Showing metabocard for LysoPC(18:0/0:0) (BMDB0010384)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-10-03 18:05:32 UTC
Update Date2020-06-04 20:09:23 UTC
BMDB IDBMDB0010384
Secondary Accession Numbers
  • BMDB0062739
  • BMDB10384
  • BMDB62739
Metabolite Identification
Common NameLysoPC(18:0/0:0)
DescriptionLysoPC(18:0/0:0) is a lysophospholipid (LyP). It is a monoglycerophospholipid in which a phosphorylcholine moiety occupies a glycerol substitution site. LysoPC(18:0/0:0), in particular, consists of one octadecanoyl chain. Lysophosphatidylcholines can have different combinations of fatty acids of varying lengths and saturation attached at the C-1 (sn-1) position. Fatty acids containing 16, 18 and 20 carbons are the most common. LysoPC(20:3(5Z,8Z,11Z)), in particular, consists of one chain of mead acid at the C-1 position. The mead acid moiety is derived from fish oils, liver and kidney. Lysophosphatidylcholine is found in small amounts in most tissues. It is formed by hydrolysis of phosphatidylcholine by the enzyme phospholipase A2, as part of the de-acylation/re-acylation cycle that controls its overall molecular species composition. It can also be formed inadvertently during extraction of lipids from tissues if the phospholipase is activated by careless handling.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(2R)-2-Hydroxy-3-(stearoyloxy)propyl 2-(trimethylazaniumyl)ethyl phosphateChEBI
1-O-Stearoyl-sn-glycero-3-phosphocholineChEBI
1-Octadecanoyl-sn-glycero-3-phosphocholineChEBI
1-Stearoyl-glycero-3-phosphocholineChEBI
1-Stearoylglycerophosphocholine (18:0)ChEBI
1-Stearoylglycerophosphocholine(18:0)ChEBI
18:0 LYSO-PCChEBI
GPCho 18:0/0:0ChEBI
GPCho(18:0/0:0)ChEBI
LPC 18:0/0:0ChEBI
LPC(18:0)ChEBI
LPC(18:0/0:0)ChEBI
LysoPC 18:0/0:0ChEBI
LysoPC(18:0)ChEBI
Lysophosphatidylcholine (18:0/0:0)ChEBI
Lysophosphatidylcholine(18:0)ChEBI
Lysophosphatidylcholine(18:0/0:0)ChEBI
PC 18:0/0:0ChEBI
PC(18:0/0:0)ChEBI
(2R)-2-Hydroxy-3-(stearoyloxy)propyl 2-(trimethylazaniumyl)ethyl phosphoric acidGenerator
LyPC(18:0)HMDB
LyPC(18:0/0:0)HMDB
LysoPC a C18:0HMDB
Stearoyl alpha-lysolecithinHMDB
StearoyllysophosphatidylcholineHMDB
1-Octadecyl-glycero-3-phosphocholineHMDB
1-Stearoyl-sn-glycero-3-phosphorylcholineHMDB
Stearoyl L-alpha-lysolecithinHMDB
1-Stearoyl-2-hydroxy-sn-glycero-3-phosphocholineHMDB
Stearoyl alpha-lysolecithin, (+-)-isomerHMDB
Stearoyl alpha-lysolecithin, (R)-isomerHMDB
1-Octadecanoyl-glycero-3-phosphocholineHMDB
1-OctadecanoylglycerophosphocholineHMDB
1-OctadecylglycerophosphocholineHMDB
1-StearoylglycerophosphocholineHMDB
1-O-Stearoyl-2-lyso-sn-glycero-3-phosphocholineHMDB
1-Octadecanoyl-3-glycerophosphorylcholineHMDB
1-Octadecanoyl-sn-glycerol-3-phosphorylcholineHMDB
1-OctadecanoyllysolecithinHMDB
1-Stearoyl-2-lysophosphatidylcholineHMDB
1-Stearoyl-3-glycerylphosphorylcholineHMDB
1-Stearoyl-GPCHMDB
1-Stearoyl-lysophosphatidylcholineHMDB
1-Stearoyl-sn-glycero-3-phosphocholineHMDB
1-Stearoyl-sn-glycerol-3-phosphatidylcholineHMDB
1-Stearoyl-sn-glycerol-3-phosphorylcholineHMDB
1-Stearoylglycero-3-phosphorylcholineHMDB
1-StearoyllysophosphatidylcholineHMDB
GPC(18:0)HMDB
GPC(18:0/0:0)HMDB
Lysophosphatidylcholine C18:0HMDB
Stearoyl L-α-lysolecithinHMDB
Stearoyl lysolecithinHMDB
Stearoyl lysophosphatidylcholineHMDB
LysoPC(18:0/0:0)Lipid Annotator, ChEBI
Chemical FormulaC26H54NO7P
Average Molecular Weight523.6832
Monoisotopic Molecular Weight523.363789599
IUPAC Name(2-{[(2R)-2-hydroxy-3-(octadecanoyloxy)propyl phosphono]oxy}ethyl)trimethylazanium
Traditional Name(2-{[(2R)-2-hydroxy-3-(octadecanoyloxy)propyl phosphono]oxy}ethyl)trimethylazanium
CAS Registry Number5655-17-4
SMILES
[H][C@@](O)(COC(=O)CCCCCCCCCCCCCCCCC)COP([O-])(=O)OCC[N+](C)(C)C
InChI Identifier
