Showing metabocard for PE(O-16:1(1Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) (BMDB0005780)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 23:18:26 UTC
Update Date2020-05-11 19:32:31 UTC
BMDB IDBMDB0005780
Secondary Accession Numbers
  • BMDB05780
Metabolite Identification
Common NamePE(O-16:1(1Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))
DescriptionPE(P-16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) 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(P-16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)), in particular, consists of one 1Z-hexadecenyl chain to the C-1 atom, and one 4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenoyl 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
GPEtn(16:0P/22:6(4Z,7Z,10Z,13Z,16Z,19Z))ChEBI
PE(P-16:0/22:6)ChEBI
1-(1-Enyl-palmitoyl)-2-docosahexaenoyl-sn-glycero-3-phosphoethanolamineHMDB
1-Alkenyl-2-acyl-glycerophosphoethanolamineHMDB
1-O-(1Z-Hexadecenyl)-2-(4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenoyl)-sn-glycero-3-phosphoethanolamineHMDB
1-(1-Enyl-palmitoyl)-2-docosahexaenoyl-gpeHMDB
GPE(38:7)HMDB
GPE(O-16:1(1Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))HMDB
GPE(O-16:1(1Z)/22:6)HMDB
GPE(O-16:1(1Z)/22:6n3)HMDB
GPE(O-16:1(1Z)/22:6W3)HMDB
GPE(p-16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))HMDB
GPE(p-16:0/22:6)HMDB
GPE(p-16:0/22:6n3)HMDB
GPE(p-16:0/22:6W3)HMDB
GPEtn(38:7)HMDB
GPEtn(O-16:1(1Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))HMDB
GPEtn(O-16:1(1Z)/22:6)HMDB
GPEtn(O-16:1(1Z)/22:6n3)HMDB
GPEtn(O-16:1(1Z)/22:6W3)HMDB
GPEtn(p-16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))HMDB
GPEtn(p-16:0/22:6)HMDB
GPEtn(p-16:0/22:6n3)HMDB
GPEtn(p-16:0/22:6W3)HMDB
PE(38:7)HMDB
PE(O-16:1(1Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))HMDB
PE(O-16:1(1Z)/22:6)HMDB
PE(O-16:1(1Z)/22:6N3)HMDB
PE(O-16:1(1Z)/22:6W3)HMDB
PE(P-16:0/22:6N3)HMDB
PE(P-16:0/22:6W3)HMDB
Phophatidylethanolamine(38:7)HMDB
Phophatidylethanolamine(O-16:1(1Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))HMDB
Phophatidylethanolamine(O-16:1(1Z)/22:6)HMDB
Phophatidylethanolamine(O-16:1(1Z)/22:6n3)HMDB
Phophatidylethanolamine(O-16:1(1Z)/22:6W3)HMDB
Phophatidylethanolamine(p-16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))HMDB
Phophatidylethanolamine(p-16:0/22:6)HMDB
Phophatidylethanolamine(p-16:0/22:6n3)HMDB
Phophatidylethanolamine(p-16:0/22:6W3)HMDB
PE(P-16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))ChEBI
Chemical FormulaC43H74NO7P
Average Molecular Weight748.0239
Monoisotopic Molecular Weight747.520290239
IUPAC Name(2-aminoethoxy)[(2R)-2-[(4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoyloxy]-3-[(1Z)-hexadec-1-en-1-yloxy]propoxy]phosphinic acid
Traditional Name2-aminoethoxy((2R)-2-[(4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoyloxy]-3-[(1Z)-hexadec-1-en-1-yloxy]propoxy)phosphinic acid
CAS Registry NumberNot Available
SMILES
[H][C@@](CO\C=C/CCCCCCCCCCCCCC)(COP(O)(=O)OCCN)OC(=O)CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CC
InChI Identifier
InChI=1S/C43H74NO7P/c1-3-5-7-9-11-13-15-17-19-20-21-22-23-24-26-28-30-32-34-36-43(45)51-42(41-50-52(46,47)49-39-37-44)40-48-38-35-33-31-29-27-25-18-16-14-12-10-8-6-4-2/h5,7,11,13,17,19,21-22,24,26,30,32,35,38,42H,3-4,6,8-10,12,14-16,18,20,23,25,27-29,31,33-34,36-37,39-41,44H2,1-2H3,(H,46,47)/b7-5-,13-11-,19-17-,22-21-,26-24-,32-30-,38-35-/t42-/m1/s1
InChI KeyWVGALBKSWOUIEZ-XNHMFJFDSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as 1-(1z-alkenyl),2-acylglycerophosphoethanolamines. These are glycerophosphoethanolamines that carry exactly one acyl chain attached to the glycerol moiety through an ester linkage at the O2-position, and one 1Z-alkenyl chain attached through an ether linkage at the O1-position.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassGlycerophospholipids
Sub ClassGlycerophosphoethanolamines
Direct Parent1-(1Z-alkenyl),2-acylglycerophosphoethanolamines
Alternative Parents
Substituents
  • 1-(1z-alkenyl),2-acylglycerophosphoethanolamine
  • Glycerol vinyl ether
  • Phosphoethanolamine
  • Fatty acid ester
  • Dialkyl phosphate
  • Fatty acyl
  • Alkyl phosphate
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Amino acid or derivatives
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Organic oxide
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Primary amine
  • Primary aliphatic amine
  • Organic oxygen compound
  • Amine
  • Carbonyl group
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
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
logP9.06ALOGPS
logP11.34ChemAxon
logS-7ALOGPS
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
Refractivity225.65 m³·mol⁻¹ChemAxon
Polarizability87 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-9022100200-594976f18eb9044bb0baView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-9031001000-a69406fa65734aa9a246View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9081011000-551a07c20a03c4cc63d1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00mt-2367510900-ce70acab848803c4fc5cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004l-9542100100-2a1ccb0a64ebaefc04a2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01t9-9101000000-c8017a6d129b66c29bb6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-3300000900-58ee7070b3c8af9a97eeView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-002e-6904820500-45039d65d3c088170182View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004l-9824100000-1682c59cd78d80d5c7f2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-4100005900-3ea506feebae75b6d698View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0btc-3100009300-1479d4fca824e9f619adView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-3896011000-6bc6ad13f2be0427662eView 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 IDHMDB0005780
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB023769
KNApSAcK IDNot Available
Chemspider ID4446616
KEGG Compound IDC00350
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID6548
PubChem Compound5283497
PDB IDNot Available
ChEBI ID90479
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available