Ligand propionate

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Basic Ligand Information

Molecular Structure
Picture of propionate (click for magnification)
Molecular Formula
BRENDA Name
InChIKey
C3H6O2
propionate
ZQLMPRRTUJBILA-MMFATTAUSA-N
Synonyms:
n-propanoate, n-propionate, proipionate, propanoate, propanoic acid, propionic acid


Show all pahtways known for Show all BRENDA pathways known for propionate

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 + propionate + CoA = AMP + diphosphate + propionyl-CoA
show the reaction diagram
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In Vivo Product in Enzyme-catalyzed Reactions (15 results)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
propionaldehyde + NAD+ + H2O = propanoate + NADH + H+
show the reaction diagram
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propionaldehyde + NAD+ + H2O = propionate + NADH + H+
show the reaction diagram
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2alpha,17alpha-diethynyl-A-nor-5alpha-androstane-2beta,17beta-diol dipropionate + 2 H2O = anordiol + 2 propanoate
show the reaction diagram
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propionylthiocholine + H2O = thiocholine + propionate
show the reaction diagram
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propionyl-CoA + H2O = CoA + propionate
show the reaction diagram
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S-propionyltrypanothione + H2O = propionate + trypanothione + H+
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(2R,3S)-2,3-dimethylmalate = pyruvate + propionic acid
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(2R,3S)-2,3-dimethylmalate = propanoate + pyruvate
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Substrate in Enzyme-catalyzed Reactions (52 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
propionic acid + 2-oxoglutarate + O2 = 2-hydroxypropionic acid + succinate + CO2
show the reaction diagram
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ATP + propionate = ADP + propionyl phosphate
show the reaction diagram
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propionate + acetate = phosphate + propionyl phosphate
show the reaction diagram
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ATP + propionate = ADP + propanoyl phosphate
show the reaction diagram
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ATP + NH3 + propionate = ADP + ?
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ATP + propionate = ADP + propionyl phosphate
show the reaction diagram
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ATP + propionate = ADP + propanoyl phosphate
show the reaction diagram
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glutaconyl-CoA + propionate = propanoyl-CoA + glutaconate
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acetyl-CoA + propionate = acetate + propanoyl-CoA
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propionate + acetoacetyl-CoA = propionyl-CoA + acetoacetate
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ATP + propanoate + CoA = AMP + diphosphate + propanoyl-CoA
show the reaction diagram
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ATP + propionate + CoA = ADP + phosphate + propionyl-CoA
show the reaction diagram
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ATP + propionate + citrate (pro-3S)-lyase = AMP + diphosphate + citrate(pro-3S)-lyase
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propionate + ATP + coenzyme A = propionyl-CoA + AMP + diphosphate
show the reaction diagram
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ATP + propionate + CoA = AMP + diphosphate + propionyl-CoA
show the reaction diagram
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ATP + propionate + CoA = ADP + phosphate + propionyl-CoA
show the reaction diagram
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ATP + propionate + CoA = ADP + phosphate + propionyl-CoA
show the reaction diagram
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Product in Enzyme-catalyzed Reactions (265 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
propionaldehyde + acceptor = propanoate + reduced acceptor
show the reaction diagram
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propanal + acceptor + H2O = propionic acid + reduced acceptor
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propionaldehyde + NAD+ + H2O = propionic acid + NADH
show the reaction diagram
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propanal + H2O + O2 = propanoate + H2O2
show the reaction diagram
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propionaldehyde + NAD+ + H2O = propionate + NADH + H+
show the reaction diagram
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propionaldehyde + NAD+ + H2O = propionate + NADH
show the reaction diagram
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propionaldehyde + NAD+ + H2O = propionate + NADH
show the reaction diagram
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propionaldehyde + NAD+ + H2O = propionate + NADH
show the reaction diagram
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propionaldehyde + NAD+ = propionate + NADH
show the reaction diagram
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propionaldehyde + NAD+ + H2O = propionic acid + NADH
show the reaction diagram
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propionaldehyde + NAD+ + H2O = propionate + NADH + 2 H+
show the reaction diagram
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propionaldehyde + NAD+ + H2O = propionate + NADH + H+
show the reaction diagram
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propionaldehyde + NADP+ + H2O = propionate + NADPH + H+
show the reaction diagram
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propionaldehyde + NAD+ + H2O = propanoate + NADH + H+
show the reaction diagram
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propionaldehyde + NAD+ + H2O = propionate + NADH + 2 H+
show the reaction diagram
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propionaldehyde + 2,6-dichlorophenolindophenol + H2O = propionate + reduced 2,6-dichlorophenolindophenol
show the reaction diagram
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acrylic acid + NADH = propanoic acid + NAD+
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propionyl-CoA + H2O = propionate + CoA
show the reaction diagram
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propionyl-CoA + H2O = propanoate + CoA
show the reaction diagram
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propionyl-CoA + citrate = propionate + (3S)-citryl-CoA
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propionyl-CoA + malonate = malonyl-CoA + propanoate
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alpha-naphthyl propionate + H2O = alpha-naphthol + propionate
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4-nitrophenyl propionate + H2O = 4-nitrophenol + propionate
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tripropionin + H2O = propionate + dipropionin
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p-nitrophenyl propionate + H2O = p-nitrophenol + propionate
show the reaction diagram
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methyl propionate = propionate + methanol
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n-propionyl salicylate + H2O = 2-hydroxybenzoate + propionate
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4-methylumbelliferyl propionate + H2O = 4-methylumbelliferone + propionate
show the reaction diagram
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4-nitrophenyl propionate + H2O = 4-nitrophenol + propionate
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propionyl-CoA + H2O = CoA + propionate
show the reaction diagram
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propionyl-CoA + H2O = propionate + CoA
show the reaction diagram
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propionyl-CoA + H2O = CoA + propionate
show the reaction diagram
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S-propionylglutathione + H2O = glutathione + propionate
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p-nitrophenyl propionate + H2O = p-nitrophenol + propionate
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propionyl agmatine + H2O = propionic acid + agmatine
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4-propionamidobutyryl-CoA + H2O = propionate + 4-aminobutyryl-CoA
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N-Propionyl-D-Leu + H2O = Propanoate + D-Leu
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N-Propionyl-D-Glu + H2O = Propanoate + D-Glu
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N-Propanoyl-D-Asp + H2O = Propanoate + D-Asp
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propanamide + H2O = propanoate + NH3
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6-(N-propionyl-alpha-D-glucosaminyl)-1-phosphatidyl-1D-myo-inositol + H2O = 6-(alpha-D-glucosaminyl)-1-phosphatidyl-1D-myo-inositol + propionate
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N-benzylpropionamide + H2O = propionate + benzylamine
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(2R,3S)-2,3-dimethylmalate = pyruvate + propionic acid
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2-methylmalonate + H+ = propionate + CO2
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4-nitrophenyl propionate + H2O = 4-nitrophenol + propionate
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ADP + phosphate + propionyl-CoA = ATP + propionate + CoA
show the reaction diagram
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Activator in Enzyme-catalyzed Reactions (18 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
2 mM, catecholase activity: 245%
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the enzyme requires only a single propionate interacting with the buried terminus of Lys16 to exhibit full activity, and it tolerates the existence of a propionate at the exposed 8-position
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increase in propionate concentration lead to increase of enzyme amount
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significant activation
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increase in propionate concentration lead to increase of enzyme amount
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hydrolase increases 50-70% by 250 mM propionate
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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 an 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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activates
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strong activation of mutant K202A
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Inhibitor in Enzyme-catalyzed Reactions (58 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
5 mM, pH 8.5, 25C, 9% inhibition
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competitive
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92 mM, pH 8, very slight inhibition
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10 mM, 41% residual activity. Incubation of alkane-grown cells with butanoate or propanoate leads to irreversible time- and O2-dependent loss of butane monooxygenase activity. Propanoate-dependent inactivation involves interaction with the catalytic site. Butane monooxygenase is protected from propanoate-dependent inactivation by the presence of its natural substrate, butane
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0.01 mM, strong inhibition
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10% inhibition at 250 mM, with dimethylglycine
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slight inhibition
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competitive inhibition versus oxaloacetate, mixed type inhibition versus acetyl-CoA; substrate acetyl-CoA, competitive; substrate oxaloacetate, competitive
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inhibits alanine transamination and lysine transamination
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80% inhibition at 11 mM
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80% residual activity at 0.5 mM
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competitive inhibition
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39% relative activity at a concentration of 0.5 mM, 63% relative activity at a concentration of 0.05 mM
61% inhibition at 0.5 mM
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competitive inhibitor; competitive inhibitor
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at 50 mM and above
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butyryl-CoA formation
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inhibits acetate activation and butyrate activation
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inhibition of wild-type enzyme
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3D Structure of Enzyme-Ligand-Complex (PDB) (75 results)

