Record Information
Version3.6
Creation Date2008-10-29 15:03:06 UTC
Update Date2013-02-09 00:25:48 UTC
HMDB IDHMDB11157
Secondary Accession NumbersNone
Metabolite Identification
Common NamePE(P-16:0e/18:1(9Z))
Description2-(9Z-octadecanoyl)-1-hexadecyl-sn-glycero-3-phosphoethanolamine is an ether lipid. Ether lipids are lipids in which one or more of the carbon atoms on glycerol is bonded to an alkyl chain via an ether linkage, as opposed to the usual ester linkage. While most phospholipids have a saturated fatty acid on C-1 and an unsaturated fatty acid on C-2 of the glycerol backbone, the fatty acid distribution at the C-1 and C-2 positions of glycerol within phospholipids is continually in flux, owing to phospholipid degradation and the continuous phospholipid remodeling that occurs while these molecules are in membranes. PEs are neutral zwitterions at physiological pH. They mostly have palmitic or stearic acid on carbon 1 and a long chain unsaturated fatty acid (e.g. 18:2, 20:4 and 22:6) on carbon 2. PE synthesis can occur via two pathways. The first requires that ethanolamine be activated by phosphorylation and then coupled to CDP. The ethanolamine is then transferred from CDP-ethanolamine to phosphatidic acid to yield PE. The second involves the decarboxylation of PS. Plasmalogens are glycerol ether phospholipids. They are of two types, alkyl ether (-O-CH2-) and alkenyl ether (-O-CH=CH-). Dihydroxyacetone phosphate (DHAP) serves as the glycerol precursor for the synthesis of plasmalogens. Three major classes of plasmalogens have been identified: choline, ethanolamine and serine derivatives. Ethanolamine plasmalogen is prevalent in myelin. Choline plasmalogen is abundant in cardiac tissue. Usually, the highest proportion of the plasmalogen form is in the ethanolamine class with rather less in choline, and commonly little or none in other phospholipids such as phosphatidylinositol. In choline plasmalogens of most tissues, a higher proportion is often of the O-alkyl rather than the O-alkenyl form, but the reverse tends to be true in heart lipids. In animal tissues, the alkyl and alkenyl moieties in both non-polar and phospholipids tend to be rather simple in composition with 16:0, 18:0 and 18:1 (double bond in position 9) predominating. Ether analogues of triacylglycerols, i.e. 1-alkyldiacyl-sn-glycerols, are present at trace levels only if at all in most animal tissues, but they can be major components of some marine lipids.
Structure
Thumb
Synonyms
  1. 2-(9Z-Octadecanoyl)-1-hexadecyl-sn-glycero-3-phosphoethanolamine
Chemical FormulaC39H78NO7P
Average Molecular Weight704.0129
Monoisotopic Molecular Weight703.551590367
IUPAC Name(2-aminoethoxy)[(2R)-3-(hexadecyloxy)-2-[(9Z)-octadec-9-enoyloxy]propoxy]phosphinic acid
Traditional IUPAC Name2-aminoethoxy(2R)-3-(hexadecyloxy)-2-[(9Z)-octadec-9-enoyloxy]propoxyphosphinic acid
CAS Registry NumberNot Available
SMILES
[H][C@@](COCCCCCCCCCCCCCCCC)(COP(O)(=O)OCCN)OC(=O)CCCCCCC\C=C/CCCCCCCC
InChI Identifier
InChI=1S/C39H78NO7P/c1-3-5-7-9-11-13-15-17-19-20-22-24-26-28-30-32-39(41)47-38(37-46-48(42,43)45-35-33-40)36-44-34-31-29-27-25-23-21-18-16-14-12-10-8-6-4-2/h17,19,38H,3-16,18,20-37,40H2,1-2H3,(H,42,43)/b19-17-/t38-/m1/s1
InChI KeyJJGMGPGKWYLISM-NPBIGWJUSA-N
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassLipids
ClassGlycerophospholipids
Sub ClassGlycerophosphoethanolamines
Other Descriptors
  • Aliphatic Acyclic Compounds
Substituents
  • Acyclic Alkene
  • Carboxylic Acid Ester
  • Dialkyl Ether
  • Fatty Acid Ester
  • Organic Hypophosphite
  • Organic Phosphite
  • Phosphoethanolamine
  • Phosphoric Acid Ester
  • Primary Aliphatic Amine (Alkylamine)
Direct ParentPhosphatidylethanolamines
Ontology
StatusExpected and Not Quantified
Origin
  • Endogenous
  • Food
Biofunction
  • Cell signaling
  • Fuel and energy storage
  • Fuel or energy source
  • Membrane integrity/stability
Application
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Extracellular
  • 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
water solubility7.300E-05 g/LALOGPS
logP8.92ALOGPS
logP11.36ChemAxon
logS-7ALOGPS
pKa (strongest acidic)1.87ChemAxon
pKa (strongest basic)10ChemAxon
physiological charge0ChemAxon
hydrogen acceptor count5ChemAxon
hydrogen donor count2ChemAxon
polar surface area117.31ChemAxon
rotatable bond count40ChemAxon
refractivity201.57ChemAxon
polarizability88.39ChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid LocationsNot Available
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB027932
KNApSAcK IDNot Available
Chemspider ID24769220
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB11157
Metagene LinkHMDB11157
METLIN IDNot Available
PubChem Compound42607455
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

Gene Name:
PLD2
Uniprot ID:
O14939
Gene Name:
PLD1
Uniprot ID:
Q13393
Gene Name:
PLSCR1
Uniprot ID:
O15162
Gene Name:
PLTP
Uniprot ID:
P55058
Gene Name:
PLD3
Uniprot ID:
Q8IV08
Gene Name:
PLD4
Uniprot ID:
Q96BZ4
Gene Name:
PLSCR2
Uniprot ID:
Q9NRY7
Gene Name:
PLSCR3
Uniprot ID:
Q9NRY6
Gene Name:
PLSCR4
Uniprot ID:
Q9NRQ2
Gene Name:
PLSCR5
Uniprot ID:
A0PG75
Gene Name:
EPT1
Uniprot ID:
Q9C0D9