagram
mandelate + O2
phenylpyruvate + H2O2
show the reaction diagram
oxidation of an L-2-hydroxy acid to a 2-oxoacid, model for the binding of L-mandelate into the active site, overview
-
-
?
thiol-glyoxylate adducts + O2
an oxalyl thioester + H2O2
show the reaction diagram
-
may be the physiological substrates
-
?
additional information
?
-
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
(S)-lactate + O2
acetate + CO2 + H2O
show the reaction diagram
(S)-lactate + O2
pyruvate + H2O2
show the reaction diagram
2-hydroxyoctanoate + O2
2-oxooctanoate + H2O2
show the reaction diagram
-
substrates for isoenzymes HAOX1, HAOX2, preferred substrate for isoenzyme HAOX3
-
?
2-hydroxypalmitate + O2
2-oxopalmitate + H2O2
show the reaction diagram
-
substrates for isoenzymes HAOX1, HAOX2
-
?
D-2 -hydroxyisocaproate + O2
2-oxoisocaproate + H2O2
show the reaction diagram
D-lactate + O2
pyruvate + H2O2
show the reaction diagram
DL-2-hydroxybutyrate + O2
2-oxobutyrate + H2O2
show the reaction diagram
DL-2-hydroxycaproate + O2
2-oxocaproate + H2O2
show the reaction diagram
DL-2-hydroxyisocaproate + O2
2-oxoisocaproate + H2O2
show the reaction diagram
DL-2-hydroxyisovalerate + O2
2-oxoisovalerate + H2O2
show the reaction diagram
DL-2-hydroxyvalerate + O2
2-oxovalerate + H2O2
show the reaction diagram
DL-glycerate + O2
? + H2O2
show the reaction diagram
-
-
-
?
DL-lactate + O2
pyruvate + H2O2
show the reaction diagram
-
-
-
?
DL-methionine + O2
? + H2O2
show the reaction diagram
-
-
-
?
glycolate + O2
glyoxylate + H2O2
show the reaction diagram
glyoxylate + O2
? + H2O2
show the reaction diagram
glyoxylate thiohemiacetals + O2
? + H2O2
show the reaction diagram
-
possible natural substrates, i.e. glyoxylate thiohemiacetals of coemzyme A, D-phosphopantetheine, D-pantetheine, N-acetylcysteamine, 2-mercaptoethanol, DL-dihydrolipoate, propane-1,3-dithiol
-
?
homoserine + O2
? + H2O2
show the reaction diagram
-
traces of activity
-
?
L-2-hydroxy-4-methylthiobutanoic acid + O2
3-(methylthio)propanoate + HCO3-
show the reaction diagram
-
oxidative decarboxylation
-
?
L-2-hydroxyisocaproate + O2
2-oxoisocaproate + H2O2
show the reaction diagram
L-alanine + O2
? + H2O2
show the reaction diagram
-
low activity
-
?
L-isoleucine + O2
? + H2O2
show the reaction diagram
-
low activity
-
?
L-lactate + O2
pyruvate + H2O2
show the reaction diagram
L-leucine + O2
? + H2O2
show the reaction diagram
L-lysine + O2
? + H2O2
show the reaction diagram
-
-
-
?
L-mandelate + O2
? + H2O2
show the reaction diagram
-
-
-
?
L-methionine + O2
? + H2O2
show the reaction diagram
L-phenylalanine + O2
? + H2O2
show the reaction diagram
-
-
-
?
L-tryptophan + O2
? + H2O2
show the reaction diagram
L-tyrosine + O2
? + H2O2
show the reaction diagram
-
-
-
?
L-valine + O2
? + H2O2
show the reaction diagram
-
low activity
-
?
lactate + O2
pyruvate + H2O2
show the reaction diagram
thiol-glyoxylate adducts + O2
an oxalyl thioester + H2O2
show the reaction diagram
-
may be the physiological substrates
-
?
additional information
?