InChI=1S/C26H54NO7P/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/h25,28H,5-24H2,1-4H3/t25-/m1/s1
InChI KeyIHNKQIMGVNPMTC-RUZDIDTESA-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
logP2.53ALOGPS
logP2.08ChemAxon
logS-6.4ALOGPS
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 Count26ChemAxon
Refractivity151.48 m³·mol⁻¹ChemAxon
Polarizability61.71 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, Positivesplash10-024u-9321010000-7c4db1d8f50345253e5eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-0f89-1900000000-4587eca1f40127997f9aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-00di-0000090000-8c56fcd29df2d9fc9c2bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-00di-0200090000-3a51011c95929ab98d63View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0000190000-41c73cffe2f1aaf160f3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000j-0001960000-94fcb8b8814d186b45b2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0gw0-1609710000-ae76bfe8f474291dc445View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0030090000-f659985c9cbbaf332a78View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-0090010000-01d93fd13edb0afa2e7aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-0090000000-ca0fc5a9d32fa941ad45View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0000090000-3069bae6fba637487e2dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-053r-0090070000-1397c10d116d343edd9eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-0090020000-274c1e62706a1695b7b9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-05fr-0000090000-0d83963fc8d256300785View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0089-0900060000-23beae7a997640f05765View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0kai-0910040000-b24aadea134c86d41382View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0000190000-db2c4daf832d5e722111View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00f0-0002990000-f2b5b69d9cc9121b1dc6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fdp-0309400000-f08bc6aa7b631fbc521eView 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
  • Placenta
  • Ruminal Fluid
  • Semimembranosus Muscle
  • Testis
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
All TissuesExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
BloodDetected and Quantified30 +/- 5 uMNot SpecifiedNot Specified
Normal
    • Aidin Foroutan, C...
 details
BloodDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
BloodDetected and Quantified14-82 uMNot SpecifiedNot Specified
Normal		 details
LiverDetected and Quantified2.1 +/- 0.4 nmol/g of tissueNot SpecifiedNot Specified
Normal
    • Aidin Foroutan, C...
 details
LiverDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
Longissimus Thoracis MuscleDetected and Quantified0.07 +/- 0.02 nmol/g of tissueNot SpecifiedNot Specified
Normal
    • Aidin Foroutan, C...
 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 Quantified0.11 +/- 0.02 uMNot SpecifiedNot Specified
Normal
    • Fozia Saleem, Sou...
 details
Ruminal FluidDetected and Quantified0.11 +/- 0.02 uMNot SpecifiedNot SpecifiedNormal
    • Fozia Saleem, Sou...
 details
Semimembranosus MuscleDetected and Quantified0.08 +/- 0.03 nmol/g of tissueNot SpecifiedNot Specified
Normal
    • Aidin Foroutan, C...
 details
TestisDetected and Quantified0.16 +/- 0.03 nmol/g of tissueNot SpecifiedNot Specified
Normal
    • Aidin Foroutan, C...
 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0010384
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB027535
KNApSAcK IDNot Available
Chemspider ID435389
KEGG Compound IDC04230
BioCyc IDCPD-8345
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound497299
PDB IDNot Available
ChEBI ID73858
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.