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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2012-09-08 14:59:44 UTC
Update Date2020-02-27 16:52:31 UTC
HMDB IDHMDB0029206
Secondary Accession Numbers
  • HMDB29206
Metabolite Identification
Common NameLysoPC(28:0/0:0)
DescriptionLysopc(28:0), also known as LysoPC a C28:0, is classified as a member of the 1-acyl-sn-glycero-3-phosphocholines. 1-acyl-sn-glycero-3-phosphocholines are glycerophosphocholines in which the glycerol is esterified with a fatty acid at O-1 position, and linked at position 3 to a phosphocholine. Lysopc(28:0) is considered to be a practically insoluble (in water) and a moderately acidic compound. Lysopc(28:0) can be found in blood. Within a cell, Lysopc(28:0) is primarily located near the membrane (predicted from logp).
Structure
Data?1582753387
Synonyms
ValueSource
LysoPC a C28:0HMDB
Chemical FormulaC36H74NO7P
Average Molecular Weight663.949
Monoisotopic Molecular Weight663.520290239
IUPAC Name(2-{[(2R)-2-hydroxy-3-(octacosanoyloxy)propyl phosphono]oxy}ethyl)trimethylazanium
Traditional Name(2-{[(2R)-2-hydroxy-3-(octacosanoyloxy)propyl phosphono]oxy}ethyl)trimethylazanium
CAS Registry NumberNot Available
SMILES
[H][C@@](O)(COC(=O)CCCCCCCCCCCCCCCCCCCCCCCCCCC)COP([O-])(=O)OCC[N+](C)(C)C
InChI Identifier
InChI=1S/C36H74NO7P/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22-23-24-25-26-27-28-29-30-36(39)42-33-35(38)34-44-45(40,41)43-32-31-37(2,3)4/h35,38H,5-34H2,1-4H3/t35-/m1/s1
InChI KeyVPAMUPUPKCTFGJ-PGUFJCEWSA-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 DescriptorsNot Available
Ontology
Physiological effect

Organoleptic effect:

Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Biological role:

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility3.6e-05 g/LALOGPS
logP5.12ALOGPS
logP6.53ChemAxon
logS-7.3ALOGPS
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 Count36ChemAxon
Refractivity197.49 m³·mol⁻¹ChemAxon
Polarizability83.68 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biospecimen Locations
  • Blood
  • Feces
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.30-1.10 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.23 +/- 0.07 uMAdult (>18 years old)BothNormal details
FecesDetected and Quantified0.22 +/- 0.1 nmol/g wet fecesAdult (>18 years old)Both
Normal
details
FecesDetected and Quantified0.21 +/- 0.11 nmol/g wet fecesAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified0.0-0.04 umol/mmol creatinineNewborn (0-30 days old)BothNormal
    • López Hernández Y...
details
UrineDetected and Quantified0.01 +/- 0.01 umol/mmol creatinineNewborn (0-30 days old)FemaleNormal
    • López Hernández Y...
details
UrineDetected and Quantified0.01 +/- 0.01 umol/mmol creatinineNewborn (0-30 days old)MaleNormal
    • López Hernández Y...
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB031399
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound131750811
PDB IDNot Available
ChEBI IDNot Available
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.