Showing metabocard for PE(16:1(9Z)/P-18:1(9Z)) (BMDB0008985)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-10-03 17:33:25 UTC
Update Date2020-05-11 19:34:48 UTC
BMDB IDBMDB0008985
Secondary Accession Numbers
  • BMDB08985
Metabolite Identification
Common NamePE(16:1(9Z)/P-18:1(9Z))
DescriptionPE(16:1(9Z)/P-18:1(9Z)) is a phosphatidylethanolamine. It is a glycerophospholipid in which a phosphorylethanolamine moiety occupies a glycerol substitution site. 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. PE(16:1(9Z)/P-18:1(9Z)), in particular, consists of one 9Z-hexadecenoyl chain to the C-1 atom, and one 1Z,9Z-octadecadienyl to the C-2 atom. While most phospholipids have a saturated fatty acid on C-1 and an unsaturated fatty acid on C-2 of the glycerol backbone, the fatty acid distribution at the C-1 and C-2 positions of glycerol within phospholipids is continually in flux, owing to phospholipid degradation and the continuous phospholipid remodeling that occurs while these molecules are in membranes. PEs are neutral zwitterions at physiological pH. They mostly have palmitic or stearic acid on carbon 1 and a long chain unsaturated fatty acid (e.g. 18:2, 20:4 and 22:6) on carbon 2. PE synthesis can occur via two pathways. The first requires that ethanolamine be activated by phosphorylation and then coupled to CDP. The ethanolamine is then transferred from CDP-ethanolamine to phosphatidic acid to yield PE. The second involves the decarboxylation of PS.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1-Palmitoleoyl-2-(1-enyl-oleoyl)-sn-glycero-3-phosphoethanolamineHMDB
GPEtn(16:1/18:1)HMDB
GPEtn(16:1n7/18:1n9)HMDB
GPEtn(16:1W7/18:1W9)HMDB
GPEtn(34:2)HMDB
PE(16:1/18:1)HMDB
PE(16:1N7/18:1N9)HMDB
PE(16:1W7/18:1W9)HMDB
PE(34:2)HMDB
Phophatidylethanolamine(16:1/18:1)HMDB
Phophatidylethanolamine(16:1n7/18:1n9)HMDB
Phophatidylethanolamine(16:1W7/18:1W9)HMDB
Phophatidylethanolamine(34:2)HMDB
(2-Aminoethoxy)[(2R)-3-[(9Z)-hexadec-9-enoyloxy]-2-[(1Z,9Z)-octadeca-1,9-dien-1-yloxy]propoxy]phosphinateHMDB
Chemical FormulaC39H74NO7P
Average Molecular Weight699.9811
Monoisotopic Molecular Weight699.520290239
IUPAC Name(2-aminoethoxy)[(2R)-3-[(9Z)-hexadec-9-enoyloxy]-2-[(1Z,9Z)-octadeca-1,9-dien-1-yloxy]propoxy]phosphinic acid
Traditional Name2-aminoethoxy(2R)-3-[(9Z)-hexadec-9-enoyloxy]-2-[(1Z,9Z)-octadeca-1,9-dien-1-yloxy]propoxyphosphinic acid
CAS Registry NumberNot Available
SMILES
[H][C@@](COC(=O)CCCCCCC\C=C/CCCCCC)(COP(O)(=O)OCCN)O\C=C/CCCCCC\C=C/CCCCCCCC
InChI Identifier
InChI=1S/C39H74NO7P/c1-3-5-7-9-11-13-15-17-18-19-21-23-25-27-29-31-34-44-38(37-47-48(42,43)46-35-33-40)36-45-39(41)32-30-28-26-24-22-20-16-14-12-10-8-6-4-2/h14,16-18,31,34,38H,3-13,15,19-30,32-33,35-37,40H2,1-2H3,(H,42,43)/b16-14-,18-17-,34-31-/t38-/m1/s1
InChI KeyKVMOASQARMCFEX-OBEJFMRTSA-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
  • Glycerol vinyl ether
  • Phosphoethanolamine
  • Fatty acid ester
  • Dialkyl phosphate
  • Fatty acyl
  • Organic phosphoric acid derivative
  • Alkyl phosphate
  • Phosphoric acid ester
  • Amino acid or derivatives
  • Carboxylic acid ester
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Organopnictogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Amine
  • Primary aliphatic amine
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Carbonyl group
  • Organic oxide
  • Organic oxygen compound
  • Primary amine
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cell membrane
  • Intracellular membrane
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP8.97ALOGPS
logP11.01ChemAxon
logS-6.9ALOGPS
pKa (Strongest Acidic)1.87ChemAxon
pKa (Strongest Basic)10ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area117.31 ŲChemAxon
Rotatable Bond Count38ChemAxon
Refractivity202.78 m³·mol⁻¹ChemAxon
Polarizability85.61 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-001i-5630539000-0fb9eb0a78de738817c4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-9020111100-09d2ce08db6d581a5a56View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-9030011000-89d51f91c0eee4af8c16View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0007-9161021000-acc721dfa1ea07314339View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udr-1190204000-cceacef3600709e81cf6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0ug3-5390101000-35cd2351414fcfdf9519View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01t9-9210000000-d25f9d9231c98dc21221View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-3000044900-c1dfc19ac1e2216081d3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-9200073000-8312570f81a6580bae33View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-5921100000-ab4c0f004593b39e0ae4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000b-4500009000-b2549800ac165ec00e42View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-002g-9860413000-0994e1fe5ba3b0133cddView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9300000000-f39286f2f89e89ea4e55View in MoNA
Biological Properties
Cellular Locations
  • Cell membrane
  • Intracellular membrane
  • Membrane
Biospecimen Locations
  • All Tissues
  • Brain
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
All TissuesExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
BrainExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0008985
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB026175
KNApSAcK IDNot Available
Chemspider ID24768471
KEGG Compound IDC00350
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound53479608
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available