Record Information
Version2.0
Creation Date2012-05-31 09:57:35 -0600
Update Date2015-06-03 15:53:12 -0600
Secondary Accession Numbers
  • ECMDB00114
Identification
Name:Glycerylphosphorylethanolamine
Description:Glycerylphosphorylethanolamine is membrane breakdown product resulting from the cleavage of the lipid group from glycerophosphoethanlomine fatty acids (i.e. phosphatidylethanolamine). Phosphatidylethanolamine is one of the major lipid constituents of E. coli.
Structure
Thumb
Synonyms:
  • 2-Aminoethyl ester 1-glycerophosphate
  • 2-Aminoethyl ester 1-Glycerophosphorate
  • 2-Aminoethyl ester 1-Glycerophosphoric acid
  • A-Glycerophosphorylethanolamine
  • Alpha-Glycerophosphorylethanolamine
  • Glycerol 3-phosphoethanolamine
  • Glycerol 3-phosphorylethanolamine
  • Glycerophosphoethanolamine
  • Glycerophosphorylethanolamine
  • Glyceryl-3-phosphorylethanolamine
  • Glycerylphosphorylethanolamine
  • GPEA
  • α-Glycerophosphorylethanolamine
Chemical Formula:C5H14NO6P
Weight:Average: 215.1415
Monoisotopic: 215.055873697
InChI Key:FRMZOWIQVCBEAC-UHFFFAOYSA-N
InChI:InChI=1S/C5H14NO6P/c7-2-1-6(13(10,11)12)3-5(9)4-8/h5,7-9H,1-4H2,(H2,10,11,12)
CAS number:1190-00-7
IUPAC Name:[(2,3-dihydroxypropyl)(2-hydroxyethyl)amino]phosphonic acid
Traditional IUPAC Name:GPEA
SMILES:OCCN(CC(O)CO)P(O)(O)=O
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as organic phosphoramides. These are organic compounds containing the phosphoric acid amide functional group.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganic acids and derivatives
Sub ClassOrganic phosphoric acids and derivatives
Direct ParentOrganic phosphoramides
Alternative Parents
Substituents
  • Organic phosphoric acid amide
  • Secondary alcohol
  • Alkanolamine
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Physical Properties
State:Solid
Charge:-2
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility29.2 mg/mLALOGPS
logP-1.9ALOGPS
logP-3.2ChemAxon
logS-0.87ALOGPS
pKa (Strongest Acidic)2.8ChemAxon
pKa (Strongest Basic)-2.6ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area121.46 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity44.53 m3·mol-1ChemAxon
Polarizability18.51 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
Adenosine triphosphate + Water + Glycerylphosphorylethanolamine > ADP + Glycerylphosphorylethanolamine + Hydrogen ion + Phosphate
Adenosine triphosphate + Water + Glycerylphosphorylethanolamine > ADP + Glycerylphosphorylethanolamine + Hydrogen ion + Phosphate
1-Acyl-sn-glycero-3-phosphoethanolamine (N-C12:0) + Water > Dodecanoate (N-C12:0) + Glycerylphosphorylethanolamine + Hydrogen ion
1-Acyl-sn-glycero-3-phosphoethanolamine (N-C14:0) + Water > Glycerylphosphorylethanolamine + Hydrogen ion + tetradecanoate (n-C14:0)
1-Acyl-sn-glycero-3-phosphoethanolamine (N-C14:1) + Water > Glycerylphosphorylethanolamine + Hydrogen ion + Tetradecenoate (N-C14:1)
1-Acyl-sn-glycero-3-phosphoethanolamine (N-C16:0) + Water > Glycerylphosphorylethanolamine + Hydrogen ion + Palmitic acid
