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Showing metabocard for LysoPC(20:4(5Z,8Z,11Z,14Z)) (HMDB10395)

Record Information
Version 3.5
Creation Date 2008-09-16 07:20:09 -0600
Update Date 2013-02-08 17:24:44 -0700
HMDB ID HMDB10395
Secondary Accession Numbers None
Metabolite Identification
Common Name LysoPC(20:4(5Z,8Z,11Z,14Z))
Description LysoPC(20:4(5Z,8Z,11Z,14Z)) 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(20:4(5Z,8Z,11Z,14Z)), in particular, consists of one chain of arachidonic acid at the C-1 position. The arachidonic acid moiety is derived from animal fats and eggs. 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-Arachidonoyl-glycero-3-phosphocholine
  2. LPC(20:4)
  3. LPC(20:4/0:0)
  4. LPC(20:4n6/0:0)
  5. LPC(20:4w6/0:0)
  6. LyPC(20:4)
  7. LyPC(20:4/0:0)
  8. LyPC(20:4n6/0:0)
  9. LyPC(20:4w6/0:0)
  10. lysoPC a C20:4
  11. LysoPC(20:4)
  12. LysoPC(20:4/0:0)
  13. LysoPC(20:4n6/0:0)
  14. LysoPC(20:4w6/0:0)
  15. Lysophosphatidylcholine(20:4)
  16. Lysophosphatidylcholine(20:4/0:0)
  17. Lysophosphatidylcholine(20:4n6/0:0)
  18. Lysophosphatidylcholine(20:4w6/0:0)
Chemical Formula C28H50NO7P
Average Molecular Weight 543.6729
Monoisotopic Molecular Weight 543.332489471
IUPAC Name (2-{[(2R)-2-hydroxy-3-[(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoyloxy]propyl phosphonato]oxy}ethyl)trimethylazanium
Traditional IUPAC Name (2-{[(2R)-2-hydroxy-3-[(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoyloxy]propyl phosphonato]oxy}ethyl)trimethylazanium
CAS Registry Number Not Available
SMILES CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(=O)OC[C@](O)([H])COP([O-])(=O)OCC[N+](C)(C)C
InChI Identifier InChI=1S/C28H50NO7P/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22-28(31)34-25-27(30)26-36-37(32,33)35-24-23-29(2,3)4/h9-10,12-13,15-16,18-19,27,30H,5-8,11,14,17,20-26H2,1-4H3/b10-9-,13-12-,16-15-,19-18-/t27-/m1/s1
InChI Key LAXQYRRMGGEGOH-JXRLJXCWSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Lipids
Class Glycerophospholipids
Sub Class Glycerophosphocholines
Other Descriptors
  • Aliphatic Acyclic Compounds
Substituents
  • Acyclic Alkene
  • 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 2.45 ALOGPS
LogP 1.52 ChemAxon
LogS -6.31 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 165.14 ChemAxon
Polarizability 60.98 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 0 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Urine
Tissue Location
  • All Tissues
Pathways Not Available
Normal Concentrations
Biofluid Status Value Age Sex Condition Comments
Blood Detected and Quantified
Article_icon
6.13 +/- 2.55 uM Adult (>18 years old) Not Specified Normal MS/MS (Biocrates)
Blood Detected and Quantified
Article_icon
8.39 +/- 0.98 uM Adult (>18 years old) Not Specified Normal LC/GC-FID (Lipomics)
Blood Detected and Quantified
Article_icon
8.394 +/- 0.976 uM Adult (>18 years old) Both Normal quantified by Lipomics Technologies, Inc.
