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Record Information
Version1.0
Creation Date2016-10-03 18:05:26 UTC
Update Date2020-05-21 16:28:40 UTC
BMDB IDBMDB0010379
Secondary Accession Numbers
  • BMDB10379
Metabolite Identification
Common NameLysoPC(14:0)
DescriptionLysoPC(14:0/0:0) is a lysophospholipid (LyP). It is a monoglycerophospholipid in which a phosphorylcholine moiety occupies a glycerol substitution site. LysoPC(14:0/0:0), in particular, consists of one tetradecanoyl chain. 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(20:3(5Z,8Z,11Z)), in particular, consists of one chain of mead acid at the C-1 position. The mead acid moiety is derived from fish oils, liver and kidney. 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
ValueSource
1-C14:0-Lysophosphatidylcholine betaineChEBI
1-Myristoyl-glycero-3-phosphocholineChEBI
1-Myristoyl-sn-glycero-3-phosphocholine betaineChEBI
1-Tetradecanoyl-sn-glycero-3-phosphocholineChEBI
1-Tetradecanoyl-sn-glycero-3-phosphocholine betaineChEBI
LPC(14:0)ChEBI
LPC(14:0/0:0)ChEBI
LyPC(14:0)ChEBI
LyPC(14:0/0:0)ChEBI
Lysophosphatidylcholine(14:0/0:0)ChEBI
PC(14:0/0:0)ChEBI
Lysophosphatidylcholine(14:0)HMDB
1-Tetradecanoyl-glycero-3-phosphocholineHMDB
LysoPC(14:0)HMDB
1-MyristoylglycerophosphocholineHMDB
1-TetradecanoylglycerophosphocholineHMDB
1-Myristoyl-GPCHMDB
1-Myristoyl-lysophosphatidylcholineHMDB
1-Myristoyl-sn-glycero-3-phosphocholineHMDB
GPC(14:0)HMDB
GPC(14:0/0:0)HMDB
LysoPC(14:0/0:0)Lipid Annotator, ChEBI
Chemical FormulaC22H46NO7P
Average Molecular Weight467.5769
Monoisotopic Molecular Weight467.301189343
IUPAC Name(2-{[(2R)-2-hydroxy-3-(tetradecanoyloxy)propyl phosphono]oxy}ethyl)trimethylazanium
Traditional Name(2-{[(2R)-2-hydroxy-3-(tetradecanoyloxy)propyl phosphono]oxy}ethyl)trimethylazanium
CAS Registry Number20559-16-4
SMILES
CCCCCCCCCCCCCC(=O)OC[C@@H](O)COP([O-])(=O)OCC[N+](C)(C)C
InChI Identifier
InChI=1S/C22H46NO7P/c1-5-6-7-8-9-10-11-12-13-14-15-16-22(25)28-19-21(24)20-30-31(26,27)29-18-17-23(2,3)4/h21,24H,5-20H2,1-4H3/t21-/m1/s1
InChI KeyVXUOFDJKYGDUJI-OAQYLSRUSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as 1-acyl-sn-glycero-3-phosphocholines. These are glycerophosphocholines in which the glycerol is esterified with a fatty acid at O-1 position, and linked at position 3 to a phosphocholine.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassGlycerophospholipids
Sub ClassGlycerophosphocholines
Direct Parent1-acyl-sn-glycero-3-phosphocholines
Alternative Parents
Substituents
  • 1-acyl-sn-glycero-3-phosphocholine
  • Phosphocholine
  • Fatty acid ester
  • Dialkyl phosphate
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Alkyl phosphate
  • Fatty acyl
  • Tetraalkylammonium salt
  • Quaternary ammonium salt
  • Secondary alcohol
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Organic oxide
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Alcohol
  • Organic oxygen compound
  • Organopnictogen compound
  • Carbonyl group
  • Organic salt
  • Amine
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
StatusDetected and Quantified
OriginNot Available
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cell membrane
  • Intracellular membrane
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP1.1ALOGPS
logP0.3ChemAxon
logS-5.8ALOGPS
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 Count22ChemAxon
Refractivity133.07 m³·mol⁻¹ChemAxon
Polarizability53.74 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0230-9411000000-7a6b8e8fd1e0609b417eView in MoNA
Biological Properties
Cellular Locations
  • Cell membrane
  • Intracellular membrane
  • Membrane
Biospecimen Locations
  • All Tissues
  • Blood
  • Liver
  • Longissimus Thoracis Muscle
  • Ruminal Fluid
  • Semimembranosus Muscle
  • Testis
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
All TissuesExpected but not QuantifiedNot ApplicableNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
BloodDetected and Quantified2.80 +/- 0.43 uMNot SpecifiedNot Specified
Normal
details
BloodDetected and Quantified3.51 +/- 2.72 uMNot SpecifiedNot Specified
Normal
details
BloodDetected and Quantified0.8+/-0.1 uMNot SpecifiedNot Specified
Normal
    • The Bovine Metabo...