1-Acyl-sn-glycero-3-phosphoethanolamine (N-C16:1) + Water > Glycerylphosphorylethanolamine + Hydrogen ion + Hexadecenoate (n-C16:1)
1-Acyl-sn-glycero-3-phosphoethanolamine (N-C18:0) + Water > Glycerylphosphorylethanolamine + Hydrogen ion + Octadecanoate (N-C18:0)
1-Acyl-sn-glycero-3-phosphoethanolamine (N-C18:1) + Water > Glycerylphosphorylethanolamine + Hydrogen ion + Octadecenoate (N-C18:1)
Glycerylphosphorylethanolamine + Water > Ethanolamine + Glycerol 3-phosphate + Hydrogen ion
Glycerylphosphorylethanolamine + Water > Ethanolamine + Glycerol 3-phosphate + Hydrogen ion
2-Acyl-sn-glycero-3-phosphoethanolamine (N-C12:0) + Water > Dodecanoate (N-C12:0) + Glycerylphosphorylethanolamine + Hydrogen ion
2-Acyl-sn-glycero-3-phosphoethanolamine (N-C12:0) + PG(12:0/12:0) > Acyl phosphatidylglycerol (N-C12:0) + Glycerylphosphorylethanolamine
2-Acyl-sn-glycero-3-phosphoethanolamine (N-C14:0) + Water > Glycerylphosphorylethanolamine + Hydrogen ion + tetradecanoate (n-C14:0)
2-Acyl-sn-glycero-3-phosphoethanolamine (N-C14:0) + PG(14:0/14:0) > Acyl phosphatidylglycerol (N-C14:0) + Glycerylphosphorylethanolamine
2-Acyl-sn-glycero-3-phosphoethanolamine (N-C14:1) + Water > Glycerylphosphorylethanolamine + Hydrogen ion + Tetradecenoate (N-C14:1)
2-Acyl-sn-glycero-3-phosphoethanolamine (N-C14:1) + PG(14:1(7Z)/14:1(7Z)) > Acyl phosphatidylglycerol (N-C14:1) + Glycerylphosphorylethanolamine
2-Acyl-sn-glycero-3-phosphoethanolamine (N-C16:0) + Water > Glycerylphosphorylethanolamine + Hydrogen ion + Palmitic acid
2-Acyl-sn-glycero-3-phosphoethanolamine (N-C16:0) + PG(16:0/16:0) > Acyl phosphatidylglycerol (N-C16:0) + Glycerylphosphorylethanolamine
2-Acyl-sn-glycero-3-phosphoethanolamine (N-C16:1) + Water > Glycerylphosphorylethanolamine + Hydrogen ion + Hexadecenoate (n-C16:1)
2-Acyl-sn-glycero-3-phosphoethanolamine (N-C16:1) + PG(16:1(9Z)/16:1(9Z)) > Acyl phosphatidylglycerol (N-C16:1) + Glycerylphosphorylethanolamine
2-Acyl-sn-glycero-3-phosphoethanolamine (N-C18:0) + Water > Glycerylphosphorylethanolamine + Hydrogen ion + Octadecanoate (N-C18:0)
2-Acyl-sn-glycero-3-phosphoethanolamine (N-C18:0) + PG(18:0/18:0) > Acyl phosphatidylglycerol (N-C18:0) + Glycerylphosphorylethanolamine
2-Acyl-sn-glycero-3-phosphoethanolamine (N-C18:1) + Water > Glycerylphosphorylethanolamine + Hydrogen ion + Octadecenoate (N-C18:1)
2-Acyl-sn-glycero-3-phosphoethanolamine (N-C18:1) + PG(18:1(11Z)/18:1(11Z)) > Acyl phosphatidylglycerol (N-C18:1) + Glycerylphosphorylethanolamine

SMPDB Pathways:Not Available
KEGG Pathways:
EcoCyc Pathways:Not Available
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MSsplash10-0udi-4900000000-8d93f4ff2c22c15490aeView in MoNA
GC-MSGC-MS Spectrum - GC-MS (3 TMS)splash10-003s-6689400000-b56cb30807ba61fbab62View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0980000000-ccf9996fb9ea623d636fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000t-5900000000-e9dcf708a81d199f0315View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0229-7900000000-b5a90feff216d218102aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03dj-1970000000-6ccb8182c976c4e3615bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9300000000-b9585a246036f404a036View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004l-9300000000-82f714d7d8fc0c0f3d6dView in MoNA