-
COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
flavin
-
dependent on
additional information
METALS and IONS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
Ag+
up to 4fold induction
Cu2+
exposure of cells to mM copper sulfate, strong induction. Highest induction at 0.3 mM, about 16-fold increase in activity. Identification of a copper-response element in the 5'-region of the LctO gene
CuSO4
induces copper regulated promoter, upregulates LctO 17fold (2D gel)
additional information
Zn2+, Fe2+, Ni2+, Mn2+, and Ca2+ have no significant effect on lctO expression
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
(R)-lactate
-
at pH 7.0
2,6-dichlorophenolindophenol
-
inhibition by excess substrate
2-hydroxybutynoate
-
inhibition of transhydrogenation reaction
2-Hydroxybutyrate
2-oxobutyrate
-
non-competitive inhibition at 5 mM
2-oxoisocaproate
-
non-competitive inhibition at 5 mM, most active inhibitor of 2-keto acids, oxidation of 2-hydroxybutyrate most sensitive
2-oxoisovalerate
-
non-competitive inhibition at 5 mM
2-oxovalerate
-
non-competitive inhibition at 5 mM
2-pyridylhydroxymethanesulfonate
-
strong inhibition between 0.1-1 mM
3-benzyl-4-[[4-(4-fluorophenyl)pyridin-2-yl]methyl]-1H-pyrazole-5-carboxylic acid
3-decyl-2,5-dioxo-4-hydroxy-3-pyrroline
-
bound to the active site in the three-dimensional structure
3-ethoxy-4-[[4-(4-fluorophenyl)pyridin-2-yl]methyl]-1H-pyrazole-5-carboxylic acid
3-ethyl-4-[[4-(4-fluorophenyl)pyridin-2-yl]methyl]-1H-pyrazole-5-carboxylic acid
3-methyl-4-(2-phenoxybenzyl)-1H-pyrazole-5-carboxylic acid
3-methyl-4-(2-phenylethyl)-1H-pyrazole-5-carboxylic acid
-
-
3-methyl-4-(3-phenoxybenzyl)-1H-pyrazole-5-carboxylic acid
3-methyl-4-(4-phenoxybenzyl)-1H-pyrazole-5-carboxylic acid
3-methyl-4-(naphthalen-1-ylmethyl)-1H-pyrazole-5-carboxylic acid
3-methyl-4-(naphthalen-2-ylmethyl)-1H-pyrazole-5-carboxylic acid
3-methyl-4-(quinolin-2-ylmethyl)-1H-pyrazole-5-carboxylic acid
3-methyl-4-[2-(trifluoromethoxy)benzyl]-1H-pyrazole-5-carboxylic acid
3-methyl-4-[2-(trifluoromethyl)benzyl]-1H-pyrazole-5-carboxylic acid
3-methyl-4-[3-(pyridin-3-yl)benzyl]-1H-pyrazole-5-carboxylic acid
3-methyl-4-[3-(pyridin-4-yl)benzyl]-1H-pyrazole-5-carboxylic acid
3-methyl-4-[3-(trifluoromethyl)benzyl]-1H-pyrazole-5-carboxylic acid
3-methyl-4-[4-(trifluoromethoxy)benzyl]-1H-pyrazole-5-carboxylic acid
3-methyl-4-[4-(trifluoromethyl)benzyl]-1H-pyrazole-5-carboxylic acid
3-methyl-4-[[4'-(trifluoromethoxy)biphenyl-3-yl]methyl]-1H-pyrazole-5-carboxylic acid
3-methyl-4-[[4'-(trifluoromethoxy)biphenyl-4-yl]methyl]-1H-pyrazole-5-carboxylic acid
