Showing metabocard for LysoPC(18:2(9Z,12Z)/0:0) (BMDB0010386)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-10-03 18:05:34 UTC
Update Date2020-06-04 20:10:48 UTC
BMDB IDBMDB0010386
Secondary Accession Numbers
  • BMDB0062752
  • BMDB10386
  • BMDB62752
Metabolite Identification
Common NameLysoPC(18:2(9Z,12Z)/0:0)
DescriptionLysopc(18:2(9Z,12Z)), also known as LPC 18:2(9Z,12Z)/0:0 or LPC(18:2n6/0:0), belongs to the class of organic compounds known as 1-acyl-sn-glycero-3-phosphocholines. These are glycerophosphocholines in which the glycerol is esterified with a fatty acid at O-1 position, and linked at position 3 to a phosphocholine. Thus, lysopc(18:2(9Z,12Z)) is considered to be a glycerophosphocholine lipid molecule. Lysopc(18:2(9Z,12Z)) is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Lysopc(18:2(9Z,12Z)) exists in all eukaryotes, ranging from yeast to humans.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1-(9Z,12Z)-Octadecadienoyl-sn-glycero-3-phosphocholineChEBI
1-(9Z,12Z-Octadecadienoyl)-glycero-3-phosphocholineChEBI
1-(9Z,12Z-Octadecadienoyl)-sn-glycero-3-phosphocholineChEBI
1-18:2-LysoPCChEBI
1-Linoleoyl-glycero-3-phosphocholineChEBI
1-Linoleoyl-GPCChEBI
1-Linoleoyl-GPC (18:2)ChEBI
1-LinoleoylglycerophosphocholineChEBI
GPC(18:2)ChEBI
GPC(18:2/0:0)ChEBI
LPC 18:2(9Z,12Z)/0:0ChEBI
LPC(18:2)ChEBI
LPC(18:2/0:0)ChEBI
LPC(18:2n6/0:0)ChEBI
LPC(18:2Omega6/0:0)ChEBI
LyPC(18:2)ChEBI
LyPC(18:2n6/0:0)ChEBI
LyPC(18:2omega6/0:0)ChEBI
LysoPC 18:2(9Z,12Z)/0:0ChEBI
LysoPC(18:2)ChEBI
LysoPC(18:2/0:0)ChEBI
LysoPC(18:2n6/0:0)ChEBI
LysoPC(18:2omega6/0:0)ChEBI
Lysophosphatidylcholine(18:2(9Z,12Z)/0:0)ChEBI
Lysophosphatidylcholine(18:2)ChEBI
Lysophosphatidylcholine(18:2/0:0)ChEBI
Lysophosphatidylcholine(18:2n6/0:0)ChEBI
Lysophosphatidylcholine(18:2omega6/0:0)ChEBI
PC 18:2(9Z,12Z)/0:0ChEBI
PC(18:2(9Z,12Z)/0:0)ChEBI
LyPC(18:2/0:0)HMDB
LysoPC(18:2(9Z,12Z))HMDB
1-Linoleoyl lysolecithinHMDB
1-Linoleoyl-sn-glycero-3-phosphorylcholineHMDB
1-Linoleoylglycerol-3-phosphorylcholineHMDB
1-LinoleoylphosphatidylcholineHMDB
LinoleoyllysolecithinHMDB
Linoleyl lysophosphatidylcholineHMDB
Lysophosphatidylcholine 18:2HMDB
1-Linoleoyl-lysophosphatidylcholineHMDB
1-Linoleoyl-sn-glycero-3-phosphocholineHMDB
GPC(18:2(9Z,12Z))HMDB
GPC(18:2(9Z,12Z)/0:0)HMDB
GPC(18:2n6)HMDB
GPC(18:2n6/0:0)HMDB
GPC(18:2W6)HMDB
GPC(18:2W6/0:0)HMDB
LPC(18:2(9Z,12Z))HMDB
LPC(18:2(9Z,12Z)/0:0)HMDB
LPC(18:2n6)HMDB
LPC(18:2W6)HMDB
LPC(18:2W6/0:0)HMDB
LysoPC(18:2n6)HMDB
LysoPC(18:2W6)HMDB
LysoPC(18:2W6/0:0)HMDB
Lysophosphatidylcholine(18:2(9Z,12Z))HMDB
Lysophosphatidylcholine(18:2n6)HMDB
Lysophosphatidylcholine(18:2W6)HMDB
Lysophosphatidylcholine(18:2W6/0:0)HMDB
LysoPC(18:2(9Z,12Z)/0:0)ChEBI
Chemical FormulaC26H50NO7P
Average Molecular Weight519.6515
Monoisotopic Molecular Weight519.332489471
IUPAC Name(2-{[(2R)-2-hydroxy-3-[(9Z,12Z)-octadeca-9,12-dienoyloxy]propyl phosphono]oxy}ethyl)trimethylazanium
Traditional Name(2-{[(2R)-2-hydroxy-3-[(9Z,12Z)-octadeca-9,12-dienoyloxy]propyl phosphono]oxy}ethyl)trimethylazanium
CAS Registry NumberNot Available
SMILES
[H][C@@](O)(COC(=O)CCCCCCC\C=C/C\C=C/CCCCC)COP([O-])(=O)OCC[N+](C)(C)C
InChI Identifier
InChI=1S/C26H50NO7P/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-26(29)32-23-25(28)24-34-35(30,31)33-22-21-27(2,3)4/h9-10,12-13,25,28H,5-8,11,14-24H2,1-4H3/b10-9-,13-12-/t25-/m1/s1
InChI KeySPJFYYJXNPEZDW-FTJOPAKQSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as 1-acyl-sn-glycero-3-phosphocholines. These are glycerophosphocholines in which the glycerol is esterified with a fatty acid at O-1 position, and linked at position 3 to a phosphocholine.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassGlycerophospholipids
Sub ClassGlycerophosphocholines
Direct Parent1-acyl-sn-glycero-3-phosphocholines
Alternative Parents
Substituents
  • 1-acyl-sn-glycero-3-phosphocholine
  • Phosphocholine
  • Fatty acid ester
  • Dialkyl phosphate
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Alkyl phosphate
  • Fatty acyl
  • Tetraalkylammonium salt
  • Quaternary ammonium salt
  • Secondary alcohol
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Organic oxide
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Alcohol
  • Organic oxygen compound
  • Organopnictogen compound
  • Carbonyl group
  • Organic salt
  • Amine
  • Hydrocarbon derivative
  • 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
logP2.22ALOGPS
logP1.36ChemAxon
logS-6.3ALOGPS
pKa (Strongest Acidic)1.86ChemAxon
pKa (Strongest Basic)-3.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area105.12 ŲChemAxon
Rotatable Bond Count24ChemAxon
Refractivity153.71 m³·mol⁻¹ChemAxon
