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Showing Compound LysoPC(15:0) (FDB027532)

Record Information
Version1.0
Creation date2011-09-21 01:26:01 UTC
Update date2019-11-26 03:21:25 UTC
Primary IDFDB027532
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameLysoPC(15:0)
DescriptionLysoPC(15:0) is a lysophospholipid (LyP). It is a monoglycerophospholipid in which a phosphorylcholine moiety occupies a glycerol substitution site. 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(15:0), in particular, consists of one chain of pentadecanoic acid at the C-1 position. The pentadecanoic acid moiety is derived from dairy products and milk fat. 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. In blood plasma significant amounts of lysophosphatidylcholine are formed by a specific enzyme system, lecithin:cholesterol acyltransferase (LCAT), which is secreted from the liver. The enzyme catalyzes the transfer of the fatty acids of position sn-2 of phosphatidylcholine to the free cholesterol in plasma, with formation of cholesterol esters and lysophosphatidylcholine. Lysophospholipids have a role in lipid signaling by acting on lysophospholipid receptors (LPL-R). LPL-R's are members of the G protein-coupled receptor family of integral membrane proteins. [HMDB]
CAS NumberNot Available
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
Predicted Properties
PropertyValueSource
Water Solubility0.00047 g/LALOGPS
logP1.46ALOGPS
logP0.75ChemAxon
logS-6ALOGPS
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 Count23ChemAxon
Refractivity137.67 m³·mol⁻¹ChemAxon
Polarizability55.85 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC23H48NO7P
IUPAC name(2-{[(2R)-2-hydroxy-3-(pentadecanoyloxy)propyl phosphono]oxy}ethyl)trimethylazanium
InChI IdentifierInChI=1S/C23H48NO7P/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-23(26)29-20-22(25)21-31-32(27,28)30-19-18-24(2,3)4/h22,25H,5-21H2,1-4H3/t22-/m1/s1
InChI KeyRJZVWDTYEWCUAR-JOCHJYFZSA-N
Isomeric SMILES[H][C@@](O)(COC(=O)CCCCCCCCCCCCCC)COP([O-])(=O)OCC[N+](C)(C)C
Average Molecular Weight481.6035
Monoisotopic Molecular Weight481.316839407
Classification
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
Physiological effect

Organoleptic effect:

Disposition

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Process

Naturally occurring process:

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Industrial application:

Biological role:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSLysoPC(15:0), 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00g1-9411000000-aa3625c1cb58a3484de8Spectrum
Predicted GC-MSLysoPC(15:0), non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSLysoPC(15:0), non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-0f89-2900000000-97a194c75d9291052ef42021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-001i-0300900000-bf094cc9a8e415fb82482021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-001i-0000900000-da67e993c1f7cbb7c8b92021-09-20View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0000190000-46669b014ca324400aad2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00kf-0090070000-c8b7250cb9c6302c146e2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-0090020000-06541d13fc52d61b89132021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0000190000-f0aee43743072cb01e612021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0f6t-0010960000-e3278f9823707de4bca02021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fdk-1718910000-6da61de50d64e691970c2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0010900000-cc0e2d15e64516dc5b792021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-0090000000-d274b16974626d7580e12021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-0090000000-7f245306cf2307c2284b2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01q9-0000900000-4650da97187f79fea93b2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-0900600000-d27bd75faee74207f0ac2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0gx0-0910400000-cda8d3880e728c981e0e2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0000900000-56d32110c312b2d9662b2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0050-0010900000-c4b9953fcfe3ab05ff0b2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0kbk-1697700000-15385d3fd3d683f609c62021-09-24View Spectrum
NMRNot Available
ChemSpider ID24694854
ChEMBL IDCHEMBL467728
KEGG Compound IDC04230
Pubchem Compound ID24779458
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB10381
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDLecithin
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
Processing...
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
Enzymes
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference