Ligand malonyl-CoA

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Basic Ligand Information

Molecular Structure
Picture of malonyl-CoA (click for magnification)
Molecular Formula
BRENDA Name
InChIKey
C24H38N7O19P3S
malonyl-CoA
LTYOQGRJFJAKNA-DVVLENMVSA-N
Synonyms:
(2) malonyl-CoA, 2-carboxyacetyl-CoA, an omega-carboxyacyl-CoA, malonyl CoA
Pathway Source
Pathways
MetaCyc
(1'S,5'S)-averufin biosynthesis, (4Z,7Z,10Z,13Z,16Z)-docosa-4,7,10,13,16-pentaenoate biosynthesis II (4-desaturase), (4Z,7Z,10Z,13Z,16Z)-docosapentaenoate biosynthesis (6-desaturase), (5R)-carbapenem carboxylate biosynthesis, (9Z)-tricosene biosynthesis more


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

Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (86 results)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
malonyl-CoA + NADPH = malonate-semialdehyde + CoA + NADP+
show the reaction diagram
-
S-adenosyl-L-methionine + malonyl-CoA = S-adenosyl-L-homocysteine + malonyl-CoA methyl ester
show the reaction diagram
-
malonyl-CoA + dephospho-CoA = CoA + malonyl-dephospho-CoA
show the reaction diagram
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malonyl-CoA + D-tryptophan = CoA + N2-malonyl-D-tryptophan
show the reaction diagram
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malonyl-CoA + 3,4-dichloroaniline = CoA + N-(3,4-dichlorophenyl)-malonamate
show the reaction diagram
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apigenin 7-O-apiosylglucoside + malonyl-CoA = apigenin 7-O-apiosylglucoside -6''-O-malonylester + CoA
show the reaction diagram
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malonyl-CoA + kaempferol 3-O-glucoside = CoA + kaempferol 3-O-glucoside malonylester
show the reaction diagram
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cinnamoyl-CoA + malonyl-CoA = 3,5-dihydroxystilbene + CoA + CO2
show the reaction diagram
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malonyl-CoA + N-methylanthraniloyl-CoA = CoA + 1,3-dihydroxy-N-methylacridone + CO2
show the reaction diagram
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malonyl-CoA + 4-coumaroyl-CoA + NADPH + H+ = CoA + isoliquiritigenin + CO2 + NADP+ + H2O
show the reaction diagram
-
malonyl-CoA + delphinidin 3-O-beta-D-glucoside = CoA + delphinidin 3-O-(6-malonyl-beta-D-glucoside)
show the reaction diagram
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a very-long-chain acyl-CoA + malonyl-CoA = a very-long-chain 3-oxoacyl-CoA + CO2 + coenzyme A
show the reaction diagram
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3 malonyl-CoA + hexanoyl-CoA = 3 CoA + 3,5,7-trioxododecanoyl-CoA + 3 CO2
show the reaction diagram
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4-coumaroyl-CoA + malonyl-CoA + H2O = 2 CoA + 4-hydroxybenzalacetone + 2 CO2
show the reaction diagram
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5 malonyl-CoA = 5 CoA + 5,7-dihydroxy-2-methyl-4H-chromen-4-one + 5 CO2 + H2O
show the reaction diagram
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3 malonyl-CoA + benzoyl-CoA = 4 CoA + 2,4,6-trihydroxybenzophenone + 3 CO2
show the reaction diagram
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7 malonyl-CoA + hexanoyl-[acyl-carrier protein] = 7 CoA + norsolorinic acid anthrone + [acyl-carrier protein] + 7 CO2 + 2 H2O
show the reaction diagram
-
malonyl-CoA + 2-aminobenzoyl-CoA = 2 CoA + 4-hydroxy-2(1H)-quinolone + CO2
show the reaction diagram
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10 malonyl-CoA = tetracenomycin F2 + 10 CoA + 10 CO2 + 2 H2O
show the reaction diagram
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acetyl-CoA + 5 malonyl-CoA + 3 NADPH + 3 H+ = 5-methyl-1-naphthoate + 6 CoA + 5 CO2 + 4 H2O + 3 NADP+
show the reaction diagram
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acetyl-CoA + 5 malonyl-CoA + 2 NADPH + 2 H+ = 2-hydroxy-5-methyl-1-naphthoate + 6 CoA + 5 CO2 + 3 H2O + 2 NADP+
show the reaction diagram
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malonyl-CoA + 5 (2S)-methylmalonyl-CoA + 5 NADPH + 5 H+ = 10-deoxymethynolide + 6 CoA + 6 CO2 + 5 NADP+ + 2 H2O
show the reaction diagram
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malonyl-CoA + 6 (2S)-methylmalonyl-CoA + 5 NADPH + 5 H+ = narbonolide + 7 CoA + 7 CO2 + 5 NADP+ + 2 H2O
show the reaction diagram
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acetyl-CoA + malonyl-CoA + [2-methylbutanoate polyketide synthase] + 2 NADPH + 2 H+ + S-adenosyl-L-methionine = (S)-2-methylbutanoyl-[2-methylbutanoate polyketide synthase] + 2 CoA + CO2 + 2 NADP+ + S-adenosyl-L-homocysteine + H2O
show the reaction diagram
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3 malonyl-CoA = phloroglucinol + 3 CO2 + 3 CoA
show the reaction diagram
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malonamoyl-[OxyC acyl-carrier protein] + malonyl-CoA = 18-carbamoyl-3,5,7,9,11,13,15,17-octaoxooctadecanoyl-[OxyC acyl-carrier protein] + CO2 + CoA
show the reaction diagram
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a medium-chain acyl-CoA + 5 malonyl-CoA + 5 (S)-methylmalonyl-CoA + 22 NADPH + 22 H+ = a mycoketide-CoA + 10 CO2 + 10 CoA + 22 NADP+ + 11 H2O
show the reaction diagram
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acetyl-CoA + 7 malonyl-CoA + 14 NADPH + 14 H+ = palmitate + 8 CoA + 7 CO2 + 14 NADP+ + 6 H2O
show the reaction diagram
acetyl-CoA + malonyl-CoA + NADH + NADPH = ?
show the reaction diagram
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8 malonyl-CoA = 8 CoA + 2,7-dihydroxy-5-[(4-hydroxy-2-oxo-2H-pyran-6-yl)methyl]-2-methyl-2,3-dihydro-4H-chromen-4-one + 2,7-dihydroxy-5-[(4-hydroxy-2-oxo-2H-pyran-6-yl)methyl]-5-methyl-2,3-dihydro-4H-chromen-4-one + 8 CO2 + H2O
show the reaction diagram
-
8 malonyl-CoA + NADPH + H+ = 8 CoA + (4E,6E,8E,10E,12E,14E)-3-hydroxyhexadeca-4,6,8,10,12,14-hexaenoic acid + NADP+ + H2O + CO2
show the reaction diagram
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In Vivo Product in Enzyme-catalyzed Reactions (6 results)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
[biotin carboxyl-carrier protein]-N6-carboxybiotinyl-L-lysine + acetyl-CoA = [biotin carboxyl-carrier protein]-N6-biotinyl-L-lysine + malonyl-CoA
show the reaction diagram
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-
acetyl-CoA + malonate = acetate + malonyl-CoA
show the reaction diagram
-
-
ATP + acetyl-CoA + HCO3- = ADP + malonyl-CoA + phosphate
show the reaction diagram
-
-

