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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2022-09-22 18:35:06 UTC
HMDB IDHMDB0000114
Secondary Accession Numbers
  • HMDB00114
Metabolite Identification
Common NameGlycerylphosphorylethanolamine
DescriptionGlycerylphosphorylethanolamine, also known as GPEA, 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. Glycerylphosphorylethanolamine is a very strong basic compound (based on its pKa).
Structure
Data?1582752112
Synonyms
ValueSource
GlycerophosphorylethanolamineChEBI
sn-Glycerol-3-phosphoethanolamineChEBI
GlycerophosphoethanolamineHMDB
GPEAHMDB
Glycerol 3-phosphoethanolamineHMDB
Glycerol 3-phosphorylethanolamineHMDB
Glycerol phosphorylethanolamineHMDB
Glyceryl-3-phosphorylethanolamineHMDB
alpha-GlycerophosphorylethanolamineHMDB
sn-Glycero-3-phosphoethanolamineHMDB
Α-glycerophosphorylethanolamineHMDB
GlycerylphosphorylethanolamineMeSH
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
Not AvailableNot 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 PropertiesNot Available
Predicted Molecular 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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+141.61330932474
DeepCCS[M-H]-137.78630932474
DeepCCS[M-2H]-175.40730932474
DeepCCS[M+Na]+150.74530932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
GlycerylphosphorylethanolamineNCCOP(O)(=O)OCC(O)CO2766.6Standard polar33892256
GlycerylphosphorylethanolamineNCCOP(O)(=O)OCC(O)CO1798.5Standard non polar33892256
GlycerylphosphorylethanolamineNCCOP(O)(=O)OCC(O)CO1882.5Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Glycerylphosphorylethanolamine,1TMS,isomer #1C[Si](C)(C)OC(CO)COP(=O)(O)OCCN1961.8Semi standard non polar33892256
Glycerylphosphorylethanolamine,1TMS,isomer #2C[Si](C)(C)OCC(O)COP(=O)(O)OCCN1951.1Semi standard non polar33892256
Glycerylphosphorylethanolamine,1TMS,isomer #3C[Si](C)(C)OP(=O)(OCCN)OCC(O)CO1950.2Semi standard non polar33892256
Glycerylphosphorylethanolamine,1TMS,isomer #4C[Si](C)(C)NCCOP(=O)(O)OCC(O)CO2056.0Semi standard non polar33892256
Glycerylphosphorylethanolamine,2TMS,isomer #1C[Si](C)(C)OCC(COP(=O)(O)OCCN)O[Si](C)(C)C2000.5Semi standard non polar33892256
Glycerylphosphorylethanolamine,2TMS,isomer #2C[Si](C)(C)OC(CO)COP(=O)(OCCN)O[Si](C)(C)C1977.3Semi standard non polar33892256
Glycerylphosphorylethanolamine,2TMS,isomer #3C[Si](C)(C)NCCOP(=O)(O)OCC(CO)O[Si](C)(C)C2049.3Semi standard non polar33892256
Glycerylphosphorylethanolamine,2TMS,isomer #4C[Si](C)(C)OCC(O)COP(=O)(OCCN)O[Si](C)(C)C1970.6Semi standard non polar33892256
Glycerylphosphorylethanolamine,2TMS,isomer #5C[Si](C)(C)NCCOP(=O)(O)OCC(O)CO[Si](C)(C)C2043.5Semi standard non polar33892256
Glycerylphosphorylethanolamine,2TMS,isomer #6C[Si](C)(C)NCCOP(=O)(OCC(O)CO)O[Si](C)(C)C2060.5Semi standard non polar33892256
Glycerylphosphorylethanolamine,2TMS,isomer #7C[Si](C)(C)N(CCOP(=O)(O)OCC(O)CO)[Si](C)(C)C2217.7Semi standard non polar33892256
Glycerylphosphorylethanolamine,3TMS,isomer #1C[Si](C)(C)OCC(COP(=O)(OCCN)O[Si](C)(C)C)O[Si](C)(C)C2002.6Semi standard non polar33892256
Glycerylphosphorylethanolamine,3TMS,isomer #1C[Si](C)(C)OCC(COP(=O)(OCCN)O[Si](C)(C)C)O[Si](C)(C)C1949.5Standard non polar33892256
Glycerylphosphorylethanolamine,3TMS,isomer #1C[Si](C)(C)OCC(COP(=O)(OCCN)O[Si](C)(C)C)O[Si](C)(C)C2636.1Standard polar33892256
Glycerylphosphorylethanolamine,3TMS,isomer #2C[Si](C)(C)NCCOP(=O)(O)OCC(CO[Si](C)(C)C)O[Si](C)(C)C2053.2Semi standard non polar33892256
