Ligand butyryl-CoA

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Basic Ligand Information

Molecular Structure
Picture of butyryl-CoA (click for magnification)
Molecular Formula
BRENDA Name
InChIKey
C25H42N7O17P3S
butyryl-CoA
CRFNGMNYKDXRTN-CITAKDKDSA-N
Synonyms:
a short-chain acyl-CoA, butanoyl-CoA, butyryl CoA, n-butanoyl-CoA, n-butyryl-CoA


Show all pahtways known for Show all BRENDA pathways known for butyryl-CoA

Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (17 results)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
butanoyl-CoA + NADH + H+ = butanal + CoA + NAD+
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butanoyl-CoA + NADH + H+ = butanal + CoA + NAD+
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butanoyl-CoA + NADH + H+ = butanal + CoA + NAD+
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butyryl-CoA + 10-deacetylbaccatin III = CoA + 10-deacetyl-10-butyrylbaccatin III
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butanoyl-CoA + phosphate = butanoylphosphate + CoA
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butanoyl-CoA + malonyl-[acyl-carrier protein] = 3-oxoheptanoyl-[acyl-carrier-protein] + CoA + CO2
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butanoyl-CoA + H2O + glyoxylate = 3-ethylmalate + CoA
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butanoyl-CoA + H2O = butanoate + CoA
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ATP + butyryl-CoA + HCO3- + H+ = ADP + glutaryl-CoA + phosphate
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In Vivo Product in Enzyme-catalyzed Reactions (13 results)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
crotonyl-CoA + NADPH = butanoyl-CoA + NADP+
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crotonyl-CoA + NADH = butanoyl-CoA + NAD+
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crotonyl-CoA + reduced acceptor = butyryl-CoA + oxidized acceptor
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butanoate + acetoacetyl-CoA = butanoyl-CoA + acetoacetate
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ATP + butyric acid + CoA = AMP + diphosphate + butyryl-CoA
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Substrate in Enzyme-catalyzed Reactions (151 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
butanoyl-CoA + 2-oxoglutarate + O2 = 2-hydroxybutanoyl-CoA + succinate + CO2
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butanoyl-CoA + NADH + H+ = butanal + CoA + NAD+
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butanoyl-CoA + NADH + H+ = butanal + CoA + NAD+
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butanoyl-CoA + 2 NAD+ + 2 reduced ferredoxin iron-sulfur cluster = (E)-but-2-enoyl-CoA + 2 NADH + 2 oxidized ferredoxin iron-sulfur cluster
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butyryl-CoA + 2,6-dichlorophenolindophenol = ?
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butyryl-CoA + O2 = trans-2-butenoyl-CoA + H2O2
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butyryl-CoA + acceptor = ? + reduced acceptor
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butyryl-CoA + oxaloacetate = ethylmalonyl-CoA + pyruvate
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butyryl-CoA + 2-hydroxy-amino-6-methyldipyrido[1,2-a: 3',2'-d]imidazole = CoA + N-(butyryloxy)-6-methylpyrido[3',2':4,5]imidazo[1,2-a]pyridin-2-amine
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butyryl-CoA + glycine = CoA + N-butyrylglycine
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butyryl-CoA + H2O = butanoate + CoA
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butyryl-CoA + malonyl-CoA = 6-propyl triacetic acid lactone + CoA
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butyryl-CoA + dihydrolipoamide = CoA + S-butyryldihydrolipoamide
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butyryl-CoA + p-nitrophenyl-beta-D-galactopyranoside = CoA + p-nitrophenyl 6-O-butyryl-beta-D-galactopyranoside
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S-adenosyl-L-methionine + butyryl-CoA = 5'-methylthioadenosine + N-butyryl-L-homoserine-1,4-lactone + CoA
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butyryl-CoA + 1,2-diacylglycerol = CoA + 1,2-diacyl-3-butyrylglycerol
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3 malonyl-CoA + butyryl-CoA = ?
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butyryl-CoA + L-carnitine = CoA + L-butyrylcarnitine
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3 malonyl-CoA + butyryl-CoA = 4 CoA + 2,4,6-trihydroxybutyrophenone + 6-propyl-4-hydroxy-2-pyrone + 3 CO2
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butyryl-CoA = 4-hydroxy-6-propyl-2-pyrone + 4-hydroxy-6-(2'-oxopentyl)-2-pyrone + 1,3,6,8-tetrahydroxynaphthalene + CoA + CO2 + H2O
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butyryl-CoA + monacolin J = (1S,3R,7S,8S,8aR)-8-[2-[(2R,4R)-4-hydroxy-6-oxotetrahydro-2H-pyran-2-yl]ethyl]-3,7-dimethyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl butanoate + CoA
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butyryl-CoA = phloroglucinol + 4-hydroxy-6-propyl-2H-pyran-2-one + CO2 + CoA
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n-butyryl-CoA + glycine = CoA + 2-amino-3-oxohexanoate
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butanoyl-CoA + malonyl-[acyl-carrier protein] = 3-oxoheptanoyl-[acyl-carrier-protein] + CoA + CO2
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butyryl-CoA + L-homoserine = CoA + O-butyryl-L-homoserine
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butyryl-CoA + [acyl-carrier protein] = CoA + butyryl-[acyl-carrier protein]
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butanoyl-CoA + D-glucosamine 6-phosphate = CoA + N-butanoyl-D-glucosamine 6-phosphate
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butyryl-CoA + malonyl-[acyl-carrier protein] = ?
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butanoyl-CoA + L-arginine = N-[(4S)-4-amino-5-oxooctyl]guanidine + CO2 + CoA
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butyryl-CoA + 1-alkyl-2-lyso-sn-glycero-3-phosphocholine = 2-butyryl-1-alkyl-sn-glycero-3-phosphocholine
