Lysolecithin (CHEM025830)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 22:37:45 UTC
Update Date2016-11-09 01:18:09 UTC
Accession NumberCHEM025830
Identification
Common NameLysolecithin
ClassSmall Molecule
DescriptionPC(18:1(9Z)/0:0), also known as lysopc 18:1(9Z)/0:0 or LPC(18:1W9/0:0), 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. Thus, PC(18:1(9Z)/0:0) is considered to be a glycerophosphocholine lipid molecule. PC(18:1(9Z)/0:0) is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. PC(18:1(9Z)/0:0) exists in all eukaryotes, ranging from yeast to humans.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
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
a 1-(9Z-Octadecenoyl)-sn-glycero-3-phosphocholineChEBI
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
Chemical FormulaC26H52NO7P
Average Molecular Mass521.667 g/mol
Monoisotopic Mass521.348 g/mol
CAS Registry NumberNot Available
IUPAC Name(2-{[(2R)-2-hydroxy-3-[(9Z)-octadec-9-enoyloxy]propyl phosphono]oxy}ethyl)trimethylazanium
Traditional Name(2-{[(2R)-2-hydroxy-3-[(9Z)-octadec-9-enoyloxy]propyl phosphono]oxy}ethyl)trimethylazanium
SMILESCCCCCCCC\C=C/CCCCCCCC(=O)OC[C@@]([H])(O)COP([O-])(=O)OCC[N+](C)(C)C
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
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 Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
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 FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-024u-9431010000-8c34065bb1a9ce8460a8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0030090000-c08a294df5c170ac8b76Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-1090010000-3f3fbc869926a73a5b72Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-0090000000-1894b105723e28dacec8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0fk9-0000090000-382efaabb1329b98f1aeSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0089-0900060000-7d4d5ee776e7a08537aeSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ue9-0910040000-b15364334c9b09b73db5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0000190000-ed1ce66db5beed8bfab7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000l-0001960000-b2d5105862a37356da93Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0gw0-1609710000-4adbedbb1f89568d7285Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0000090000-f6a072a97b578a3bd0b0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-053r-0090070000-f56fc89aebf13639f1aeSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-0090020000-be75beb7bf742731dc1eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0000190000-37dcc74901c1425d0392Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0190-0002990000-c8110d0a5e4476020596Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0frj-0309400000-cd464845573077fb0e9fSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0002815
FooDB IDFDB005287
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID17240641
ChEBI ID28610
PubChem Compound ID16081932
Kegg Compound IDNot Available
YMDB IDYMDB01190
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation)
2. Chung, Guk Hoon; Kim, Sun Ki; Rhee, Joon Shick; Han, Jeong Joon. Process for preparing lysophospholipids using enzymes. U.S. (2001), 8 pp.
3. Frasch SC, Zemski-Berry K, Murphy RC, Borregaard N, Henson PM, Bratton DL: Lysophospholipids of different classes mobilize neutrophil secretory vesicles and induce redundant signaling through G2A. J Immunol. 2007 May 15;178(10):6540-8.
4. Yang J, Zhao X, Liu X, Wang C, Gao P, Wang J, Li L, Gu J, Yang S, Xu G: High performance liquid chromatography-mass spectrometry for metabonomics: potential biomarkers for acute deterioration of liver function in chronic hepatitis B. J Proteome Res. 2006 Mar;5(3):554-61.
5. Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043.
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=25584012
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=25642819