3-methyl-4-[[4'-(trifluoromethyl)biphenyl-3-yl]methyl]-1H-pyrazole-5-carboxylic acid
3-methyl-4-[[4'-(trifluoromethyl)biphenyl-4-yl]methyl]-1H-pyrazole-5-carboxylic acid
4-(1-benzofuran-2-ylmethyl)-3-methyl-1H-pyrazole-5-carboxylic acid
4-(1-benzothiophen-2-ylmethyl)-3-methyl-1H-pyrazole-5-carboxylic acid
4-(3-carbamoylbenzyl)-3-methyl-1H-pyrazole-5-carboxylic acid
4-(3-carboxybenzyl)-3-methyl-1H-pyrazole-5-carboxylic acid
4-(3-cyanobenzyl)-3-methyl-1H-pyrazole-5-carboxylic acid
4-(3-fluorobenzyl)-3-methyl-1H-pyrazole-5-carboxylic acid
4-(4'-fluorobiphenyl-3-yl)-3-methyl-1H-pyrazole-5-carboxylic acid
4-(4'-fluorobiphenyl-4-yl)-3-methyl-1H-pyrazole-5-carboxylic acid
4-(4-carbamoylbenzyl)-3-methyl-1H-pyrazole-5-carboxylic acid
4-(4-carboxybenzyl)-3-methyl-1H-pyrazole-5-carboxylic acid
4-(4-cyanobenzyl)-3-methyl-1H-pyrazole-5-carboxylic acid
4-(4-fluorobenzyl)-3-methyl-1H-pyrazole-5-carboxylic acid
4-(4-fluorophenyl)-3-methyl-1H-pyrazole-5-carboxylic acid
4-(biphenyl-3-ylmethyl)-3-methyl-1H-pyrazole-5-carboxylic acid
-
-
4-carboxy-5-(1-pentyl)hexylsulfanyl-1,2,3-triazole
-
bound to the active site in the three-dimensional structure
4-carboxy-5-dodecylsulfanyl-1,2,3-triazole
-
-
4-chloromercuribenzoate
4-[(2'-fluorobiphenyl-3-yl)methyl]-3-methyl-1H-pyrazole-5-carboxylic acid
4-[(3'-fluorobiphenyl-3-yl)methyl]-3-methyl-1H-pyrazole-5-carboxylic acid
4-[(4'-carbamoylbiphenyl-3-yl)methyl]-3-methyl-1H-pyrazole-5-carboxylic acid
4-[(4'-carboxybiphenyl-3-yl)methyl]-3-methyl-1H-pyrazole-5-carboxylic acid
4-[(4'-cyanobiphenyl-3-yl)methyl]-3-methyl-1H-pyrazole-5-carboxylic acid
4-[(4'-fluorobiphenyl-2-yl)methyl]-3-methyl-1H-pyrazole-5-carboxylic acid
4-[(4'-fluorobiphenyl-3-yl)methyl]-3-methyl-1H-pyrazole-5-carboxylic acid
4-[(4'-fluorobiphenyl-4-yl)methyl]-3-methyl-1H-pyrazole-5-carboxylic acid
4-[2-(4'-fluorobiphenyl-3-yl)ethyl]-3-methyl-1H-pyrazole-5-carboxylic acid
4-[2-(4'-fluorobiphenyl-4-yl)ethyl]-3-methyl-1H-pyrazole-5-carboxylic acid
4-[2-(4-fluorophenyl)ethyl]-3-methyl-1H-pyrazole-5-carboxylic acid
4-[2-(biphenyl-4-yl)ethyl]-3-methyl-1H-pyrazole-5-carboxylic acid
-
-
4-[[4'-(2-amino-2-oxoethyl)biphenyl-3-yl]methyl]-3-methyl-1H-pyrazole-5-carboxylic acid
4-[[4-(4-fluorophenyl)pyridin-2-yl]methyl]-3-(2-phenylethyl)-1H-pyrazole-5-carboxylic acid
4-[[4-(4-fluorophenyl)pyridin-2-yl]methyl]-3-(propan-2-yl)-1H-pyrazole-5-carboxylic acid
4-[[4-(4-fluorophenyl)pyridin-2-yl]methyl]-3-phenyl-1H-pyrazole-5-carboxylic acid
8-hydroxyquinoline
acetate
arsenate
-
inhibition of glycolate-ferricyanide or glyoxylate-ferricyanide assay above 0.1 M