References
References:
  • Fallbrook A, Turenne SD, Mamalias N, Kish SJ, Ross BM: Phosphatidylcholine and phosphatidylethanolamine metabolites may regulate brain phospholipid catabolism via inhibition of lysophospholipase activity. Brain Res. 1999 Jul 10;834(1-2):207-10. Pubmed: 10407117
  • Jensen JE, Drost DJ, Menon RS, Williamson PC: In vivo brain (31)P-MRS: measuring the phospholipid resonances at 4 Tesla from small voxels. NMR Biomed. 2002 Aug;15(5):338-47. Pubmed: 12203225
  • Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
  • Kish SJ, Robitaille Y, Ball M, Gilbert J, Deck JH, Chang LJ, Schut L: Glycerophosphoethanolamine concentration is elevated in brain of patients with dominantly inherited olivopontocerebellar atrophy. Neurosci Lett. 1990 Dec 11;120(2):209-11. Pubmed: 2293106
  • Nelson C, Moffat B, Jacobsen N, Henzel WJ, Stults JT, King KL, McMurtrey A, Vandlen R, Spencer SA: Glycerophosphorylethanolamine (GPEA) identified as an hepatocyte growth stimulator in liver extracts. Exp Cell Res. 1996 Nov 25;229(1):20-6. Pubmed: 8940245
  • Nitsch RM, Blusztajn JK, Pittas AG, Slack BE, Growdon JH, Wurtman RJ: Evidence for a membrane defect in Alzheimer disease brain. Proc Natl Acad Sci U S A. 1992 Mar 1;89(5):1671-5. Pubmed: 1311847
  • Perry TL, Hansen S, Gandham SS: Postmortem changes of amino compounds in human and rat brain. J Neurochem. 1981 Feb;36(2):406-10. Pubmed: 7463068
  • Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. Pubmed: 19212411
Synthesis Reference:Tronconi, Giovanni. Process for the chromatographic isolation of 1-(a)-glycerylphosphorylcholine and of L-(a)-glycerylphosphorylethanolamine. PCT Int. Appl. (1990), 18 pp.
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI IDNot Available
HMDB IDHMDB00114
Pubchem Compound ID123874
Kegg IDC01233
ChemSpider ID17215919
Wikipedia IDNot Available
BioCyc IDNot Available

Enzymes

General function:
Lipid transport and metabolism
Specific function:
2-lysophosphatidylcholine + H(2)O = glycerophosphocholine + a carboxylate
Gene Name:
pldB
Uniprot ID:
P07000
Molecular weight:
38978
Reactions
2-lysophosphatidylcholine + H(2)O = glycerophosphocholine + a carboxylate.
General function:
Involved in glycerophosphodiester phosphodiesterase activity
Specific function:
Glycerophosphoryl diester phosphodiesterase hydrolyzes deacylated phospholipids to G3P and the corresponding alcohols
Gene Name:
glpQ
Uniprot ID:
P09394
Molecular weight:
40843
Reactions
A glycerophosphodiester + H(2)O = an alcohol + sn-glycerol 3-phosphate.
General function:
Involved in hydrolase activity
Specific function:
Hydrolyzes only long chain acyl thioesters (C12-C18). Specificity similar to chymotrypsin
Gene Name:
tesA
Uniprot ID:
P0ADA1
Molecular weight:
23622
Reactions
2-lysophosphatidylcholine + H(2)O = glycerophosphocholine + a carboxylate.