EC NUMBER
ENZYME 3D STRUCTURE

Enzyme Kinetic Parameters

kcat Value (Turnover Number) (30 results)

EC NUMBER
TURNOVER NUMBER [1/S]
TURNOVER NUMBER MAXIMUM [1/S]
COMMENTARY
LITERATURE
108
-
pH 7.5, 25C
14.2
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pH 7.0, 25C
190
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at pH 7.3 and 37C
5.6
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pH 8.5, 45C
190
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pH 7.3, 37C, propionyl-CoA-forming direction, with propionate

KM Value (65 results)

EC NUMBER
KM VALUE [MM]
KM VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
14.3
-
pH 7.5, 30C
26
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pH 7.2, 30C
16
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cosubstrate glutaconyl-CoA
3.2
-
pH 7.5, 25C
628
-
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3850
-
pH 7.0, 25C
80
-
pH 8.5, 30C, recombinant enzyme
0.12
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pH 8.5, 45C
29
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pH 7.3, 37C, propionyl-CoA-forming direction, with propionate

Ki Value (17 results)

EC NUMBER
KI VALUE [MM]
KI VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
28
-
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250
-
pH 6.5, 30C
0.003
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9.9
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pH 7.6, 25C, recombinant wild-type enzyme

IC50 Value (3 results)

EC NUMBER
IC50 VALUE
IC50 VALUE MAXIMUM
COMMENTARY
LITERATURE
0.025
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IC50: 0.025 mM

References & Links

Links to other databases for propionate

ChEBI
PubChem
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PubChem