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Record Information
Version1.0
Creation Date2016-09-30 23:46:21 UTC
Update Date2020-05-21 16:28:40 UTC
BMDB IDBMDB0007883
Secondary Accession Numbers
  • BMDB07883
Metabolite Identification
Common NamePC(14:0/20:4(5Z,8Z,11Z,14Z))
DescriptionPC(14:0/20:4(5Z,8Z,11Z,14Z)), also known as phosphatidylcholine(14:0/20:4) or gpcho(14:0/20:4), belongs to the class of organic compounds known as phosphatidylcholines. These are glycerophosphocholines in which the two free -OH are attached to one fatty acid each through an ester linkage. Thus, PC(14:0/20:4(5Z,8Z,11Z,14Z)) is considered to be a glycerophosphocholine lipid molecule. PC(14:0/20:4(5Z,8Z,11Z,14Z)) is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. PC(14:0/20:4(5Z,8Z,11Z,14Z)) exists in all eukaryotes, ranging from yeast to humans. PC(14:0/20:4(5Z,8Z,11Z,14Z)) participates in a number of enzymatic reactions, within cattle. In particular, S-Adenosylhomocysteine and PC(14:0/20:4(5Z,8Z,11Z,14Z)) can be biosynthesized from S-adenosylmethionine and pe-nme2(14:0/20:4(5Z,8Z,11Z,14Z)) through its interaction with the enzyme phosphatidylethanolamine N-methyltransferase. Furthermore, Cytidine monophosphate and PC(14:0/20:4(5Z,8Z,11Z,14Z)) can be biosynthesized from CDP-choline and DG(14:0/20:4(5Z,8Z,11Z,14Z)/0:0) through its interaction with the enzyme choline/ethanolaminephosphotransferase. Finally, PC(14:0/20:4(5Z,8Z,11Z,14Z)) and L-serine can be converted into choline and PS(14:0/20:4(5Z,8Z,11Z,14Z)); which is mediated by the enzyme phosphatidylserine synthase. In cattle, PC(14:0/20:4(5Z,8Z,11Z,14Z)) is involved in a couple of metabolic pathways, which include phosphatidylcholine biosynthesis PC(14:0/20:4(5Z,8Z,11Z,14Z)) pathway and phosphatidylethanolamine biosynthesis pe(14:0/20:4(5Z,8Z,11Z,14Z)) pathway.
Structure
Thumb
Synonyms
ValueSource
1-Myristoyl-2-arachidonoyl-sn-glycero-3-phosphocholineChEBI
1-Tetradecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphocholineChEBI
GPCho(14:0/20:4)ChEBI
GPCho(14:0/20:4n6)ChEBI
GPCho(14:0/20:4W6)ChEBI
PC(14:0/20:4)ChEBI
PC(14:0/20:4n6)ChEBI
PC(14:0/20:4W6)ChEBI
Phosphatidylcholine(14:0/20:4)ChEBI
Phosphatidylcholine(14:0/20:4n6)ChEBI
Phosphatidylcholine(14:0/20:4W6)ChEBI
GPCho(34:4)HMDB
PC(34:4)HMDB
LecithinHMDB
Phosphatidylcholine(34:4)HMDB
PC(14:0/20:4(5Z,8Z,11Z,14Z))Lipid Annotator
Chemical FormulaC42H76NO8P
Average Molecular Weight754.0285
Monoisotopic Molecular Weight753.530854925
IUPAC Name(2-{[(2R)-2-[(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoyloxy]-3-(tetradecanoyloxy)propyl phosphonato]oxy}ethyl)trimethylazanium
Traditional Namelecithin
CAS Registry NumberNot Available
SMILES
CCCCCCCCCCCCCC(=O)OC[C@]([H])(COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC
InChI Identifier
InChI=1S/C42H76NO8P/c1-6-8-10-12-14-16-18-19-20-21-22-23-25-27-29-31-33-35-42(45)51-40(39-50-52(46,47)49-37-36-43(3,4)5)38-48-41(44)34-32-30-28-26-24-17-15-13-11-9-7-2/h14,16,19-20,22-23,27,29,40H,6-13,15,17-18,21,24-26,28,30-39H2,1-5H3/b16-14-,20-19-,23-22-,29-27-/t40-/m1/s1
InChI KeySRQSAJRUMDQMMS-NLDJLLEISA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as phosphatidylcholines. These are glycerophosphocholines in which the two free -OH are attached to one fatty acid each through an ester linkage.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassGlycerophospholipids
Sub ClassGlycerophosphocholines
Direct ParentPhosphatidylcholines
Alternative Parents
Substituents
  • Diacylglycero-3-phosphocholine
  • Phosphocholine
  • Fatty acid ester
  • Dialkyl phosphate
  • Dicarboxylic acid or derivatives
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Alkyl phosphate
  • Fatty acyl
  • Quaternary ammonium salt
  • Tetraalkylammonium salt
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic nitrogen compound
  • Carbonyl group
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxide
  • Organopnictogen compound
  • Amine
  • Organic salt
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
  • Exogenous
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
logP5.36ALOGPS
logP7.56ChemAxon
logS-7.4ALOGPS
pKa (Strongest Acidic)1.86ChemAxon
pKa (Strongest Basic)-6.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area111.19 ŲChemAxon
Rotatable Bond Count38ChemAxon
Refractivity229.53 m³·mol⁻¹ChemAxon
Polarizability89.94 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-8191331300-e09b2465ca6875a71d90View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-3390010000-0639ab49a1263cdee172View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-7290011000-8bec9f02630c5adc0da6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0zi0-0092000300-fb8e5f8e6cf0caa4c67eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-056r-0191001000-5ad30a59a3f2abd37194View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-056r-5293000000-20b4c6327140f214686aView in MoNA
Biological Properties
Cellular Locations
  • Cell membrane
  • Intracellular membrane
  • Membrane
Biospecimen Locations
  • All Tissues
  • Milk
  • Ruminal Fluid
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
All TissuesExpected but not QuantifiedNot ApplicableNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
MilkDetected and Quantified0.081 +/- 0.004 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified0.10 +/- 0.01 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified0.13 +/- 0.01 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified0.074 +/- 0.004 uMNot SpecifiedNot Specified
Normal
details
Ruminal FluidDetected and Quantified0.009 +/- 0.003 uMNot SpecifiedNot Specified
Normal
    • Fozia Saleem, Sou...
details
Abnormal Concentrations
Not Available
HMDB IDHMDB0007883
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound24778634
PDB IDNot Available
ChEBI ID86102
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. A. Foroutan et al. (2019). A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation). Journal of Agricultural and Food Chemistry.

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
General function:
Not Available
Specific function:
Catalyzes a base-exchange reaction in which the polar head group of phosphatidylethanolamine (PE) or phosphatidylcholine (PC) is replaced by L-serine. In membranes, PTDSS1 catalyzes mainly the conversion of phosphatidylcholine. Also converts, in vitro and to a lesser extent, phosphatidylethanolamine (By similarity).
Gene Name:
PTDSS1
Uniprot ID:
Q2KHY9
Molecular weight:
55416.0
Reactions
PC(14:0/20:4(5Z,8Z,11Z,14Z)) + L-Serine → Choline + PS(14:0/20:4(5Z,8Z,11Z,14Z))details