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Identification
YMDB IDYMDB01194
NamePE(14:0/0:0)
SpeciesSaccharomyces cerevisiae
StrainBrewer's yeast
DescriptionLysoPE(14:0) 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.
Structure
Thumb
Synonyms
  • 1-myristoyl-2-hydroxy-sn-glycero-3-phosphoethanolamine
  • LPE(14:0)
  • LPE(14:0/0:0)
  • Lyso-PE(14:0)
  • Lyso-PE(14:0/0:0)
  • LysoPE(14:0)
  • LysoPE(14:0/0:0)
  • Lysophosphatidylethanolamine(14:0)
  • Lysophosphatidylethanolamine(14:0/0:0)
  • tetradecanoyl-lysophosphatidylethanolamine
  • 1-Tetradecanoyl-sn-glycero-3-phosphoethanolamine
  • 1-Tetradecanoyl-sn-glycero-3-phosphoethanolamine zwitterion
  • LPE (14:0/0:0)
  • 1-Tetradecanoyl-2-hydroxy-sn-glycero-3-phosphoethanolamine
CAS number19805-23-3
WeightAverage: 425.4972
Monoisotopic: 425.254239151
InChI KeyRPXHXZNGZBHSMJ-GOSISDBHSA-N
InChIInChI=1S/C19H40NO7P/c1-2-3-4-5-6-7-8-9-10-11-12-13-19(22)25-16-18(21)17-27-28(23,24)26-15-14-20/h18,21H,2-17,20H2,1H3,(H,23,24)/t18-/m1/s1
IUPAC Name(2-aminoethoxy)[(2R)-2-hydroxy-3-(tetradecanoyloxy)propoxy]phosphinic acid
Traditional IUPAC Name2-aminoethoxy(2R)-2-hydroxy-3-(tetradecanoyloxy)propoxyphosphinic acid
Chemical FormulaC19H40NO7P
SMILES[H][C@@](O)(COC(=O)CCCCCCCCCCCCC)COP(O)(=O)OCCN
Chemical Taxonomy
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
Physical Properties
StateSolid
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility0.0071 g/LALOGPS
logP3.25ALOGPS
logP2.64ChemAxon
logS-4.8ALOGPS
pKa (Strongest Acidic)1.87ChemAxon
pKa (Strongest Basic)10ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area128.31 ŲChemAxon
Rotatable Bond Count21ChemAxon
Refractivity108.21 m³·mol⁻¹ChemAxon
Polarizability47.97 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular LocationsNot Available
Organoleptic PropertiesNot Available
SMPDB Pathways
Lysolipid incorporation into ERPW002532 ThumbThumb?image type=greyscaleThumb?image type=simple
Lysolipid incorporation into ER PC(14:0/14:0)PW002783 ThumbThumb?image type=greyscaleThumb?image type=simple
Lysolipid incorporation into ER PC(16:1(11Z)/16:1(11Z))PW002786 ThumbThumb?image type=greyscaleThumb?image type=simple
Lysolipid incorporation into ER PC(18:2(9Z,11Z)/18:2(9Z,11Z))PW002789 ThumbThumb?image type=greyscaleThumb?image type=simple
Lysolipid incorporation into MitochondriaPW002531 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG PathwaysNot Available
SMPDB Reactions
PE(14:0/0:0) PE(14:0/14:0)
Adenosine triphosphate + water + PE(14:0/0:0)ADP + phosphate + PE(14:0/0:0)
Adenosine triphosphate + water + PE(14:0/0:0)ADP + phosphate + PE(14:0/0:0)
PE(14:0/0:0)PE(14:0/14:0)
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 ID84299
HMDB IDHMDB11500
Pubchem Compound ID89229
Kegg IDNot Available
ChemSpider ID7826020
FOODB IDFDB028216
Wikipedia IDNot Available
BioCyc IDNot Available

Transporters

General function:
Involved in nucleotide binding
Specific function:
This magnesium-dependent enzyme catalyzes the hydrolysis of ATP coupled with the transport of phospholipids. Required for protein transport from Golgi to vacuoles
Gene Name:
DNF2
Uniprot ID:
Q12675
Molecular weight:
182617.0
Reactions
ATP + H(2)O + phospholipid(In) → ADP + phosphate + phospholipid(Out).
General function:
Involved in nucleotide binding
Specific function:
This magnesium-dependent enzyme catalyzes the hydrolysis of ATP coupled with the transport of phospholipids (Potential)
Gene Name:
DNF1
Uniprot ID:
P32660
Molecular weight:
177796.0
Reactions
ATP + H(2)O + phospholipid(In) → ADP + phosphate + phospholipid(Out).