Glycerylphosphorylethanolamine,3TMS,isomer #2C[Si](C)(C)NCCOP(=O)(O)OCC(CO[Si](C)(C)C)O[Si](C)(C)C2070.8Standard non polar33892256
Glycerylphosphorylethanolamine,3TMS,isomer #2C[Si](C)(C)NCCOP(=O)(O)OCC(CO[Si](C)(C)C)O[Si](C)(C)C2733.4Standard polar33892256
Glycerylphosphorylethanolamine,3TMS,isomer #3C[Si](C)(C)NCCOP(=O)(OCC(CO)O[Si](C)(C)C)O[Si](C)(C)C2065.8Semi standard non polar33892256
Glycerylphosphorylethanolamine,3TMS,isomer #3C[Si](C)(C)NCCOP(=O)(OCC(CO)O[Si](C)(C)C)O[Si](C)(C)C2095.9Standard non polar33892256
Glycerylphosphorylethanolamine,3TMS,isomer #3C[Si](C)(C)NCCOP(=O)(OCC(CO)O[Si](C)(C)C)O[Si](C)(C)C2415.1Standard polar33892256
Glycerylphosphorylethanolamine,3TMS,isomer #4C[Si](C)(C)OC(CO)COP(=O)(O)OCCN([Si](C)(C)C)[Si](C)(C)C2230.6Semi standard non polar33892256
Glycerylphosphorylethanolamine,3TMS,isomer #4C[Si](C)(C)OC(CO)COP(=O)(O)OCCN([Si](C)(C)C)[Si](C)(C)C2161.9Standard non polar33892256
Glycerylphosphorylethanolamine,3TMS,isomer #4C[Si](C)(C)OC(CO)COP(=O)(O)OCCN([Si](C)(C)C)[Si](C)(C)C2831.8Standard polar33892256
Glycerylphosphorylethanolamine,3TMS,isomer #5C[Si](C)(C)NCCOP(=O)(OCC(O)CO[Si](C)(C)C)O[Si](C)(C)C2064.1Semi standard non polar33892256
Glycerylphosphorylethanolamine,3TMS,isomer #5C[Si](C)(C)NCCOP(=O)(OCC(O)CO[Si](C)(C)C)O[Si](C)(C)C2083.2Standard non polar33892256
Glycerylphosphorylethanolamine,3TMS,isomer #5C[Si](C)(C)NCCOP(=O)(OCC(O)CO[Si](C)(C)C)O[Si](C)(C)C2369.1Standard polar33892256
Glycerylphosphorylethanolamine,3TMS,isomer #6C[Si](C)(C)OCC(O)COP(=O)(O)OCCN([Si](C)(C)C)[Si](C)(C)C2217.0Semi standard non polar33892256
Glycerylphosphorylethanolamine,3TMS,isomer #6C[Si](C)(C)OCC(O)COP(=O)(O)OCCN([Si](C)(C)C)[Si](C)(C)C2177.3Standard non polar33892256
Glycerylphosphorylethanolamine,3TMS,isomer #6C[Si](C)(C)OCC(O)COP(=O)(O)OCCN([Si](C)(C)C)[Si](C)(C)C2780.1Standard polar33892256
Glycerylphosphorylethanolamine,3TMS,isomer #7C[Si](C)(C)OP(=O)(OCCN([Si](C)(C)C)[Si](C)(C)C)OCC(O)CO2215.6Semi standard non polar33892256
Glycerylphosphorylethanolamine,3TMS,isomer #7C[Si](C)(C)OP(=O)(OCCN([Si](C)(C)C)[Si](C)(C)C)OCC(O)CO2163.3Standard non polar33892256
Glycerylphosphorylethanolamine,3TMS,isomer #7C[Si](C)(C)OP(=O)(OCCN([Si](C)(C)C)[Si](C)(C)C)OCC(O)CO2522.5Standard polar33892256
Glycerylphosphorylethanolamine,4TMS,isomer #1C[Si](C)(C)NCCOP(=O)(OCC(CO[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C2066.6Semi standard non polar33892256
Glycerylphosphorylethanolamine,4TMS,isomer #1C[Si](C)(C)NCCOP(=O)(OCC(CO[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C2108.8Standard non polar33892256
Glycerylphosphorylethanolamine,4TMS,isomer #1C[Si](C)(C)NCCOP(=O)(OCC(CO[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C2226.9Standard polar33892256
Glycerylphosphorylethanolamine,4TMS,isomer #2C[Si](C)(C)OCC(COP(=O)(O)OCCN([Si](C)(C)C)[Si](C)(C)C)O[Si](C)(C)C2234.8Semi standard non polar33892256
Glycerylphosphorylethanolamine,4TMS,isomer #2C[Si](C)(C)OCC(COP(=O)(O)OCCN([Si](C)(C)C)[Si](C)(C)C)O[Si](C)(C)C2189.1Standard non polar33892256
Glycerylphosphorylethanolamine,4TMS,isomer #2C[Si](C)(C)OCC(COP(=O)(O)OCCN([Si](C)(C)C)[Si](C)(C)C)O[Si](C)(C)C2561.9Standard polar33892256
Glycerylphosphorylethanolamine,4TMS,isomer #3C[Si](C)(C)OC(CO)COP(=O)(OCCN([Si](C)(C)C)[Si](C)(C)C)O[Si](C)(C)C2233.1Semi standard non polar33892256
Glycerylphosphorylethanolamine,4TMS,isomer #3C[Si](C)(C)OC(CO)COP(=O)(OCCN([Si](C)(C)C)[Si](C)(C)C)O[Si](C)(C)C2206.8Standard non polar33892256
Glycerylphosphorylethanolamine,4TMS,isomer #3C[Si](C)(C)OC(CO)COP(=O)(OCCN([Si](C)(C)C)[Si](C)(C)C)O[Si](C)(C)C2334.1Standard polar33892256