General function:
Involved in nucleotide binding
Specific function:
Part of the ABC transporter complex UgpABCE involved in sn-glycerol-3-phosphate import. Responsible for energy coupling to the transport system (Probable). Can also transport glycerophosphoryl diesters
Gene Name:
ugpC
Uniprot ID:
P10907
Molecular weight:
39524
Reactions
ATP + H(2)O + glycerol-3-phosphate(Out) = ADP + phosphate + glycerol-3-phosphate(In).
General function:
Involved in glycerophosphodiester phosphodiesterase activity
Specific function:
Glycerophosphoryl diester phosphodiesterase hydrolyzes deacylated phospholipids to G3P and the corresponding alcohols
Gene Name:
ugpQ
Uniprot ID:
P10908
Molecular weight:
27409
Reactions
A glycerophosphodiester + H(2)O = an alcohol + sn-glycerol 3-phosphate.
General function:
Involved in transporter activity
Specific function:
Part of the binding-protein-dependent transport system for sn-glycerol-3-phosphate; probably responsible for the translocation of the substrate across the membrane
Gene Name:
ugpA
Uniprot ID:
P10905
Molecular weight:
33264
General function:
Involved in transporter activity
Specific function:
Part of the binding-protein-dependent transport system for sn-glycerol-3-phosphate; probably responsible for the translocation of the substrate across the membrane
Gene Name:
ugpE
Uniprot ID:
P10906
Molecular weight:
31499
General function:
Involved in transporter activity
Specific function:
sn-glycerol-3-phosphate and glycerophosphoryl diester- binding protein interacts with the binding protein-dependent transport system ugpACE
Gene Name:
ugpB
Uniprot ID:
P0AG80
Molecular weight:
48448

Transporters

General function:
Involved in nucleotide binding
Specific function:
Part of the ABC transporter complex UgpABCE involved in sn-glycerol-3-phosphate import. Responsible for energy coupling to the transport system (Probable). Can also transport glycerophosphoryl diesters
Gene Name:
ugpC
Uniprot ID:
P10907
Molecular weight:
39524
Reactions
ATP + H(2)O + glycerol-3-phosphate(Out) = ADP + phosphate + glycerol-3-phosphate(In).
General function:
Involved in transporter activity
Specific function:
Part of the binding-protein-dependent transport system for sn-glycerol-3-phosphate; probably responsible for the translocation of the substrate across the membrane
Gene Name:
ugpA
Uniprot ID:
P10905
Molecular weight:
33264
General function:
Involved in transporter activity
Specific function:
Part of the binding-protein-dependent transport system for sn-glycerol-3-phosphate; probably responsible for the translocation of the substrate across the membrane
Gene Name:
ugpE
Uniprot ID:
P10906
Molecular weight:
31499
General function:
Involved in transporter activity
Specific function:
Non-specific porin
Gene Name:
ompN
Uniprot ID:
P77747
Molecular weight:
41220
General function:
Involved in transporter activity
Specific function:
Uptake of inorganic phosphate, phosphorylated compounds, and some other negatively charged solutes
Gene Name:
phoE
Uniprot ID:
P02932
Molecular weight:
38922
General function:
Involved in transporter activity
Specific function:
OmpF is a porin that forms passive diffusion pores which allow small molecular weight hydrophilic materials across the outer membrane. It is also a receptor for the bacteriophage T2
Gene Name:
ompF
Uniprot ID:
P02931
Molecular weight:
39333
General function:
Involved in transporter activity
Specific function:
sn-glycerol-3-phosphate and glycerophosphoryl diester- binding protein interacts with the binding protein-dependent transport system ugpACE
Gene Name:
ugpB
Uniprot ID:
P0AG80
Molecular weight:
48448
General function:
Involved in transporter activity
Specific function:
Forms passive diffusion pores which allow small molecular weight hydrophilic materials across the outer membrane
Gene Name:
ompC
Uniprot ID:
P06996
Molecular weight:
40368