Ligand butyric acid

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Basic Ligand Information

Molecular Structure
Picture of butyric acid (click for magnification)
Molecular Formula
BRENDA Name
InChIKey
C4H8O2
butyric acid
FERIUCNNQQJTOY-UHFFFAOYSA-N
Synonyms:
Butanoate, butanoic acid, Butyrate, n-butanoate, n-butanoic acid, n-Butyrate, n-butyric acid, propanecarboxylic acid, Sodiumbutyrate


Show all pahtways known for Show all BRENDA pathways known for butyric acid

Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (5 results)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
ATP + butanoate = ADP + butanoyl phosphate
show the reaction diagram
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butanoate + acetoacetyl-CoA = butanoyl-CoA + acetoacetate
show the reaction diagram
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ATP + butyric acid + CoA = AMP + diphosphate + butyryl-CoA
show the reaction diagram
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In Vivo Product in Enzyme-catalyzed Reactions (16 results)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
butyraldehyde + NAD+ + H2O = butyrate + NADH + H+
show the reaction diagram
-
-
butyryl-CoA + acetate = butanoate + acetyl-CoA
show the reaction diagram
-
-
tributyrin + H2O = dibutyrin + butyrate
show the reaction diagram
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butanoyl-CoA + H2O = butanoate + CoA
show the reaction diagram
-
-
butyramide + H2O = n-butyrate + NH3
show the reaction diagram
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nonane-4,6-dione + H2O = pentan-2-one + butanoate
show the reaction diagram
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Substrate in Enzyme-catalyzed Reactions (35 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
butyric acid + 2-oxoglutarate + O2 = 2-hydroxy-4-butyric acid + succinate + CO2
show the reaction diagram
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butyric acid + ATP + NADPH + H+ = butyraldehyde + AMP + diphosphate + NADP+
show the reaction diagram
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ATP + butyrate = ADP + butyryl phosphate
show the reaction diagram
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diphosphate + butyrate = phosphate + butyryl phosphate
show the reaction diagram
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ATP + butanoate = ADP + butanoyl phosphate
show the reaction diagram
-
ATP + butyrate = ADP + butanoyl phosphate
show the reaction diagram
-
ATP + butanoate = ADP + butanoyl phosphate
show the reaction diagram
-
glutaconyl-CoA + butyrate = butyryl-CoA + glutaconate
show the reaction diagram
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butanol + butanoate = butyl butanoate + H2O
show the reaction diagram
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butanol + butanoate = butyl butanoate + H2O
show the reaction diagram
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ATP + butyrate + CoA = AMP + diphosphate + butyryl-CoA
show the reaction diagram
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GTP + butyrate + CoA = GDP + phosphate + butyryl-CoA
show the reaction diagram
-
ATP + butyrate + CoA = AMP + diphosphate + butyryl-CoA
show the reaction diagram
-
ATP + butyrate + CoA = AMP + diphosphate + butyryl-CoA
show the reaction diagram
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butyrate + ATP + coenzyme A = butyryl-CoA + AMP + diphosphate
show the reaction diagram
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ATP + butyrate + CoA = AMP + diphosphate + butyryl-CoA
show the reaction diagram
-
ATP + butyrate + CoA = ADP + phosphate + butyryl-CoA
show the reaction diagram
-
ATP + butanoate + CoA = ADP + phosphate + butanoyl-CoA
show the reaction diagram
-
ATP + butyrate + CoA = ADP + phosphate + butyryl-CoA
show the reaction diagram
-
ATP + butyrate + CoA = ADP + phosphate + butyryl-CoA
show the reaction diagram
-

