Showing metabocard for PC(20:0/14:1(9Z)) (BMDB0008263)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-10-03 17:17:23 UTC
Update Date2020-06-04 20:44:23 UTC
BMDB IDBMDB0008263
Secondary Accession Numbers
  • BMDB08263
Metabolite Identification
Common NamePC(20:0/14:1(9Z))
DescriptionPC(20:0/14:1(9Z)), also known as PC(34:1) or lecithin, 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(20:0/14:1(9Z)) is considered to be a glycerophosphocholine lipid molecule. PC(20:0/14:1(9Z)) is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. PC(20:0/14:1(9Z)) exists in all eukaryotes, ranging from yeast to humans.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
PC(20:0/14:1(9Z))Lipid Annotator
PC(34:1)Lipid Annotator, HMDB
Phosphatidylcholine(34:1)Lipid Annotator, HMDB
LecithinLipid Annotator, HMDB
Phosphatidylcholine(20:0/14:1)Lipid Annotator, HMDB
1-arachidonyl-2-myristoleoyl-sn-glycero-3-phosphocholineLipid Annotator, HMDB
GPCho(20:0/14:1)Lipid Annotator, HMDB
PC(20:0/14:1)Lipid Annotator, HMDB
1-eicosanoyl-2-(9Z-tetradecenoyl)-sn-glycero-3-phosphocholineLipid Annotator, HMDB
GPCho(34:1)Lipid Annotator, HMDB
Chemical FormulaC42H82NO8P
Average Molecular Weight760.0761
Monoisotopic Molecular Weight759.577805117
IUPAC Name(2-{[(2R)-3-(icosanoyloxy)-2-[(9Z)-tetradec-9-enoyloxy]propyl phosphonato]oxy}ethyl)trimethylazanium
Traditional Namelecithin
CAS Registry NumberNot Available
SMILES
CCCCCCCCCCCCCCCCCCCC(=O)OC[C@]([H])(COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCC\C=C/CCCC
InChI Identifier
InChI=1S/C42H82NO8P/c1-6-8-10-12-14-16-18-19-20-21-22-23-25-26-28-30-32-34-41(44)48-38-40(39-50-52(46,47)49-37-36-43(3,4)5)51-42(45)35-33-31-29-27-24-17-15-13-11-9-7-2/h13,15,40H,6-12,14,16-39H2,1-5H3/b15-13-/t40-/m1/s1
InChI KeyHUTFJQFEXOTHFG-LLVYEJTBSA-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
logP5.61ALOGPS
logP8.64ChemAxon
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 Count41ChemAxon
Refractivity226.18 m³·mol⁻¹ChemAxon
Polarizability94.05 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, Negativesplash10-0bvl-0095001400-63622013d08d335231ddView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03dl-0098002000-941d53d3b8dc07c9a9aaView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-06vl-5293100000-7deb3486d9ae7f8bdd52View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0000000900-5c2654109ac5e1768f70View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0062042900-a8249877b9ac3ec44b2aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03di-1039000000-c5dae421f2260a0d55ecView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0000000900-b3c6e728ecd1d8ae0cd1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-0011000900-977431a0f5ef59817087View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03i6-0099000900-6d15ff6da7e535a6716eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001a-8191141400-17e781a3aab061473623View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ka5-4391020100-fe03241c5765e174503cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fs9-9164021000-1db88577f42dbe2ea706View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0000000900-c437fa62968cd6370d11View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-0000000900-5d47ab6a1cc6748bc9e4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-0101490300-9145839c0baaff67fb74View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0000000900-fc5ea85eb3704fac1e2aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03e9-0600000900-91dd06610a8a97fa32c6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-1900230300-94bd04db609f7a93f865View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0000000900-122890d5f0b74a98dbf8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-0000000900-03d1b99daac1f51a0754View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0002-0600490200-8c0b0d7255f258dddecbView 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 Quantified26 +/- 1 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified16.1 +/- 0.5 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified17.0 +/- 0.2 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified22 +/- 1 uMNot SpecifiedNot Specified
Normal		 details
Ruminal FluidDetected and Quantified0.227 +/- 0.120 uMNot SpecifiedNot Specified
Normal
    • Fozia Saleem, Sou...
 details
Ruminal FluidDetected and Quantified0.231 +/- 0.165 uMNot SpecifiedNot Specified
Normal
    • Fozia Saleem, Sou...
 details
Ruminal FluidDetected and Quantified0.14 +/- 0.145 uMNot SpecifiedNot Specified
Normal
    • Fozia Saleem, Sou...
 details
Ruminal FluidDetected and Quantified0.312 +/- 0.284 uMNot SpecifiedNot Specified
Normal
    • Fozia Saleem, Sou...
 details
Ruminal FluidDetected and Quantified0.027 uMNot SpecifiedNot Specified
Normal		 details
Ruminal FluidDetected and Quantified0.03 uMNot SpecifiedNot Specified
Normal		 details
Ruminal FluidDetected and Quantified0.034 uMNot SpecifiedNot Specified
Normal		 details
Ruminal FluidDetected and Quantified0.3 uMNot SpecifiedNot Specified
Normal		 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0008263
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID24766925
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound52923053
PDB IDNot Available
ChEBI IDNot Available
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.