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Record Information
Version4.0
StatusDetected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2019-08-07 15:42:37 UTC
HMDB IDHMDB0000114
Secondary Accession Numbers
  • HMDB00114
Metabolite Identification
Common NameGlycerylphosphorylethanolamine
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
Data?1565192557
Synonyms
ValueSource
GlycerophosphorylethanolamineChEBI
sn-Glycerol-3-phosphoethanolamineChEBI
GlycerophosphoethanolamineMeSH
GlycerylphosphorylethanolamineMeSH
GPEAHMDB
Glycerol 3-phosphoethanolamineHMDB
Glycerol 3-phosphorylethanolamineHMDB
Glycerol phosphorylethanolamineHMDB
Glyceryl-3-phosphorylethanolamineHMDB
alpha-GlycerophosphorylethanolamineHMDB
sn-Glycero-3-phosphoethanolamineHMDB
α-GlycerophosphorylethanolamineHMDB
Chemical FormulaC5H14NO6P
Average Molecular Weight215.1415
Monoisotopic Molecular Weight215.055873697
IUPAC Name(2-aminoethoxy)(2,3-dihydroxypropoxy)phosphinic acid
Traditional Nameglycerophosphorylethanolamine
CAS Registry Number1190-00-7
SMILES
NCCOP(O)(=O)OCC(O)CO
InChI Identifier
InChI=1S/C5H14NO6P/c6-1-2-11-13(9,10)12-4-5(8)3-7/h5,7-8H,1-4,6H2,(H,9,10)
InChI KeyJZNWSCPGTDBMEW-UHFFFAOYSA-N
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
Ontology
Disposition

Source:

Biological location:

Process

Naturally occurring process:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility29.2 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
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
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Feces
Tissue Locations
  • Brain
  • Liver
  • Prostate
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB021895
KNApSAcK IDNot Available
Chemspider ID110410
KEGG Compound IDC01233
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID5151
PubChem Compound123874
PDB IDNot Available
ChEBI ID52330
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceTronconi, 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
General References
  1. 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 ]
  2. 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 ]
  3. 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 ]
  4. 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 ]
  5. 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 ]
  6. 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 ]
  7. 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. doi: 10.1038/nature07762. [PubMed:19212411 ]

Enzymes

General function:
Involved in hydrolase activity
Specific function:
Hydrolyzes fatty acids from S-acylated cysteine residues in proteins such as trimeric G alpha proteins or HRAS. Has depalmitoylating activity and also low lysophospholipase activity.
Gene Name:
LYPLA1
Uniprot ID:
O75608
Molecular weight:
24669.355
General function:
Involved in phosphatidylcholine-sterol O-acyltransferase activity
Specific function:
Has transacylase and calcium-independent phospholipase A2 activity. Catalyzes the formation of 1-O-acyl-N-acetylsphingosine and the concomitant release of a lyso-phospholipid (By similarity). May have weak lysophospholipase activity.
Gene Name:
PLA2G15
Uniprot ID:
Q8NCC3
Molecular weight:
Not Available
General function:
Involved in metabolic process
Specific function:
Selectively hydrolyzes arachidonyl phospholipids in the sn-2 position releasing arachidonic acid. Together with its lysophospholipid activity, it is implicated in the initiation of the inflammatory response.
Gene Name:
PLA2G4A
Uniprot ID:
P47712
Molecular weight:
85210.19
General function:
Involved in hydrolase activity
Specific function:
May hydrolyze fatty acids from S-acylated cysteine residues in proteins such as trimeric G alpha proteins or HRAS. Has lysophospholipase activity (By similarity). Deacylates GAP43.
Gene Name:
LYPLA2
Uniprot ID:
O95372
Molecular weight:
24736.71
General function:
Involved in sugar binding
Specific function:
May have both lysophospholipase and carbohydrate-binding activities.
Gene Name:
CLC
Uniprot ID:
Q05315
Molecular weight:
16452.785
General function:
Involved in glycerophosphodiester phosphodiesterase activity
Specific function:
Has glycerophosphoinositol phosphodiesterase activity. Has little or no activity towards glycerophosphocholine. GDE1 activity can be modulated by G-protein signaling pathways (By similarity).
Gene Name:
GDE1
Uniprot ID:
Q9NZC3
Molecular weight:
37718.04
General function:
Involved in immune response
Specific function:
Not Available
Gene Name:
HLA-B
Uniprot ID:
Q95372
Molecular weight:
21058.9