Showing metabocard for PC(18:4(6Z,9Z,12Z,15Z)/16:0) (BMDB0008232)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-10-03 17:16:44 UTC
Update Date2020-06-04 19:20:12 UTC
BMDB IDBMDB0008232
Secondary Accession Numbers
  • BMDB08232
Metabolite Identification
Common NamePC(18:4(6Z,9Z,12Z,15Z)/16:0)
DescriptionPC(18:4(6Z,9Z,12Z,15Z)/16:0), also known as phosphatidylcholine(18:4/16:0) or gpcho(18:4/16:0), 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(18:4(6Z,9Z,12Z,15Z)/16:0) is considered to be a glycerophosphocholine lipid molecule. PC(18:4(6Z,9Z,12Z,15Z)/16:0) is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. PC(18:4(6Z,9Z,12Z,15Z)/16:0) exists in all eukaryotes, ranging from yeast to humans.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1-Stearidonoyl-2-palmitoyl-sn-glycero-3-phosphocholineHMDB
Gpcho(18:4/16:0)HMDB
Gpcho(18:4n3/16:0)HMDB
Gpcho(18:4W3/16:0)HMDB
Gpcho(34:4)HMDB
LecithinHMDB
PC Aa C34:4HMDB
PC(18:4/16:0)HMDB
PC(18:4n3/16:0)HMDB
PC(18:4W3/16:0)HMDB
PC(34:4)HMDB
Phosphatidylcholine(18:4/16:0)HMDB
Phosphatidylcholine(18:4n3/16:0)HMDB
Phosphatidylcholine(18:4W3/16:0)HMDB
Phosphatidylcholine(34:4)HMDB
1-(6Z,9Z,12Z,15Z-Octadecatetraenoyl)-2-hexadecanoyl-sn-glycero-3-phosphocholineHMDB
PC(18:4(6Z,9Z,12Z,15Z)/16:0)Lipid Annotator
Chemical FormulaC42H76NO8P
Average Molecular Weight754.0285
Monoisotopic Molecular Weight753.530854925
IUPAC Name(2-{[(2R)-2-(hexadecanoyloxy)-3-[(6Z,9Z,12Z,15Z)-octadeca-6,9,12,15-tetraenoyloxy]propyl phosphonato]oxy}ethyl)trimethylazanium
Traditional Namelecithin
CAS Registry NumberNot Available
SMILES
CCCCCCCCCCCCCCCC(=O)O[C@]([H])(COC(=O)CCCC\C=C/C\C=C/C\C=C/C\C=C/CC)COP([O-])(=O)OCC[N+](C)(C)C
InChI Identifier
InChI=1S/C42H76NO8P/c1-6-8-10-12-14-16-18-20-21-23-24-26-28-30-32-34-41(44)48-38-40(39-50-52(46,47)49-37-36-43(3,4)5)51-42(45)35-33-31-29-27-25-22-19-17-15-13-11-9-7-2/h8,10,14,16,20-21,24,26,40H,6-7,9,11-13,15,17-19,22-23,25,27-39H2,1-5H3/b10-8-,16-14-,21-20-,26-24-/t40-/m1/s1
InChI KeyYWDDIWXKFJEMKF-JTZVLWBESA-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
logP5.34ALOGPS
logP7.56ChemAxon
logS-7.4ALOGPS
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 Count38ChemAxon
Refractivity229.53 m³·mol⁻¹ChemAxon
Polarizability89.37 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, Positivesplash10-000i-7190321300-b86321f4aa4c72048a0dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-3291010000-1860fa0366fc7cf821f7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001r-9284020000-29758c22d853c7649c11View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0pdi-0090000200-b413c074589c5d3d4660View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-056r-0090001000-dbe63a6031d5141a10f0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a6r-3090000000-ac73f5755fb4eefc5382View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0000000900-fb17bd89e0dbf4476c66View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-0000000900-d42a6dc7b67679b57a97View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fb9-0100390200-f5dc92756e74ef08c8c3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0000000900-fd248ad900d1f4236853View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0030000900-dab5e5e46040945149a3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a9i-0090000400-cfcc1f1dc71cb4900f29View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0000000900-117f3fc6982fc425d794View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-0000000900-e0182f758af441932884View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0007-0500190100-3bb08c32575fff188412View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0000000900-58a43ac72477d144a720View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0zfr-0092032700-1b3b7ea4e5a76cf45991View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-056r-4190200000-8c78b8a7e5407a14d931View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0000000900-b98e9d2d756a1104b321View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ue9-0600000900-d92091f9cf400c110537View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001j-1900321200-39890f0802e66a4c3ee5View 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 Quantified0.081 +/- 0.004 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified0.10 +/- 0.01 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified0.13 +/- 0.01 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified0.074 +/- 0.004 uMNot SpecifiedNot Specified
Normal		 details
Ruminal FluidDetected and Quantified0.009 +/- 0.003 uMNot SpecifiedNot Specified
Normal
    • Fozia Saleem, Sou...
 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0008232
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB025422
KNApSAcK IDNot Available
Chemspider ID24766894
KEGG Compound IDC00157
BioCyc ID PHOSPHATIDYLCHOLINE
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound52922891
PDB IDNot Available
ChEBI ID89416
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.