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PE(P-18:0/20:4(5Z,8Z,11Z,14Z)) (FDB112225)

Record Information
Version1.0
Creation date2020-04-20 17:58:16 UTC
Update date2020-04-21 18:03:02 UTC
Primary IDFDB112225
Secondary Accession NumbersNot Available
Chemical Information
FooDB NamePE(P-18:0/20:4(5Z,8Z,11Z,14Z))
DescriptionPE(P-18:0/20:4(5Z,8Z,11Z,14Z)) 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-18:0/20:4(5Z,8Z,11Z,14Z)), in particular, consists of one 1Z-octadecenyl chain to the C-1 atom, and one 5Z,8Z,11Z,14Z-eicosatetraenoyl 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.
CAS NumberNot Available
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
Not AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility6.4e-05 g/LALOGPS
logP9.4ALOGPS
logP12.06ChemAxon
logS-7.1ALOGPS
pKa (Strongest Acidic)1.87ChemAxon
pKa (Strongest Basic)10ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area117.31 ŲChemAxon
Rotatable Bond Count40ChemAxon
Refractivity223.41 m³·mol⁻¹ChemAxon
Polarizability90.28 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC43H78NO7P
IUPAC name(2-aminoethoxy)[(2R)-2-[(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoyloxy]-3-[(1Z)-octadec-1-en-1-yloxy]propoxy]phosphinic acid
InChI IdentifierInChI=1S/C43H78NO7P/c1-3-5-7-9-11-13-15-17-19-21-22-24-26-28-30-32-34-36-43(45)51-42(41-50-52(46,47)49-39-37-44)40-48-38-35-33-31-29-27-25-23-20-18-16-14-12-10-8-6-4-2/h11,13,17,19,22,24,28,30,35,38,42H,3-10,12,14-16,18,20-21,23,25-27,29,31-34,36-37,39-41,44H2,1-2H3,(H,46,47)/b13-11-,19-17-,24-22-,30-28-,38-35-/t42-/m1/s1
InChI KeyURPXXNCTXCOATD-FXMFQVEGSA-N
Isomeric SMILES[H][C@@](CO\C=C/CCCCCCCCCCCCCCCC)(COP(O)(=O)OCCN)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC
Average Molecular Weight752.0557
Monoisotopic Molecular Weight751.551590367
Classification
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
  • 1-(alk-1-enyl)-2-acyl-sn-glycero-3-phosphoethanolamine (CHEBI:79207 )
  • 1-(1Z-alkenyl),2-acylglycerophosphoethanolamines (LMGP02030003 )
Ontology
OntologyNo ontology term
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MSNot Available
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-9021101200-09deeefa2d4acc25b4672017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-9031001000-4eab33bf274405f871522017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9053002000-3bd90e2a302a4ac607772017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-3375600900-3567dfd8fb570a78d29d2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004l-9551300100-48d9fed485f0b81638642017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01t9-9100000000-56001c4ee49886d1ba032017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-3000006900-5408a4cb69aa5ad7df272021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0c03-7100039200-d776b540c3b61929b4852021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-3932310000-1606a2bb4e452e4455612021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-3300000900-c521f75762a51af60f3b2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udm-4631900300-7e505f4bd4a4fc79948e2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0f96-9712200000-e8cc9485e88ebbe382d92021-09-22View Spectrum
NMRNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound IDNot Available
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference