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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2014-04-16 20:46:07 UTC
Update Date2019-11-21 17:06:52 UTC
HMDB IDHMDB0061700
Secondary Accession Numbers
  • HMDB0062711
  • HMDB61700
  • HMDB62711
Metabolite Identification
Common NameLysoPC(0:0/18:2(9Z,12Z))
DescriptionLysoPC(0:0/18:2(9Z,12Z)) is a lysophosphatidylcholine, which is a lysophospholipid. The term 'lysophospholipid' (LPL) refers to any phospholipid that is missing one of its two O-acyl chains. Thus, LPLs have a free alcohol in either the sn-1 or sn-2 position. The prefix 'lyso-' comes from the fact that lysophospholipids were originally found to be hemolytic however it is now used to refer generally to phospholipids missing an acyl chain. LPLs are usually the result of phospholipase A-type enzymatic activity on regular phospholipids such as phosphatidylcholine or phosphatidic acid, although they can also be generated by the acylation of glycerophospholipids or the phosphorylation of monoacylglycerols. 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. There is also a phospholipase A1, which is able to cleave the sn-1 ester bond. Lysophosphatidylcholine has pro-inflammatory properties in vitro and it is known to be a pathological component of oxidized lipoproteins (LDL) in plasma and of atherosclerotic lesions. Recently, it has been found to have some functions in cell signalling, and specific receptors (coupled to G proteins) have been identified. It activates the specific phospholipase C that releases diacylglycerols and inositol triphosphate with resultant increases in intracellular Ca2+ and activation of protein kinase C. It also activates the mitogen-activated protein kinase in certain cell types. Lysophosphatidylcholines can have different combinations of fatty acids of varying lengths and saturation attached at the C-1 (sn-1) or C-2 (sn-2) position. LysoPC(0:0/18:2(9Z,12Z)), in particular, consists of one chain of linoleic acid at the C-2 position.
Structure
Data?1574356012
Synonyms
ValueSource
2-(9Z,12Z-Octadecadienoyl)-sn-glycero-3-phosphocholineChEBI
2-LinoleoyllysophosphatidylcholineChEBI
LPC[0:0/18:2(omega-6)]ChEBI
2-Linoleoyl-GPCHMDB
2-Linoleoyl-lysophosphatidylcholineHMDB
2-Linoleoyl-sn-glycero-3-phosphocholineHMDB
2-Linoleoyl-sn-glycero-3-phosphorylcholineHMDB
GPC(0:0/18:2(9Z,12Z))HMDB
GPC(0:0/18:2n6)HMDB
GPC(0:0/18:2w6)HMDB
GPC(18:2(9Z,12Z))HMDB
GPC(18:2)HMDB
GPC(18:2n6)HMDB
GPC(18:2w6)HMDB
LPC(0:0/18:2(9Z,12Z))HMDB
LPC(0:0/18:2n6)HMDB
LPC(0:0/18:2w6)HMDB
LPC(18:2(9Z,12Z))HMDB
LPC(18:2)HMDB
LPC(18:2n6)HMDB
LPC(18:2w6)HMDB
LysoPC(0:0/18:2(9Z,12Z))HMDB
LysoPC(0:0/18:2n6)HMDB
LysoPC(0:0/18:2w6)HMDB
LysoPC(18:2(9Z,12Z))HMDB
LysoPC(18:2)HMDB
LysoPC(18:2n6)HMDB
LysoPC(18:2w6)HMDB
Lysophosphatidylcholine(0:0/18:2(9Z,12Z))HMDB
Lysophosphatidylcholine(0:0/18:2n6)HMDB
Lysophosphatidylcholine(0:0/18:2w6)HMDB
Lysophosphatidylcholine(18:2(9Z,12Z))HMDB
Lysophosphatidylcholine(18:2)HMDB
Lysophosphatidylcholine(18:2n6)HMDB
Lysophosphatidylcholine(18:2w6)HMDB
Chemical FormulaC26H50NO7P
Average Molecular Weight519.66
Monoisotopic Molecular Weight519.332489952
IUPAC Name(2-{[(2R)-3-hydroxy-2-[(9Z,12Z)-octadeca-9,12-dienoyloxy]propyl phosphono]oxy}ethyl)trimethylazanium
Traditional Name(2-{[(2R)-3-hydroxy-2-[(9Z,12Z)-octadeca-9,12-dienoyloxy]propyl phosphono]oxy}ethyl)trimethylazanium
CAS Registry Number27304-12-7
SMILES
CCCCC\C=C/C\C=C/CCCCCCCC(=O)O[C@H](CO)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)34-25(23-28)24-33-35(30,31)32-22-21-27(2,3)4/h9-10,12-13,25,28H,5-8,11,14-24H2,1-4H3/b10-9-,13-12-/t25-/m1/s1
InChI KeyLSUXCWJOIAWGOU-FTJOPAKQSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as 2-acyl-sn-glycero-3-phosphocholines. These are glycerophosphocholines in which the glycerol is esterified with a fatty acid at O-2 position, and linked at position 3 to a phosphocholine.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassGlycerophospholipids
Sub ClassGlycerophosphocholines
Direct Parent2-acyl-sn-glycero-3-phosphocholines
Alternative Parents
Substituents
  • 2-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
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Organic oxide
  • Alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Organopnictogen compound
  • Organic oxygen compound
  • Primary alcohol
  • Carbonyl group
  • Organic salt
  • Amine
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effect

Organoleptic effect:

Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Biological role:

Industrial application:

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
Water Solubility0.00033 g/LALOGPS
logP2.18ALOGPS
logP1.36ChemAxon
logS-6.3ALOGPS
pKa (Strongest Acidic)1.86ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area105.12 ŲChemAxon
Rotatable Bond Count24ChemAxon
Refractivity153.71 m³·mol⁻¹ChemAxon
Polarizability58.91 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Not Available
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID30785783
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound71768169
PDB IDNot Available
ChEBI ID76084
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Divecha N, Irvine RF: Phospholipid signaling. Cell. 1995 Jan 27;80(2):269-78. [PubMed:7834746 ]
  2. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  3. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  4. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  5. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  6. Cevc, Gregor (1993). Phospholipids Handbook. Marcel Dekker.
  7. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.