Record Information
Version1.0
Creation date2010-04-08 22:06:37 UTC
Update date2019-11-26 03:00:28 UTC
Primary IDFDB005287
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameLysolecithin
DescriptionLysophosphatidylcholines (LPC), also called lysolecithins, are a class of chemical compounds which are derived from phosphatidylcholines. They result from partial hydrolysis of phosphatidylcholines, which removes one of the fatty acid groups. The hydrolysis is generally the result of the enzymatic action of phospholipase A2. LPC is present as a minor phospholipid in the cell membrane (<=3%) and in the blood plasma (8-12%). Since LPCs are quickly metabolized by lysophosholypase and LPC-acyltransferase, they last only shortly in vivo. [Wikipedia]. Lysolecithin is found in many foods, some of which are cardamom, cucumber, common buckwheat, and rice.
CAS Number3542-29-8
Structure
Thumb
Synonyms
SynonymSource
1-(9Z-Octadecenoyl)-sn-glycero-3-phosphocholineChEBI
1-Oleoyl-2-hydroxy-sn-glycero-3-phosphocholineChEBI
1-Oleoyl-sn-glycero-3-phosphorylcholineChEBI
1-OleoylglycerophosphocholineChEBI
3-Oleoyl-rac-glycerol-1-phosphorylcholineChEBI
LPC 18:1ChEBI
LPC 18:1(9Z)/0:0ChEBI
LPC(18:1(9Z)/0:0)ChEBI
LysoPC 18:1(9Z)/0:0ChEBI
Lysophosphatidylcholine 18:1ChEBI
Lysophosphatidylcholine(18:1(9Z)/0:0)ChEBI
PC 18:1(9Z)/0:0ChEBI
PC(18:1(9Z)/0:0)ChEBI
1-Oleoyl-glycero-3-phosphocholineHMDB
LysoPC(18:1/0:0)HMDB
LysoPC(18:1(9Z))HMDB
Lysophosphatidylcholine(18:1)HMDB
LysoPC(18:1)HMDB
LyPC(18:1/0:0)HMDB
LyPC(18:1)HMDB
LPC(18:1/0:0)HMDB
LPC(18:1)HMDB
1-(9Z-Octadecenoyl)-glycero-3-phosphocholineHMDB
Lysophosphatidylcholine(18:1/0:0)HMDB
1-(9Z)-Octadecenoyl-sn-glycero-3-phosphocholineHMDB
1-Oleoyl-sn-glycero-3-phosphocholineHMDB
Choline phosphate (ester) 3-ester with 1-monooleinHMDB
Choline phosphate 3-ester with 1-monooleinHMDB
Gpcho(18:1(9Z)/0:0)[rac]HMDB
LPC(18:1n9/0:0)HMDB
LPC(18:1W9/0:0)HMDB
LyPC(18:1W9/0:0)HMDB
LysoPC a C18:1HMDB
LysoPC(18:1n9/0:0)HMDB
LysoPC(18:1W9/0:0)HMDB
Lysophosphatidylcholine(18:1n9/0:0)HMDB
Lysophosphatidylcholine(18:1W9/0:0)HMDB
LysoPIC(18:1/0:0)HMDB
Olein-1-mono-3-phosphate ester with cholineHMDB
Oleoyl lysolecithinHMDB
Oleoyl lysophosphatidylcholineHMDB
1-(cis-9-Octadecenoyl)-sn-glycero-3-phosphocholineHMDB
1-OGPCHMDB
1-Oleoyl lysophosphatidylcholineHMDB
1-Oleoyl-lysopcHMDB
1-O-Oleoyl-sn-glycero-3-phosphocholineHMDB
1-Oleoyl-2-hydroxy-sn-glycerol-3-phosphocholineHMDB
1-Oleoyl-GPCHMDB
1-Oleoyl-lysophosphatidylcholineHMDB
1-Oleoyl-sn-glycerol-3-phosphatidylcholineHMDB
1-Oleoyl-sn-glycerol-3-phosphorylcholineHMDB
GPC(18:1(9Z))HMDB
GPC(18:1(9Z)/0:0)HMDB
GPC(18:1)HMDB
GPC(18:1n9)HMDB
GPC(18:1n9/0:0)HMDB
GPC(18:1W9)HMDB
GPC(18:1W9/0:0)HMDB
LPC(18:1(9Z))HMDB
LPC(18:1n9)HMDB
LPC(18:1W9)HMDB
LysoPC(18:1n9)HMDB
LysoPC(18:1W9)HMDB
Lysophosphatidylcholine C18:1HMDB
Lysophosphatidylcholine(18:1(9Z))HMDB
Lysophosphatidylcholine(18:1n9)HMDB
Lysophosphatidylcholine(18:1W9)HMDB
LysoPC(18:1(9Z)/0:0)ChEBI
1-Acyl-2-lyso-phosphatidylcholinemanual
1-O-Acyl-sn-glycero-3-phosphocholinemanual
2-Lysolecithinmanual
2-Lysophosphatidylcholinemanual
alpha-Acylglycerophosphocholinemanual
LPCmanual
Lysolecithinsmanual
Lysophosphatidylcholinesmanual
Predicted Properties
PropertyValueSource
Water Solubility0.00028 g/LALOGPS
logP2.38ALOGPS
logP1.72ChemAxon
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 Count25ChemAxon
Refractivity152.59 m³·mol⁻¹ChemAxon
Polarizability60.02 ųChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC26H52NO7P
IUPAC name(2-{[(2R)-2-hydroxy-3-[(9Z)-octadec-9-enoyloxy]propyl phosphono]oxy}ethyl)trimethylazanium
InChI IdentifierInChI=1S/C26H52NO7P/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/h12-13,25,28H,5-11,14-24H2,1-4H3/b13-12-/t25-/m1/s1
InChI KeyYAMUFBLWGFFICM-PTGWMXDISA-N
Isomeric SMILESCCCCCCCC\C=C/CCCCCCCC(=O)OC[C@@]([H])(O)COP([O-])(=O)OCC[N+](C)(C)C
Average Molecular Weight521.6673
Monoisotopic Molecular Weight521.348139535
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

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
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 KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-024u-9431010000-8c34065bb1a9ce8460a8JSpectraViewer
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDC04230
Pubchem Compound IDNot Available
Pubchem Substance ID6900
ChEBI ID17504
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDLYSOLECITHIN|LYSOPHOSPHATIDYLCHOLINE
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 IDLysophosphatidylcholine
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
immunostimulant50847 A substance that augments, stimulates, activates, potentiates, or modulates the immune response at either the cellular or humoral level. A classical agent (Freund's adjuvant, BCG, Corynebacterium parvum, et al.) contains bacterial antigens. It could also be endogenous (e.g., histamine, interferon, transfer factor, tuftsin, interleukin-1). Its mode of action is either non-specific, resulting in increased immune responsiveness to a wide variety of antigens, or antigen-specific, i.e., affecting a restricted type of immune response to a narrow group of antigens. The therapeutic efficacy is related to its antigen-specific immunoadjuvanticity.DUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).