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n-butyryl-CoA + glycine = CoA + N-butyrylglycine
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butyryl-CoA + phosphate = CoA + butyryl phosphate
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butyryl-CoA + 13-hydroxylupanine = CoA + 13-butyryloxylupanine
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n-butyryl-CoA + malonyl-CoA = bisnoryangonin-type and p-coumaroyltriacetic acid lactone-type pyrones + CoA + CO2
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2-oxo-3-methylbutanoate + butanoyl-CoA + H2O = 3-ethyl-2-hydroxy-2-isopropylsuccinic acid + CoA
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butanoyl-CoA + H2O + oxaloacetate = (2S,3S)-2-hydroxyhexane-1,2,3-tricarboxylate + CoA
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butanoyl-CoA + H2O + glyoxylate = 3-ethylmalate + CoA
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glyoxylate + butyryl-CoA + H2O = 2-oxohexanedioic acid + CoA
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butyryl-CoA + propanoate = ?
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butyryl-CoA + citrate = butyrate + (3S)-citryl-CoA
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butyryl-CoA + 3-hydroxy-3-methylglutarate = butyrate + 3-hydroxy-3-methylglutaryl-CoA
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butyryl-CoA + malonate = malonyl-CoA + butanoate
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butyryl-CoA + H2O = butanoate + CoA
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butyryl-CoA + H2O = butanoate + CoA
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butanoyl-CoA = isobutanoyl-CoA
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ADP + phosphate + butyryl-CoA = ATP + butyrate + CoA
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Product in Enzyme-catalyzed Reactions (87 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
n-butyraldehyde + coenzyme A + NADP+ = n-butyryl-CoA + NADPH + H+
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butyraldehyde + CoA + NAD+ = butyryl-CoA + NADH + H+
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2-oxopentanoate + NAD+ + CoA = butanoyl-CoA + CO2 + NADH
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2-ketovalerate + CoA + benzyl viologen = butanoyl-CoA + CO2 + reduced benzyl viologen
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crotonyl-CoA + NADPH + H+ = butanoyl-CoA + NADP+
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crotonyl-CoA + NADPH = butanoyl-CoA + NADP+
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crotonyl-CoA + NADPH + H+ = butyryl-CoA + NADP+
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crotonyl-CoA + NADPH + H+ = butanoyl-CoA + NADP+
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butyryl-L-carnitine + CoA = butyryl-CoA + L-carnitine
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3-oxohexanoyl-CoA + CoA = acetyl-CoA + butyryl-CoA
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CoA + 3-oxohexanoyl-CoA = acetyl-CoA + butanoyl-CoA
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CoA + butyryl phosphate = butyryl-CoA + phosphate
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n-butyrylcarnitine + CoASH = n-butyryl-CoA + carnitine
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glutaconyl-CoA + butyrate = butyryl-CoA + glutaconate
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(S)-ethylmalonyl-CoA = butanoyl-CoA + CO2
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isobutanoyl-CoA = butanoyl-CoA
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ATP + butyrate + CoA = AMP + diphosphate + butyryl-CoA
show the reaction diagram
557,
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GTP + butyrate + CoA = GDP + phosphate + butyryl-CoA
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ATP + butyrate + CoA = AMP + diphosphate + butyryl-CoA
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ATP + butyrate + CoA = AMP + diphosphate + butyryl-CoA
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butyrate + ATP + coenzyme A = butyryl-CoA + AMP + diphosphate
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ATP + butyrate + CoA = AMP + diphosphate + butyryl-CoA
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ATP + butyrate + CoA = ADP + phosphate + butyryl-CoA
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ATP + butanoate + CoA = ADP + phosphate + butanoyl-CoA
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ATP + butyrate + CoA = ADP + phosphate + butyryl-CoA
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ATP + butyrate + CoA = ADP + phosphate + butyryl-CoA
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glutaryl-CoA + Na+[side 1] = butyryl-CoA + CO2 + Na+[side 2]
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Activator in Enzyme-catalyzed Reactions (3 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
activates
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Inhibitor in Enzyme-catalyzed Reactions (33 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
0.1 mM, 50% inhibition
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about 30% residual activity at 2.5 mM
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synthase III mutants C122Aand C122Q: inhibition of decarboxylation activity in presence of
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0.1 mM, 28% inhibtion
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0.4 mM, in presence of 100 mM L-glutamine, 50% loss of activity
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dead-end inhibition pattern
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1 mM, 42% inhibition
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at high concentrations
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non-competitive inhibition
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competitive
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0.1 mM, 29% inhibition
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R207Q and Y89F/R207Q mutants show conversion of adenosylcobalamin to hydroxycobalamin, indicating inactivation of the enzyme. No changes in wild-type and Y89F-mutant