Product in Enzyme-catalyzed Reactions (417 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
1-butanol + 2 NAD+ + H2O = butanoic acid + 2 NADH + 2 H+
show the reaction diagram
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butanal + acceptor + H2O = butanoic acid + reduced acceptor
show the reaction diagram
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butanal + H2O + O2 = butanoate + H2O2
show the reaction diagram
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butyraldehyde + NAD+ + H2O = butyrate + NADH + H+
show the reaction diagram
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butyraldehyde + NAD+ + H2O = butanoate + NADH
show the reaction diagram
-
-
butyraldehyde + NAD(P)+ + H2O = n-butanoate + NAD(P)H + H+
show the reaction diagram
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-
n-butyraldehyde + NAD+ + H2O = n-butyrate + NADH
show the reaction diagram
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-
butyraldehyde + NAD+ = butyrate + NADH
show the reaction diagram
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butyraldehyde + NAD+ + H2O = butyrate + NADH + 2 H+
show the reaction diagram
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-
n-butanal + NADP+ + H2O = butanoate + NADPH + 2 H+
show the reaction diagram
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-
butyraldehyde + NAD+ + H2O = butanoate + NADH + H+
show the reaction diagram
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-
butyraldehyde + NAD+ + H2O = butyrate + NADH + 2 H+
show the reaction diagram
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-
butyraldehyde + H2O + oxidized ferredoxin = butyrate + H+ + reduced ferredoxin
show the reaction diagram
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butyraldehyde + H2O + oxidized methyl viologen = butyrate + H+ + reduced methyl viologen
show the reaction diagram
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-
butyraldehyde + H2O + benzylviologen = butanoate + reduced benzylviologen
show the reaction diagram
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L-dihydroorotate + crotonate = orotate + butanoate
show the reaction diagram
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butyryl-CoA + H2O = butanoate + CoA
show the reaction diagram
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N2-butyryl-L-ornithine + H2O = L-ornithine + butyric acid
show the reaction diagram
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p-nitrophenol butyrate + H2O = p-nitrophenol + butyric acid
show the reaction diagram
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4-nitrophenyl butyrate + glutathione = S-(4-nitrophenyl)glutathione + butyrate
show the reaction diagram
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butyryl-CoA + citrate = butyrate + (3S)-citryl-CoA
show the reaction diagram
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butyryl-CoA + 3-hydroxy-3-methylglutarate = butyrate + 3-hydroxy-3-methylglutaryl-CoA
show the reaction diagram
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butyryl-CoA + malonate = malonyl-CoA + butanoate
show the reaction diagram
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methylbutyrate + H2O = methanol + butanoate
show the reaction diagram
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4-nitrophenyl butanoate + H2O = 4-nitrophenol + butanoate
show the reaction diagram
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butyryl-L-carnitine + H2O = butyrate + L-carnitine
show the reaction diagram
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4-nitrophenyl butyrate + H2O = 4-nitrophenol + butyrate
show the reaction diagram
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methyl butyrate = butyrate + methanol
show the reaction diagram
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hexadecanyl butyrate + H2O = hexadecanol + butyrate
show the reaction diagram
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phorbol 12,13-dibutanoate + H2O = phorbol 13-butanoate + butanoate
show the reaction diagram
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4-methylumbelliferyl butyrate + H2O = 4-methylumbelliferone + butyrate
show the reaction diagram
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4-nitrophenyl butanoate + H2O = 4-nitrophenol + butanoate
show the reaction diagram
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p-nitrophenyl butyrate + H2O = butyrate + p-nitrophenol
show the reaction diagram
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p-nitrophenyl butyrate + H2O = 4-nitrophenol + butyrate
show the reaction diagram
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4-nitrophenyl butyrate + H2O = 4-nitrophenol + butyrate
show the reaction diagram
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butyryl-CoA + H2O = butanoate + CoA
show the reaction diagram
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-
S-butyrylglutathione + H2O = glutathione + butanoate
show the reaction diagram
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2,3-diketo-1-phosphohexane + H2O = 2-ketopentanoate + formate + glyoxylate + butyrate
show the reaction diagram
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2-naphthyl butyrate + H2O = 2-naphthol + butanoate
show the reaction diagram
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N6-butyryl-L-lysine + H2O = L-lysine + butanoate
show the reaction diagram
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N-methylbutyramide + H2O = methylamine + butyric acid
show the reaction diagram
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4-nitrophenylbutyrate + H2O = 4-nitrophenol + butyrate
show the reaction diagram
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butyramide + H2O = butyric acid + NH3
show the reaction diagram
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N-Butyl-D-Leu + H2O = Butanoate + D-Leu
show the reaction diagram
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N-Butyl-D-Glu + H2O = Butanoate + D-Glu
show the reaction diagram
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N-Butanoyl-D-Asp + H2O = Butanoate + D-Asp
show the reaction diagram
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butanamide + H2O = butanoate + NH3
show the reaction diagram
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6-(N-butanoyl-alpha-D-glucosaminyl)-1-phosphatidyl-1D-myo-inositol + H2O = 6-(alpha-D-glucosaminyl)-1-phosphatidyl-1D-myo-inositol + butanoate
show the reaction diagram
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n-butyronitrile + H2O = n-butyric acid + NH3
show the reaction diagram
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2,4-diketoheptanoate + H2O = pyruvate + butanoate
show the reaction diagram
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ADP + phosphate + butyryl-CoA = ATP + butyrate + CoA
show the reaction diagram
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Activator in Enzyme-catalyzed Reactions (9 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
induction of enzyme expression, erythroleukemia cells
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significantly increase of enzyme activity and expression in human colon cancer cell line HT-29
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highly activating for the wild-type enzyme
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in pH-controlled cultures, the addition of 20 mM acetate promotes a more vigorous solventogenic fermentation
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if a carboxylic acid, such as acetate, is omitted from the reaction using the pure enzyme, no enzyme activity is found. As soon as a carboxylic acid is added, the decarboxylation starts immediately. The enzyme activity is increased with the number of carbon atoms, rising from formate to butyrate. Above four carbon atoms, the activity decreases. Pimelate, butyrate and propionate are the strongest activators
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activation of mutant K202A
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Inhibitor in Enzyme-catalyzed Reactions (60 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
IC50 0.032 mM, pH 6.5
-
IC50: 13.6 mM
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incubation of alkane-grown cells with butanoate or propanoate leads to irreversible time- and O2-dependent loss of butane monooxygenase activity
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50% inhibition at 250 mM, with dimethylglycine
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72% inhibition at 11 mM
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IC50: 0.055 mM
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slight inhibition of the reverse reaction, competitive versus benzylamine, noncompetitive versus formate
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decreases PEPC activity and restricts the stimulation by abscisic acid
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at 200 mM and above
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propanoate-CoA formation
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competitive inhibitor of benzoate
-
-
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slight inhibition of wild-type enzyme
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500 mM, 44% inhibition
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3D Structure of Enzyme-Ligand-Complex (PDB) (13 results)

