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Human Metabolome Database Version 3.5

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Showing metabocard for PG(18:3(9Z,12Z,15Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) (HMDB10689)

Record Information
Version 3.5
Creation Date 2008-09-25 07:35:46 -0600
Update Date 2013-02-08 17:25:34 -0700
HMDB ID HMDB10689
Secondary Accession Numbers None
Metabolite Identification
Common Name PG(18:3(9Z,12Z,15Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))
Description PG(18:3(9Z,12Z,15Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) is a phosphatidylglycerol or glycerophospholipid (PG or GP). It is a glycerophospholipid in which a phosphoglycerol moiety occupies a glycerol substitution site. As is the case with diacylglycerols, phosphatidylglycerols can have many different combinations of fatty acids of varying lengths and saturation attached at the C-1 and C-2 positions. Fatty acids containing 16, 18 and 20 carbons are the most common. PG(18:3(9Z,12Z,15Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)), in particular, consists of one chain of a-linolenic acid at the C-1 position and one chain of docosahexaenoic acid at the C-2 position. The a-linolenic acid moiety is derived from seed oils, especially canola and soybean oil, while the docosahexaenoic acid moiety is derived from fish oils. Phosphatidylglycerol is present at a level of 1-2% in most animal tissues, but it can be the second most abundant phospholipid in lung surfactant at up to 11% of the total. It is well established that the concentration of phosphatidylglycerol increases during fetal development. Phosphatidylglycerol may be present in animal tissues merely as a precursor for diphosphatidylglycerol (cardiolipin). Phosphatidylglycerol is formed from phosphatidic acid by a sequence of enzymatic reactions that proceeds via the intermediate, cytidine diphosphate diacylglycerol (CDP-diacylglycerol). Bioynthesis proceeds by condensation of phosphatidic acid and cytidine triphosphate with elimination of pyrophosphate via the action of phosphatidate cytidyltransferase (or CDP-synthase). CDP-diacylglycerol then reacts with glycerol-3-phosphate via phosphatidylglycerophosphate synthase to form 3-sn-phosphatidyl-1'-sn-glycerol 3'-phosphoric acid, with the release of cytidine monophosphate (CMP). Finally, phosphatidylglycerol is formed by the action of specific phosphatases. While most phospholipids have a saturated fatty acid on C-1 and an unsaturated fatty acid on C-2 of the glycerol backbone, the fatty acid distribution at the C-1 and C-2 positions of glycerol within phospholipids is continually in flux, owing to phospholipid degradation and the continuous phospholipid remodeling that occurs while these molecules are in membranes. PGs have a net charge of -1 at physiological pH and are found in high concentration in mitochondrial membranes and as components of pulmonary surfactant. PG also serves as a precursor for the synthesis of cardiolipin. PG is synthesized from CDP-diacylglycerol and glycerol-3-phosphate.
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. 1-(9Z,12Z,15Z-Octadeatrienoyl)-2-(4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenoyl)-sn-glycero-3-phospho-(1'-glycerol)
  2. 1-a-Linolenoyl-2-docosahexaenoyl-sn-glycero-3-phosphoglycerol
  3. 1-alpha-Linolenoyl-2-docosahexaenoyl-sn-glycero-3-phosphoglycerol
  4. GPG(18:3/22:6)
  5. GPG(18:3n3/22:6n3)
  6. GPG(18:3w3/22:6w3)
  7. GPG(40:9)
  8. PG(18:3/22:6)
  9. PG(18:3n3/22:6n3)
  10. PG(18:3w3/22:6w3)
  11. PG(40:9)
  12. Phosphatidylglycerol(18:3/22:6)
  13. Phosphatidylglycerol(18:3n3/22:6n3)
  14. Phosphatidylglycerol(18:3w3/22:6w3)
  15. Phosphatidylglycerol(40:9)
Chemical Formula C46H73O10P
Average Molecular Weight 817.0396
Monoisotopic Molecular Weight 816.494135068
IUPAC Name [(2S)-2,3-dihydroxypropoxy][(2R)-2-[(4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoyloxy]-3-[(9Z,12Z,15Z)-octadeca-9,12,15-trienoyloxy]propoxy]phosphinic acid
Traditional IUPAC Name (2S)-2,3-dihydroxypropoxy(2R)-2-[(4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoyloxy]-3-[(9Z,12Z,15Z)-octadeca-9,12,15-trienoyloxy]propoxyphosphinic acid
CAS Registry Number Not Available
SMILES [H][C@](O)(CO)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCC\C=C/C\C=C/C\C=C/CC)OC(=O)CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CC
InChI Identifier InChI=1S/C46H73O10P/c1-3-5-7-9-11-13-15-17-19-20-21-22-24-26-28-30-32-34-36-38-46(50)56-44(42-55-57(51,52)54-40-43(48)39-47)41-53-45(49)37-35-33-31-29-27-25-23-18-16-14-12-10-8-6-4-2/h5-8,11-14,17-19,21-23,26,28,32,34,43-44,47-48H,3-4,9-10,15-16,20,24-25,27,29-31,33,35-42H2,1-2H3,(H,51,52)/b7-5-,8-6-,13-11-,14-12-,19-17-,22-21-,23-18-,28-26-,34-32-/t43-,44+/m0/s1
InChI Key CXLZYQKWZLBZEB-JRJQDFDNSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Lipids
Class Glycerophospholipids
Sub Class Glycerophosphoglycerols
Other Descriptors
  • Aliphatic Acyclic Compounds
  • Glycerophosphoglycerols
Substituents
  • 1,2 Diol
  • Acyclic Alkene
  • Carboxylic Acid Ester
  • Dicarboxylic Acid Derivative
  • Fatty Acid Ester
  • Monosaccharide Phosphate
  • Organic Hypophosphite
  • Organic Phosphite
  • Phosphoric Acid Ester
  • Primary Alcohol
  • Saccharide
  • Secondary Alcohol
  • Triose Monosaccharide
Direct Parent Phosphatidylglycerols
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 1.290E-04 g/L ALOGPS
LogP 7.50 ALOGPS
LogP 11.24 ChemAxon
LogS -6.80 ALOGPS
pKa (strongest acidic) 1.89 ChemAxon
pKa (strongest basic) -3 ChemAxon
Hydrogen Acceptor Count 6 ChemAxon
Hydrogen Donor Count 3 ChemAxon
Polar Surface Area 148.82 A2 ChemAxon
Rotatable Bond Count 39 ChemAxon
Refractivity 242.17 ChemAxon
Polarizability 92.21 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge -1 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid Locations
  • Blood
Tissue Location
  • All Tissues
Pathways Not Available
Normal Concentrations
Biofluid Status Value Age Sex Condition Comments
Blood Detected and Quantified
Article_icon
0.116 +/- 0.019 uM Adult (>18 years old) Both Normal Not Available
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 FDB027839
KNApSAcK ID Not Available
Chemspider ID 24768188 Link_out
KEGG Compound ID Not Available
BioCyc ID Not Available
BiGG ID Not Available
Wikipedia Link Not Available
NuGOwiki Link HMDB10689 Link_out
Metagene Link HMDB10689 Link_out
METLIN ID Not Available
PubChem Compound 52926689 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-CoA:lysophosphatidylglycerol acyltransferase 1
Reactions:
    Gene Name: LPGAT1
    Uniprot ID: Q92604 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA