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Identification
YMDB IDYMDB00757
NameGlycerylphosphorylethanolamine
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
Descriptionsn-glycero-3-phosphoethanolamine belongs to the class of organic compounds known as glycerophosphoethanolamines. These are glycerolipids characterized by an ethanolamine ester of glycerophosphoric acid. 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 atoms. sn-glycero-3-phosphoethanolamine is a very strong basic compound (based on its pKa).
Structure
Thumb
Synonyms
  • 2-aminoethyl ester 1-Glycerophosphoric acid
  • a-Glycerophosphorylethanolamine
  • alpha-Glycerophosphorylethanolamine
  • Glycerol 3-phosphoethanolamine
  • Glycerol 3-phosphorylethanolamine
  • Glycerophosphoethanolamine
  • Glycerophosphorylethanolamine
  • Glyceryl-3-phosphorylethanolamine
  • Glycerylphosphorylethanolamine
  • GPEA
  • sn-glycero-3-Phosphoethanolamine
  • sn-Glycerol-3-phosphoethanolamine
  • Glycerol phosphorylethanolamine
  • α-Glycerophosphorylethanolamine
CAS numberNot Available
WeightAverage: 215.1415
Monoisotopic: 215.055873697
InChI KeyJZNWSCPGTDBMEW-UHFFFAOYSA-N
InChIInChI=1S/C5H14NO6P/c6-1-2-11-13(9,10)12-4-5(8)3-7/h5,7-8H,1-4,6H2,(H,9,10)
IUPAC Name(2-aminoethoxy)(2,3-dihydroxypropoxy)phosphinic acid
Traditional IUPAC Nameglycerophosphorylethanolamine
Chemical FormulaC5H14NO6P
SMILES[H]C(O)(CO)COP(O)(=O)OCCN
Chemical Taxonomy
Description belongs to the class of organic compounds known as glycerophosphoethanolamines. These are glycerolipids characterized by an ethanolamine ester of glycerophosphoric acid. 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 atoms.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassGlycerophospholipids
Sub ClassGlycerophosphoethanolamines
Direct ParentGlycerophosphoethanolamines
Alternative Parents
Substituents
  • Sn-glycero-3-phosphoethanolamine
  • Phosphoethanolamine
  • Dialkyl phosphate
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Alkyl phosphate
  • Secondary alcohol
  • 1,2-diol
  • Primary amine
  • Primary alcohol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxide
  • Primary aliphatic amine
  • Organic nitrogen compound
  • Amine
  • Organopnictogen compound
  • Alcohol
  • 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 Solubility36.5 g/LALOGPS
logP-2.3ALOGPS
logP-3.4ChemAxon
logS-0.77ALOGPS
pKa (Strongest Acidic)1.87ChemAxon
pKa (Strongest Basic)10ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area122.24 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity43.82 m³·mol⁻¹ChemAxon
Polarizability19.07 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • cell envelope
Organoleptic PropertiesNot Available
SMPDB PathwaysNot Available
KEGG PathwaysNot Available
SMPDB ReactionsNot Available
KEGG Reactions
Glycerylphosphorylethanolamine + fatty acid ↔ water + PE(14:0/16:1(9Z))
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0gwf-5900000000-55796a83071cae1bff8bJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-9110000000-687d834f521d42c7e36cJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-9100000000-f3f7dcb5cdd10c48a24aJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052f-9000000000-750b47541e6949c8a75fJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-2950000000-9e71c620f3a5db1afe86JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004l-9700000000-823f904dfffc25785d54JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-fdc87551301ed4f6a009JSpectraViewer
References
References:
  • Herrgard, M. J., Swainston, N., Dobson, P., Dunn, W. B., Arga, K. Y., Arvas, M., Bluthgen, N., Borger, S., Costenoble, R., Heinemann, M., Hucka, M., Le Novere, N., Li, P., Liebermeister, W., Mo, M. L., Oliveira, A. P., Petranovic, D., Pettifer, S., Simeonidis, E., Smallbone, K., Spasic, I., Weichart, D., Brent, R., Broomhead, D. S., Westerhoff, H. V., Kirdar, B., Penttila, M., Klipp, E., Palsson, B. O., Sauer, U., Oliver, S. G., Mendes, P., Nielsen, J., Kell, D. B. (2008). "A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology." Nat Biotechnol 26:1155-1160.18846089
  • Angus, W. W., Lester, R. L. (1975). "The regulated catabolism of endogenous and exogenous phosphatidylinositol by Saccharomyces cerevisiae leading to extracellular glycerophosphorylinositol and inositol." J Biol Chem 250:22-30.166987
  • Lee, K. S., Patton, J. L., Fido, M., Hines, L. K., Kohlwein, S. D., Paltauf, F., Henry, S. A., Levin, D. E. (1994). "The Saccharomyces cerevisiae PLB1 gene encodes a protein required for lysophospholipase and phospholipase B activity." J Biol Chem 269:19725-19730.8051052
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID52330
HMDB IDHMDB0000114
Pubchem Compound ID123874
Kegg IDC01233
ChemSpider ID110410
FOODB IDFDB021895
Wikipedia IDNot Available
BioCyc IDNot Available

Enzymes

General function:
Involved in metabolic process
Specific function:
Sequentially removes both fatty acyl groups from diacylglycerophospholipids and therefore has both phospholipase A and lysophospholipase activities. Substrate preference is phosphatidylserine > phosphatidylinositol >> phosphatidylcholine > phosphatidylethanolamine
Gene Name:
PLB1
Uniprot ID:
P39105
Molecular weight:
71666.60156
Reactions
2-lysophosphatidylcholine + H(2)O → glycerophosphocholine + a carboxylate.