Atebrin
-
long chain oxidase, 72-76% inhibition at 1 mM, short chain oxidase: 68-76% inhibition at 1 mM
benzaldehyde
-
50% inhibition at 2 mM
bipyridine
-
strong inhibition
Butyrate
-
-
caproate
-
mixed-type non-competitive inhibition
chloride
-
inhibits the enzyme at high concentrations
Cibacron blue 3GA
-
at a concentration higher than 0.001 mM is a normal competitive inhibitor, at concentrations below 0.001 mM the inhibition is time-, dye- and pH-dependent
cysteine
-
28-38% inhibition of glycolate oxidation at 1 mM
diethyldithiocarbamate
dihydrolipoate
-
competitive inhibition of 2-hydroxybutyrate oxidation
diphenylglycolic acid
Dithionite
-
reduction of FMN
DL-2-hydroxy-3-butynoate
-
irreversible inactivation after 25 turnovers, covalent addition to the coenzyme
DL-2-hydroxy-3-heptynoate
-
inactivation after18000 turnovers
DL-2-hydroxy-3-hexynoate
-
inactivation after 8500 turnovers
DL-2-hydroxy-3-octynoate
-
inactivation after 15000 turnovers
DL-2-hydroxy-3-pentynoate
-
inactivation after 4800 turnovers
DL-2-hydroxyisocaproate
-
marked inhibition above 50 mM
DL-2-hydroxyvalerate
-
marked inhibition above 50 mM
DL-beta-Phenyllactate
-
short chain oxidase: 10% inhibition of glycolate oxidation, 81% inhibition of L-2-hydroxisocaproate oxidation at 10 mM
DL-Lipoate
-
long chain oxidase, 35% inhibition at 0.24 mM, short chain oxidase: 46-52% inhibition at 0.01 mM
DL-vinylglycolate
-
slight inactivation after 10000 turnovers
glycolate
glyoxylate
Heptanoate
-
-
hexanoate
-
-
hydoxylamine
-
66-67% inhibition at 5 mM
hydroxylamine
-
50% inhibition at 5 mM, competitive
iodoacetamide
-
inhibition at 50 mM
iodoacetate
L-leucine
L-Mandelate
L-phenylalanine
-
long chain oxidase, 43% inhibition at 33 mM
malonate
-
-
Mandelate
-
-
NAD+
-
competitive
o-Iodosobenzoate
o-phenanthroline
oxalate
Oxamate
-
mixed-type non-competitive inhibition
phosphate
Propionate
pyruvate
Quinacrine
-
6% inhibition at 1 mM
rotenone
-
50% inhibition at 0.1 mM
sodium sulfite
-
reduces FMN
succinate
trans-cinnamate
-
competitive inhibition
valerate
-
-
additional information
ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
arsenate
-
increasing activity up to 0.1 M, inhibition of ferricyanide-linked assay above 0.1 M
ascorbate
-
17.5-26% activation at 1 mM
CuSO4
200 microM for 45 min induces copper regulated promoter
EDTA
-
slight activation for short and long chain oxidases
isocitrate
phosphate
-
increasing activity up to 0.1 M, inhibition of ferricyanide-linked assay above 0.1 M
succinate
-
strong, bundle sheath isoform