Substrate in Enzyme-catalyzed Reactions (379 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
malonyl-CoA + NADPH = malonate-semialdehyde + CoA + NADP+
show the reaction diagram
-
S-adenosyl-L-methionine + malonyl-CoA = S-adenosyl-L-homocysteine + malonyl-CoA methyl ester
show the reaction diagram
-
malonyl-CoA + dephospho-CoA = CoA + malonyl-dephospho-CoA
show the reaction diagram
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[biotin carboxyl-carrier protein 87]-N6-biotinyl-L-lysine + malonyl-CoA = [biotin carboxyl-carrier protein 87]-N6-carboxybiotinyl-L-lysine + acetyl-CoA
show the reaction diagram
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malonyl-CoA + anthranilate = CoA + N-malonylanthranilate
show the reaction diagram
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malonyl-CoA + 2-hydroxy-amino-6-methyldipyrido[1,2-a: 3',2'-d]imidazole = CoA + N-malonyloxyamino-6-methyldipyrido[1,2-a: 3',2'-d]imidazole
show the reaction diagram
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malonyl-CoA + L-carnitine = malonyl-L-carnitine + CoA
show the reaction diagram
-
malonyl-CoA + 4-coumaroyl-CoA + NADPH + H+ = CoA + isoliquiritigenin + CO2 + NADP+ + H2O
show the reaction diagram
-
malonyl-CoA + lauroyl-CoA = ?
show the reaction diagram
-
malonyl-CoA + dephospho-CoA = CoA + malonyl-dephospho-CoA
show the reaction diagram
-
malvidin 3-O-beta-D-glucoside + malonyl-CoA = CoA + malvidin 3-O-(6-O-malonyl)-beta-D-glucoside
show the reaction diagram
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5 malonyl-CoA = 5 CoA + 5,7-dihydroxy-2-methyl-4H-chromen-4-one + 5 CO2 + H2O
show the reaction diagram
-
malonyl-CoA + 2-aminobenzoyl-CoA = 2 CoA + 4-hydroxy-2(1H)-quinolone + CO2
show the reaction diagram
-
10 malonyl-CoA = tetracenomycin F2 + 10 CoA + 10 CO2 + 2 H2O
show the reaction diagram
-
acetyl-CoA + 5 malonyl-CoA + 3 NADPH + 3 H+ = 5-methyl-1-naphthoate + 6 CoA + 5 CO2 + 4 H2O + 3 NADP+
show the reaction diagram
-
acetyl-CoA + 5 malonyl-CoA + 2 NADPH + 2 H+ = 2-hydroxy-5-methyl-1-naphthoate + 6 CoA + 5 CO2 + 3 H2O + 2 NADP+
show the reaction diagram
-
malonyl-CoA + 5 (2S)-methylmalonyl-CoA + 5 NADPH + 5 H+ = 10-deoxymethynolide + 6 CoA + 6 CO2 + 5 NADP+ + 2 H2O
show the reaction diagram
-
malonyl-CoA + 6 (2S)-methylmalonyl-CoA + 5 NADPH + 5 H+ = narbonolide + 7 CoA + 7 CO2 + 5 NADP+ + 2 H2O
show the reaction diagram
-
acetyl-CoA + malonyl-CoA + [2-methylbutanoate polyketide synthase] + 2 NADPH + 2 H+ + S-adenosyl-L-methionine = (S)-2-methylbutanoyl-[2-methylbutanoate polyketide synthase] + 2 CoA + CO2 + 2 NADP+ + S-adenosyl-L-homocysteine + H2O
show the reaction diagram
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3 malonyl-CoA = phloroglucinol + 3 CO2 + 3 CoA
show the reaction diagram
-
malonamoyl-[OxyC acyl-carrier protein] + malonyl-CoA = 18-carbamoyl-3,5,7,9,11,13,15,17-octaoxooctadecanoyl-[OxyC acyl-carrier protein] + CO2 + CoA
show the reaction diagram
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malonyl-CoA + (S)-1-aminoethylphosphonic acid = CoA + ?
show the reaction diagram
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6 malonyl-CoA + 5 NADPH + NADH + 6 H+ = (2E,5S,6E,8E,10E)-5-hydroxydodeca-2,6,8,10-tetraenal + 6 CoA + 5 NADP+ + NAD+ + 6 CO2 + 4 H2O
show the reaction diagram
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4-nitrobenzoyl-CoA + malonyl-CoA + 4 (S)-methylmalonyl-CoA + 4 NADPH + 4 H+ = demethylluteothin + 5 CO2 + 6 CoA + 4 NADP+ + 3 H2O
show the reaction diagram
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4-nitrobenzoyl-CoA + malonyl-CoA + 6 (S)-methylmalonyl-CoA + 6 NADPH + 4 H+ = demethyldeoxyspectinabilin + 7 CO2 + 8 CoA + 6 NADP+ + 5 H2O
show the reaction diagram
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lauroyl-CoA + malonyl-CoA = ?
show the reaction diagram
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malonyl-CoA + L-homoserine = CoA + O-malonyl-L-homoserine
show the reaction diagram
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malonyl-CoA + L-(-)carnitine = malonylcarnitine + CoASH
show the reaction diagram
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8 malonyl-CoA = 8 CoA + 2,7-dihydroxy-5-[(4-hydroxy-2-oxo-2H-pyran-6-yl)methyl]-2-methyl-2,3-dihydro-4H-chromen-4-one + 2,7-dihydroxy-5-[(4-hydroxy-2-oxo-2H-pyran-6-yl)methyl]-5-methyl-2,3-dihydro-4H-chromen-4-one + 8 CO2 + H2O
show the reaction diagram
