Human Metabolome Database Version 3.5

Showing metabocard for LysoPC(16:0) (HMDB10382)

Record Information
Version 3.5
Creation Date 2008-09-16 07:19:56 -0600
Update Date 2013-02-08 17:24:42 -0700
HMDB ID HMDB10382
Secondary Accession Numbers None
Metabolite Identification
Common Name LysoPC(16:0)
Description LysoPC(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
Download: MOL | SDF | PDB | SMILES | InChI
Display: 2D Structure | 3D Structure
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 Formula C24H50NO7P
Average Molecular Weight 495.6301
Monoisotopic Molecular Weight 495.332489471
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 Number Not 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 Key ASWBNKHCZGQVJV-HSZRJFAPSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Lipids
Class Glycerophospholipids
Sub Class Glycerophosphocholines
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 Parent Lysophosphatidylcholines
Ontology
Status Detected 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
State Solid
Experimental Properties
Property Value Reference
Melting Point Not Available Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
Water Solubility 3.680E-04 g/L ALOGPS
LogP 1.83 ALOGPS
LogP 1.19 ChemAxon
LogS -6.17 ALOGPS
pKa (strongest acidic) 1.86 ChemAxon
pKa (strongest basic) -3.4 ChemAxon
Hydrogen Acceptor Count 4 ChemAxon
Hydrogen Donor Count 1 ChemAxon
Polar Surface Area 105.12 A2 ChemAxon
Rotatable Bond Count 24 ChemAxon
Refractivity 142.27 ChemAxon
Polarizability 57.99 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 0 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • All Tissues
Pathways
Name SMPDB Link KEGG Link
Phospholipid Biosynthesis SMP00025 map00564 Link_out
Normal Concentrations
Biofluid Status Value Age Sex Condition Reference
Blood Detected and Quantified
141 +/- 50 uM Adult (>18 years old) Not Specified Comment Normal
Blood Detected and Quantified
106.6 +/- 16.73 uM Adult (>18 years old) Not Specified Comment Normal
Blood Detected and Quantified
106.598 +/- 16.732 uM Adult (>18 years old) Both Comment Normal
Urine Detected and Quantified
0.014 umol/mmol creatinine Adult (>18 years old) Both Comment Normal
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
DrugBank Metabolite ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB027533
KNApSAcK ID Not Available
Chemspider ID 405287 Link_out
KEGG Compound ID C04230 Link_out
BioCyc ID PHOSPHATIDYLCHOLINE Link_out
BiGG ID Not Available
Wikipedia Link Lecithin Link_out
NuGOwiki Link HMDB10382 Link_out
Metagene Link HMDB10382 Link_out
METLIN ID Not Available
PubChem Compound 460602 Link_out
PDB ID Not Available
ChEBI ID Not Available
References
Synthesis Reference Not Available
Material Safety Data Sheet (MSDS) Not Available
General References Not Available

Enzymes
Name: Acyl-protein thioesterase 1
Reactions: Not Available
Gene Name: LYPLA1
Uniprot ID: O75608 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Group XV phospholipase A2
Reactions: Not Available
Gene Name: PLA2G15
Uniprot ID: Q8NCC3 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Calcium-dependent phospholipase A2
Reactions: Not Available
Gene Name: PLA2G5
Uniprot ID: P39877 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Group IIF secretory phospholipase A2
Reactions: Not Available
Gene Name: PLA2G2F
Uniprot ID: Q9BZM2 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytosolic phospholipase A2
Reactions: Not Available
Gene Name: PLA2G4A
Uniprot ID: P47712 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Phospholipase A2
Reactions: Not Available
Gene Name: PLA2G1B
Uniprot ID: P04054 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Group XIIB secretory phospholipase A2-like protein
Reactions: Not Available
Gene Name: PLA2G12B
Uniprot ID: Q9BX93 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Group 10 secretory phospholipase A2
Reactions: Not Available
Gene Name: PLA2G10
Uniprot ID: O15496 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Group IIE secretory phospholipase A2
Reactions: Not Available
Gene Name: PLA2G2E
Uniprot ID: Q9NZK7 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Acyl-protein thioesterase 2
Reactions: Not Available
Gene Name: LYPLA2
Uniprot ID: O95372 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: 85/88 kDa calcium-independent phospholipase A2
Reactions: Not Available
Gene Name: PLA2G6
Uniprot ID: O60733 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Phosphatidylcholine-sterol acyltransferase
Reactions: Not Available
Gene Name: LCAT
Uniprot ID: P04180 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Eosinophil lysophospholipase
Reactions: Not Available
Gene Name: CLC
Uniprot ID: Q05315 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Group IID secretory phospholipase A2
Reactions: Not Available
Gene Name: PLA2G2D
Uniprot ID: Q9UNK4 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Platelet-activating factor acetylhydrolase
Reactions: Not Available
Gene Name: PLA2G7
Uniprot ID: Q13093 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Platelet-activating factor acetylhydrolase IB subunit gamma
Reactions: Not Available
Gene Name: PAFAH1B3
Uniprot ID: Q15102 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Platelet-activating factor acetylhydrolase IB subunit beta
Reactions: Not Available
Gene Name: PAFAH1B2
Uniprot ID: P68402 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Group 3 secretory phospholipase A2
Reactions: Not Available
Gene Name: PLA2G3
Uniprot ID: Q9NZ20 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Platelet-activating factor acetylhydrolase 2, cytoplasmic
Reactions: Not Available
Gene Name: PAFAH2
Uniprot ID: Q99487 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Lysophospholipid acyltransferase 5
Reactions: Not Available
Gene Name: LPCAT3
Uniprot ID: Q6P1A2 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Lysophosphatidylcholine acyltransferase 1
Reactions: Not Available
Gene Name: LPCAT1
Uniprot ID: Q8NF37 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Lysophosphatidylcholine acyltransferase 2
Reactions: Not Available
Gene Name: LPCAT2
Uniprot ID: Q7L5N7 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: 60 kDa lysophospholipase
Reactions: Not Available
Gene Name: ASPG
Uniprot ID: Q86U10 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Phospholipase B1, membrane-associated
Reactions: Not Available
Gene Name: PLB1
Uniprot ID: Q6P1J6 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytosolic phospholipase A2 beta
Reactions: Not Available
Gene Name: PLA2G4B
Uniprot ID: P0C869 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA