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

IdentificationTaxonomyPhysical propertiesSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-10-03 18:05:34 UTC
Update Date2020-06-04 20:10:48 UTC
MCDB ID BMDB0010386
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
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
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-03kl-9431010000-c20360afbdedc9d9232f2017-10-06View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0000190000-3c86eb832bb0e5b457ff2021-09-22View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0190-0002990000-61bb2de3bf360b7c57842021-09-22View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0frl-0309400000-703f583c1dec34d853632021-09-22View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0fk9-0000090000-971f1431e3c2228b9f5d2021-09-22View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0089-0900060000-dd4dca9634d21e863fe42021-09-22View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ue9-0910040000-75b3d9cd99357a6300432021-09-22View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0030090000-9b4f9f161f1e634d70b62021-09-22View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-1090010000-2378656ce1b1501e42df2021-09-22View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-1090000000-ed0e0c463537d6bd8f932021-09-22View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0000190000-85bff21ad2f9c91a74472021-09-24View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001l-0001960000-38c8f8d665d29a3102862021-09-24View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0pcr-1609710000-e08a75389116b197e7742021-09-24View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0000090000-7d81a037787f63d958552021-09-24View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0fb9-0090070000-6e0343e152dc3c713a982021-09-24View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-0090020000-20568d21d5462d55a6c02021-09-24View Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, H2O, predicted)Not Available2022-08-22View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Not Available2022-08-22View Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, H2O, predicted)Not Available2022-08-22View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Not Available2022-08-22View Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, H2O, predicted)Not Available2022-08-22View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Not Available2022-08-22View Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, H2O, predicted)Not Available2022-08-22View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Not Available2022-08-22View Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, predicted)Not Available2022-08-22View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Not Available2022-08-22View Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, H2O, predicted)Not Available2022-08-22View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Not Available2022-08-22View Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, H2O, predicted)Not Available2022-08-22View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Not Available2022-08-22View Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, H2O, predicted)Not Available2022-08-22View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Not Available2022-08-22View Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, H2O, predicted)Not Available2022-08-22View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Not Available2022-08-22View Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, H2O, predicted)Not Available2022-08-22View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Not Available2022-08-22View Spectrum
Concentrations
StatusValueReferenceDetails
Detected and Quantified0.181 +/- 0.002 uM details
Detected and Quantified0.164 +/- 0.004 uM details
Detected and Quantified0.19 +/- 0.01 uM details
Detected and Quantified0.185 +/- 0.004 uM details
HMDB IDHMDB0010386
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB 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.