Glycerylphosphorylethanolamine,4TMS,isomer #4C[Si](C)(C)OCC(O)COP(=O)(OCCN([Si](C)(C)C)[Si](C)(C)C)O[Si](C)(C)C2219.2Semi standard non polar33892256
Glycerylphosphorylethanolamine,4TMS,isomer #4C[Si](C)(C)OCC(O)COP(=O)(OCCN([Si](C)(C)C)[Si](C)(C)C)O[Si](C)(C)C2203.8Standard non polar33892256
Glycerylphosphorylethanolamine,4TMS,isomer #4C[Si](C)(C)OCC(O)COP(=O)(OCCN([Si](C)(C)C)[Si](C)(C)C)O[Si](C)(C)C2298.6Standard polar33892256
Glycerylphosphorylethanolamine,5TMS,isomer #1C[Si](C)(C)OCC(COP(=O)(OCCN([Si](C)(C)C)[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C2226.7Semi standard non polar33892256
Glycerylphosphorylethanolamine,5TMS,isomer #1C[Si](C)(C)OCC(COP(=O)(OCCN([Si](C)(C)C)[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C2212.8Standard non polar33892256
Glycerylphosphorylethanolamine,5TMS,isomer #1C[Si](C)(C)OCC(COP(=O)(OCCN([Si](C)(C)C)[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C2198.3Standard polar33892256
Glycerylphosphorylethanolamine,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(CO)COP(=O)(O)OCCN2179.4Semi standard non polar33892256
Glycerylphosphorylethanolamine,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OCC(O)COP(=O)(O)OCCN2174.8Semi standard non polar33892256
Glycerylphosphorylethanolamine,1TBDMS,isomer #3CC(C)(C)[Si](C)(C)OP(=O)(OCCN)OCC(O)CO2189.1Semi standard non polar33892256
Glycerylphosphorylethanolamine,1TBDMS,isomer #4CC(C)(C)[Si](C)(C)NCCOP(=O)(O)OCC(O)CO2280.2Semi standard non polar33892256
Glycerylphosphorylethanolamine,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OCC(COP(=O)(O)OCCN)O[Si](C)(C)C(C)(C)C2392.5Semi standard non polar33892256
Glycerylphosphorylethanolamine,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(CO)COP(=O)(OCCN)O[Si](C)(C)C(C)(C)C2367.4Semi standard non polar33892256
Glycerylphosphorylethanolamine,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)NCCOP(=O)(O)OCC(CO)O[Si](C)(C)C(C)(C)C2470.4Semi standard non polar33892256
Glycerylphosphorylethanolamine,2TBDMS,isomer #4CC(C)(C)[Si](C)(C)OCC(O)COP(=O)(OCCN)O[Si](C)(C)C(C)(C)C2372.3Semi standard non polar33892256
Glycerylphosphorylethanolamine,2TBDMS,isomer #5CC(C)(C)[Si](C)(C)NCCOP(=O)(O)OCC(O)CO[Si](C)(C)C(C)(C)C2465.4Semi standard non polar33892256
Glycerylphosphorylethanolamine,2TBDMS,isomer #6CC(C)(C)[Si](C)(C)NCCOP(=O)(OCC(O)CO)O[Si](C)(C)C(C)(C)C2495.3Semi standard non polar33892256
Glycerylphosphorylethanolamine,2TBDMS,isomer #7CC(C)(C)[Si](C)(C)N(CCOP(=O)(O)OCC(O)CO)[Si](C)(C)C(C)(C)C2617.2Semi standard non polar33892256
Glycerylphosphorylethanolamine,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OCC(COP(=O)(OCCN)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C2591.7Semi standard non polar33892256
Glycerylphosphorylethanolamine,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OCC(COP(=O)(OCCN)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C2465.6Standard non polar33892256
Glycerylphosphorylethanolamine,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OCC(COP(=O)(OCCN)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C2781.1Standard polar33892256
Glycerylphosphorylethanolamine,3TBDMS,isomer #2CC(C)(C)[Si](C)(C)NCCOP(=O)(O)OCC(CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C2668.5Semi standard non polar33892256
Glycerylphosphorylethanolamine,3TBDMS,isomer #2CC(C)(C)[Si](C)(C)NCCOP(=O)(O)OCC(CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C2641.5Standard non polar33892256
