Showing metabocard for PC(22:0/20:2(11Z,14Z)) (BMDB0008539)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-10-03 17:23:46 UTC
Update Date2020-06-04 19:11:06 UTC
BMDB IDBMDB0008539
Secondary Accession Numbers
  • BMDB08539
Metabolite Identification
Common NamePC(22:0/20:2(11Z,14Z))
DescriptionPC(22:0/20:2(11Z,14Z)) is a phosphatidylchloline (PC). It is a glycerophospholipid in which a phosphorylcholine moiety occupies a glycerol substitution site. As is the case with diacylglycerols, phosphatidylcholines can have many different combinations of fatty acids of varying lengths and saturation attached to the C-1 and C-2 positions. PC(22:0/20:2(11Z,14Z)), in particular, consists of one docosanoyl chain to the C-1 atom, and one 11Z,14Z-eicosadienoyl to the C-2 atom. In E. coli, PCs can be found in the integral component of the cell outer membrane. They are hydrolyzed by Phospholipases to a 2-acylglycerophosphocholine and a carboxylate.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
Phosphatidylcholine(22:0/20:2)Lipid Annotator, HMDB
PC(22:0/20:2)Lipid Annotator, HMDB
GPCho(22:0/20:2)Lipid Annotator, HMDB
Phosphatidylcholine(42:2)Lipid Annotator, HMDB
LecithinLipid Annotator, HMDB
GPCho(42:2)Lipid Annotator, HMDB
PC(42:2)Lipid Annotator, HMDB
PC(22:0/20:2(11Z,14Z))Lipid Annotator
1-docosanoyl-2-(11Z,14Z-eicosadienoyl)-sn-glycero-3-phosphocholineLipid Annotator, HMDB
1-behenoyl-2-eicosadienoyl-sn-glycero-3-phosphocholineLipid Annotator, HMDB
gpcho(22:0/20:2n6)HMDB
gpcho(22:0/20:2W6)HMDB
PC Aa C42:2HMDB
PC(22:0/20:2n6)HMDB
PC(22:0/20:2W6)HMDB
Phosphatidylcholine(22:0/20:2n6)HMDB
Phosphatidylcholine(22:0/20:2W6)HMDB
Chemical FormulaC50H96NO8P
Average Molecular Weight870.2729
Monoisotopic Molecular Weight869.687355565
IUPAC Name(2-{[(2R)-3-(docosanoyloxy)-2-[(11Z,14Z)-icosa-11,14-dienoyloxy]propyl phosphonato]oxy}ethyl)trimethylazanium
Traditional Namelecithin
CAS Registry NumberNot Available
SMILES
CCCCCCCCCCCCCCCCCCCCCC(=O)OC[C@]([H])(COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCCC\C=C/C\C=C/CCCCC
InChI Identifier
InChI=1S/C50H96NO8P/c1-6-8-10-12-14-16-18-20-22-24-25-27-28-30-32-34-36-38-40-42-49(52)56-46-48(47-58-60(54,55)57-45-44-51(3,4)5)59-50(53)43-41-39-37-35-33-31-29-26-23-21-19-17-15-13-11-9-7-2/h15,17,21,23,48H,6-14,16,18-20,22,24-47H2,1-5H3/b17-15-,23-21-/t48-/m1/s1
InChI KeyLFYYYSNBZJRBSA-HHITYQTISA-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
logP6.63ALOGPS
logP11.84ChemAxon
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 Count48ChemAxon
Refractivity264.11 m³·mol⁻¹ChemAxon
Polarizability109.73 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, Positivesplash10-0079-9045041140-ce3fae6216d6bb908c1eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-007x-6398031110-67b2bdfc575400425940View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001s-9077002100-be74002d3266301fb585View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00ri-0019000030-49a8f8bf1081a2269bc7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0019000100-1cb1aea6197f514ce8ddView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052r-5059100000-9c3caec3c61457e3fec5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0000000090-68ac673f23e394c3c146View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00e9-0600000090-d18782d551cf189f549cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-1900041030-b50abf00a5992e900c44View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0000000009-7cbfab51475788a607c8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0003000009-9c939bb480626247dbdaView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-14ii-0009000004-4afed0eaaff58edc29f0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0000000090-e605ed621546773b38cfView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-0000000090-1f36656371040c902947View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4k-0900161930-f02c200202b3bbe897c8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0000000090-c336174e69b9e1796bbaView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01bi-0016003090-812197ac268958b5aa2cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052r-3009100000-ac85b89ed44d4ca329f1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0000000090-1a99a84a66e8fb9335ddView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-0000000090-3c6b6ad511895debb4a6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00mx-0100197030-823af935e30860aec8dbView 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 Quantified0.007 +/- 0.002 uMNot SpecifiedNot Specified
Normal
    • Fozia Saleem, Sou...
 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0008539
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID24767200
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available