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Human Metabolome Database Version 3.5

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Showing metabocard for LysoPC(17:0) (HMDB12108)

Record Information
Version 3.5
Creation Date 2009-03-25 09:15:54 -0600
Update Date 2013-02-08 17:28:16 -0700
HMDB ID HMDB12108
Secondary Accession Numbers None
Metabolite Identification
Common Name LysoPC(17:0)
Description LysoPC(17:0) 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(17:0), in particular, consists of one chain of margaric acid at the C-1 position. The margaric acid moiety is derived from butter, milk and fat of ruminants. 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 | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. 1-Heptadecanoyl-glycero-3-phosphocholine
  2. LPC(17:0)
  3. LPC(17:0/0:0)
  4. LyPC(17:0)
  5. LyPC(17:0/0:0)
  6. lysoPC a C17:0
  7. LysoPC(17:0)
  8. LysoPC(17:0/0:0)
  9. Lysophosphatidylcholine(17:0)
  10. Lysophosphatidylcholine(17:0/0:0)
Chemical Formula C25H52NO7P
Average Molecular Weight 509.6566
Monoisotopic Molecular Weight 509.348139535
IUPAC Name (2-{[(2R)-3-(heptadecanoyloxy)-2-hydroxypropyl phosphonato]oxy}ethyl)trimethylazanium
Traditional IUPAC Name (2-{[(2R)-3-(heptadecanoyloxy)-2-hydroxypropyl phosphonato]oxy}ethyl)trimethylazanium
CAS Registry Number Not Available
SMILES [H][C@@](O)(COC(=O)CCCCCCCCCCCCCCCC)COP([O-])(=O)OCC[N+](C)(C)C
InChI Identifier InChI=1S/C25H52NO7P/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-25(28)31-22-24(27)23-33-34(29,30)32-21-20-26(2,3)4/h24,27H,5-23H2,1-4H3/t24-/m1/s1
InChI Key SRRQPVVYXBTRQK-XMMPIXPASA-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 2.890E-04 g/L ALOGPS
LogP 2.18 ALOGPS
LogP 1.64 ChemAxon
LogS -6.29 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 25 ChemAxon
Refractivity 146.87 ChemAxon
Polarizability 60.03 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 0 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid Locations
  • Blood
  • Urine
Tissue Location Not Available
Pathways Not Available
Normal Concentrations
Biofluid Status Value Age Sex Condition Comments
Blood Detected and Quantified
Article_icon
2.55 +/- 1.08 uM Adult (>18 years old) Not Specified Normal MS/MS (Biocrates)
Urine Detected and Quantified
Article_icon
0.0032 (0.0008-0.0087) umol/mmol creatinine Adult (>18 years old) Both Normal by DFI-MS/MS (Biocrates kit)
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB028772
KNApSAcK ID Not Available
Chemspider ID 24694752 Link_out
KEGG Compound ID C04230 Link_out
BioCyc ID Not Available
BiGG ID Not Available
Wikipedia Link Not Available
NuGOwiki Link HMDB12108 Link_out
Metagene Link HMDB12108 Link_out
METLIN ID Not Available
PubChem Compound 24779463 Link_out
PDB ID Not Available
ChEBI ID 580913 Link_out
References
Synthesis Reference Not Available
Material Safety Data Sheet (MSDS) Not Available
General References
  1. Cai S, Huo T, Li N, Xiong Z, Li F: Lysophosphatidylcholine-biomarker of Metformin action: studied using UPLC/MS/MS. Biomed Chromatogr. 2009 Mar 24. Pubmed: 19309761 Link_out
Enzymes
Name: Cytosolic phospholipase A2
Reactions:
  • 2-lysophosphatidylcholine + H2O = glycerophosphocholine + a carboxylate [RN:R07291]
Gene Name: PLA2G4A
Uniprot ID: P47712 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Eosinophil lysophospholipase
Reactions:
  • 2-lysophosphatidylcholine + H2O = glycerophosphocholine + a carboxylate [RN:R07291]
Gene Name: CLC
Uniprot ID: Q05315 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Platelet-activating factor acetylhydrolase
Reactions:
  • 1-alkyl-2-acetyl-sn-glycero-3-phosphocholine + H2O = 1-alkyl-sn-glycero-3-phosphocholine + acetate [RN:R04452]
Gene Name: PLA2G7
Uniprot ID: Q13093 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Platelet-activating factor acetylhydrolase IB subunit gamma
Reactions:
  • 1-alkyl-2-acetyl-sn-glycero-3-phosphocholine + H2O = 1-alkyl-sn-glycero-3-phosphocholine + acetate [RN:R04452]
Gene Name: PAFAH1B3
Uniprot ID: Q15102 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Platelet-activating factor acetylhydrolase IB subunit beta
Reactions:
  • 1-alkyl-2-acetyl-sn-glycero-3-phosphocholine + H2O = 1-alkyl-sn-glycero-3-phosphocholine + acetate [RN:R04452]
Gene Name: PAFAH1B2
Uniprot ID: P68402 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Platelet-activating factor acetylhydrolase 2, cytoplasmic
Reactions:
  • 1-alkyl-2-acetyl-sn-glycero-3-phosphocholine + H2O = 1-alkyl-sn-glycero-3-phosphocholine + acetate [RN:R04452]
Gene Name: PAFAH2
Uniprot ID: Q99487 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Lysophospholipid acyltransferase 5
Reactions:
  • acyl-CoA + 1-acyl-sn-glycero-3-phosphocholine = CoA + 1,2-diacyl-sn-glycero-3-phosphocholine [RN:R01318]
Gene Name: LPCAT3
Uniprot ID: Q6P1A2 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Lysophosphatidylcholine acyltransferase 1
Reactions:
  • acetyl-CoA + 1-alkyl-sn-glycero-3-phosphocholine = CoA + 2-acetyl-1-alkyl-sn-glycero-3-phosphocholine [RN:R03437]
Gene Name: LPCAT1
Uniprot ID: Q8NF37 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Lysophosphatidylcholine acyltransferase 2
Reactions:
  • acetyl-CoA + 1-alkyl-sn-glycero-3-phosphocholine = CoA + 2-acetyl-1-alkyl-sn-glycero-3-phosphocholine [RN:R03437]
Gene Name: LPCAT2
Uniprot ID: Q7L5N7 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: 60 kDa lysophospholipase
Reactions:
  • L-asparagine + H2O = L-aspartate + NH3 [RN:R00485]
Gene Name: ASPG
Uniprot ID: Q86U10 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Phospholipase B1, membrane-associated
Reactions:
  • 2-lysophosphatidylcholine + H2O = glycerophosphocholine + a carboxylate [RN:R07291]
Gene Name: PLB1
Uniprot ID: Q6P1J6 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA