Record Information
Version1.0
Creation date2011-09-21 01:26:04 UTC
Update date2015-07-21 06:59:08 UTC
Primary IDFDB027535
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameLysoPC(18:0)
DescriptionLysoPC(18:0) 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(18:0), in particular, consists of one chain of stearic acid at the C-1 position. The stearic acid moiety is derived from animal fats, coco butter and sesame oil. 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 Number5655-17-4
Structure
Thumb
Synonyms
SynonymSource
(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(18:0/0:0)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
LysoPC(18:0)Lipid Annotator
(2R)-2-Hydroxy-3-(stearoyloxy)propyl 2-(trimethylazaniumyl)ethyl ateChEBI
(2R)-2-Hydroxy-3-(stearoyloxy)propyl 2-(trimethylazaniumyl)ethyl ic acidGenerator
1-O-Stearoyl-sn-glycero-3-ocholineChEBI
1-Octadecanoyl-sn-glycero-3-ocholineChEBI
1-Stearoyl-glycero-3-ocholineChEBI
1-stearoyl-glycero-3-phosphocholinehmdb
Lysoatidylcholine(18:0)ChEBI
Lysoatidylcholine(18:0/0:0)ChEBI
Predicted Properties
PropertyValueSource
Water Solubility0.00023 g/LALOGPS
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
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC26H54NO7P
IUPAC name(2-{[(2R)-2-hydroxy-3-(octadecanoyloxy)propyl phosphono]oxy}ethyl)trimethylazanium
InChI IdentifierInChI=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
Isomeric SMILES[H][C@@](O)(COC(=O)CCCCCCCCCCCCCCCCC)COP([O-])(=O)OCC[N+](C)(C)C
Average Molecular Weight523.6832
Monoisotopic Molecular Weight523.363789599
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
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-024u-9321010000-7c4db1d8f50345253e5eView in MoNA
ChemSpider ID435389
ChEMBL IDCHEMBL3093101
KEGG Compound IDC04230
Pubchem Compound ID497299
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB10384
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET 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
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
Enzymes
NameGene NameUniProt ID
60 kDa lysophospholipaseASPGQ86U10
Eosinophil lysophospholipaseCLCQ05315
Platelet-activating factor acetylhydrolasePLA2G7Q13093
Platelet-activating factor acetylhydrolase IB subunit gammaPAFAH1B3Q15102
Platelet-activating factor acetylhydrolase IB subunit betaPAFAH1B2P68402
Platelet-activating factor acetylhydrolase 2, cytoplasmicPAFAH2Q99487
Acyl-protein thioesterase 1LYPLA1O75608
Acyl-protein thioesterase 2LYPLA2O95372
Phosphatidylcholine-sterol acyltransferaseLCATP04180
Lysophospholipid acyltransferase 5LPCAT3Q6P1A2
Lysophosphatidylcholine acyltransferase 2LPCAT2Q7L5N7
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference