Showing metabocard for PC(20:1(11Z)/18:2(9Z,12Z)) (BMDB0008303)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-10-03 17:18:11 UTC
Update Date2020-06-04 19:31:42 UTC
BMDB IDBMDB0008303
Secondary Accession Numbers
  • BMDB08303
Metabolite Identification
Common NamePC(20:1(11Z)/18:2(9Z,12Z))
DescriptionPC(20:1(11Z)/18:2(9Z,12Z)), also known as PC(20:1/18:2) or phosphatidylcholine(38:3), 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)/18:2(9Z,12Z)) is considered to be a glycerophosphocholine lipid molecule. PC(20:1(11Z)/18:2(9Z,12Z)) is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. PC(20:1(11Z)/18:2(9Z,12Z)) exists in all eukaryotes, ranging from yeast to humans.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
PC(20:1/18:2)HMDB
Phosphatidylcholine(38:3)HMDB
1-Eicosenoyl-2-linoleoyl-sn-glycero-3-phosphocholineHMDB
PC(38:3)HMDB
LecithinHMDB
GPCho(38:3)HMDB
Phosphatidylcholine(20:1/18:2)HMDB
1-(11-Eicosenoyl)-2-(9Z,12Z-octadecadienoyl)-sn-glycero-3-phosphocholineHMDB
GPCho(20:1/18:2)HMDB
PC(20:1(11Z)/18:2(9Z,12Z))Lipid Annotator
Chemical FormulaC46H86NO8P
Average Molecular Weight812.1507
Monoisotopic Molecular Weight811.609105245
IUPAC Name(2-{[(2R)-3-[(11Z)-icos-11-enoyloxy]-2-[(9Z,12Z)-octadeca-9,12-dienoyloxy]propyl phosphonato]oxy}ethyl)trimethylazanium
Traditional Namelecithin
CAS Registry NumberNot Available
SMILES
CCCCCCCC\C=C/CCCCCCCCCC(=O)OC[C@]([H])(COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCC\C=C/C\C=C/CCCCC
InChI Identifier
InChI=1S/C46H86NO8P/c1-6-8-10-12-14-16-18-20-22-23-25-26-28-30-32-34-36-38-45(48)52-42-44(43-54-56(50,51)53-41-40-47(3,4)5)55-46(49)39-37-35-33-31-29-27-24-21-19-17-15-13-11-9-7-2/h15,17,20-22,24,44H,6-14,16,18-19,23,25-43H2,1-5H3/b17-15-,22-20-,24-21-/t44-/m1/s1
InChI KeyKJDCENXZHMAYTN-VHWCKNCUSA-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
logP6.02ALOGPS
logP9.7ChemAxon
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 Count43ChemAxon
Refractivity246.82 m³·mol⁻¹ChemAxon
Polarizability99.22 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, Positivesplash10-01q3-8091041220-e8e03000480b1c90cad3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01p6-4292011100-048b90044ebedfe05bb1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00li-9086002100-382c0ee0acf5e623a9f0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0bvl-0095000040-6ba81254f3a019e82086View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0098000200-9feef843dfb7644be9f7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-056u-4092000000-fc31b9766a5056e2fbcfView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0000000090-5cb49c7c039e3d7fca35View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-0000000190-e562dcc8ad422ebb1e79View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udk-0900369110-5b3d91cac166864c28f0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0000000090-b1ba273f95f6293d0145View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0011000090-f27598e3628b771fd86aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a92-0099000090-3a8aaad373376cbdbe43View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0000000090-5d09de4c7b02b1d770beView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03e9-0600000090-3e7228ae930b29d5cacbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0f89-1900041210-32546e7292bacb03dc7fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0000000090-6fea64f934a34fc28e70View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-0064004290-67dd96760664b9dd8d95View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-3049100000-0b4d257e226413962aa1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0000000090-5004d6181bff1df70870View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-0000000190-fc85ca9ecf02ec9d7566View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052r-0200498220-5d433843ab523d4373d8View in MoNA
Biological Properties
Cellular Locations
  • Cell membrane
  • Intracellular membrane
  • Membrane
Biospecimen Locations
  • All Tissues
  • Milk
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
All TissuesExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
MilkDetected and Quantified0.25 +/- 0.01 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified0.320 +/- 0.003 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified0.375 +/- 0.001 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified0.226 +/- 0.004 uMNot SpecifiedNot Specified
Normal		 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0008303
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound52923115
PDB IDNot Available
ChEBI ID89105
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.