details
LiverDetected but not QuantifiedNot ApplicableNot SpecifiedNot Specified
Normal
details
LiverDetected and Quantified0.09+/-0.01 nmol/g of tissueNot SpecifiedNot Specified
Normal
    • The Bovine Metabo...
details
Longissimus Thoracis MuscleDetected and Quantified0.07+/-0.01 nmol/g of tissueNot SpecifiedNot Specified
Normal
    • The Bovine Metabo...
details
Ruminal FluidDetected and Quantified6+/-3 uMNot SpecifiedNot Specified
Normal
    • The Bovine Metabo...
details
Semimembranosus MuscleDetected and Quantified0.07+/-0.01 nmol/g of tissueNot SpecifiedNot Specified
Normal
    • The Bovine Metabo...
details
TestisDetected and Quantified0.09+/-0.01 nmol/g of tissueNot SpecifiedNot Specified
Normal
    • The Bovine Metabo...
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified5.59 +/- 0.52 uMNot SpecifiedNot Specified
Transition disease/1 wk after parturition
details
BloodDetected and Quantified5.62 +/- 0.39 uMNot SpecifiedNot Specified
Transition disease/1 wk after parturition
details
HMDB IDHMDB0010379
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB027530
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound460604
PDB IDNot Available
ChEBI ID64489
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Involved in calcium ion binding
Specific function:
Has primarily calcium-dependent phospholipase and lysophospholipase activities, with a major role in membrane lipid remodeling and biosynthesis of lipid mediators of the inflammatory response (By similarity). Plays an important role in embryo implantation and parturition through its ability to trigger prostanoid production (By similarity). Preferentially hydrolyzes the ester bond of the fatty acyl group attached at sn-2 position of phospholipids (phospholipase A2 activity). Selectively hydrolyzes sn-2 arachidonoyl group from membrane phospholipids, providing the precursor for eicosanoid biosynthesis via the cyclooxygenase pathway. In an alternative pathway of eicosanoid biosynthesis, hydrolyzes sn-2 fatty acyl chain of eicosanoid lysophopholipids to release free bioactive eicosanoids. Hydrolyzes the ester bond of the fatty acyl group attached at sn-1 position of phospholipids (phospholipase A1 activity) only if an ether linkage rather than an ester linkage is present at the sn-2 position. This hydrolysis is not stereospecific. Has calcium-independent phospholipase A2 and lysophospholipase activities in the presence of phosphoinositides. Has O-acyltransferase activity. Catalyzes the transfer of fatty acyl chains from phospholipids to a primary hydroxyl group of glycerol (sn-1 or sn-3), potentially contributing to monoacylglycerol synthesis (By similarity).
Gene Name:
PLA2G4A
Uniprot ID:
A4IFJ5
Molecular weight:
85350.0
Reactions
PC(14:0/20:4(5Z,8Z,11Z,14Z)) + Water → Arachidonic acid + LysoPC(14:0)details