Showing metabocard for PC(O-16:0/20:5(5Z,8Z,11Z,14Z,17Z)) (BMDB0062815)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2018-08-29 17:12:03 UTC
Update Date2020-06-04 19:13:59 UTC
BMDB IDBMDB0062815
Secondary Accession Numbers
  • BMDB62815
Metabolite Identification
Common NamePC(O-16:0/20:5(5Z,8Z,11Z,14Z,17Z))
DescriptionPC(O-16:0/20:5(5Z,8Z,11Z,14Z,17Z)) 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-16:0/20:5(5Z,8Z,11Z,14Z,17Z)) is considered to be a glycerophosphocholine lipid molecule. PC(O-16:0/20:5(5Z,8Z,11Z,14Z,17Z)) is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1-Hexadecyl-2-eicosapentaenoyl-GPCHMDB
1-Hexadecyl-2-eicosapentaenoyl-sn-glycero-3-phosphocholineHMDB
1-Hexadecyl-2-eicosapentaenoyl-sn-glycero-phosphatidylcholineHMDB
2-O-(5,8,11,14,17-Eicosapentaenoyl)-1-O-hexadecylglycero-3-phosphocholineHMDB
GPC(16:0/20:5)HMDB
GPC(16:0/20:5n3)HMDB
GPC(16:0/20:5W3)HMDB
GPC(36:5)HMDB
GPC(O-16:0/20:5(5Z,8Z,11Z,14Z,17Z))HMDB
GPCho(16:0/20:5)HMDB
GPCho(16:0/20:5n3)HMDB
GPCho(16:0/20:5W3)HMDB
GPCho(36:5)HMDB
GPCho(O-16:0/20:5(5Z,8Z,11Z,14Z,17Z))HMDB
PC(16:0/20:5)HMDB
PC(16:0/20:5n3)HMDB
PC(16:0/20:5W3)HMDB
PC(36:5)HMDB
Phosphatidylcholine(16:0/20:5)HMDB
Phosphatidylcholine(16:0/20:5n3)HMDB
Phosphatidylcholine(16:0/20:5W3)HMDB
Phosphatidylcholine(36:5)HMDB
Phosphatidylcholine(O-16:0/20:5(5Z,8Z,11Z,14Z,17Z))HMDB
PC(O-16:0/20:5(5Z,8Z,11Z,14Z,17Z))HMDB
Chemical FormulaC44H80NO7P
Average Molecular Weight766.098
Monoisotopic Molecular Weight765.567240918
IUPAC Name(2-{[(2R)-3-(hexadecyloxy)-2-[(5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaenoyloxy]propyl phosphono]oxy}ethyl)trimethylazanium
Traditional Name(2-{[(2R)-3-(hexadecyloxy)-2-[(5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaenoyloxy]propyl phosphono]oxy}ethyl)trimethylazanium
CAS Registry NumberNot Available
SMILES
CCCCCCCCCCCCCCCCOC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CC
InChI Identifier
InChI=1S/C44H80NO7P/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/h8,10,14,16,20,22,24-25,29,31,43H,6-7,9,11-13,15,17-19,21,23,26-28,30,32-42H2,1-5H3/b10-8-,16-14-,22-20-,25-24-,31-29-/t43-/m1/s1
InChI KeyYHSSHPWVFALMBA-IARQOZKNSA-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
logP6ALOGPS
logP8.46ChemAxon
logS-7.4ALOGPS
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 Count39ChemAxon
Refractivity240.1 m³·mol⁻¹ChemAxon
Polarizability93.52 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-0000000090-1097a3dda9c044f6ac84View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0000000090-1097a3dda9c044f6ac84View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0udr-0009201910-5cebdba8431ae0fd987eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0000000900-15e652a3c47d2e3a33b1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-0000000900-15e652a3c47d2e3a33b1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00lr-1900340700-0bc7315745fe9b7dd281View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0000000900-74925401eb11a223000fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-0021010900-a5be6944c15382c1f06dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0ufr-4295100000-585561ee08617548115fView in MoNA
Biological Properties
Cellular Locations
  • Cell membrane
  • Intracellular membrane
  • Membrane
Biospecimen Locations
  • Milk
  • Ruminal Fluid
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
MilkDetected and Quantified0.041 +/- 0.003 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified0.062 +/- 0.003 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified0.066 +/- 0.002 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified0.041 +/- 0.003 uMNot SpecifiedNot Specified
Normal		 details
Ruminal FluidDetected and Quantified0.022 +/- 0.003 uMNot SpecifiedNot Specified
Normal
    • Fozia Saleem, Sou...
 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0039528
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB097418
KNApSAcK IDNot Available
Chemspider ID8660716
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound10485310
PDB IDNot Available
ChEBI ID86437
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.