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malonyl-CoA + an [acyl-carrier protein] = CoA + a methylmalonyl-[acyl-carrier protein]
show the reaction diagram
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8 malonyl-CoA + NADPH + H+ = 8 CoA + (4E,6E,8E,10E,12E,14E)-3-hydroxyhexadeca-4,6,8,10,12,14-hexaenoic acid + NADP+ + H2O + CO2
show the reaction diagram
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2-oxo-3-methylbutanoate + malonyl-CoA + H2O = 2-hydroxy-3-metylbutane-11,2-tricarboxyl acid + CoA
show the reaction diagram
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malonyl-CoA + apo-[acyl-carrier protein] = ? + holo-[acyl-carrier protein]
show the reaction diagram
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malonyl-CoA + malonate = malonyl-CoA + malonate
show the reaction diagram
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malonyl-CoA = malonate + CoA
show the reaction diagram
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malonyl-CoA + H2O = malonate + CoA
show the reaction diagram
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malonyl-CoA + H2O = malonate + CoA
show the reaction diagram
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malonyl-CoA + H2O = malonate + CoA
show the reaction diagram
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malonyl-CoA + H2O = CoA + malonate
show the reaction diagram
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malonyl-CoA + H2O = ?
show the reaction diagram
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malonyl-CoA + H+ = acetyl-CoA + CO2
show the reaction diagram
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Malonyl-CoA = Acetyl-CoA + CO2
show the reaction diagram
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Product in Enzyme-catalyzed Reactions (27 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
malonate semialdehyde + coenzyme A + NADP+ = malonyl-CoA + NADPH + H+
show the reaction diagram
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acetyl-CoA + oxaloacetate = malonyl-CoA + pyruvate
show the reaction diagram
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apiin + malonyl-CoA = apigenin 7-O-apiosylglucoside -6''-O-malonylester + malonyl-CoA
show the reaction diagram
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-
malonyl-L-carnitine + CoA = malonyl-CoA + L-carnitine
show the reaction diagram
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-
malonylcarnitine + CoASH = malonyl-CoA + L-(-)carnitine
show the reaction diagram
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-
ATP + malonate + CoA = ADP + phosphate + malonyl-CoA
show the reaction diagram
-
-
ATP + acetyl-CoA + HCO3- = ADP + phosphate + malonyl-CoA
show the reaction diagram
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ATP + acetyl-CoA + HCO3- = ADP + malonyl-CoA + phosphate
show the reaction diagram
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Activator in Enzyme-catalyzed Reactions (4 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
15% activation at 0.005 mM
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activates enzyme activity 1.36fold
-
activation in decreasing order: acetyl-CoA, n-propanyl-CoA, n-butanoyl-CoA, malonyl-CoA/ CoA, acetoacetyl-CoA, oleoyl-CoA
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Inhibitor in Enzyme-catalyzed Reactions (85 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
2.4 mM, no inhibition of NADP+-dependent reaction, 14% inhibition of NAD+-dependent reaction
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inhibition of mitochondrial enzyme and cytosolic enzyme to a much lower extent than with acetyl-CoA
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non-competitive
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noncompetitive inhibitor
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inhibition of MCT1 at 0.01 mM and inhibition of both isozymes at 0.02 mM and 0.04 mM; inhibits both MCT1 and MCT2
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0.1 mM, 11 inhibtion
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competitive, malonyl-transferase reaction
0.4 mM, 70% inhibition
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0.2 mM, 83% residual activity
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competitive inhibition
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3D Structure of Enzyme-Ligand-Complex (PDB) (4 results)

