Showing metabocard for PC(O-16:0/20:3(8Z,11Z,14Z)) (BMDB0062813)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2018-08-29 17:12:01 UTC
Update Date2020-06-04 19:24:52 UTC
BMDB IDBMDB0062813
Secondary Accession Numbers
  • BMDB62813
Metabolite Identification
Common NamePC(O-16:0/20:3(8Z,11Z,14Z))
DescriptionPC(O-16:0/20:3(8Z,11Z,14Z)) belongs to the class of organic compounds known as 1-alkyl,2-acylglycero-3-phosphocholines. These are glycerophosphocholines that carry exactly one acyl chain attached to the glycerol moiety through an ester linkage at the O2-position, and one alkyl chain attached through an ether linkage at the O1-position. Thus, PC(O-16:0/20:3(8Z,11Z,14Z)) is considered to be a glycerophosphocholine lipid molecule. PC(O-16:0/20:3(8Z,11Z,14Z)) is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1-Hexadecyl-2-dihomo-gamma-linolenoyl-GPCHMDB
1-Hexadecyl-2-dihomo-gamma-linolenoyl-sn-glycero-3-phosphocholineHMDB
1-Hexadecyl-2-dihomo-gamma-linolenoyl-sn-glycero-phosphatidylcholineHMDB
GPC(16:0/20:3)HMDB
GPC(16:0/20:3n6)HMDB
GPC(16:0/20:3W6)HMDB
GPC(36:3)HMDB
GPC(O-16:0/20:3(8Z,11Z,14Z))HMDB
GPCho(16:0/20:3)HMDB
GPCho(16:0/20:3n6)HMDB
GPCho(16:0/20:3W6)HMDB
GPCho(36:3)HMDB
GPCho(O-16:0/20:3(8Z,11Z,14Z))HMDB
PC(16:0/20:3)HMDB
PC(16:0/20:3n6)HMDB
PC(16:0/20:3W6)HMDB
PC(36:3)HMDB
Phosphatidylcholine(16:0/20:3)HMDB
Phosphatidylcholine(16:0/20:3n6)HMDB
Phosphatidylcholine(16:0/20:3W6)HMDB
Phosphatidylcholine(36:3)HMDB
Phosphatidylcholine(O-16:0/20:3(8Z,11Z,14Z))HMDB
1-O-Hexadecyl-2-O-dihomogammalinolenoylglycero-3-phosphocholineHMDB
PC(O-16:0/20:3(8Z,11Z,14Z))HMDB
Chemical FormulaC44H84NO7P
Average Molecular Weight770.13
Monoisotopic Molecular Weight769.598541047
IUPAC Name(2-{[(2R)-3-(hexadecyloxy)-2-[(8Z,11Z,14Z)-icosa-8,11,14-trienoyloxy]propyl phosphono]oxy}ethyl)trimethylazanium
Traditional Name(2-{[(2R)-3-(hexadecyloxy)-2-[(8Z,11Z,14Z)-icosa-8,11,14-trienoyloxy]propyl phosphono]oxy}ethyl)trimethylazanium
CAS Registry NumberNot Available
SMILES
CCCCCCCCCCCCCCCCOC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCC\C=C/C\C=C/C\C=C/CCCCC
InChI Identifier
InChI=1S/C44H84NO7P/c1-6-8-10-12-14-16-18-20-22-23-24-25-27-29-31-33-35-37-44(46)52-43(42-51-53(47,48)50-40-38-45(3,4)5)41-49-39-36-34-32-30-28-26-21-19-17-15-13-11-9-7-2/h14,16,20,22,24-25,43H,6-13,15,17-19,21,23,26-42H2,1-5H3/b16-14-,22-20-,25-24-/t43-/m1/s1
InChI KeyVYKSGWCIVDQIQR-MEAIPJDCSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as 1-alkyl,2-acylglycero-3-phosphocholines. These are glycerophosphocholines that carry exactly one acyl chain attached to the glycerol moiety through an ester linkage at the O2-position, and one alkyl chain attached through an ether linkage at the O1-position.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassGlycerophospholipids
Sub ClassGlycerophosphocholines
Direct Parent1-alkyl,2-acylglycero-3-phosphocholines
Alternative Parents
Substituents
  • 1-alkyl,2-acylglycero-3-phosphocholine
  • Phosphocholine
  • Fatty acid ester
  • Dialkyl phosphate
  • Glycerol ether
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Fatty acyl
  • Alkyl phosphate
  • Tetraalkylammonium salt
  • Quaternary ammonium salt
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Dialkyl ether
  • Ether
  • Monocarboxylic acid or derivatives
  • Organonitrogen compound
  • Organopnictogen compound
  • Organic oxygen compound
  • Carbonyl group
  • Amine
  • Organic nitrogen compound
  • Organooxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organic salt
  • 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
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP6.09ALOGPS
logP9.19ChemAxon
logS-7.6ALOGPS
pKa (Strongest Acidic)1.86ChemAxon
pKa (Strongest Basic)-4.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area94.12 ŲChemAxon
Rotatable Bond Count41ChemAxon
Refractivity237.86 m³·mol⁻¹ChemAxon
Polarizability95.6 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, Negativesplash10-0udi-0000000090-3d6811548a7d3de72b59View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0000000090-3d6811548a7d3de72b59View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4o-0009201910-3fd38c3971ff1449284eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0000000900-a77b4361de0929ecf0e7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0031010900-1025f1dd73d3255326ceView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-6059300000-bcaee9c73c84136c8007View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0000000900-f8446695140eef013859View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-0000000900-f8446695140eef013859View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0089-1900340700-1e4a7fc5d8d959a9febdView in MoNA
Biological Properties
Cellular Locations
  • Cell membrane
  • Intracellular membrane
  • Membrane
Biospecimen Locations
  • Milk
  • Ruminal Fluid
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
MilkDetected and Quantified0.25 +/- 0.01 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified0.275 +/- 0.001 uMNot SpecifiedNot Specified
Normal		 details
Ruminal FluidDetected and Quantified0.012 +/- 0.05 uMNot SpecifiedNot Specified
Normal
    • Fozia Saleem, Sou...
 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0039527
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB097470
KNApSAcK IDNot Available
Chemspider ID24958570
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound16759365
PDB IDNot Available
ChEBI ID86436
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.