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Human Metabolome Database Version 3.5

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Showing metabocard for PE(P-16:0e/0:0) (HMDB11152)

Record Information
Version 3.5
Creation Date 2008-10-29 08:50:28 -0600
Update Date 2013-02-08 17:25:47 -0700
HMDB ID HMDB11152
Secondary Accession Numbers None
Metabolite Identification
Common Name PE(P-16:0e/0:0)
Description 1-(1Z-hexadecenyl)-sn-glycero-3-phosphoethanolamine is an phospho-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
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. 1-(1Z-Hexadecenyl)-sn-glycero-3-phosphoethanolamine
  2. 2-Azaniumylethyl [(2R)-3-[(E)-hexadec-1-enoxy]-2-hydroxy-propyl] phosphate
  3. LysoPE(dm16:0e)
Chemical Formula C21H44NO6P
Average Molecular Weight 437.5509
Monoisotopic Molecular Weight 437.290624657
IUPAC Name (2-aminoethoxy)[(2R)-3-[(1Z)-hexadec-1-en-1-yloxy]-2-hydroxypropoxy]phosphinic acid
Traditional IUPAC Name 2-aminoethoxy(2R)-3-[(1Z)-hexadec-1-en-1-yloxy]-2-hydroxypropoxyphosphinic acid
CAS Registry Number Not Available
SMILES [H][C@@](O)(CO\C=C/CCCCCCCCCCCCCC)COP(O)(=O)OCCN
InChI Identifier InChI=1S/C21H44NO6P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-17-26-19-21(23)20-28-29(24,25)27-18-16-22/h15,17,21,23H,2-14,16,18-20,22H2,1H3,(H,24,25)/b17-15-/t21-/m1/s1
InChI Key QYTPGOPLNFESQC-NUTQULCTSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Lipids
Class Glycerophospholipids
Sub Class Glycerophosphoethanolamines
Other Descriptors
  • Aliphatic Acyclic Compounds
Substituents
  • Enol Ether
  • Organic Hypophosphite
  • Organic Phosphite
  • Phosphoethanolamine
  • Phosphoric Acid Ester
  • Primary Aliphatic Amine (Alkylamine)
  • Secondary Alcohol
Direct Parent Other Glycerophosphoethanolamines
Ontology
Status Expected 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
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 0.0026 g/L ALOGPS
LogP 4.63 ALOGPS
LogP 3.92 ChemAxon
LogS -5.23 ALOGPS
pKa (strongest acidic) 1.87 ChemAxon
pKa (strongest basic) 10 ChemAxon
Hydrogen Acceptor Count 5 ChemAxon
Hydrogen Donor Count 3 ChemAxon
Polar Surface Area 111.24 A2 ChemAxon
Rotatable Bond Count 22 ChemAxon
Refractivity 117.75 ChemAxon
Polarizability 50.65 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 0 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid Locations Not Available
Tissue Location Not Available
Pathways Not Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB027927
KNApSAcK ID Not Available
Chemspider ID 24769219 Link_out
KEGG Compound ID Not Available
BioCyc ID Not Available
BiGG ID Not Available
Wikipedia Link Not Available
NuGOwiki Link HMDB11152 Link_out
Metagene Link HMDB11152 Link_out
METLIN ID Not Available
PubChem Compound 42607469 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: Phospholipase D2
Reactions:
  • a phosphatidylcholine + H2O = choline + a phosphatidate [RN:R01310]
Gene Name: PLD2
Uniprot ID: O14939 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Phospholipase D1
Reactions:
  • a phosphatidylcholine + H2O = choline + a phosphatidate [RN:R01310]
Gene Name: PLD1
Uniprot ID: Q13393 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Probable phospholipid-transporting ATPase IG
Reactions:
  • ATP + H2O + phospholipidin = ADP + phosphate + phospholipidout [RN:R00086]
Gene Name: ATP11C
Uniprot ID: Q8NB49 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Probable phospholipid-transporting ATPase IH
Reactions:
  • ATP + H2O + phospholipidin = ADP + phosphate + phospholipidout [RN:R00086]
Gene Name: ATP11A
Uniprot ID: P98196 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Probable phospholipid-transporting ATPase VA
Reactions:
  • ATP + H2O + phospholipidin = ADP + phosphate + phospholipidout [RN:R00086]
Gene Name: ATP10A
Uniprot ID: O60312 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Probable phospholipid-transporting ATPase IC
Reactions:
  • ATP + H2O + phospholipidin = ADP + phosphate + phospholipidout [RN:R00086]
Gene Name: ATP8B1
Uniprot ID: O43520 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Probable phospholipid-transporting ATPase IIA
Reactions:
  • ATP + H2O + phospholipidin = ADP + phosphate + phospholipidout [RN:R00086]
Gene Name: ATP9A
Uniprot ID: O75110 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Probable phospholipid-transporting ATPase VD
Reactions:
  • ATP + H2O + phospholipidin = ADP + phosphate + phospholipidout [RN:R00086]
Gene Name: ATP10D
Uniprot ID: Q9P241 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Probable phospholipid-transporting ATPase IB
Reactions:
  • ATP + H2O + phospholipidin = ADP + phosphate + phospholipidout [RN:R00086]
Gene Name: ATP8A2
Uniprot ID: Q9NTI2 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Probable phospholipid-transporting ATPase IA
Reactions:
