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Identification
YMDB IDYMDB02213
NameLysoPC(20:4(5Z,8Z,11Z,14Z))
SpeciesSaccharomyces cerevisiae
StrainBrewer's yeast
DescriptionLysoPC(20:4(5Z,8Z,11Z,14Z)) is a lysophospholipid (LyP). It is a monoglycerophospholipid in which a phosphorylcholine moiety occupies a glycerol substitution site. Lysophosphatidylcholines can have different combinations of fatty acids of varying lengths and saturation attached at the C-1 (sn-1) position. Fatty acids containing 16, 18 and 20 carbons are the most common. LysoPC(20:4(5Z,8Z,11Z,14Z)), in particular, consists of one chain of arachidonic acid at the C-1 position. The arachidonic acid moiety is derived from animal fats and eggs. Lysophosphatidylcholine is found in small amounts in most tissues. It is formed by hydrolysis of phosphatidylcholine by the enzyme phospholipase A2, as part of the de-acylation/re-acylation cycle that controls its overall molecular species composition. It can also be formed inadvertently during extraction of lipids from tissues if the phospholipase is activated by careless handling.
Structure
Thumb
Synonyms
  • 1-arachidonoyl-glycero-3-phosphocholine
  • LPC(20:4)
  • LPC(20:4/0:0)
  • LPC(20:4n6/0:0)
  • LPC(20:4w6/0:0)
  • LyPC(20:4)
  • LyPC(20:4/0:0)
  • LyPC(20:4n6/0:0)
  • LyPC(20:4w6/0:0)
  • LysoPC(20:4)
  • LysoPC(20:4/0:0)
  • LysoPC(20:4n6/0:0)
  • Lysophosphatidylcholine(20:4)
  • Lysophosphatidylcholine(20:4/0:0)
  • Lysophosphatidylcholine(20:4n6/0:0)
  • Lysophosphatidylcholine(20:4w6/0:0)
  • LysoPC(20:4w6/0:0)
  • 1-(5Z,8Z,11Z,14Z-Eicosatetraenoyl)-sn-glycero-3-phosphocholine
  • 1-Arachidonoyl-glycero-3-phosphocholine
  • 1-Arachidonoyl-GPC
  • GPC(20:4n6)
  • LPC 20:4(5Z,8Z,11Z,14Z)/0:0
  • LPC(20:4(5Z,8Z,11Z,14Z)/0:0)
  • LysoPC 20:4(5Z,8Z,11Z,14Z)/0:0
  • LysoPC(20:4(5Z,8Z,11Z,14Z)/0:0)
  • Lysophosphatidylcholine(20:4(5Z,8Z,11Z,14Z)/0:0)
  • PC 20:4(5Z,8Z,11Z,14Z)/0:0
  • PC(20:4(5Z,8Z,11Z,14Z)/0:0)
  • LPC(20:4)
  • LPC(20:4/0:0)
  • LPC(20:4n6/0:0)
  • LPC(20:4W6/0:0)
  • LyPC(20:4)
  • LyPC(20:4/0:0)
  • LyPC(20:4n6/0:0)
  • LyPC(20:4W6/0:0)
  • LysoPC a C20:4
  • LysoPC(20:4)
  • LysoPC(20:4/0:0)
  • LysoPC(20:4n6/0:0)
  • Lysophosphatidylcholine(20:4)
  • Lysophosphatidylcholine(20:4/0:0)
  • Lysophosphatidylcholine(20:4n6/0:0)
  • Lysophosphatidylcholine(20:4W6/0:0)
  • LysoPC(20:4(5Z,8Z,11Z,14Z))
  • 1-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-glycero-3-phosphocholine
CAS numberNot Available
WeightAverage: 543.6729
Monoisotopic: 543.332489471
InChI KeyLAXQYRRMGGEGOH-HHHXNRCGSA-N
InChIInChI=1S/C28H50NO7P/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22-28(31)34-25-27(30)26-36-37(32,33)35-24-23-29(2,3)4/h9-10,12-13,15-16,18-19,27,30H,5-8,11,14,17,20-26H2,1-4H3/t27-/m1/s1
IUPAC Name(2-{[(2R)-2-hydroxy-3-(icosa-5,8,11,14-tetraenoyloxy)propyl phosphonato]oxy}ethyl)trimethylazanium
Traditional IUPAC Name(2-{[(2R)-2-hydroxy-3-(icosa-5,8,11,14-tetraenoyloxy)propyl phosphonato]oxy}ethyl)trimethylazanium
Chemical FormulaC28H50NO7P
SMILESCCCCCC=CCC=CCC=CCC=CCCCC(=O)OC[C@@H](O)COP([O-])(=O)OCC[N+](C)(C)C
Chemical Taxonomy
Physical Properties
StateSolid
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility0.00029 g/LALOGPS
logP2.45ALOGPS
logP1.52ChemAxon
logS-6.3ALOGPS
pKa (Strongest Acidic)1.86ChemAxon
pKa (Strongest Basic)-3.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area105.12 ŲChemAxon
Rotatable Bond Count24ChemAxon
Refractivity165.14 m³·mol⁻¹ChemAxon
Polarizability61.4 ųChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular LocationsNot Available
Organoleptic PropertiesNot Available
SMPDB Pathways
Lysolipid incorporation into ER PC(20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))PW002790 ThumbThumb?image type=greyscaleThumb?image type=simple
Lysolipid incorporation into Mitochondria PC(20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))PW002798 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG PathwaysNot Available
SMPDB Reactions
LysoPC(20:4(5Z,8Z,11Z,14Z)) + waterGlycerophosphocholine + a carboxylate
LysoPC(20:4(5Z,8Z,11Z,14Z))PC(20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))
KEGG ReactionsNot Available
Concentrations
Intracellular Concentrations
Intracellular ConcentrationSubstrateGrowth ConditionsStrainCitation
0.033 ± 0.00165 µM YEB media with 0.5 mM glucoseaerobicBrewer's yeastExperimentally Determined
Not Available
Conversion Details Here
Extracellular ConcentrationsNot Available
Spectra
Spectra
References
References:Not Available
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID74344
HMDB IDHMDB10395
Pubchem Compound ID24779476
Kegg IDC04230
ChemSpider ID24766532
FOODB IDFDB027546
Wikipedia IDNot Available
BioCyc IDNot Available

Enzymes

General function:
Involved in metabolic process
Specific function:
Intracellular phospholipase B that catalyzes the double deacylation of phosphatidylcholine (PC) to glycerophosphocholine (GroPCho). Plays an important role in membrane lipid homeostasis. Responsible for the rapid PC turnover in response to inositol, elevated temperatures, or when choline is present in the growth medium
Gene Name:
NTE1
Uniprot ID:
Q04958
Molecular weight:
187131.0
Reactions
2-lysophosphatidylcholine + H(2)O → glycerophosphocholine + a carboxylate.