Showing metabocard for PC(20:4(8Z,11Z,14Z,17Z)/22:1(13Z)) (BMDB0008480)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-10-03 17:22:34 UTC
Update Date2020-06-04 19:13:45 UTC
BMDB IDBMDB0008480
Secondary Accession Numbers
  • BMDB08480
Metabolite Identification
Common NamePC(20:4(8Z,11Z,14Z,17Z)/22:1(13Z))
DescriptionPC(20:4(8Z,11Z,14Z,17Z)/22:1(13Z)), also known as pc(20:4(8z,11z,14z,17z)/22:1(13z)) or pc(20:4(8z,11z,14z,17z)/22:1(13z)), 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(20:4(8Z,11Z,14Z,17Z)/22:1(13Z)) is possibly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). PC(20:4(8Z,11Z,14Z,17Z)/22:1(13Z)) participates in a number of enzymatic reactions, within cattle. In particular, S-Adenosylhomocysteine and PC(20:4(8Z,11Z,14Z,17Z)/22:1(13Z)) can be biosynthesized from S-adenosylmethionine and pe-nme2(20:4(8Z,11Z,14Z,17Z)/22:1(13Z)); which is catalyzed by the enzyme phosphatidylethanolamine N-methyltransferase. Furthermore, Cytidine monophosphate and PC(20:4(8Z,11Z,14Z,17Z)/22:1(13Z)) can be biosynthesized from CDP-choline and DG(20:4(8Z,11Z,14Z,17Z)/22:1(13Z)/0:0); which is catalyzed by the enzyme choline/ethanolaminephosphotransferase. Finally, PC(20:4(8Z,11Z,14Z,17Z)/22:1(13Z)) and L-serine can be converted into choline and PS(20:4(8Z,11Z,14Z,17Z)/22:1(13Z)); which is mediated by the enzyme phosphatidylserine synthase. In cattle, PC(20:4(8Z,11Z,14Z,17Z)/22:1(13Z)) is involved in a couple of metabolic pathways, which include phosphatidylcholine biosynthesis PC(20:4(8Z,11Z,14Z,17Z)/22:1(13Z)) pathway and phosphatidylethanolamine biosynthesis pe(20:4(8Z,11Z,14Z,17Z)/22:1(13Z)) pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
GPCho(42:5)Lipid Annotator, HMDB
Phosphatidylcholine(42:5)Lipid Annotator, HMDB
PC(42:5)Lipid Annotator, HMDB
Phosphatidylcholine(20:4/22:1)Lipid Annotator, HMDB
PC(20:4(8Z,11Z,14Z,17Z)/22:1(13Z))Lipid Annotator
1-eicsoatetraenoyl-2-erucoyl-sn-glycero-3-phosphocholineLipid Annotator, HMDB
LecithinLipid Annotator, HMDB
PC(20:4/22:1)Lipid Annotator, HMDB
1-(8Z,11Z,14Z,17Z-eicosapentaenoyl)-2-(13Z-docosenoyl)-sn-glycero-3-phosphocholineLipid Annotator, HMDB
GPCho(20:4/22:1)Lipid Annotator, HMDB
Chemical FormulaC50H90NO8P
Average Molecular Weight864.2253
Monoisotopic Molecular Weight863.640405373
IUPAC Name(2-{[(2R)-2-[(13Z)-docos-13-enoyloxy]-3-[(8Z,11Z,14Z,17Z)-icosa-8,11,14,17-tetraenoyloxy]propyl phosphonato]oxy}ethyl)trimethylazanium
Traditional Namelecithin
CAS Registry NumberNot Available
SMILES
CCCCCCCC\C=C/CCCCCCCCCCCC(=O)O[C@]([H])(COC(=O)CCCCCC\C=C/C\C=C/C\C=C/C\C=C/CC)COP([O-])(=O)OCC[N+](C)(C)C
InChI Identifier
InChI=1S/C50H90NO8P/c1-6-8-10-12-14-16-18-20-22-24-25-27-29-31-33-35-37-39-41-43-50(53)59-48(47-58-60(54,55)57-45-44-51(3,4)5)46-56-49(52)42-40-38-36-34-32-30-28-26-23-21-19-17-15-13-11-9-7-2/h9,11,15,17,20-23,28,30,48H,6-8,10,12-14,16,18-19,24-27,29,31-47H2,1-5H3/b11-9-,17-15-,22-20-,23-21-,30-28-/t48-/m1/s1
InChI KeyPTYNPEDSBXJXNP-LDJXKJQGSA-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
StatusDetected and 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
logP6.57ALOGPS
logP10.75ChemAxon
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 Count45ChemAxon
Refractivity267.46 m³·mol⁻¹ChemAxon
Polarizability105.29 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, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0000000090-73fe852ed61e302a2cb9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03e9-0600000090-281d890ea0e8836732dbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-1900041030-2bc86bb2bd94c5a784c8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0000000090-344839f57bddcfdd86d2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0j4r-0028003090-1d7e9c6988ebc6972ec7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0pbi-6129300000-69e1d8fdce943ae5ea96View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0000000090-c972580dac208541e718View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-0000000090-b2a23e6a03be044b0644View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0080-0100197030-19d842cbbae20d281cf5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0000000090-82ae7ff734adbb08a56bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0003000090-13855b000599df0aa1fcView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0ue2-0009000040-1d3b731d64e3922c55c2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0000000090-c3fe53523ee4b4e26624View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0000000090-a457985afb9547a01dddView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udk-0900161930-06f8f822a00429800f28View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0000000090-cdf661fb9eb1035829efView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03e9-0600000090-650dff136c294b9b5366View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-1900041030-67de1dbcbb5c2cd63bddView in MoNA
Biological Properties
Cellular Locations
  • Cell membrane
  • Intracellular membrane
  • Membrane
Biospecimen Locations
  • All Tissues
  • Ruminal Fluid
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
All TissuesExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
Ruminal FluidDetected and Quantified0.076 +/- 0.013 uMNot SpecifiedNot Specified
Normal
    • Fozia Saleem, Sou...
 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0008480
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID24767141
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound53479099
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available