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.0052 - 103
(S)-Lactate
0.033
2,6-dichlorophenolindophenol
-
-
0.045
2-Hydroxyoctanoate
-
isoenzyme HAOX3
0.75
2-mercaptoethanol-glyoxylate adduct
-
-
-
0.04
2-oxo-octanoate
-
-
4.4
Bromopyruvate
-
transhydrogenation reaction
2.2
coenzyme A-glyoxylate adduct
-
-
0.28
dichlorophenolindophenol
-
cosubstrate: glycolate
4
DL-2-hydroxy-3-butynoate
-
-
0.38
DL-2-hydroxy-3-heptynoate
-
-
7
DL-2-hydroxy-3-hexynoate
-
-
0.14
DL-2-hydroxy-3-octynoate
-
-
9
DL-2-hydroxy-3-pentynoate
-
-
0.7 - 1.1
DL-2-hydroxy-4-methylthiobutanoic acid
0.6 - 14
DL-2-Hydroxybutyrate
0.15 - 3.2
DL-2-hydroxycaproate
0.6
DL-2-hydroxyisocaproate
8
DL-2-hydroxyisovalerate
-
-
0.25 - 13
DL-2-hydroxyvalerate
0.7 - 28
DL-3-chlorolactate
18 - 27
DL-alpha-hydroxy-n-butyrate
5.5 - 10
DL-alpha-hydroxy-n-valerate
71
DL-alpha-phenyllactate
-
-
5 - 53
DL-glycerate
2.04 - 2.5
DL-hydroxybutyrate
27
DL-lactate
-
-
4
DL-methionine
-
pH 7.5
0.1
DL-phenyllactate
-
pH 7.0 and 7.5
10
DL-vinylglycolate
-
-
7.14
glycerate
-
pH 8.0
0.0056 - 2.1
glycolate
1.41 - 3.4
glyoxylate
0.046
L-2-hydroxy octanoate
-
1.36
L-2-hydroxy palmitate
-
1.82
L-2-hydroxy-4-methylthiobutanoic acid
-
-
2.4
L-2-hydroxy-beta-methylvalerate
-
long chain oxidase
0.3 - 2.5
L-2-Hydroxyisocaproate
140
L-alpha-hydroxy-beta-methylvalerate
-
A95G mutant
125
L-alpha-hydroxy-isovalerate
-
A95G mutant
1.9
L-alpha-hydroxyphenyllactate
-
-
2.2
L-beta-Phenyllactate
-
long chain oxidase
0.34 - 16.5
L-lactate
5.3 - 15
L-leucine
90
L-lysine
-
-
0.16 - 20
L-Mandelate
53
L-methionine
-
-
0.09 - 0.13
L-Phenyllactate
35 - 40
L-tryptophan
0.4
N-acetylcysteamine-glyoxylate adduct
-
-
0.022 - 0.64
O2
0.7
pantetheine-glyoxylate adduct
-
-
0.03
propane-1,3-dithiol-glyoxylate adduct
-
-
-
additional information
additional information
TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.08
2-oxo-octanoate
Homo sapiens
-
-
0.36
Bromopyruvate
Rattus sp.
-
transhydrogenation reaction
1.9 - 2.1
DL-2-hydroxy-4-methylthiobutanoic acid
0.76
DL-2-Hydroxybutyrate
Rattus sp.
-
-
1.66 - 2
DL-hydroxybutyrate
54.1
flavin
Homo sapiens
-
pH 7.0, 30C, flavin reduction
1.04
glycerate
Spinacia oleracea
-
pH 8.0
0.33 - 31.2
glycolate
0.7 - 0.83
glyoxylate
0.99
L-2-hydroxy octanoate
Rattus norvegicus
Q07523
-
0.34
L-2-hydroxy palmitate
Rattus norvegicus
Q07523
-
0.74
L-2-hydroxy-4-methylthiobutanoic acid
Gallus gallus
-
-
2 - 2.4
L-2-Hydroxyisocaproate
0.26 - 4.7
L-lactate
0.014
L-leucine
Rattus sp.
-
isozymes beta1 and beta2
0.11 - 2.51
L-Mandelate
0.59 - 0.7
L-Phenyllactate
0.52 - 4.7
O2
additional information
additional information