Glycerylphosphorylethanolamine,3TBDMS,isomer #2CC(C)(C)[Si](C)(C)NCCOP(=O)(O)OCC(CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C2917.7Standard polar33892256
Glycerylphosphorylethanolamine,3TBDMS,isomer #3CC(C)(C)[Si](C)(C)NCCOP(=O)(OCC(CO)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C2679.3Semi standard non polar33892256
Glycerylphosphorylethanolamine,3TBDMS,isomer #3CC(C)(C)[Si](C)(C)NCCOP(=O)(OCC(CO)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C2602.7Standard non polar33892256
Glycerylphosphorylethanolamine,3TBDMS,isomer #3CC(C)(C)[Si](C)(C)NCCOP(=O)(OCC(CO)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C2672.5Standard polar33892256
Glycerylphosphorylethanolamine,3TBDMS,isomer #4CC(C)(C)[Si](C)(C)OC(CO)COP(=O)(O)OCCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2860.9Semi standard non polar33892256
Glycerylphosphorylethanolamine,3TBDMS,isomer #4CC(C)(C)[Si](C)(C)OC(CO)COP(=O)(O)OCCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2704.7Standard non polar33892256
Glycerylphosphorylethanolamine,3TBDMS,isomer #4CC(C)(C)[Si](C)(C)OC(CO)COP(=O)(O)OCCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2956.1Standard polar33892256
Glycerylphosphorylethanolamine,3TBDMS,isomer #5CC(C)(C)[Si](C)(C)NCCOP(=O)(OCC(O)CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C2682.8Semi standard non polar33892256
Glycerylphosphorylethanolamine,3TBDMS,isomer #5CC(C)(C)[Si](C)(C)NCCOP(=O)(OCC(O)CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C2621.9Standard non polar33892256
Glycerylphosphorylethanolamine,3TBDMS,isomer #5CC(C)(C)[Si](C)(C)NCCOP(=O)(OCC(O)CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C2655.4Standard polar33892256
Glycerylphosphorylethanolamine,3TBDMS,isomer #6CC(C)(C)[Si](C)(C)OCC(O)COP(=O)(O)OCCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2858.6Semi standard non polar33892256
Glycerylphosphorylethanolamine,3TBDMS,isomer #6CC(C)(C)[Si](C)(C)OCC(O)COP(=O)(O)OCCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2734.5Standard non polar33892256
Glycerylphosphorylethanolamine,3TBDMS,isomer #6CC(C)(C)[Si](C)(C)OCC(O)COP(=O)(O)OCCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2936.7Standard polar33892256
Glycerylphosphorylethanolamine,3TBDMS,isomer #7CC(C)(C)[Si](C)(C)OP(=O)(OCCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)OCC(O)CO2851.2Semi standard non polar33892256
Glycerylphosphorylethanolamine,3TBDMS,isomer #7CC(C)(C)[Si](C)(C)OP(=O)(OCCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)OCC(O)CO2685.2Standard non polar33892256
Glycerylphosphorylethanolamine,3TBDMS,isomer #7CC(C)(C)[Si](C)(C)OP(=O)(OCCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)OCC(O)CO2737.7Standard polar33892256
Glycerylphosphorylethanolamine,4TBDMS,isomer #1CC(C)(C)[Si](C)(C)NCCOP(=O)(OCC(CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C2900.6Semi standard non polar33892256
Glycerylphosphorylethanolamine,4TBDMS,isomer #1CC(C)(C)[Si](C)(C)NCCOP(=O)(OCC(CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C2756.7Standard non polar33892256
Glycerylphosphorylethanolamine,4TBDMS,isomer #1CC(C)(C)[Si](C)(C)NCCOP(=O)(OCC(CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C2622.3Standard polar33892256
Glycerylphosphorylethanolamine,4TBDMS,isomer #2CC(C)(C)[Si](C)(C)OCC(COP(=O)(O)OCCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3110.1Semi standard non polar33892256
Glycerylphosphorylethanolamine,4TBDMS,isomer #2CC(C)(C)[Si](C)(C)OCC(COP(=O)(O)OCCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C2895.7Standard non polar33892256
