Record Information
Version1.0
Creation date2011-09-21 01:36:18 UTC
Update date2015-07-21 06:59:21 UTC
Primary IDFDB028219
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameLysoPE(16:0/0:0)
DescriptionLysoPE(16:0/0:0) is a lysophosphatidylethanolamine or a lysophospholipid. The term 'lysophospholipid' (LPL) refers to any phospholipid that is missing one of its two O-acyl chains. Thus, LPLs have a free alcohol in either the sn-1 or sn-2 position. The prefix 'lyso-' comes from the fact that lysophospholipids were originally found to be hemolytic however it is now used to refer generally to phospholipids missing an acyl chain. LPLs are usually the result of phospholipase A-type enzymatic activity on regular phospholipids such as phosphatidylcholine or phosphatidic acid, although they can also be generated by the acylation of glycerophospholipids or the phosphorylation of monoacylglycerols. Some LPLs serve important signaling functions such as lysophosphatidic acid. Lysophosphatidylethanolamines (LPEs) can function as plant growth regulators with several diverse uses. (LPEs) are approved for outdoor agricultural use to accelerate ripening and improve the quality of fresh produce. They are also approved for indoor use to preserve stored crops and commercial cut flowers. As a breakdown product of phosphatidylethanolamine (PE), LPE is present in cells of all organisms. [HMDB]
CAS NumberNot Available
Structure
Thumb
Synonyms
SynonymSource
1-Hexadecanoyl-sn-glycero-3-phosphoethanolamineChEBI
1-Palmitoyl-gpeChEBI
1-Palmitoyl-gpe (16:0)ChEBI
1-Palmitoyl-sn-glycero-3-phosphoethanolamine zwitterionChEBI
2-Ammonioethyl (2R)-2-hydroxy-3-(palmitoyloxy)propyl phosphateChEBI
GPE(16:0)ChEBI
GPE(16:0/0:0)ChEBI
PE(16:0/0:0)ChEBI
2-Ammonioethyl (2R)-2-hydroxy-3-(palmitoyloxy)propyl phosphoric acidGenerator
1-Palmitoyl-2-hydroxy-sn-glycero-3-phosphoethanolamineHMDB
Hexadecanoyl-lysophosphatidylethanolamineHMDB
LPE(16:0)HMDB
LPE(16:0/0:0)HMDB
Lyso-pe(16:0)HMDB
Lyso-pe(16:0/0:0)HMDB
LysoPE(16:0)HMDB
Lysophosphatidylethanolamine(16:0)HMDB
Lysophosphatidylethanolamine(16:0/0:0)HMDB
1-Hexadecanoyl-2-hydroxy-sn-glycero-3-phosphoethanolamineHMDB
1-HexadecanoylglycerophosphoethanolamineHMDB
1-Palmitoyl-2-hydroxy-sn-glycero-3-phosphatidylethanolamineHMDB
1-Palmitoyl-3-glycerylphosphorylethanolamineHMDB
1-Palmitoyl-sn-glycero-3-phosphoethanolamineHMDB
1-Palmitoyl-sn-glycerol-3-L-alpha-phosphorylethanolamineHMDB
1-Palmitoyl-sn-glycerol-3-L-α-phosphorylethanolamineHMDB
1-Palmitoyl-sn-glycerol-3-phosphylethanolamineHMDB
1-Palmitoyl-sn-glycerophosphatidylethanolamineHMDB
1-Palmitoylglycero-3-phosphorylethanolamineHMDB
1-PalmitoylglycerophosphoethanolamineHMDB
3-Palmitoyl-DL-glycerol-1-phosphorylethanolamineHMDB
Palmitoyl lysophosphatidylethanolamineHMDB
1-Palmitoyl-lysophosphatidylethanolamineHMDB
LysoPE(16:0/0:0)Lipid Annotator
1-Hexadecanoyl-sn-glycero-3-oethanolamineChEBI
1-Palmitoyl-2-hydroxy-sn-glycero-3-oethanolamineHMDB
1-palmitoyl-2-hydroxy-sn-glycero-3-phosphoethanolaminehmdb
1-Palmitoyl-sn-glycero-3-oethanolamine zwitterionChEBI
2-Ammonioethyl (2R)-2-hydroxy-3-(palmitoyloxy)propyl ateChEBI
2-Ammonioethyl (2R)-2-hydroxy-3-(palmitoyloxy)propyl ic acidGenerator
Lyso-PE(16:0/0:0)hmdb
Lysoatidylethanolamine(16:0/0:0)HMDB
Predicted Properties
PropertyValueSource
Water Solubility0.0024 g/LALOGPS
logP4.1ALOGPS
logP3.53ChemAxon
logS-5.3ALOGPS
pKa (Strongest Acidic)1.87ChemAxon
pKa (Strongest Basic)10ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area128.31 ŲChemAxon
Rotatable Bond Count23ChemAxon
Refractivity117.41 m³·mol⁻¹ChemAxon
Polarizability52.25 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC21H44NO7P
IUPAC name(2-aminoethoxy)[(2R)-3-(hexadecanoyloxy)-2-hydroxypropoxy]phosphinic acid
InChI IdentifierInChI=1S/C21H44NO7P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-21(24)27-18-20(23)19-29-30(25,26)28-17-16-22/h20,23H,2-19,22H2,1H3,(H,25,26)/t20-/m1/s1
InChI KeyYVYMBNSKXOXSKW-HXUWFJFHSA-N
Isomeric SMILES[H][C@@](O)(COC(=O)CCCCCCCCCCCCCCC)COP(O)(=O)OCCN
Average Molecular Weight453.5503
Monoisotopic Molecular Weight453.285539279
Classification
Description belongs to the class of organic compounds known as 1-acyl-sn-glycero-3-phosphoethanolamines. These are glycerophoethanolamines in which the glycerol is esterified with a fatty acid at O-1 position, and linked at position 3 to a phosphoethanolamine.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassGlycerophospholipids
Sub ClassGlycerophosphoethanolamines
Direct Parent1-acyl-sn-glycero-3-phosphoethanolamines
Alternative Parents
Substituents
  • 1-monoacyl-sn-glycero-3-phosphoethanolamine
  • Phosphoethanolamine
  • Fatty acid ester
  • Dialkyl phosphate
  • Organic phosphoric acid derivative
  • Fatty acyl
  • Alkyl phosphate
  • Phosphoric acid ester
  • Amino acid or derivatives
  • Carboxylic acid ester
  • Secondary alcohol
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Organonitrogen compound
  • Hydrocarbon derivative
  • Alcohol
  • Primary aliphatic amine
  • Organic oxide
  • Organopnictogen compound
  • Organic nitrogen compound
  • Carbonyl group
  • Organic oxygen compound
  • Amine
  • Organooxygen compound
  • Primary amine
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effect

Organoleptic effect:

Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0gvo-3920100000-42e56a40b9f2f651e243JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-03mi-4290100000-9d4961833a31a61505d2JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-9110200000-adac1ea4ba52b6c32a6aJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-9120000000-9cc034fa9a4c6eeac716JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9210000000-1e7e20f5d5acdebdbeadJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0pbi-1290500000-c144e6d1cc68b4901cb6JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a73-6490000000-d52a88743171a228301cJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01t9-9110000000-93d9fa86c2fd00af0101JSpectraViewer
ChemSpider ID7826019
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID9547069
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB11503
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
Pathways
NameSMPDB LinkKEGG Link
Phospholipid BiosynthesisSMP00025 map00564
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference