Record Information
Version3.6
Creation Date2008-09-16 13:19:56 UTC
Update Date2013-02-09 00:24:42 UTC
HMDB IDHMDB10382
Secondary Accession NumbersNone
Metabolite Identification
Common NameLysoPC(16:0)
DescriptionLysoPC(16:0) 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(16:0), in particular, consists of one chain of palmitic acid at the C-1 position. The palmitic acid moiety is derived from fish oils, milk fats, vegetable oils and animal fats. 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.
Structure
Thumb
Synonyms
  1. 1-Palmitoyl-glycero-3-phosphocholine
  2. 1-Palmitoyl-lysophosphatidylcholine
  3. LPC(16:0)
  4. LPC(16:0/0:0)
  5. LyPC(16:0)
  6. LyPC(16:0/0:0)
  7. lysoPC a C16:0
  8. LysoPC(16:0)
  9. LysoPC(16:0/0:0)
  10. Lysophosphatidylcholine(16:0)
  11. Lysophosphatidylcholine(16:0/0:0)
Chemical FormulaC24H50NO7P
Average Molecular Weight495.6301
Monoisotopic Molecular Weight495.332489471
IUPAC Name(2-{[(2R)-3-(hexadecanoyloxy)-2-hydroxypropyl phosphonato]oxy}ethyl)trimethylazanium
Traditional IUPAC Name(2-{[(2R)-3-(hexadecanoyloxy)-2-hydroxypropyl phosphonato]oxy}ethyl)trimethylazanium
CAS Registry NumberNot Available
SMILES
[H][C@@](O)(COC(=O)CCCCCCCCCCCCCCC)COP([O-])(=O)OCC[N+](C)(C)C
InChI Identifier
InChI=1S/C24H50NO7P/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/h23,26H,5-22H2,1-4H3/t23-/m1/s1
InChI KeyASWBNKHCZGQVJV-HSZRJFAPSA-N
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassLipids
ClassGlycerophospholipids
Sub ClassGlycerophosphocholines
Other Descriptors
  • Aliphatic Acyclic Compounds
  • Monoacylglycerophosphocholines(Lipidmaps)
Substituents
  • Carboxylic Acid Ester
  • Choline
  • Fatty Acid Ester
  • Glycero 3 Phosphocholine
  • Organic Hypophosphite
  • Organic Phosphite
  • Phosphocholine
  • Phosphoethanolamine
  • Phosphoric Acid Ester
  • Quaternary Ammonium Salt
  • Secondary Alcohol
Direct ParentLysophosphatidylcholines
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
  • Food
Biofunction
  • Cell signaling
  • Energy source
  • Fuel and energy storage
  • Fuel or energy source
  • Membrane component
  • Membrane integrity/stability
Application
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Extracellular
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
water solubility3.680E-04 g/LALOGPS
logP1.83ALOGPS
logP1.19ChemAxon
logS-6.2ALOGPS
pKa (strongest acidic)1.86ChemAxon
pKa (strongest basic)-3.4ChemAxon
physiological charge0ChemAxon
hydrogen acceptor count4ChemAxon
hydrogen donor count1ChemAxon
polar surface area105.12ChemAxon
rotatable bond count24ChemAxon
refractivity142.27ChemAxon
polarizability57.99ChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • All Tissues
Pathways
NameSMPDB LinkKEGG Link
Phospholipid BiosynthesisSMP00025map00564
Normal Concentrations
BiofluidStatusValueAgeSexConditionReference
BloodDetected and Quantified141 +/- 50 uMAdult (>18 years old)Not SpecifiedCommentNormal
BloodDetected and Quantified106.6 +/- 16.73 uMAdult (>18 years old)Not SpecifiedCommentNormal
BloodDetected and Quantified106.598 +/- 16.732 uMAdult (>18 years old)BothCommentNormal
UrineDetected and Quantified0.014 umol/mmol creatinineAdult (>18 years old)BothCommentNormal
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB027533
KNApSAcK IDNot Available
Chemspider ID405287
KEGG Compound IDC04230
BioCyc ID PHOSPHATIDYLCHOLINE
BiGG IDNot Available
Wikipedia LinkLecithin
NuGOwiki LinkHMDB10382
Metagene LinkHMDB10382
METLIN IDNot Available
PubChem Compound460602
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

Gene Name:
LYPLA1
Uniprot ID:
O75608
Gene Name:
PLA2G15
Uniprot ID:
Q8NCC3
Gene Name:
PLA2G5
Uniprot ID:
P39877
Gene Name:
PLA2G2F
Uniprot ID:
Q9BZM2
Gene Name:
PLA2G4A
Uniprot ID:
P47712
Gene Name:
PLA2G1B
Uniprot ID:
P04054
Gene Name:
PLA2G10
Uniprot ID:
O15496
Gene Name:
PLA2G2E
Uniprot ID:
Q9NZK7
Gene Name:
LYPLA2
Uniprot ID:
O95372
Gene Name:
CLC
Uniprot ID:
Q05315
Gene Name:
PLA2G2D
Uniprot ID:
Q9UNK4
Gene Name:
PLA2G3
Uniprot ID:
Q9NZ20
Gene Name:
LPCAT3
Uniprot ID:
Q6P1A2
Gene Name:
ASPG
Uniprot ID:
Q86U10
Gene Name:
PLA2G4B
Uniprot ID:
P0C869