Human Metabolome Database Version 3.5

Showing metabocard for PE(O-16:1(1Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) (HMDB05780)

Record Information
Version 3.5
Creation Date 2006-05-22 08:17:42 -0600
Update Date 2013-02-08 17:14:17 -0700
HMDB ID HMDB05780
Secondary Accession Numbers
  • HMDB11361
Metabolite Identification
Common Name PE(O-16:1(1Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))
Description PE(O-16:1(1Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) 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(dm16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) 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(dm16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)), in particular, consists of one chain of plasmalogen 16:0 at the C-1 position and one chain of docosahexaenoic acid at the C-2 position. The plasmalogen 16:0 moiety is derived from animal fats, liver and kidney, while the docosahexaenoic acid moiety is derived from fish oils. 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
Download: MOL | SDF | PDB | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. 1-(1-Enyl-palmitoyl)-2-docosahexaenoyl-sn-glycero-3-phosphoethanolamine
  2. 1-Alkenyl-2-acyl-glycerophosphoethanolamine
  3. 1-O-(1Z-Hexadecenyl)-2-(4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenoyl)-sn-glycero-3-phosphoethanolamine
  4. GPEtn(16:0/22:6)
  5. GPEtn(16:0/22:6n3)
  6. GPEtn(16:0/22:6w3)
  7. GPEtn(16:0p/22:6(4Z,7Z,10Z,13Z,16Z,19Z))
  8. GPEtn(38:6)
  9. PE(16:0/22:6)
  10. PE(16:0/22:6n3)
  11. PE(16:0/22:6w3)
  12. PE(38:6)
  13. PE(dm16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))
  14. Phophatidylethanolamine(16:0/22:6)
  15. Phophatidylethanolamine(16:0/22:6n3)
  16. Phophatidylethanolamine(16:0/22:6w3)
  17. Phophatidylethanolamine(38:6)
Chemical Formula C43H74NO7P
Average Molecular Weight 748.0239
Monoisotopic Molecular Weight 747.520290239
IUPAC Name (2-aminoethoxy)[(2R)-2-[(4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoyloxy]-3-[(1Z)-hexadec-1-en-1-yloxy]propoxy]phosphinic acid
Traditional IUPAC Name 2-aminoethoxy(2R)-2-[(4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoyloxy]-3-[(1Z)-hexadec-1-en-1-yloxy]propoxyphosphinic acid
CAS Registry Number Not Available
SMILES [H][C@@](CO\C=C/CCCCCCCCCCCCCC)(COP(O)(=O)OCCN)OC(=O)CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CC
InChI Identifier InChI=1S/C43H74NO7P/c1-3-5-7-9-11-13-15-17-19-20-21-22-23-24-26-28-30-32-34-36-43(45)51-42(41-50-52(46,47)49-39-37-44)40-48-38-35-33-31-29-27-25-18-16-14-12-10-8-6-4-2/h5,7,11,13,17,19,21-22,24,26,30,32,35,38,42H,3-4,6,8-10,12,14-16,18,20,23,25,27-29,31,33-34,36-37,39-41,44H2,1-2H3,(H,46,47)/b7-5-,13-11-,19-17-,22-21-,26-24-,32-30-,38-35-/t42-/m1/s1
InChI Key WVGALBKSWOUIEZ-XNHMFJFDSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Lipids
Class Glycerophospholipids
Sub Class Glycerophosphoethanolamines
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 Parent Lysophosphatidylethanolamines
Ontology
Status Expected 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
State Solid
Experimental Properties
Property Value Reference
Melting Point Not Available Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
Water Solubility 6.850E-05 g/L ALOGPS
LogP 9.06 ALOGPS
LogP 11.34 ChemAxon
LogS -7.04 ALOGPS
pKa (strongest acidic) 1.87 ChemAxon
pKa (strongest basic) 10 ChemAxon
Hydrogen Acceptor Count 5 ChemAxon
Hydrogen Donor Count 2 ChemAxon
Polar Surface Area 117.31 A2 ChemAxon
Rotatable Bond Count 38 ChemAxon
Refractivity 225.65 ChemAxon
Polarizability 87 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 0 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid Locations Not Available
Tissue Location
  • All Tissues
  • Brain
Pathways Not Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Predicted Concentrations Help
Biofluid Value Original age Original sex Original condition Comments
Blood 20.784 +/- 17.189 uM Adult (>18 years old) Both Normal (Upper Limit) Concentration data updated from parsing Nick's...
Blood 0.98848 +/- 0.17696 uM Adult (>18 years old) Both Normal (Most Probable) Concentration data updated from parsing Nick's...
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
DrugBank Metabolite ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB023769
KNApSAcK ID Not Available
Chemspider ID 4446616 Link_out
KEGG Compound ID C00350 Link_out
BioCyc ID 1-Alkenyl-2-acyl-glyceroPethamines Link_out
BiGG ID Not Available
Wikipedia Link Not Available
NuGOwiki Link HMDB05780 Link_out
Metagene Link HMDB05780 Link_out
METLIN ID 6548 Link_out
PubChem Compound 5283497 Link_out
PDB ID Not Available
ChEBI ID Not Available
References
Synthesis Reference Not Available
Material Safety Data Sheet (MSDS) Not Available
General References Not Available

