Ligand lysophosphatidylcholine

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Basic Ligand Information

Molecular Structure
Picture of lysophosphatidylcholine (click for magnification)
Molecular Formula
BRENDA Name
InChIKey
C12H25NO7PR
lysophosphatidylcholine
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
LITERATURE
REACTION DIAGRAM
PROVEN IN VIVO REACTION
ENZYME 3D STRUCTURE
show the reaction diagram
lysophosphatidylcholine = ?
-
show the reaction diagram
lysophosphatidylcholine + H2O = choline + 2-lysophosphatidate
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In Vivo Product in Enzyme-catalyzed Reactions (9 results)

EC NUMBER
LITERATURE
REACTION DIAGRAM
PROVEN IN VIVO REACTION
ENZYME 3D STRUCTURE
-
show the reaction diagram
acyl-CoA + glycerophosphocholine = CoA + 1-acyl-sn-glycero-3-phosphocholine
-
-
show the reaction diagram
phosphatidylcholine + H2O = 1-acylglycerophosphocholine + a carboxylate
-
show the reaction diagram
phosphatidylcholine + H2O = lysophosphatidylcholine + a carboxylate
-

Substrate in Enzyme-catalyzed Reactions (69 results)

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

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

Activator in Enzyme-catalyzed Reactions (39 results)

COMMENTARY
EC NUMBER
LITERATURE
ENZYME 3D STRUCTURE

Inhibitor in Enzyme-catalyzed Reactions (43 results)

COMMENTARY
EC NUMBER
LITERATURE
ENZYME 3D STRUCTURE
completely elimination of activity
-
activation at low concentrations, optimum at 0.075 mM, inhibitory above 0.2 mM
-
activation, at low concentrations, inhibition above 0.2 mM
-
high concentration, lung enzyme
-
above 0.1 mM, C10-C16, competitive inhibition
-
non competitive
-
inhibition of LCAT activity
-
both enantiomers, inhibition reversed by albumin
-
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
-
generated as a consequence of the activation of cytosolic phospholipase A2 by protein kinase C-alpha and p38 mitogen-activated protein kinase
-
competitive with respect to the lipid activator, 50% inhibition at 0.025 mM in the presence of phosphatidylcholine/oleic acid
-
99% inhibition of L-form, only partial inhibition of H-form
-
the solubilized but not the microsomal enzyme is strongly inhibited
-
1 mM, 89% inhibition
-
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
-
inhibitory plasma compounds, profile determination by mass spectroscopy, overview
-
strongly inhibitory
-
competitive inhibition at low concentration of palmitoyl-CoA
strongly inhibitory
-
50% inhibition is produced by 7% molar
-
C12, C14 and C16 lysophosphatidylcholines give progressive inhibition with increasing chain length
-
50% inhibition at 0.05 mM
-
ceramide synthesis activity, 10 mol%, moderate inhibition
-
10 microg/ml, about 35% relative activity
-
activity is significantly decreased in cells treated with lysophosphatidylcholine (0.005 mg/ml) for 48 h, 0.001-0.005 mM probucol or 0.001 mM pyrrolidindithiocarbamate significantly attenuate inhibition of DDAH activity by lysophosphatidylcholine
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Enzyme Kinetic Parameters

kcat Value (Turnover Number) (3 results)

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

KM Value (35 results)

COMMENTARY
EC NUMBER
KM VALUE [MM]
KM VALUE MAXIMUM [MM]
LITERATURE
-
0.027
-
at 20°C
0.012
-
at 5°C
0.058
-
cooperativity: Hill number 1.7
0.0131
-
enzyme from heart mitochondria
0.0124
-
pH 8.0, 30°C, AtMAGL4
0.25
-
constant water activity of 0.22
4.9
-
substrate concentration between 0.015-0.2 mM
0.022
-
at low substrate concentrations
0.083
-
at high substrate concentrations
0.26
-
soluble isozyme, pH 8.0, 37°C
2
-
in presence of 0.25 mM Zn2+
0.55
-
pH 7.4, temperature not specified in the publication
1
-
kinetic analysis of recombinant autotaxin/lysoPLD using [14C] lysophosphatidylcholine substrate
0.1
-
in presence of 10 mM L-histidine
0.66
-
in presence of 0.25 mM Zn2+ plus 10 mM L-histidine
0.47
-
at 4 mM Ca2+
1
-
in the presence of Triton X-100
1.07
-
-
1.67
-
at 40 mM Ca2+
3
-
at pH 7.4 and 37°C
0.00082
-
-
8.3
-

Ki Value (1 result)

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

References & Links

Links to other databases for lysophosphatidylcholine

ChEBI
PubChem
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