Showing metabocard for PC(O-18:0/20:4(5Z,8Z,11Z,14Z)) (BMDB0062830)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2018-08-29 17:12:17 UTC
Update Date2020-06-04 19:16:21 UTC
BMDB IDBMDB0062830
Secondary Accession Numbers
  • BMDB62830
Metabolite Identification
Common NamePC(O-18:0/20:4(5Z,8Z,11Z,14Z))
DescriptionPC(O-18:0/20:4(8Z,11Z,14Z,17Z)) 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(O-18:0/20:4(8Z,11Z,14Z,17Z)), in particular, consists of one octadecyl chain to the C-1 atom, and one 8Z,11Z,14Z,17Z-eicosapentaenoyl 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
1-O-Octadecyl-2-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-sn-glycero-3-phosphocholineChEBI
1-Octadecyl-2-(5Z,8Z,11Z,14Z)-icosatetraenoyl-sn-glycero-3-phosphocholineChEBI
1-Octadecyl-2-(5Z,8Z,11Z,14Z)-icosatetraenoyl-sn-phosphatidylcholineChEBI
1-Octadecyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphocholineChEBI
1-Octadecyl-2-arachidonoyl-sn-glycero-3-phosphocholineChEBI
1-Stearyl-2-eicsoatetraenoyl-sn-glycero-3-phosphocholineChEBI
PC(O-18:0/20:4(5Z,8Z,11Z,14Z))ChEBI
PC(O-18:0/20:4)ChEBI
1-Stearyl-2-eicsoateHMDB
1-Stearyl-2-eicsoic acidHMDB
Gpcho(18:0/20:4)HMDB
Gpcho(18:0/20:4n3)HMDB
Gpcho(18:0/20:4W3)HMDB
Gpcho(38:4)HMDB
LecithinHMDB
PC Ae C38:4HMDB
PC(18:0/20:4)HMDB
PC(18:0/20:4n3)HMDB
PC(18:0/20:4W3)HMDB
PC(38:4)HMDB
PC(O-38:4)HMDB
Phosphatidylcholine(18:0/20:4)HMDB
Phosphatidylcholine(18:0/20:4n3)HMDB
Phosphatidylcholine(18:0/20:4W3)HMDB
Phosphatidylcholine(38:4)HMDB
1-Octadecanyl-2-(8Z,11Z,14Z,17Z-eicosapentaenoyl)-sn-glycero-3-phosphocholineHMDB
PC(o-18:0/20:4(8Z,11Z,14Z,17Z))Lipid Annotator
Chemical FormulaC46H86NO7P
Average Molecular Weight796.1513
Monoisotopic Molecular Weight795.614190623
IUPAC Name(2-{[(2R)-2-[(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoyloxy]-3-(octadecyloxy)propyl phosphono]oxy}ethyl)trimethylazanium
Traditional Name(2-{[(2R)-2-[(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoyloxy]-3-(octadecyloxy)propyl phosphono]oxy}ethyl)trimethylazanium
CAS Registry NumberNot Available
SMILES
[H][C@@](COCCCCCCCCCCCCCCCCCC)(COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC
InChI Identifier
InChI=1S/C46H86NO7P/c1-6-8-10-12-14-16-18-20-22-24-25-27-29-31-33-35-37-39-46(48)54-45(44-53-55(49,50)52-42-40-47(3,4)5)43-51-41-38-36-34-32-30-28-26-23-21-19-17-15-13-11-9-7-2/h14,16,20,22,25,27,31,33,45H,6-13,15,17-19,21,23-24,26,28-30,32,34-44H2,1-5H3/b16-14-,22-20-,27-25-,33-31-/t45-/m1/s1
InChI KeyGBNPCIWXLWZJGA-IGBSIYCFSA-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
logP6.39ALOGPS
logP9.71ChemAxon
logS-7.5ALOGPS
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 Count42ChemAxon
Refractivity248.18 m³·mol⁻¹ChemAxon
Polarizability98.74 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-9152211400-8370d318fc2953751ef6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0gw0-4292002100-2f6cbef42ce9e3607e36View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-9085003100-ea7aabc04029a789a066View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0f6x-0034000900-70f18db23e1ca106d72fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0frf-2093203600-0d4be29b4830823a0cabView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0ug0-6094200000-b8e2919f82587bc81b4eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0000000090-a8777a162743af0cfcd5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-0000000090-a8777a162743af0cfcd5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0vi0-0006300910-7a5f39eea6d9e38d6589View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0000000900-6787195d11ad42096df1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-0000000900-6787195d11ad42096df1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001j-1900141700-9845a38ebea24d73c905View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0000000900-396b53711a21a76df333View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-0022011900-1656d87f9cc3d7ecb3a7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0udi-5169100000-fb8ae0602aa1569e58d0View in MoNA
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • All Tissues
  • Ruminal Fluid
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
All TissuesExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
Ruminal FluidDetected and Quantified0.034 +/- 0.026 uMNot SpecifiedNot Specified
Normal
    • Fozia Saleem, Sou...
 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0013420
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB029420
KNApSAcK IDNot Available
Chemspider ID4947105
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound6443065
PDB IDNot Available
ChEBI ID75245
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.