Record Information
Version1.0
Creation date2011-09-21 01:26:03 UTC
Update date2019-11-26 03:21:25 UTC
Primary IDFDB027534
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameLysoPC(16:1(9Z))
DescriptionLysoPC(16:1(9Z)) 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(16:1(9Z)), in particular, consists of one chain of palmitoleic acid at the C-1 position. The palmitoleic acid moiety is derived from animal fats and vegetable oils. 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 Number76790-27-7
Structure
Thumb
Synonyms
SynonymSource
1-(9Z-Hexadecenoyl)-sn-glycero-3-ocholineChEBI
1-Palmitoleoyl-glycero-3-ocholineChEBI
1-palmitoleoyl-glycero-3-phosphocholinehmdb
1-Palmitoleoyl-glyceroocholineChEBI
LPC 16:1(9Z)/0:0ChEBI
LPC(16:1(9Z)/0:0)ChEBI
LPC(16:1)hmdb
LPC(16:1/0:0)hmdb
LPC(16:1n7/0:0)hmdb
LPC(16:1w7/0:0)hmdb
LyPC(16:1)hmdb
LyPC(16:1/0:0)hmdb
LyPC(16:1n7/0:0)hmdb
LyPC(16:1w7/0:0)hmdb
Lysoatidylcholine(16:1(9Z)/0:0)ChEBI
Lysoatidylcholine(16:1)HMDB
Lysoatidylcholine(16:1/0:0)HMDB
Lysoatidylcholine(16:1N7/0:0)HMDB
Lysoatidylcholine(16:1W7/0:0)HMDB
LysoPC 16:1(9Z)/0:0ChEBI
LysoPC a C16:1HMDB
LysoPC(16:1(9Z)/0:0)ChEBI
LysoPC(16:1)hmdb
LysoPC(16:1/0:0)hmdb
LysoPC(16:1n7/0:0)hmdb
LysoPC(16:1w7/0:0)hmdb
Lysophosphatidylcholine(16:1)hmdb
Lysophosphatidylcholine(16:1/0:0)hmdb
Lysophosphatidylcholine(16:1n7/0:0)hmdb
Lysophosphatidylcholine(16:1w7/0:0)hmdb
PC 16:1(9Z)/0:0ChEBI
PC(16:1(9Z)/0:0)ChEBI
Predicted PropertiesNot Available
Chemical FormulaC24H48NO7P
IUPAC name
InChI IdentifierInChI=1S/C24H48NO7P/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-24(27)30-21-23(26)22-32-33(28,29)31-20-19-25(2,3)4/h10-11,23,26H,5-9,12-22H2,1-4H3/t23-/m1/s1
InChI KeyLFUDDCMNKWEORN-HSZRJFAPSA-N
Isomeric SMILESCCCCCCC=CCCCCCCCC(=O)OC[C@@H](O)COP([O-])(=O)OCC[N+](C)(C)C
Average Molecular Weight493.6142
Monoisotopic Molecular Weight493.316839407
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 DescriptorsNot Available
Ontology
OntologyNo ontology term
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
EI-MS/GC-MSNot Available
MS/MSNot Available
NMRNot Available
ChemSpider ID24766525
ChEMBL IDNot Available
KEGG Compound IDC04230
Pubchem Compound ID24779461
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB10383
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
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