3D Structure of Enzyme-Ligand-Complex (PDB) (33 results)

Enzyme Kinetic Parameters

kcat Value (Turnover Number) (67 results)

EC NUMBER
TURNOVER NUMBER [1/S]
TURNOVER NUMBER MAXIMUM [1/S]
COMMENTARY
LITERATURE
0.19
-
recombinant enzyme, pH 7.15, 30°C
3.37
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recombinant enzyme, pH 7.15, 30°C
2
8
pH 7.5, 22-25°C
2
8
pH 7.5, temperature not specified in the publication
0.225
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0.133
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using recombinant enzyme, electron acceptor: electron-transferring flavoprotein
0.05
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pH 8.8, 25°C, recombinant enzyme
0.011
0.012
pH 5.5, 30°C, dependent on product formed
0.3
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in 50 mM HEPES, pH 7.5 and 0.1 mM 4,4'-dithiodipyridine, at pH 7.8 and 25°C
10.8
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didomain construct, pH not specified in the publication, 25°C
38.2
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pH 7.4, 30ºC
0.0033
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pH 6.6, 30°C, wild-type enzyme

KM Value (144 results)

EC NUMBER
KM VALUE [MM]
KM VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
0.256
-
recombinant enzyme, pH 7.15, 30°C
0.01
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pH 7.5, 22-25°C
0.0067
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0.01
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pH 7.5, temperature not specified in the publication
0.25
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0.221
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p-nitrophenyl-beta-D-galactopyranoside
0.016
0.025
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0.0861
0.0889
pH 5.5, 30°C, dependent on product formed
1.59
-
pH 7.9, 25°C
12
-
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0.0006
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pH 7, 30°C
0.0083
-
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0.046
-
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130
-
-
0.058
-
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1.16
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in 50 mM HEPES, pH 7.5 and 0.1 mM 4,4'-dithiodipyridine, at pH 7.8 and 25°C
0.00164
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didomain construct, pH not specified in the publication, 25°C
0.4
-
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0.022
-
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1.3
-
pH 8.0, 25°C, isolated transferase
0.41
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pH 8, 37°C, Vmax: 44 micromol/min/mg, wild-type
0.007
0.02
estimated from rates at lower and higher substrate concentration
0.057
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pH 7.4, 30ºC
3.34
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pH 6.6, 30°C, wild-type enzyme

Ki Value (14 results)

EC NUMBER
KI VALUE [MM]
KI VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
1.45
-
inhbition of CO/acetyl-CoA exchange reaction
0.005
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1.3
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at pH 8.5 and 30°C
0.033
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pH 8.0
2.6
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pH 6.0, 30°C

IC50 Value (1 result)

EC NUMBER
IC50 VALUE
IC50 VALUE MAXIMUM
COMMENTARY
LITERATURE
1
-
pH 7.5, 30°C

References & Links

Links to other databases for butyryl-CoA

ChEBI
PubChem
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PubChem