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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2012-10-30 10:32:48 UTC
Update Date2022-09-22 18:34:27 UTC
HMDB IDHMDB0059660
Secondary Accession Numbers
  • HMDB59660
Metabolite Identification
Common Namesn-glycero-3-Phosphoethanolamine
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
ValueSource
GlycerophosphoethanolamineChEBI
GlycerylphosphorylethanolamineHMDB
GlycerophosphorylethanolamineHMDB
sn-Glycerol-3-phosphoethanolamineHMDB
Chemical FormulaC5H14NO6P
Average Molecular Weight215.1415
Monoisotopic Molecular Weight215.055873697
IUPAC Name(2-aminoethoxy)[(2S)-2,3-dihydroxypropoxy]phosphinic acid
Traditional Name2-aminoethoxy(2S)-2,3-dihydroxypropoxyphosphinic acid
CAS Registry NumberNot Available
SMILES
NCCO[P@@](O)(=O)OC[C@@H](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)/t5-/m0/s1
InChI KeyJZNWSCPGTDBMEW-YFKPBYRVSA-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
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M-H]-MetCCS_train_neg138.95530932474
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedCancer patients undergoing total body irradiation details
UrineDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedCancer patients undergoing total body irradiation details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB03484
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID4573608
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5459861
PDB IDNot Available
ChEBI ID16929
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  2. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  3. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  4. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  5. Divecha N, Irvine RF: Phospholipid signaling. Cell. 1995 Jan 27;80(2):269-78. [PubMed:7834746 ]
  6. Cevc, Gregor (1993). Phospholipids Handbook. Marcel Dekker.
  7. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

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
Reactions
1-Acyl-sn-glycero-3-phosphoethanolamine + Water → Fatty acid + sn-glycero-3-Phosphoethanolaminedetails
General function:
Involved in hydrolase activity
Specific function:
Membrane-associated phospholipase. Exhibits a calcium-independent broad substrate specificity including phospholipase A2/lysophospholipase activity. Preferential hydrolysis at the sn-2 position of diacylphospholipids and diacyglycerol, whereas it shows no positional specificity toward triacylglycerol. Exhibits also esterase activity toward p-nitrophenyl. May act on the brush border membrane to facilitate the absorption of digested lipids (By similarity).
Gene Name:
PLB1
Uniprot ID:
Q6P1J6
Molecular weight:
161711.9
Reactions
1-Acyl-sn-glycero-3-phosphoethanolamine + Water → Fatty acid + sn-glycero-3-Phosphoethanolaminedetails
2-Acyl-sn-glycero-3-phosphoethanolamine + Water → Fatty acid + sn-glycero-3-Phosphoethanolaminedetails
General function:
Involved in metabolic process
Specific function:
Phospholipase B that deacylates intracellular phosphatidylcholine (PtdCho), generating glycerophosphocholine (GroPtdCho). This deacylation occurs at both sn-2 and sn-1 positions of PtdCho. Its specific chemical modification by certain organophosphorus (OP) compounds leads to distal axonopathy.
Gene Name:
PNPLA6
Uniprot ID:
Q8IY17
Molecular weight:
150952.43
Reactions
1-Acyl-sn-glycero-3-phosphoethanolamine + Water → Fatty acid + sn-glycero-3-Phosphoethanolaminedetails
2-Acyl-sn-glycero-3-phosphoethanolamine + Water → Fatty acid + sn-glycero-3-Phosphoethanolaminedetails
General function:
Not Available
Specific function:
Serine hydrolase, whose specific chemical modification by certain organophosphorus (OP) compounds leads to distal axonopathy (By similarity).
Gene Name:
PNPLA7
Uniprot ID:
Q6ZV29
Molecular weight:
Not Available
Reactions
1-Acyl-sn-glycero-3-phosphoethanolamine + Water → Fatty acid + sn-glycero-3-Phosphoethanolaminedetails
2-Acyl-sn-glycero-3-phosphoethanolamine + Water → Fatty acid + sn-glycero-3-Phosphoethanolaminedetails
General function:
Not Available
Specific function:
Enzyme catalyzing the degradation of lysoplasmalogen. Lysoplasmalogens are formed by the hydrolysis of the abundant membrane glycerophospholipids plasmalogens. May control the respective levels of plasmalogens and lysoplasmalogens in cells and modulate cell membrane properties.
Gene Name:
TMEM86B
Uniprot ID:
Q8N661
Molecular weight:
24351.695
Reactions
1-(1-alkenyl)-sn-glycero-3-phosphoethanolamine + Water → an aldehyde + sn-glycero-3-Phosphoethanolaminedetails