Showing metabocard for PC(O-16:0/18:1(9Z)) (BMDB0062808)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2018-08-29 17:11:56 UTC
Update Date2020-06-04 20:41:36 UTC
BMDB IDBMDB0062808
Secondary Accession Numbers
  • BMDB62808
Metabolite Identification
Common NamePC(O-16:0/18:1(9Z))
DescriptionPC(O-16:0/18:1(9Z)), also known as GPC(O-16:0/18:1) or PC(O-32:1), 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-16:0/18:1(9Z)) is considered to be a glycerophosphocholine lipid molecule. PC(O-16:0/18:1(9Z)) is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1-Hexadecyl-2-(9Z-octadecenoyl)-sn-glycero-3-phosphocholineChEBI
1-Hexadecyl-2-oleoyl-sn-glycero-3-phosphocholineChEBI
1-O-Hexadecyl-2-(9Z-octadecenoyl)-sn-glycero-3-phosphocholineChEBI
1-Palmityl-2-oleoyl-GPCChEBI
1-Palmityl-2-oleoyl-GPC (O-16:0/18:1)ChEBI
1-Palmityl-2-oleoyl-sn-glycero-3-phosphocholineChEBI
1-Palmityl-2-palmitoleoyl-sn-glycero-3-phosphocholineChEBI
GPC(O-16:0/18:1)ChEBI
PC(O-16:0/18:1)ChEBI
PC(O-32:1)ChEBI
1-O-Hexadecyl-2-(9Z)-octadecenoyl-sn-glycero-3-phosphocholineChEBI
1-O-Hexadecyl-2-(9Z)-octadecenoyl-sn-phosphatidylcholine betaineChEBI
PC O-16:0/18:1(N-9)ChEBI
Chemical FormulaC42H84NO7P
Average Molecular Weight746.0926
Monoisotopic Molecular Weight745.598540559
IUPAC Name(2-{[(2R)-3-(hexadecyloxy)-2-[(9Z)-octadec-9-enoyloxy]propyl phosphono]oxy}ethyl)trimethylazanium
Traditional Name(2-{[(2R)-3-(hexadecyloxy)-2-[(9Z)-octadec-9-enoyloxy]propyl phosphono]oxy}ethyl)trimethylazanium
CAS Registry Number79645-38-8
SMILES
[H][C@@](COCCCCCCCCCCCCCCCC)(COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCC\C=C/CCCCCCCC
InChI Identifier
InChI=1S/C42H84NO7P/c1-6-8-10-12-14-16-18-20-22-23-25-27-29-31-33-35-42(44)50-41(40-49-51(45,46)48-38-36-43(3,4)5)39-47-37-34-32-30-28-26-24-21-19-17-15-13-11-9-7-2/h20,22,41H,6-19,21,23-40H2,1-5H3/b22-20-/t41-/m1/s1
InChI KeySIEDNCDNGMIKST-IYEJTHTFSA-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
OriginNot Available
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
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
logP5.92ALOGPS
logP9.02ChemAxon
logS-7.7ALOGPS
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
Refractivity226.43 m³·mol⁻¹ChemAxon
Polarizability94.09 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Milk
  • Ruminal Fluid
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
MilkDetected and Quantified1.18 +/- 0.02 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified1.45 +/- 0.03 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified1.88 +/- 0.02 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified1.19 +/- 0.01 uMNot SpecifiedNot Specified
Normal		 details
Ruminal FluidDetected and Quantified0.01 +/- 0.005 uMNot SpecifiedNot Specified
Normal
    • Fozia Saleem, Sou...
 details
Ruminal FluidDetected and Quantified0.01 +/- 0.005 uMNot SpecifiedNot Specified
Normal
    • Fozia Saleem, Sou...
 details
Ruminal FluidDetected and Quantified0.01 +/- 0.009 uMNot SpecifiedNot Specified
Normal
    • Fozia Saleem, Sou...
 details
Ruminal FluidDetected and Quantified0.025 +/- 0.015 uMNot SpecifiedNot Specified
Normal
    • Fozia Saleem, Sou...
 details
Ruminal FluidDetected and Quantified0.007 uMNot SpecifiedNot Specified
Normal		 details
Ruminal FluidDetected and Quantified0.01 uMNot SpecifiedNot Specified
Normal		 details
Ruminal FluidDetected and Quantified0.012 uMNot SpecifiedNot Specified
Normal		 details
Ruminal FluidDetected and Quantified0.021 uMNot SpecifiedNot Specified
Normal		 details
Abnormal Concentrations
Not Available
HMDB IDNot Available
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 Compound24779266
PDB IDNot Available
ChEBI ID34112
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.