Record Information
Version3.6
Creation Date2006-05-22 14:17:42 UTC
Update Date2013-02-09 00:14:17 UTC
HMDB IDHMDB05779
Secondary Accession Numbers
  • HMDB11385
Metabolite Identification
Common NamePE(O-18:1(1Z)/20:4(5Z,8Z,11Z,14Z))
DescriptionPE(O-18:1(1Z)/20:4(5Z,8Z,11Z,14Z)) is a class of glycerophospholipid in which a phosphorylethanolamine moiety occupies a glycerol substitution site. As is the case with diacylglycerols, glycerophosphocholines can have many different combinations of fatty acids of varying lengths and saturation attached at the SN-1 and SN-2 positions. fatty acids containing 16, 18 and 20 carbons are the most common. (LipidMAPS)PE(dm18:0/20:4(5Z,8Z,11Z,14Z)) is a phosphatidylethanolamine (PE or GPEtn). It is a glycerophospholipid in which a phosphorylethanolamine moiety occupies a glycerol substitution site. As is the case with diacylglycerols, glycerophosphoethanolamines can have many different combinations of fatty acids of varying lengths and saturation attached at the C-1 and C-2 positions. Fatty acids containing 16, 18 and 20 carbons are the most common. PE(dm18:0/20:4(5Z,8Z,11Z,14Z)), in particular, consists of one chain of plasmalogen 18:0 at the C-1 position and one chain of arachidonic acid at the C-2 position. The plasmalogen 18:0 moiety is derived from animal fats, liver and kidney, while the arachidonic acid moiety is derived from animal fats and eggs. Phospholipids, are ubiquitous in nature and are key components of the lipid bilayer of cells, as well as being involved in metabolism and signaling.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. 1-(1-Enyl-stearoyl)-2-arachidonoyl-sn-glycero-3-phosphoethanolamine
  2. 1-(1Z-Octadecenyl)-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphoethanolamine
  3. 1-Alkenyl-2-acyl-glycerophosphoethanolamine
  4. GPEtn(18:0/20:4)
  5. GPEtn(18:0/20:4n6)
  6. GPEtn(18:0/20:4w6)
  7. GPEtn(38:4)
  8. PE(18:0/20:4)
  9. PE(18:0/20:4n6)
  10. PE(18:0/20:4w6)
  11. PE(38:4)
  12. PE(dm18:0/20:4(5Z,8Z,11Z,14Z))
  13. Phophatidylethanolamine(18:0/20:4)
  14. Phophatidylethanolamine(18:0/20:4n6)
  15. Phophatidylethanolamine(18:0/20:4w6)
  16. Phophatidylethanolamine(38:4)
  17. [R-(all-Z)]-5,8,11,14-Eicosatetraenoate
  18. [R-(all-Z)]-5,8,11,14-Eicosatetraenoic acid
  19. [R-(all-Z)]-5,8,11,14-Eicosatetraenoic acid 1-[[[(2-aminoethoxy)hydroxyphosphinyl]oxy]methyl]-2-(1-octadecenyloxy)ethyl ester
Chemical FormulaC43H78NO7P
Average Molecular Weight752.0557
Monoisotopic Molecular Weight751.551590367
IUPAC Name(2-aminoethoxy)[(2R)-2-[(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoyloxy]-3-[(1Z)-octadec-1-en-1-yloxy]propoxy]phosphinic acid
Traditional IUPAC Name2-aminoethoxy(2R)-2-[(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoyloxy]-3-[(1Z)-octadec-1-en-1-yloxy]propoxyphosphinic acid
CAS Registry Number103597-60-0
SMILES
[H][C@@](CO\C=C/CCCCCCCCCCCCCCCC)(COP(O)(=O)OCCN)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC
InChI Identifier
InChI=1S/C43H78NO7P/c1-3-5-7-9-11-13-15-17-19-21-22-24-26-28-30-32-34-36-43(45)51-42(41-50-52(46,47)49-39-37-44)40-48-38-35-33-31-29-27-25-23-20-18-16-14-12-10-8-6-4-2/h11,13,17,19,22,24,28,30,35,38,42H,3-10,12,14-16,18,20-21,23,25-27,29,31-34,36-37,39-41,44H2,1-2H3,(H,46,47)/b13-11-,19-17-,24-22-,30-28-,38-35-/t42-/m1/s1
InChI KeyURPXXNCTXCOATD-FXMFQVEGSA-N
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassLipids
ClassGlycerophospholipids
Sub ClassGlycerophosphoethanolamines
Other Descriptors
  • Aliphatic Acyclic Compounds
Substituents
  • Acyclic Alkene
  • Carboxylic Acid Ester
  • Enol Ether
  • Fatty Acid Ester
  • Organic Hypophosphite
  • Organic Phosphite
  • Phosphoethanolamine
  • Phosphoric Acid Ester
  • Primary Aliphatic Amine (Alkylamine)
Direct ParentLysophosphatidylethanolamines
Ontology
StatusExpected and Not Quantified
Origin
  • Endogenous
  • Food
Biofunction
  • Cell signaling
  • Energy source
  • Fuel and energy storage
  • Fuel or energy source
  • Membrane component
  • 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 solubility6.380E-05 g/LALOGPS
logP9.4ALOGPS
logP12.06ChemAxon
logS-7.1ALOGPS
pKa (strongest acidic)1.87ChemAxon
pKa (strongest basic)10ChemAxon
physiological charge0ChemAxon
hydrogen acceptor count5ChemAxon
hydrogen donor count2ChemAxon
polar surface area117.31ChemAxon
rotatable bond count40ChemAxon
refractivity223.41ChemAxon
polarizability90.74ChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid LocationsNot Available
Tissue Location
  • All Tissues
  • Brain
PathwaysNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Predicted Concentrations Help
BiofluidValueOriginal ageOriginal sexOriginal conditionComments
Blood28.29 +/- 21.925 uMAdult (>18 years old)BothNormal (Upper Limit)Concentration data updated from parsing Nick's...
Blood3.71733 +/- 0.67887 uMAdult (>18 years old)BothNormal (Most Probable)Concentration data updated from parsing Nick's...
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 IDFDB023768
KNApSAcK IDNot Available
Chemspider ID7826008
KEGG Compound IDC00350
BioCyc ID1-Alkenyl-2-acyl-glyceroPethamines
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB05779
Metagene LinkHMDB05779
METLIN ID6548
PubChem Compound9547058
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

Gene Name:
PLA2G5
Uniprot ID:
P39877
Gene Name:
PLA2G2F
Uniprot ID:
Q9BZM2
Gene Name:
PLA2G4A
Uniprot ID:
P47712
Gene Name:
PLA2G1B
Uniprot ID:
P04054
Gene Name:
PLA2G10
Uniprot ID:
O15496
Gene Name:
PLA2G2E
Uniprot ID:
Q9NZK7
Gene Name:
PLA2G2D
Uniprot ID:
Q9UNK4
Gene Name:
PLD2
Uniprot ID:
O14939
Gene Name:
PLD1
Uniprot ID:
Q13393
Gene Name:
PLA2G3
Uniprot ID:
Q9NZ20
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
Gene Name:
PLA2G4B
Uniprot ID:
P0C869
Gene Name:
Not Available
Uniprot ID:
Q59EA4