Glycerylphosphorylethanolamine,4TBDMS,isomer #2CC(C)(C)[Si](C)(C)OCC(COP(=O)(O)OCCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C2826.5Standard polar33892256
Glycerylphosphorylethanolamine,4TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC(CO)COP(=O)(OCCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3072.0Semi standard non polar33892256
Glycerylphosphorylethanolamine,4TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC(CO)COP(=O)(OCCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C2838.8Standard non polar33892256
Glycerylphosphorylethanolamine,4TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC(CO)COP(=O)(OCCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C2656.7Standard polar33892256
Glycerylphosphorylethanolamine,4TBDMS,isomer #4CC(C)(C)[Si](C)(C)OCC(O)COP(=O)(OCCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3071.2Semi standard non polar33892256
Glycerylphosphorylethanolamine,4TBDMS,isomer #4CC(C)(C)[Si](C)(C)OCC(O)COP(=O)(OCCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C2843.6Standard non polar33892256
Glycerylphosphorylethanolamine,4TBDMS,isomer #4CC(C)(C)[Si](C)(C)OCC(O)COP(=O)(OCCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C2643.2Standard polar33892256
Glycerylphosphorylethanolamine,5TBDMS,isomer #1CC(C)(C)[Si](C)(C)OCC(COP(=O)(OCCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3313.0Semi standard non polar33892256
Glycerylphosphorylethanolamine,5TBDMS,isomer #1CC(C)(C)[Si](C)(C)OCC(COP(=O)(OCCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C2985.7Standard non polar33892256
Glycerylphosphorylethanolamine,5TBDMS,isomer #1CC(C)(C)[Si](C)(C)OCC(COP(=O)(OCCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C2658.5Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Glycerylphosphorylethanolamine GC-MS (Non-derivatized) - 70eV, Positivesplash10-0gwf-5900000000-55796a83071cae1bff8b2016-09-22Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Glycerylphosphorylethanolamine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Glycerylphosphorylethanolamine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Glycerylphosphorylethanolamine GC-MS (TMS_1_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Glycerylphosphorylethanolamine GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Glycerylphosphorylethanolamine GC-MS (TMS_1_3) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Glycerylphosphorylethanolamine GC-MS (TMS_1_4) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Glycerylphosphorylethanolamine GC-MS (TMS_2_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Glycerylphosphorylethanolamine GC-MS (TMS_2_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Glycerylphosphorylethanolamine GC-MS (TMS_2_3) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Glycerylphosphorylethanolamine GC-MS (TMS_2_4) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Glycerylphosphorylethanolamine GC-MS (TMS_2_5) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Glycerylphosphorylethanolamine GC-MS (TMS_2_6) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Glycerylphosphorylethanolamine GC-MS (TMS_2_7) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Glycerylphosphorylethanolamine GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Glycerylphosphorylethanolamine GC-MS (TBDMS_1_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Glycerylphosphorylethanolamine GC-MS (TBDMS_1_3) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Glycerylphosphorylethanolamine GC-MS (TBDMS_1_4) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Glycerylphosphorylethanolamine