Polarizability58.75 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-03kl-9431010000-c20360afbdedc9d9232fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0000190000-3c86eb832bb0e5b457ffView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0190-0002990000-61bb2de3bf360b7c5784View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0frl-0309400000-703f583c1dec34d85363View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0fk9-0000090000-971f1431e3c2228b9f5dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0089-0900060000-dd4dca9634d21e863fe4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ue9-0910040000-75b3d9cd99357a630043View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0030090000-9b4f9f161f1e634d70b6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-1090010000-2378656ce1b1501e42dfView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-1090000000-ed0e0c463537d6bd8f93View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0000190000-85bff21ad2f9c91a7447View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001l-0001960000-38c8f8d665d29a310286View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0pcr-1609710000-e08a75389116b197e774View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0000090000-7d81a037787f63d95855View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0fb9-0090070000-6e0343e152dc3c713a98View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-0090020000-20568d21d5462d55a6c0View in MoNA
1D NMR13C NMR Spectrum (1D, 100 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 1000 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 200 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 300 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 500 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 600 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 700 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 800 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 900 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Cell membrane
  • Intracellular membrane
  • Membrane
Biospecimen Locations
  • All Tissues
  • Blood
  • Liver
  • Longissimus Thoracis Muscle
  • Milk
  • Placenta
  • Ruminal Fluid
  • Semimembranosus Muscle
  • Testis
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
All TissuesExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
BloodDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
BloodDetected and Quantified15 +/- 3 uMNot SpecifiedNot Specified
Normal
    • Aidin Foroutan, C...
 details
BloodDetected and Quantified30-186 uMNot SpecifiedNot Specified
Normal		 details
BloodDetected and Quantified4.31 +/- 2.3 uMNot SpecifiedNot Specified
Normal		 details
BloodDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
LiverDetected and Quantified1.1 +/- 0.3 nmol/g of tissueNot SpecifiedNot Specified
Normal
    • Aidin Foroutan, C...
 details
LiverDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
Longissimus Thoracis MuscleDetected and Quantified0.3 +/- 0.1 nmol/g of tissueNot SpecifiedNot Specified
Normal
    • Aidin Foroutan, C...
 details
MilkDetected and Quantified0.181 +/- 0.002 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified0.164 +/- 0.004 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified0.19 +/- 0.01 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified0.185 +/- 0.004 uMNot SpecifiedNot Specified
Normal		 details
PlacentaExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
Ruminal FluidDetected and Quantified0.2 +/- 0.1 uMNot SpecifiedNot Specified
Normal
    • Aidin Foroutan, C...
 details
Ruminal FluidDetected and Quantified0.16 +/- 0.04 uMNot SpecifiedNot Specified
Normal
    • Fozia Saleem, Sou...
 details
Ruminal FluidDetected and Quantified0.09 +/- 0.04 uMNot SpecifiedNot SpecifiedNormal
    • Fozia Saleem, Sou...
 details
Semimembranosus MuscleDetected and Quantified0.4 +/- 0.1 nmol/g of tissueNot SpecifiedNot Specified
Normal
    • Aidin Foroutan, C...
 details
TestisDetected and Quantified0.41 +/- 0.13 nmol/g of tissueNot SpecifiedNot Specified
Normal
    • Aidin Foroutan, C...
 details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Heat stress		 details
BloodDetected and Quantified13.2 +/- 2.46 uMNot SpecifiedNot Specified
Transition disease/1 wk after parturition		 details
HMDB IDHMDB0010386
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB030316
KNApSAcK IDNot Available
Chemspider ID9181014
KEGG Compound IDNot Available
BioCyc IDCPD-8347
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound11005824
PDB IDNot Available
ChEBI ID28733
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.