  • ATP + H2O + phospholipidin = ADP + phosphate + phospholipidout [RN:R00086]
Gene Name: ATP8A1
Uniprot ID: Q9Y2Q0 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Probable phospholipid-transporting ATPase IM
Reactions:
  • ATP + H2O + phospholipidin = ADP + phosphate + phospholipidout [RN:R00086]
Gene Name: ATP8B4
Uniprot ID: Q8TF62 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Probable phospholipid-transporting ATPase IF
Reactions:
  • ATP + H2O + phospholipidin = ADP + phosphate + phospholipidout [RN:R00086]
Gene Name: ATP11B
Uniprot ID: Q9Y2G3 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Probable phospholipid-transporting ATPase IK
Reactions:
  • ATP + H2O + phospholipidin = ADP + phosphate + phospholipidout [RN:R00086]
Gene Name: ATP8B3
Uniprot ID: O60423 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Phospholipid scramblase 1
Reactions:
    Gene Name: PLSCR1
    Uniprot ID: O15162 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: Phosphatidylserine decarboxylase proenzyme
    Reactions:
    • phosphatidyl-L-serine = phosphatidylethanolamine + CO2 [RN:R02055]
    Gene Name: PISD
    Uniprot ID: Q9UG56 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: Phospholipid transfer protein
    Reactions:
      Gene Name: PLTP
      Uniprot ID: P55058 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Choline/ethanolaminephosphotransferase 1
      Reactions:
      • CDP-choline + 1,2-diacyl-sn-glycerol = CMP + a phosphatidylcholine [RN:R01321]
      Gene Name: CEPT1
      Uniprot ID: Q9Y6K0 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Phospholipase D3
      Reactions:
      • a phosphatidylcholine + H2O = choline + a phosphatidate [RN:R01310]
      Gene Name: PLD3
      Uniprot ID: Q8IV08 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Phospholipase D4
      Reactions:
      • a phosphatidylcholine + H2O = choline + a phosphatidate [RN:R01310]
      Gene Name: PLD4
      Uniprot ID: Q96BZ4 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Phospholipid scramblase 2
      Reactions:
        Gene Name: PLSCR2
        Uniprot ID: Q9NRY7 Link_out
        Protein Sequence: FASTA
        Gene Sequence: FASTA
        Name: Phospholipid scramblase 3
        Reactions:
          Gene Name: PLSCR3
          Uniprot ID: Q9NRY6 Link_out
          Protein Sequence: FASTA
          Gene Sequence: FASTA
          Name: Phospholipid scramblase 4
          Reactions:
            Gene Name: PLSCR4
            Uniprot ID: Q9NRQ2 Link_out
            Protein Sequence: FASTA
            Gene Sequence: FASTA
            Name: Phospholipid scramblase family member 5
            Reactions:
              Gene Name: PLSCR5
              Uniprot ID: A0PG75 Link_out
              Protein Sequence: FASTA
              Gene Sequence: FASTA
              Name: Probable phospholipid-transporting ATPase VB
              Reactions:
              • ATP + H2O + phospholipidin = ADP + phosphate + phospholipidout [RN:R00086]
              Gene Name: ATP10B
              Uniprot ID: O94823 Link_out
              Protein Sequence: FASTA
              Gene Sequence: FASTA
              Name: Probable phospholipid-transporting ATPase ID
              Reactions:
              • ATP + H2O + phospholipidin = ADP + phosphate + phospholipidout [RN:R00086]
              Gene Name: ATP8B2
              Uniprot ID: P98198 Link_out
              Protein Sequence: FASTA
              Gene Sequence: FASTA
              Name: Abhydrolase domain-containing protein 4
              Reactions:
                Gene Name: ABHD4
                Uniprot ID: Q8TB40 Link_out
                Protein Sequence: FASTA
                Gene Sequence: FASTA
                Name: N-acyl-phosphatidylethanolamine-hydrolyzing phospholipase D
                Reactions:
                  Gene Name: NAPEPLD
                  Uniprot ID: Q6IQ20 Link_out
                  Protein Sequence: FASTA
                  Gene Sequence: FASTA
                  Name: Phosphatidylethanolamine-binding protein 1
                  Reactions:
                    Gene Name: PEBP1
                    Uniprot ID: P30086 Link_out
                    Protein Sequence: FASTA
                    Gene Sequence: FASTA
                    Name: Phosphatidylethanolamine-binding protein 4
                    Reactions:
                      Gene Name: PEBP4
                      Uniprot ID: Q96S96 Link_out
                      Protein Sequence: FASTA
                      Gene Sequence: FASTA
                      Name: Ethanolaminephosphotransferase 1
                      Reactions:
                      • CDP-ethanolamine + 1,2-diacyl-sn-glycerol = CMP + a phosphatidylethanolamine [RN:R02057]
                      Gene Name: EPT1
                      Uniprot ID: Q9C0D9 Link_out
                      Protein Sequence: FASTA
                      Gene Sequence: FASTA