Showing metabocard for PC(20:5(5Z,8Z,11Z,14Z,17Z)/18:3(9Z,12Z,15Z)) (BMDB0008502)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-10-03 17:23:01 UTC
Update Date2020-05-11 18:46:43 UTC
BMDB IDBMDB0008502
Secondary Accession Numbers
  • BMDB08502
Metabolite Identification
Common NamePC(20:5(5Z,8Z,11Z,14Z,17Z)/18:3(9Z,12Z,15Z))
DescriptionPC(20:5(5Z,8Z,11Z,14Z,17Z)/18:3(9Z,12Z,15Z)) is a phosphatidylchloline (PC). It is a glycerophospholipid in which a phosphorylcholine moiety occupies a glycerol substitution site. As is the case with diacylglycerols, phosphatidylcholines can have many different combinations of fatty acids of varying lengths and saturation attached to the C-1 and C-2 positions. PC(20:5(5Z,8Z,11Z,14Z,17Z)/18:3(9Z,12Z,15Z)), in particular, consists of one 5Z,8Z,11Z,14Z,17Z-eicosapentaenoyl chain to the C-1 atom, and one 9Z,12Z,15Z-octadecatrienoyl to the C-2 atom. In E. coli, PCs can be found in the integral component of the cell outer membrane. They are hydrolyzed by Phospholipases to a 2-acylglycerophosphocholine and a carboxylate.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
PC(20:5/18:3)HMDB
Phosphatidylcholine(20:5/18:3)HMDB
PC(38:8)HMDB
1-Eicosapentaenoyl-2-a-linolenoyl-sn-glycero-3-phosphocholineHMDB
LecithinHMDB
Phosphatidylcholine(38:8)HMDB
GPCho(20:5/18:3)HMDB
1-(5Z,8Z,11Z,14Z,17Z-Eicosapentaenoyl)-2-(9Z,12Z,15Z-octadeatrienoyl)-sn-glycero-3-phosphocholineHMDB
GPCho(38:8)HMDB
PC(20:5(5Z,8Z,11Z,14Z,17Z)/18:3(9Z,12Z,15Z))Lipid Annotator
Chemical FormulaC46H76NO8P
Average Molecular Weight802.0713
Monoisotopic Molecular Weight801.530854925
IUPAC Name(2-{[(2R)-3-[(5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaenoyloxy]-2-[(9Z,12Z,15Z)-octadeca-9,12,15-trienoyloxy]propyl phosphonato]oxy}ethyl)trimethylazanium
Traditional Namelecithin
CAS Registry NumberNot Available
SMILES
CC\C=C/C\C=C/C\C=C/CCCCCCCC(=O)O[C@]([H])(COC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CC)COP([O-])(=O)OCC[N+](C)(C)C
InChI Identifier
InChI=1S/C46H76NO8P/c1-6-8-10-12-14-16-18-20-22-23-25-26-28-30-32-34-36-38-45(48)52-42-44(43-54-56(50,51)53-41-40-47(3,4)5)55-46(49)39-37-35-33-31-29-27-24-21-19-17-15-13-11-9-7-2/h8-11,14-17,20-22,24-26,30,32,44H,6-7,12-13,18-19,23,27-29,31,33-43H2,1-5H3/b10-8-,11-9-,16-14-,17-15-,22-20-,24-21-,26-25-,32-30-/t44-/m1/s1
InChI KeyVYIXUVZBGLOKLY-BZKFZLIYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as phosphatidylcholines. These are glycerophosphocholines in which the two free -OH are attached to one fatty acid each through an ester linkage.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassGlycerophospholipids
Sub ClassGlycerophosphocholines
Direct ParentPhosphatidylcholines
Alternative Parents
Substituents
  • Diacylglycero-3-phosphocholine
  • Phosphocholine
  • Fatty acid ester
  • Dialkyl phosphate
  • Dicarboxylic acid or derivatives
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Alkyl phosphate
  • Fatty acyl
  • Quaternary ammonium salt
  • Tetraalkylammonium salt
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic nitrogen compound
  • Carbonyl group
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxide
  • Organopnictogen compound
  • Amine
  • Organic salt
  • 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
logP5.29ALOGPS
logP7.89ChemAxon
logS-7.4ALOGPS
pKa (Strongest Acidic)1.86ChemAxon
pKa (Strongest Basic)-6.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area111.19 ŲChemAxon
Rotatable Bond Count38ChemAxon
Refractivity252.4 m³·mol⁻¹ChemAxon
Polarizability92.62 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, Positivesplash10-0udi-0000000090-995b8b141412c1caed55View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ue9-0600000090-604f889dd658b2836d98View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-1900041210-8f46eef6978a04837fc4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0000000090-01d0b76202d73b3bc4b3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-0000000190-9d71cf1852ac551a73d5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0008-0900369110-7abb30fa821dacbb5dc9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0000000090-8193a8b7c937ea1db289View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-0000000190-279d352228b79793cfb6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05ea-0200498220-c45d915d8bcaf48f0d0cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0000000090-f0f467767c3209b31bd3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ue9-0600000090-c6f1233975478adc0957View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-1900041210-a367d571c9b6272068f1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0000000090-da873b341982db7cc4d9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0084005390-2bdae9a84e26270c32dbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0ufr-4194401000-2dd43341d69614929f9dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0000000090-b2c8c2732ebc305daed0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0011000090-e46f7537232aec84dca8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0uii-0099000090-da657e6c5cd203933d87View in MoNA
Biological Properties
Cellular Locations
  • Cell membrane
  • Intracellular membrane
  • Membrane
Biospecimen Locations
  • All Tissues
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
All TissuesExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0008502
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound52923357
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available