Cerebrospinal Fluid (CSF) Detected and Quantified
Article_icon
0.024 +/- 0.007 uM Adult (>18 years old) Not Specified Normal Not Available
Urine Detected and Quantified
Article_icon
0.002 (0.0005-0.0038) 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 FDB027546
KNApSAcK ID Not Available
Chemspider ID 21403155 Link_out
KEGG Compound ID C04230 Link_out
BioCyc ID PHOSPHATIDYLCHOLINE Link_out
BiGG ID Not Available
Wikipedia Link Lecithin Link_out
NuGOwiki Link HMDB10395 Link_out
Metagene Link HMDB10395 Link_out
METLIN ID Not Available
PubChem Compound 24779476 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:
    Gene Name: LYPLA1
    Uniprot ID: O75608 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: Group XV phospholipase A2
    Reactions:
      Gene Name: PLA2G15
      Uniprot ID: Q8NCC3 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Calcium-dependent phospholipase A2
      Reactions:
      • phosphatidylcholine + H2O = 1-acylglycerophosphocholine + a carboxylate [RN:R01313]
      Gene Name: PLA2G5
      Uniprot ID: P39877 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Group IIF secretory phospholipase A2
      Reactions:
      • phosphatidylcholine + H2O = 1-acylglycerophosphocholine + a carboxylate [RN:R01313]
      Gene Name: PLA2G2F
      Uniprot ID: Q9BZM2 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      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: Phospholipase A2
      Reactions:
      • phosphatidylcholine + H2O = 1-acylglycerophosphocholine + a carboxylate [RN:R01313]
      Gene Name: PLA2G1B
      Uniprot ID: P04054 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Group XIIB secretory phospholipase A2-like protein
      Reactions:
        Gene Name: PLA2G12B
        Uniprot ID: Q9BX93 Link_out
        Protein Sequence: FASTA
        Gene Sequence: FASTA
        Name: Group 10 secretory phospholipase A2
        Reactions:
        • phosphatidylcholine + H2O = 1-acylglycerophosphocholine + a carboxylate [RN:R01313]
        Gene Name: PLA2G10
        Uniprot ID: O15496 Link_out
        Protein Sequence: FASTA
        Gene Sequence: FASTA
        Name: Group IIE secretory phospholipase A2
        Reactions:
        • phosphatidylcholine + H2O = 1-acylglycerophosphocholine + a carboxylate [RN:R01313]
        Gene Name: PLA2G2E
        Uniprot ID: Q9NZK7 Link_out
        Protein Sequence: FASTA
        Gene Sequence: FASTA
        Name: Acyl-protein thioesterase 2
        Reactions:
          Gene Name: LYPLA2
          Uniprot ID: O95372 Link_out
          Protein Sequence: FASTA
          Gene Sequence: FASTA
          Name: 85 kDa calcium-independent phospholipase A2
          Reactions:
          • phosphatidylcholine + H2O = 1-acylglycerophosphocholine + a carboxylate [RN:R01313]
          Gene Name: PLA2G6
          Uniprot ID: O60733 Link_out
          Protein Sequence: FASTA
          Gene Sequence: FASTA
          Name: Phosphatidylcholine-sterol acyltransferase
          Reactions:
          • phosphatidylcholine + a sterol = 1-acylglycerophosphocholine + a sterol ester [RN:R02114]
          Gene Name: LCAT
          Uniprot ID: P04180 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: Group IID secretory phospholipase A2
          Reactions:
          • phosphatidylcholine + H2O = 1-acylglycerophosphocholine + a carboxylate [RN:R01313]
          Gene Name: PLA2G2D
          Uniprot ID: Q9UNK4 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: Group 3 secretory phospholipase A2
          Reactions:
          • phosphatidylcholine + H2O = 1-acylglycerophosphocholine + a carboxylate [RN:R01313]
          Gene Name: PLA2G3
          Uniprot ID: Q9NZ20 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
          Name: Cytosolic phospholipase A2 beta
          Reactions:
          • phosphatidylcholine + H2O = 1-acylglycerophosphocholine + a carboxylate [RN:R01313]
          Gene Name: PLA2G4B
          Uniprot ID: P0C869 Link_out
          Protein Sequence: FASTA
          Gene Sequence: FASTA