Enzyme Kinetic Parameters

kcat Value (Turnover Number) (105 results)

EC NUMBER
TURNOVER NUMBER [1/S]
TURNOVER NUMBER MAXIMUM [1/S]
COMMENTARY
LITERATURE
0.058
-
pH 7.0, 30°C, recombinant His-tagged BPS
0.0296
-
pH 8.0, 30°C, recombinant wild-type enzyme
0.55
-
pH 8.5, temperature not specified in the publication
0.92
-
pH 6.5, 30°C
0.0112
-
pH 7.5, 37°C, recombinant enzyme
1.7
-
pH 7.8, 22°C
0.4
-
cosubstrate: (S)-1-aminoethylphosphonic acid, pH 7.5, 25°C
0.102
-
mutant enzyme S726F, at pH 7.0 and 30°C
0.12
-
25°C, pH 7.5

KM Value (236 results)

EC NUMBER
KM VALUE [MM]
KM VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
0.035
-
-
1.9
-
pH 6.0
0.005
-
-
0.004
-
-
0.005
-
-
0.033
-
-
0.5
-
-
0.007
-
-
0.028
-
pH 8.0, 25°C; pH 8.0, 30°C, reaction with acetyl-CoA and malonyl-CoA; pH 8.0, 30°C, reaction with malonyl-CoA, without acetyl-CoA
0.0069
-
pH 8.5, temperature not specified in the publication
0.588
-
pH 6.5, 30°C
0.0084
-
pH 7.5, 37°C, recombinant enzyme
0.0027
-
pH 7.8, 22°C
0.05
-
cosubstrate: (S)-1-aminoethylphosphonic acid, pH 7.5, 25°C
0.1176
-
mutant enzyme S726F, at pH 7.0 and 30°C
0.017
-
25°C, pH 7.5
0.5
-
-
0.7
-
pH 6.0, 30°C
1.2
-
-

Ki Value (13 results)

EC NUMBER
KI VALUE [MM]
KI VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
TABLE ID
0.4
-
24°C, pH 7.8, inhibition of NAD+-dependent reaction
1694
0.021
-
-
2516
0.021
-
pH and temperature not specified in the publication
2870
0.6
-
pH 6.0, 30°C
18211
1.6
-
recombinant enzyme, pH 8.0, 30°C
18164
66.63
-
pH and temperature not specified in the publication
34985
0.009
-
-
42579

IC50 Value (53 results)

EC NUMBER
IC50 VALUE
IC50 VALUE MAXIMUM
COMMENTARY
LITERATURE
0.017
-
-

References & Links