Showing metabocard for PC(18:3(9Z,12Z,15Z)/20:1(11Z)) (BMDB0008209)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-10-03 17:16:09 UTC
Update Date2020-06-04 19:40:05 UTC
BMDB IDBMDB0008209
Secondary Accession Numbers
  • BMDB08209
Metabolite Identification
Common NamePC(18:3(9Z,12Z,15Z)/20:1(11Z))
DescriptionPC(18:3(9Z,12Z,15Z)/20:1(11Z)), also known as gpcho(38:4) or phosphatidylcholine(38:4), 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(18:3(9Z,12Z,15Z)/20:1(11Z)) is considered to be a glycerophosphocholine lipid molecule. PC(18:3(9Z,12Z,15Z)/20:1(11Z)) is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. PC(18:3(9Z,12Z,15Z)/20:1(11Z)) exists in all eukaryotes, ranging from yeast to humans. PC(18:3(9Z,12Z,15Z)/20:1(11Z)) participates in a number of enzymatic reactions, within cattle. In particular, S-Adenosylhomocysteine and PC(18:3(9Z,12Z,15Z)/20:1(11Z)) can be biosynthesized from S-adenosylmethionine and pe-nme2(18:3(9Z,12Z,15Z)/20:1(11Z)); which is mediated by the enzyme phosphatidylethanolamine N-methyltransferase. Furthermore, Cytidine monophosphate and PC(18:3(9Z,12Z,15Z)/20:1(11Z)) can be biosynthesized from CDP-choline and DG(18:3(9Z,12Z,15Z)/20:1(11Z)/0:0) through its interaction with the enzyme choline/ethanolaminephosphotransferase. Finally, PC(18:3(9Z,12Z,15Z)/20:1(11Z)) and L-serine can be converted into choline and PS(18:3(9Z,12Z,15Z)/20:1(11Z)) through its interaction with the enzyme phosphatidylserine synthase. In cattle, PC(18:3(9Z,12Z,15Z)/20:1(11Z)) is involved in a couple of metabolic pathways, which include phosphatidylcholine biosynthesis PC(18:3(9Z,12Z,15Z)/20:1(11Z)) pathway and phosphatidylethanolamine biosynthesis pe(18:3(9Z,12Z,15Z)/20:1(11Z)) pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
GPCho(38:4)HMDB
PC(38:4)HMDB
Phosphatidylcholine(38:4)HMDB
GPCho(18:3/20:1)HMDB
Phosphatidylcholine(18:3/20:1)HMDB
LecithinHMDB
PC(18:3/20:1)HMDB
1-(9Z,12Z,15Z-Octadeatrienoyl)-2-(11-eicosenoyl)-sn-glycero-3-phosphocholineHMDB
1-a-Linolenoyl-2-eicosenoyl-sn-glycero-3-phosphocholineHMDB
PC(18:3(9Z,12Z,15Z)/20:1(11Z))Lipid Annotator
Chemical FormulaC46H84NO8P
Average Molecular Weight810.1348
Monoisotopic Molecular Weight809.593455181
IUPAC Name(2-{[(2R)-2-[(11Z)-icos-11-enoyloxy]-3-[(9Z,12Z,15Z)-octadeca-9,12,15-trienoyloxy]propyl phosphonato]oxy}ethyl)trimethylazanium
Traditional Namelecithin
CAS Registry NumberNot Available
SMILES
CCCCCCCC\C=C/CCCCCCCCCC(=O)O[C@]([H])(COC(=O)CCCCCCC\C=C/C\C=C/C\C=C/CC)COP([O-])(=O)OCC[N+](C)(C)C
InChI Identifier
InChI=1S/C46H84NO8P/c1-6-8-10-12-14-16-18-20-22-23-25-27-29-31-33-35-37-39-46(49)55-44(43-54-56(50,51)53-41-40-47(3,4)5)42-52-45(48)38-36-34-32-30-28-26-24-21-19-17-15-13-11-9-7-2/h9,11,15,17,20-22,24,44H,6-8,10,12-14,16,18-19,23,25-43H2,1-5H3/b11-9-,17-15-,22-20-,24-21-/t44-/m1/s1
InChI KeyWAZYDHAWJWFGBD-LMJTUUMUSA-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
logP6.01ALOGPS
logP9.33ChemAxon
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 Count42ChemAxon
Refractivity247.94 m³·mol⁻¹ChemAxon
Polarizability98.29 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, Positivesplash10-03el-9082041220-99927559f57c987d74e9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01ox-4292011200-f4c368f127cbf32e79d4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00kr-8095002100-21efafd7ea0bd42b1182View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0092000030-a111d458799b6f901f58View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-056r-0090000100-ce24ab0b12ecc35d4ee6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a6u-4092000000-e86c8beef09999ac6a2aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0000000090-fa334b794ce842b59d7bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0075004390-c15ec8a7231650658e6fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-056r-7295500000-e14643d6ed8da0f387aaView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0000000090-b25dca7fc1b5373b3809View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-0000000190-58e0c5d29433cc0e7cdfView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-053r-0200498220-14dc3a3c48f3de1d2dbaView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0000000090-20235538cb799e7cb64eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-0011000090-dc16fd0049ce9e8a5506View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a96-0099000090-f8fe23d48c947e4e3986View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0000000090-12f7c14a559d8169eb4cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03e9-0600000090-4e1c9c4510d5cf1106a3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0f89-1900041210-37ba45e80d34fbcbda95View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0000000090-bd4db731926b5d2cbe56View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-0000000190-c053420ce1420abe1479View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0002-0900369110-435b8d5ed9d087ed466fView in MoNA
Biological Properties
Cellular Locations
  • Cell membrane
  • Intracellular membrane
  • Membrane
Biospecimen Locations
  • All Tissues
  • Milk
  • Ruminal Fluid
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
All TissuesExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
MilkDetected and Quantified0.55 +/- 0.01 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified0.58 +/- 0.01 uMNot SpecifiedNot Specified
Normal		 details
Ruminal FluidDetected and Quantified0.033 +/- 0.008 uMNot SpecifiedNot Specified
Normal
    • Fozia Saleem, Sou...
 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0008209
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB025399
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound52922857
PDB IDNot Available
ChEBI ID89444
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.