Enzymes
Name: Calcium-dependent phospholipase A2
Reactions: Not Available
Gene Name: PLA2G5
Uniprot ID: P39877 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Group IIF secretory phospholipase A2
Reactions: Not Available
Gene Name: PLA2G2F
Uniprot ID: Q9BZM2 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytosolic phospholipase A2
Reactions: Not Available
Gene Name: PLA2G4A
Uniprot ID: P47712 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Phospholipase A2
Reactions: Not Available
Gene Name: PLA2G1B
Uniprot ID: P04054 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Group XIIB secretory phospholipase A2-like protein
Reactions: Not Available
Gene Name: PLA2G12B
Uniprot ID: Q9BX93 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Group 10 secretory phospholipase A2
Reactions: Not Available
Gene Name: PLA2G10
Uniprot ID: O15496 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Group IIE secretory phospholipase A2
Reactions: Not Available
Gene Name: PLA2G2E
Uniprot ID: Q9NZK7 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: 85/88 kDa calcium-independent phospholipase A2
Reactions: Not Available
Gene Name: PLA2G6
Uniprot ID: O60733 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Group IID secretory phospholipase A2
Reactions: Not Available
Gene Name: PLA2G2D
Uniprot ID: Q9UNK4 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Phospholipase D2
Reactions: Not Available
Gene Name: PLD2
Uniprot ID: O14939 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Phosphatidylethanolamine N-methyltransferase
Reactions: Not Available
Gene Name: PEMT
Uniprot ID: Q9UBM1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Phospholipase D1
Reactions: Not Available
Gene Name: PLD1
Uniprot ID: Q13393 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Group 3 secretory phospholipase A2
Reactions: Not Available
Gene Name: PLA2G3
Uniprot ID: Q9NZ20 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Probable phospholipid-transporting ATPase IG
Reactions: Not Available
Gene Name: ATP11C
Uniprot ID: Q8NB49 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Probable phospholipid-transporting ATPase IH
Reactions: Not Available
Gene Name: ATP11A
Uniprot ID: P98196 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Probable phospholipid-transporting ATPase VA
Reactions: Not Available
Gene Name: ATP10A
Uniprot ID: O60312 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Probable phospholipid-transporting ATPase IC
Reactions: Not Available
Gene Name: ATP8B1
Uniprot ID: O43520 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Probable phospholipid-transporting ATPase IIA
Reactions: Not Available
Gene Name: ATP9A
Uniprot ID: O75110 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Probable phospholipid-transporting ATPase VD
Reactions: Not Available
Gene Name: ATP10D
Uniprot ID: Q9P241 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Probable phospholipid-transporting ATPase IB
Reactions: Not Available
Gene Name: ATP8A2
Uniprot ID: Q9NTI2 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Probable phospholipid-transporting ATPase IA
Reactions: Not Available
Gene Name: ATP8A1
Uniprot ID: Q9Y2Q0 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Probable phospholipid-transporting ATPase IM
Reactions: Not Available
Gene Name: ATP8B4
Uniprot ID: Q8TF62 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Probable phospholipid-transporting ATPase IF
Reactions: Not Available
Gene Name: ATP11B
Uniprot ID: Q9Y2G3 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Probable phospholipid-transporting ATPase IK
Reactions: Not Available
Gene Name: ATP8B3
Uniprot ID: O60423 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Phospholipid scramblase 1
Reactions: Not Available
Gene Name: PLSCR1
Uniprot ID: O15162 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Phosphatidylserine decarboxylase proenzyme
Reactions: Not Available
Gene Name: PISD
Uniprot ID: Q9UG56 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Phospholipid transfer protein
Reactions: Not Available
Gene Name: PLTP
Uniprot ID: P55058 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Choline/ethanolaminephosphotransferase 1
Reactions: Not Available
Gene Name: CEPT1
Uniprot ID: Q9Y6K0 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Phospholipase D3
Reactions: Not Available
Gene Name: PLD3
Uniprot ID: Q8IV08 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Phospholipase D4
Reactions: Not Available
Gene Name: PLD4
Uniprot ID: Q96BZ4 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Phospholipid scramblase 2
Reactions: Not Available
Gene Name: PLSCR2
Uniprot ID: Q9NRY7 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Phospholipid scramblase 3
Reactions: Not Available
Gene Name: PLSCR3
Uniprot ID: Q9NRY6 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Phospholipid scramblase 4
Reactions: Not Available
Gene Name: PLSCR4
Uniprot ID: Q9NRQ2 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Phospholipid scramblase family member 5
Reactions: Not Available
Gene Name: PLSCR5
Uniprot ID: A0PG75 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Probable phospholipid-transporting ATPase VB
Reactions: Not Available
Gene Name: ATP10B
Uniprot ID: O94823 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Probable phospholipid-transporting ATPase ID
Reactions: Not Available
Gene Name: ATP8B2
Uniprot ID: P98198 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Abhydrolase domain-containing protein 4
Reactions: Not Available
Gene Name: ABHD4
Uniprot ID: Q8TB40 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: N-acyl-phosphatidylethanolamine-hydrolyzing phospholipase D
Reactions: Not Available
Gene Name: NAPEPLD
Uniprot ID: Q6IQ20 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Phosphatidylethanolamine-binding protein 1
Reactions: Not Available
Gene Name: PEBP1
Uniprot ID: P30086 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Phosphatidylethanolamine-binding protein 4
Reactions: Not Available
Gene Name: PEBP4
Uniprot ID: Q96S96 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Ethanolaminephosphotransferase 1
Reactions: Not Available
Gene Name: EPT1
Uniprot ID: Q9C0D9 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytosolic phospholipase A2 beta
Reactions: Not Available
Gene Name: PLA2G4B
Uniprot ID: P0C869 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Phospholipase D1 variant
Reactions: Not Available
Gene Name: Not Available
Uniprot ID: Q59EA4 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA