Ligand lysophosphatidylcholine

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Basic Ligand Information

Molecular Structure
Picture of lysophosphatidylcholine (click for magnification)
Molecular Formula
BRENDA Name
InChIKey
C12H25NO7PR
lysophosphatidylcholine
KFNRNFXZFIRNEO-NSHDSACASA-N
Synonyms:
1-acrylglycerophosphocholine, 1-acyl-2-lysophosphatidycholine, 1-acyl-2-lysophosphatidylcholine, 1-acyl-glycero-3-phosphorylcholine, 1-acyl-glycerophosphocholine, 1-acyl-lysophosphatidylcholine, 1-acyl-sn-glycero-3-phosphocholine, 1-acyl-sn-glycero-3-phosphorylcholine, 1-acyl-sn-glycerol-3-phosphocholine, 1-acylglycerol-3-phosphorylcholine, 1-acylglycerophosphocholine, 1-acylglyceryl phosphorylcholine, 2-lyso-phosphatidylcholine, 2-lysolecithin, 2-lysophosphatidylcholine, lyso-phosphatidylcholine, lysocholinephospholipid, lysolecithin, lysolecithin analogs, lysophophatidylcholine, lysophosphatidyl choline, lysophosphatidylcholines


Show all pahtways known for Show all BRENDA pathways known for lysophosphatidylcholine

Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (15 results)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
lysophosphatidylcholine = ?
show the reaction diagram
-
lysophosphatidylcholine + H2O = choline + 2-lysophosphatidate
show the reaction diagram
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In Vivo Product in Enzyme-catalyzed Reactions (9 results)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
acyl-CoA + glycerophosphocholine = CoA + 1-acyl-sn-glycero-3-phosphocholine
show the reaction diagram
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-
phosphatidylcholine + H2O = 1-acylglycerophosphocholine + a carboxylate
show the reaction diagram
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-
phosphatidylcholine + H2O = lysophosphatidylcholine + a carboxylate
show the reaction diagram
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Substrate in Enzyme-catalyzed Reactions (69 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
lyso-phosphatidylcholine + O2 = ?
show the reaction diagram
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1-Acyl-glycerophosphocholine + diacylcholine glycerolipid = ?
show the reaction diagram
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acyl-CoA + lysophosphatidylcholine = CoA + acyllysophosphatidylcholine
show the reaction diagram
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1-acylglyceryl phosphorylcholine + lecithin = lecithin + 1-acylglyceryl phosphorylcholine
show the reaction diagram
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lysophosphatidylcholine + CMP = ?
show the reaction diagram
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lysophosphatidylcholine + H2O = fatty acid + glycerophosphocholine
show the reaction diagram
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lysophosphatidylcholine + H2O = ?
show the reaction diagram
-
2-lysophosphatidylcholine + H2O = choline + 2-lysophosphatidate
show the reaction diagram
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ATP + H2O + lysophosphatidylcholine/out = ADP + phosphate + lysophosphatidylcholine/in
show the reaction diagram
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Product in Enzyme-catalyzed Reactions (50 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
3-sn-phosphatidylcholine + dolichol = 1-acyl-sn-glycero-3-phosphocholine + acyldolichol
show the reaction diagram
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acyl-CoA + glycerophosphocholine = CoA + 1-acyl-sn-glycero-3-phosphocholine
show the reaction diagram
-
-
phosphatidylcholine + H2O = lysophosphatidylcholine + fatty acid
show the reaction diagram
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1-acyl-2-oleoyl-sn-glycerol-3-phosphocholine + H2O = 1-acylglycerol-3-phosphorylcholine + oleic acid
show the reaction diagram
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1-palmitoyl-2-(5-oxo)valeroyl-sn-glycero-3-phosphocholine + H2O = lysophosphatidylcholine + ?
show the reaction diagram
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3-Lysolecithin = 2-Lysolecithin
show the reaction diagram
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ATP + H2O + lysophosphatidylcholine/out = ADP + phosphate + lysophosphatidylcholine/in
show the reaction diagram
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-

Activator in Enzyme-catalyzed Reactions (39 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
lysolecithin, stimulates
-
activation
-
aprrox. 0.3%, 150% activation of activity in chromatophore extracts
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inhibition in presence of digitonin, stimulation in absence of digitonin within a certain concentration range
-
activation
-
activates
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activation
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C16-18 acyl derivatives of lysophosphatidylcholine stimulate the activity of enzyme form A more extensively than the C14 acyl derivative, and the C12 acyl derivative is without effect on enzyme form A
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activation of phospholipids in the order of decreasing efficiency: phosphatidylcholine, lysophosphatidylcholine, phosphatidylethanolamine, phosphatidylserine, sphingomyelin
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increases activity
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stimulates at low subsolubilizing concentrations, membrane-solubilizing concentrations lead to nearly complete inactivation
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slight activation, 0.2 mM
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activate
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0.5 mM, activation of phospholipase B activity to 132% of control
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activates
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stimulation
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stimulation
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in heparin-capacitated spermatozoa, the addition of lysophosphatidylcholine produces a significant increase (about 7fold) in acrosin activity
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stimulates
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Inhibitor in Enzyme-catalyzed Reactions (43 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
completely elimination of activity
-
non competitive
-
inhibits 68% of the enzyme activity at 30 microM
-
inhibition at high concentrations due to its detergent effect
-
inhibition in presence of digitonin, stimulation in absence of digitonin within a certain concentration range
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increases Km and reduces Vmax of the enzyme with triaclyglyrol substrates, not with monoacylglycerols, the activity is completely restored by addition of taurodeoxycholine or phospholipid
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inhibitory plasma compounds, profile determination by mass spectroscopy, overview
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50% inhibition at 0.05 mM
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ceramide synthesis activity, 10 mol%, moderate inhibition
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Enzyme Kinetic Parameters

kcat Value (Turnover Number) (3 results)

EC NUMBER
TURNOVER NUMBER [1/S]
TURNOVER NUMBER MAXIMUM [1/S]
COMMENTARY
LITERATURE
13
-
37°C, pH 7.5
2.5
-
soluble isozyme, pH 8.0, 37°C
0.032
-
pH 7.4, temperature not specified in the publication

KM Value (35 results)

EC NUMBER
KM VALUE [MM]
KM VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
0.25
-
pH 8.0, 30°C, AtMAGL4
4.9
-
constant water activity of 0.22
2
-
soluble isozyme, pH 8.0, 37°C

Ki Value (1 result)

EC NUMBER
KI VALUE [MM]
KI VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
0.93
-
-

References & Links

Links to other databases for lysophosphatidylcholine

ChEBI
PubChem
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PubChem