Showing metabocard for PC(20:1(11Z)/20:1(11Z)) (BMDB0008308)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
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Record Information
Version1.0
Creation Date2016-10-03 17:18:18 UTC
Update Date2020-06-04 19:29:34 UTC
BMDB IDBMDB0008308
Secondary Accession Numbers
  • BMDB08308
Metabolite Identification
Common NamePC(20:1(11Z)/20:1(11Z))
DescriptionPC(20:1(11Z)/20:1(11Z)), also known as gpcho(20:1n9/20:1n9) or gpcho(40:2), 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. Thus, PC(20:1(11Z)/20:1(11Z)) is considered to be a glycerophosphocholine lipid molecule. PC(20:1(11Z)/20:1(11Z)) is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. PC(20:1(11Z)/20:1(11Z)) exists in all eukaryotes, ranging from yeast to humans. PC(20:1(11Z)/20:1(11Z)) participates in a number of enzymatic reactions, within cattle. In particular, S-Adenosylhomocysteine and PC(20:1(11Z)/20:1(11Z)) can be biosynthesized from S-adenosylmethionine and pe-nme2(20:1(11Z)/20:1(11Z)) through its interaction with the enzyme phosphatidylethanolamine N-methyltransferase. Furthermore, Cytidine monophosphate and PC(20:1(11Z)/20:1(11Z)) can be biosynthesized from CDP-choline and DG(20:1(11Z)/20:1(11Z)/0:0); which is mediated by the enzyme choline/ethanolaminephosphotransferase. Finally, PC(20:1(11Z)/20:1(11Z)) and L-serine can be converted into choline and PS(20:1(11Z)/20:1(11Z)); which is mediated by the enzyme phosphatidylserine synthase. In cattle, PC(20:1(11Z)/20:1(11Z)) is involved in a couple of metabolic pathways, which include phosphatidylcholine biosynthesis PC(20:1(11Z)/20:1(11Z)) pathway and phosphatidylethanolamine biosynthesis pe(20:1(11Z)/20:1(11Z)) pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
Chemical FormulaC48H92NO8P
Average Molecular Weight842.2197
Monoisotopic Molecular Weight841.656055437
IUPAC Name(2-{[(2R)-2,3-bis[(11Z)-icos-11-enoyloxy]propyl phosphono]oxy}ethyl)trimethylazanium
Traditional Name(2-{[(2R)-2,3-bis[(11Z)-icos-11-enoyloxy]propyl phosphono]oxy}ethyl)trimethylazanium
CAS Registry NumberNot Available
SMILES
[H][C@@](COC(=O)CCCCCCCCC\C=C/CCCCCCCC)(COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCCC\C=C/CCCCCCCC
InChI Identifier
InChI=1S/C48H92NO8P/c1-6-8-10-12-14-16-18-20-22-24-26-28-30-32-34-36-38-40-47(50)54-44-46(45-56-58(52,53)55-43-42-49(3,4)5)57-48(51)41-39-37-35-33-31-29-27-25-23-21-19-17-15-13-11-9-7-2/h20-23,46H,6-19,24-45H2,1-5H3/b22-20-,23-21-/t46-/m1/s1
InChI KeyAEUCYCQYAUFAKH-DITNKEBASA-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
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
logP6.37ALOGPS
logP10.95ChemAxon
logS-7.6ALOGPS
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 Count46ChemAxon
Refractivity254.91 m³·mol⁻¹ChemAxon
Polarizability105 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, Positivesplash10-001u-9042061140-dce66103287b052c101aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0f7x-6394041110-5201bb7880378e8c9eeeView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fs9-9047016200-92713194f63fda8879a4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-052f-0079000170-8afb0aea8c699c928191View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4l-0069100200-d6487356b92a1c95bc0eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a6u-8189400000-40512a3a8e2545068f33View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0000000090-22004a077e65cf532e85View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-0000000190-063b8600b5379c7321f0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014r-0200249220-5801cb362ed91d9144d3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0000000090-4b489c53edd2019c68bfView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-052f-0008004290-8d74a12daa721b0ffe34View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-1009200000-633af349b8fafb005e58View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0000000090-7798f4de22a79938254aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-0001000090-c596d6f684547a9c47d7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a90-0009000090-74508f25d7ee38cf98abView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0000000090-334ce021df69056ff46bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-0000000090-b86490a18567af168853View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000t-0900139030-689fd37677e52c0dcc11View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0000000090-22c680cb0cae12530752View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000x-0600000090-2ed5ce7d2651aa92b053View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-1900021120-7b95c8fba4eafaf4642fView in MoNA
Biological Properties
Cellular Locations
  • Cell membrane
  • Intracellular membrane
  • Membrane
Biospecimen Locations
  • All Tissues
  • Blood
  • Liver
  • Longissimus Thoracis Muscle
  • Milk
  • Semimembranosus Muscle
  • Testis
Pathways
Normal Concentrations
Abnormal Concentrations
Not Available
HMDB IDHMDB0008308
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB025498
KNApSAcK IDNot Available
Chemspider ID24766969
KEGG Compound IDC00157
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound24779063
PDB IDNot Available
ChEBI ID86198
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. A. Foroutan et al. (2019). A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation). Journal of Agricultural and Food Chemistry.