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Identification
YMDB IDYMDB01198
NamePE(16:0/16:0)
SpeciesSaccharomyces cerevisiae
StrainBrewer's yeast
DescriptionPE(16:0/16:0) is a phosphatidylethanolamine. 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 to the C-1 and C-2 positions. PE(16:0/16:0), in particular, consists of two hexadecanoyl chains at positions C-1 and C-2. 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.
Structure
Thumb
Synonyms
  • (3-Phosphatidyl)-ethanolamine
  • (3-Phosphatidyl)ethanolamine
  • 1-Acyl-2-acyl-sn-glycero-3-phosphoethanolamine
  • 1,2-diacyl-sn-glycero-3-phosphoethanolamine
  • 1,2-dipalmitoyl-rac-glycero-3-phosphoethanolamine
  • Cephalin
  • GPEtn(16:0/16:0)
  • GPEtn(32:0)
  • O-(1-beta-Acyl-2-acyl-sn-glycero-3-phospho)ethanolamine
  • Palmitin, 1,2-di-, 2-aminoethyl hydrogen phosphate
  • PE(16:0/16:0)
  • PE(32:0)
  • Phophatidylethanolamine(16:0/16:0)
  • Phophatidylethanolamine(32:0)
  • Phosphatidylethanolamine
  • phosphatidylethanolamines
  • 1,2-Dihexadecanoyl-sn-glycero-3-phosphoethanolamine
  • 1,2-Dipalmitoyl-sn-glycero-3-phosphoethanolamine zwitterion
  • 2-Ammonioethyl (2R)-2,3-bis(palmitoyloxy)propyl phosphate
  • 2-Ammonioethyl (2R)-2,3-bis(palmitoyloxy)propyl phosphoric acid
  • 1,2-Dipalmitoyl-rac-glycerophosphoethanolamine
  • DHPE
  • DPPE
  • 1,2-Dihexadecyl-sn-glycero-3-phosphoethanolamine
  • 1,2-Dipalmitoyl-3-phosphatidylethanolamine
  • 1,2-Dipalmitoyl-3-phosphatidylethanolamine, (+-)-isomer
  • 1,2-Dipalmitoyl-3-phosphatidylethanolamine, ion(1-)
  • Dipalmitoyl cephalin
  • Phosphatidylethanolamine dipalmitoate
  • 1,2-Dipalmitoyl-3-phosphatidylethanolamine, (R)-isomer
  • Dipalmitoyl phosphatidylethanolamine
  • 1,2-Dihexadecanoyl-rac-glycero-3-phosphoethanolamine
  • 1,2-Dipalmitoyl-sn-glycero-3-phosphoethanolamine
CAS number5681-36-7
WeightAverage: 691.972
Monoisotopic: 691.515205345
InChI KeySLKDGVPOSSLUAI-PGUFJCEWSA-N
InChIInChI=1S/C37H74NO8P/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-36(39)43-33-35(34-45-47(41,42)44-32-31-38)46-37(40)30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h35H,3-34,38H2,1-2H3,(H,41,42)/t35-/m1/s1
IUPAC Name(2-aminoethoxy)[(2R)-2,3-bis(hexadecanoyloxy)propoxy]phosphinic acid
Traditional IUPAC Name2-aminoethoxy((2R)-2,3-bis(hexadecanoyloxy)propoxy)phosphinic acid
Chemical FormulaC37H74NO8P
SMILES[H][C@@](COC(=O)CCCCCCCCCCCCCCC)(COP(O)(=O)OCCN)OC(=O)CCCCCCCCCCCCCCC
Chemical Taxonomy
Description belongs to the class of organic compounds known as phosphatidylethanolamines. These are glycerophosphoetahnolamines in which two fatty acids are bonded to the glycerol moiety through ester linkages.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassGlycerophospholipids
Sub ClassGlycerophosphoethanolamines
Direct ParentPhosphatidylethanolamines
Alternative Parents
Substituents
  • Diacylglycero-3-phosphoethanolamine
  • Phosphoethanolamine
  • Fatty acid ester
  • Dialkyl phosphate
  • Dicarboxylic acid or derivatives
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Alkyl phosphate
  • Fatty acyl
  • Amino acid or derivatives
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Organopnictogen compound
  • Organic oxygen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Amine
  • Primary aliphatic amine
  • Organic nitrogen compound
  • Primary amine
  • Carbonyl group
  • Organic oxide
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateSolid
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility9.5e-05 g/LALOGPS
logP8.08ALOGPS
logP10.45ChemAxon
logS-6.9ALOGPS
pKa (Strongest Acidic)1.87ChemAxon
pKa (Strongest Basic)10ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area134.38 ŲChemAxon
Rotatable Bond Count39ChemAxon
Refractivity191 m³·mol⁻¹ChemAxon
Polarizability85.57 ųChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular LocationsNot Available
Organoleptic PropertiesNot Available
SMPDB Pathways
Glycerophospholipid metabolismPW002493 ThumbThumb?image type=greyscaleThumb?image type=simple
Lysolipid incorporation into ER PC(16:0/16:0)PW002784 ThumbThumb?image type=greyscaleThumb?image type=simple
Lysolipid incorporation into Mitochondria PC(16:0/16:0)PW002753 ThumbThumb?image type=greyscaleThumb?image type=simple
Phosphatidylcholine biosynthesis PC(16:0/16:0)PW002885 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
Glycerophospholipid metabolismec00564 Map00564
Glycosylphosphatidylinositol(GPI)-anchor biosynthesisec00563 Map00563
SMPDB Reactions
DG(16:0/16:0/0:0) + CDP-EthanolamineCytidine monophosphate + hydron + PE(16:0/16:0)
PE(16:0/0:0) PE(16:0/16:0)
PE(16:0/16:0) + S-Adenosyl-L-methioninePE-NMe(16:0/16:0) + hydron + S-Adenosylhomocysteine
KEGG ReactionsNot Available
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
References
References:
  • Ejsing, C. S., Sampaio, J. L., Surendranath, V., Duchoslav, E., Ekroos, K., Klemm, R. W., Simons, K., Shevchenko, A. (2009). "Global analysis of the yeast lipidome by quantitative shotgun mass spectrometry." Proc Natl Acad Sci U S A 106:2136-2141.19174513
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID16038
HMDB IDHMDB08923
Pubchem Compound ID65109
Kegg IDC00350
ChemSpider ID393103
FOODB IDFDB026113
WikipediaLecithin
BioCyc IDL-1-PHOSPHATIDYL-ETHANOLAMINE

Enzymes

General function:
Involved in phosphatidylethanolamine N-methyltransferas
Specific function:
S-adenosyl-L-methionine + phosphatidylethanolamine = S-adenosyl-L-homocysteine + phosphatidyl-N-methylethanolamine
Gene Name:
PEM1
Uniprot ID:
P05374
Molecular weight:
101203.0
Reactions
S-adenosyl-L-methionine + phosphatidylethanolamine → S-adenosyl-L-homocysteine + phosphatidyl-N-methylethanolamine.