GC-MS (TBDMS_2_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Glycerylphosphorylethanolamine GC-MS (TBDMS_2_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Glycerylphosphorylethanolamine GC-MS (TBDMS_2_3) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Glycerylphosphorylethanolamine GC-MS (TBDMS_2_4) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Glycerylphosphorylethanolamine GC-MS (TBDMS_2_5) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Glycerylphosphorylethanolamine GC-MS (TBDMS_2_6) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Glycerylphosphorylethanolamine GC-MS (TBDMS_2_7) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Glycerylphosphorylethanolamine 10V, Positive-QTOFsplash10-0006-9110000000-687d834f521d42c7e36c2015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Glycerylphosphorylethanolamine 20V, Positive-QTOFsplash10-0006-9100000000-f3f7dcb5cdd10c48a24a2015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Glycerylphosphorylethanolamine 40V, Positive-QTOFsplash10-052f-9000000000-750b47541e6949c8a75f2015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Glycerylphosphorylethanolamine 10V, Negative-QTOFsplash10-03di-2950000000-9e71c620f3a5db1afe862015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Glycerylphosphorylethanolamine 20V, Negative-QTOFsplash10-004l-9700000000-823f904dfffc25785d542015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Glycerylphosphorylethanolamine 40V, Negative-QTOFsplash10-004i-9000000000-fdc87551301ed4f6a0092015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Glycerylphosphorylethanolamine 10V, Positive-QTOFsplash10-0006-9710000000-e0cffde8c86999d55b582021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Glycerylphosphorylethanolamine 20V, Positive-QTOFsplash10-0007-9100000000-3885584fdb3534a0f84e2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Glycerylphosphorylethanolamine 40V, Positive-QTOFsplash10-0006-9000000000-36cf29cb44eeb3400dfa2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Glycerylphosphorylethanolamine 10V, Negative-QTOFsplash10-0h00-9460000000-32cd47677e60fcdcf1012021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Glycerylphosphorylethanolamine 20V, Negative-QTOFsplash10-004i-9300000000-30cffc727549756341602021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Glycerylphosphorylethanolamine 40V, Negative-QTOFsplash10-004i-9000000000-ca30e71e114ea66730882021-09-24Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Blood
  • Feces
  • Urine
Tissue Locations
  • Brain
  • Liver
  • Placenta
  • Prostate
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedAdult (>18 years old)BothAsthma details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothAsthma details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB 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 IDM02913
MarkerDB IDNot Available
Good Scents 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. 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 ]
  2. 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 ]
  3. 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 ]
  4. 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 ]
  5. 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 ]
  6. 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 ]
  7. 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 ]
  8. Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]

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