Showing metabocard for PC(o-22:0/18:3(9Z,12Z,15Z)) (BMDB0013446)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-10-03 18:40:43 UTC
Update Date2020-06-04 20:40:03 UTC
BMDB IDBMDB0013446
Secondary Accession Numbers
  • BMDB13446
Metabolite Identification
Common NamePC(o-22:0/18:3(9Z,12Z,15Z))
DescriptionPC(o-22:0/18:3(9Z,12Z,15Z)) 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-22:0/18:3(9Z,12Z,15Z)), in particular, consists of one docosanyl chain to the C-1 atom, and one 9Z,12Z,15Z-octadecatrienoyl 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
PC(40:3)Lipid Annotator, HMDB
GPCho(22:0/18:3)Lipid Annotator, HMDB
PC(22:0/18:3)Lipid Annotator, HMDB
PC(o-22:0/18:3(9Z,12Z,15Z))Lipid Annotator
1-Behenyl-2-a-linolenoyl-sn-glycero-3-phosphocholineLipid Annotator, HMDB
LecithinLipid Annotator, HMDB
Phosphatidylcholine(22:0/18:3)Lipid Annotator, HMDB
GPCho(40:3)Lipid Annotator, HMDB
1-docosanyl-2-(9Z,12Z,15Z-octadeatrienoyl)-sn-glycero-3-phosphocholineLipid Annotator, HMDB
Phosphatidylcholine(40:3)Lipid Annotator, HMDB
1-Behenyl-2-alpha-linolenoyl-sn-glycero-3-phosphocholineHMDB
gpcho(22:0/18:3n3)HMDB
gpcho(22:0/18:3W3)HMDB
PC Ae C40:3HMDB
PC(22:0/18:3n3)HMDB
PC(22:0/18:3W3)HMDB
PC(O-40:3)HMDB
Phosphatidylcholine(22:0/18:3n3)HMDB
Phosphatidylcholine(22:0/18:3W3)HMDB
Chemical FormulaC48H92NO7P
Average Molecular Weight826.2203
Monoisotopic Molecular Weight825.661140815
IUPAC Name(2-{[(2R)-3-(docosyloxy)-2-[(9Z,12Z,15Z)-octadeca-9,12,15-trienoyloxy]propyl phosphonato]oxy}ethyl)trimethylazanium
Traditional Name(2-{[(2R)-3-(docosyloxy)-2-[(9Z,12Z,15Z)-octadeca-9,12,15-trienoyloxy]propyl phosphonato]oxy}ethyl)trimethylazanium
CAS Registry NumberNot Available
SMILES
CCCCCCCCCCCCCCCCCCCCCCOC[C@]([H])(COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCC\C=C/C\C=C/C\C=C/CC
InChI Identifier
InChI=1S/C48H92NO7P/c1-6-8-10-12-14-16-18-20-22-23-24-25-26-28-30-32-34-36-38-40-43-53-45-47(46-55-57(51,52)54-44-42-49(3,4)5)56-48(50)41-39-37-35-33-31-29-27-21-19-17-15-13-11-9-7-2/h9,11,15,17,21,27,47H,6-8,10,12-14,16,18-20,22-26,28-46H2,1-5H3/b11-9-,17-15-,27-21-/t47-/m1/s1
InChI KeyCPEAXNSICHTTDR-BKMBJBKQSA-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
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP6.71ALOGPS
logP10.97ChemAxon
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 Count45ChemAxon
Refractivity256.27 m³·mol⁻¹ChemAxon
Polarizability104.63 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, Positivesplash10-002r-9152032130-df4444cd642e27437597View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0913-6398022210-fd17b5968acff7d979b7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00m0-9067002200-3d2ca3e75349c5bd90e6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00fr-0082000390-76a696d5cac59a2c9512View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00b9-2085200920-313d9c8609c6b4a73d5fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-5092200000-c81ededefaa94295aeffView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0000000090-f4b978280786ee4886cbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-0000000090-f4b978280786ee4886cbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00o0-1900061160-18bfabef238e7ce34968View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0000000090-24336b3dd18126a5fabbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-0051002290-a953a8d54594917b8d6cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-5094300000-3d06ac6d00b9b8a4d704View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0000000090-2a1b8d84ae4b0f39a8d0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-0000000090-2a1b8d84ae4b0f39a8d0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01tb-0070120920-9e52aa2e51a3bf6991e0View in MoNA
Biological Properties
Cellular Locations
  • Cell membrane
  • Intracellular membrane
  • Membrane
Biospecimen Locations
  • All Tissues
  • Ruminal Fluid
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
All TissuesExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
Ruminal FluidDetected and Quantified0.002 uMNot SpecifiedNot Specified
Normal		 details
Ruminal FluidDetected and Quantified0.002 uMNot SpecifiedNot Specified
Normal		 details
Ruminal FluidDetected and Quantified0.004 uMNot SpecifiedNot Specified
Normal		 details
Ruminal FluidDetected and Quantified0.005 uMNot SpecifiedNot Specified
Normal		 details
Ruminal FluidDetected and Quantified0.012 +/- 0.004 uMNot SpecifiedNot Specified
Normal
    • Fozia Saleem, Sou...
 details
Ruminal FluidDetected and Quantified0.012 +/- 0.006 uMNot SpecifiedNot Specified
Normal
    • Fozia Saleem, Sou...
 details
Ruminal FluidDetected and Quantified0.014 +/- 0.005 uMNot SpecifiedNot Specified
Normal
    • Fozia Saleem, Sou...
 details
Ruminal FluidDetected and Quantified0.018 +/- 0.003 uMNot SpecifiedNot Specified
Normal
    • Fozia Saleem, Sou...
 details
Ruminal FluidDetected and Quantified0.018 +/- 0.003 uMNot SpecifiedNot Specified
Normal
    • Fozia Saleem, Sou...
 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0013446
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB029446
KNApSAcK IDNot Available
Chemspider ID35032628
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound53481747
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available