Enzyme Kinetic Parameters

kcat Value (Turnover Number) (17 results)

EC NUMBER
TURNOVER NUMBER [1/S]
TURNOVER NUMBER MAXIMUM [1/S]
COMMENTARY
LITERATURE
60
-
pH 7.5, 25°C
9.7
-
pH 8.5, 30°C, recombinant enzyme

KM Value (36 results)

EC NUMBER
KM VALUE [MM]
KM VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
0.8
-
-
16.9
-
pH 7.5, 30°C
35.2
-
pH 7.5, 25°C
150
-
cosubstrate glutaconyl-CoA
0.8
-
pH 7.5, 25°C
0.22
-
-
24.4
-
pH 8.5, 30°C, recombinant enzyme
5
-
pH not specified in the publication, temperature not specified in the publication

Ki Value (10 results)

EC NUMBER
KI VALUE [MM]
KI VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
3.6
-
non-competitive, glycolate oxidation
0.002
-
-

IC50 Value (11 results)

EC NUMBER
IC50 VALUE
IC50 VALUE MAXIMUM
COMMENTARY
LITERATURE
0.032
-
IC50 0.032 mM, pH 6.5
13.6
-
IC50: 13.6 mM
0.055
-
IC50: 0.055 mM
275
-
pH 7.0, 25°C

References & Links

Links to other databases for butyric acid

ChEBI
PubChem
ChEBI
PubChem