Showing metabocard for PC(20:5(5Z,8Z,11Z,14Z,17Z)/24:0) (BMDB0008519)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-10-03 17:23:22 UTC
Update Date2020-05-11 18:46:57 UTC
BMDB IDBMDB0008519
Secondary Accession Numbers
  • BMDB08519
Metabolite Identification
Common NamePC(20:5(5Z,8Z,11Z,14Z,17Z)/24:0)
DescriptionPC(20:5(5Z,8Z,11Z,14Z,17Z)/24:0), also known as pc(20:5(5z,8z,11z,14z,17z)/24:0) or pc(20:5(5z,8z,11z,14z,17z)/24:0), 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. PC(20:5(5Z,8Z,11Z,14Z,17Z)/24:0) is possibly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). PC(20:5(5Z,8Z,11Z,14Z,17Z)/24:0) participates in a number of enzymatic reactions, within cattle. In particular, S-Adenosylhomocysteine and PC(20:5(5Z,8Z,11Z,14Z,17Z)/24:0) can be biosynthesized from S-adenosylmethionine and pe-nme2(20:5(5Z,8Z,11Z,14Z,17Z)/24:0); which is catalyzed by the enzyme phosphatidylethanolamine N-methyltransferase. Furthermore, Cytidine monophosphate and PC(20:5(5Z,8Z,11Z,14Z,17Z)/24:0) can be biosynthesized from CDP-choline and DG(20:5(5Z,8Z,11Z,14Z,17Z)/24:0/0:0); which is mediated by the enzyme choline/ethanolaminephosphotransferase. Finally, PC(20:5(5Z,8Z,11Z,14Z,17Z)/24:0) and L-serine can be converted into choline and PS(20:5(5Z,8Z,11Z,14Z,17Z)/24:0); which is catalyzed by the enzyme phosphatidylserine synthase. In cattle, PC(20:5(5Z,8Z,11Z,14Z,17Z)/24:0) is involved in a couple of metabolic pathways, which include phosphatidylcholine biosynthesis PC(20:5(5Z,8Z,11Z,14Z,17Z)/24:0) pathway and phosphatidylethanolamine biosynthesis pe(20:5(5Z,8Z,11Z,14Z,17Z)/24:0) pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
Phosphatidylcholine(20:5/24:0)Lipid Annotator, HMDB
Phosphatidylcholine(44:5)Lipid Annotator, HMDB
1-eicosapentaenoyl-2-lignoceroyl-sn-glycero-3-phosphocholineLipid Annotator, HMDB
GPCho(44:5)Lipid Annotator, HMDB
GPCho(20:5/24:0)Lipid Annotator, HMDB
PC(20:5(5Z,8Z,11Z,14Z,17Z)/24:0)Lipid Annotator
LecithinLipid Annotator, HMDB
PC(44:5)Lipid Annotator, HMDB
1-(5Z,8Z,11Z,14Z,17Z-eicosapentaenoyl)-2-tetracosanoyl-sn-glycero-3-phosphocholineLipid Annotator, HMDB
PC(20:5/24:0)Lipid Annotator, HMDB
Chemical FormulaC52H94NO8P
Average Molecular Weight892.2784
Monoisotopic Molecular Weight891.671705501
IUPAC Name(2-{[(2R)-3-[(5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaenoyloxy]-2-(tetracosanoyloxy)propyl phosphonato]oxy}ethyl)trimethylazanium
Traditional Namelecithin
CAS Registry NumberNot Available
SMILES
CCCCCCCCCCCCCCCCCCCCCCCC(=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/C52H94NO8P/c1-6-8-10-12-14-16-18-20-22-24-25-26-27-29-31-33-35-37-39-41-43-45-52(55)61-50(49-60-62(56,57)59-47-46-53(3,4)5)48-58-51(54)44-42-40-38-36-34-32-30-28-23-21-19-17-15-13-11-9-7-2/h9,11,15,17,21,23,30,32,36,38,50H,6-8,10,12-14,16,18-20,22,24-29,31,33-35,37,39-49H2,1-5H3/b11-9-,17-15-,23-21-,32-30-,38-36-/t50-/m1/s1
InChI KeyGBFFTGGMKNBBJH-CNIZVWBJSA-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 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
logP6.92ALOGPS
logP11.64ChemAxon
logS-7.5ALOGPS
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 Count47ChemAxon
Refractivity276.66 m³·mol⁻¹ChemAxon
Polarizability109.44 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, Positivesplash10-0006-0000000090-8d8f6bd546daea05e8b2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000x-0600000090-a85d2e13385646bc2771View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-1900031130-12627ae909fc1d259590View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0000000090-ca2cf245de34535993edView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-0000000090-ff54be8c98bfdc9a0fe6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-015j-0200292840-ee9606a0bf576a3eb5f3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0000000009-e0cc34089e053ec3237cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-0000000019-0864db6e2814667125e6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001k-0900143911-75fbf1f79206b3d2d1ecView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0000000090-1a66b19ce8dba1efede5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000y-0026003090-6dcd19545be774b7387eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0udi-7289700000-842a30c8fb93690b5d43View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0000000090-857a5c6b02fde01e8f93View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000x-0600000090-e91b90f929664a44ff3aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-1900031130-eb85c7777d6acef43536View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0000000009-aff872dcbd9a4b587b4aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-0003000009-fa379764b657e5238cf1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0vmi-0009000004-fca8ed113a7a54735091View 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 IDHMDB0008519
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID24767180
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound53479135
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available