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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2008-09-25 13:34:26 UTC
Update Date2017-12-07 02:27:48 UTC
HMDB IDHMDB0010610
Secondary Accession Numbers
  • HMDB10610
Metabolite Identification
Common NamePG(18:0/20:4(5Z,8Z,11Z,14Z))
DescriptionPG(18:0/20:4(5Z,8Z,11Z,14Z)) 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(18:0/20:4(5Z,8Z,11Z,14Z)), in particular, consists of one chain of stearic acid at the C-1 position and one chain of arachidonic acid at the C-2 position. The stearic acid moiety is derived from animal fats, coco butter and sesame oil, while the arachidonic acid moiety is derived from animal fats and eggs. 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
Synonyms
ValueSource
1-Octadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phospho-(1'-glycerol)ChEBI
1-Stearoyl-2-arachidonoyl-sn-glycero-3-phosphoglycerolChEBI
GPG(18:0/20:4)ChEBI
PG(18:0/20:4)ChEBI
GPG(18:0/20:4N6)HMDB
GPG(18:0/20:4W6)HMDB
GPG(38:4)HMDB
PG(18:0/20:4N6)HMDB
PG(18:0/20:4W6)HMDB
PG(38:4)HMDB
Phosphatidylglycerol(18:0/20:4)HMDB
Phosphatidylglycerol(18:0/20:4n6)HMDB
Phosphatidylglycerol(18:0/20:4W6)HMDB
Phosphatidylglycerol(38:4)HMDB
1-octadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphoglycerol; PG(18:0/20:4)Lipid Annotator
PG(18:0/20:4(5Z,8Z,11Z,14Z))Lipid Annotator
1-octadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphoglycerolLipid Annotator
Chemical FormulaC44H79O10P
Average Molecular Weight799.0658
Monoisotopic Molecular Weight798.54108526
IUPAC Name[(2S)-2,3-dihydroxypropoxy][(2R)-2-[(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoyloxy]-3-(octadecanoyloxy)propoxy]phosphinic acid
Traditional Name(2S)-2,3-dihydroxypropoxy(2R)-2-[(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoyloxy]-3-(octadecanoyloxy)propoxyphosphinic acid
CAS Registry NumberNot Available
SMILES
[H][C@](O)(CO)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCCCCCCCCCCC)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC
InChI Identifier
InChI=1S/C44H79O10P/c1-3-5-7-9-11-13-15-17-19-20-22-24-26-28-30-32-34-36-44(48)54-42(40-53-55(49,50)52-38-41(46)37-45)39-51-43(47)35-33-31-29-27-25-23-21-18-16-14-12-10-8-6-4-2/h11,13,17,19,22,24,28,30,41-42,45-46H,3-10,12,14-16,18,20-21,23,25-27,29,31-40H2,1-2H3,(H,49,50)/b13-11-,19-17-,24-22-,30-28-/t41-,42+/m0/s1
InChI KeyGGSONEYZZWVXFY-QPQYMHNXSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as phosphatidylglycerols. These are glycerophosphoglycerols in which two fatty acids are bonded to the 1-glycerol moiety through ester linkages. As is the case with diacylglycerols, phosphatidylglycerols can have many different combinations of fatty acids of varying lengths and saturation attached to the C-1 and C-2 positions.
KingdomChemical entities
Super ClassOrganic compounds
ClassLipids and lipid-like molecules
Sub ClassGlycerophospholipids
Direct ParentPhosphatidylglycerols
Alternative Parents
Substituents
  • 1,2-diacylglycerophosphoglycerol
  • Fatty acid ester
  • Dialkyl phosphate
  • Dicarboxylic acid or derivatives
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Alkyl phosphate
  • Fatty acyl
  • 1,2-diol
  • Carboxylic acid ester
  • Secondary alcohol
  • Carboxylic acid derivative
  • Organic oxide
  • Organooxygen compound
  • Alcohol
  • Organic oxygen compound
  • Primary alcohol
  • Carbonyl group
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

  Tissue and substructures:

  Cell and elements:

Source:

  Biological:

    Animal:

Route of exposure:

  Enteral:

Role

Biological role:

Industrial application:

  Food and nutrition:

Process

Naturally occurring process:

  Biological process:

    Cellular process:

    Biochemical pathway:

    Chemical reaction:

    Biochemical process:

Physiological effect

Organoleptic effect:

  Touch:

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 Solubility7.9e-05 g/LALOGPS
logP8.48ALOGPS
logP12.16ChemAxon
logS-7ALOGPS
pKa (Strongest Acidic)1.89ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area148.82 ŲChemAxon
Rotatable Bond Count42ChemAxon
Refractivity227.38 m³·mol⁻¹ChemAxon
Polarizability95.46 ųChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00nk-3091422700-cc69d42758bf4185e87fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05r9-4192211300-86730290e26859fdb6c7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-056r-8095202100-166630615b0ac6ef3307View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0fsj-1192110400-017eb45cca47c97eca3eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00o0-5290100100-a0068f2603ce63d80324View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9020000000-8333999a52e56fabba23View in MoNA
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid Locations
  • Blood
Tissue Location
  • All Tissues
Pathways
NameSMPDB/PathwhizKEGG
Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/16:1(9Z)/16:1(9Z))Pw029121Pw029121 greyscalePw029121 simpleNot Available
Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/16:1(9Z)/18:0)Pw029122Pw029122 greyscalePw029122 simpleNot Available
Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z))Pw029123Pw029123 greyscalePw029123 simpleNot Available
Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/18:0/20:4(5Z,8Z,11Z,14Z))Pw029124Pw029124 greyscalePw029124 simpleNot Available
Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/18:0/22:5(4Z,7Z,10Z,13Z,16Z))Pw029125Pw029125 greyscalePw029125 simpleNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.191 +/- 0.026 uMAdult (>18 years old)BothNormal details
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 IDFDB027760
KNApSAcK IDNot Available
Chemspider ID24768109
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound24779553
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  2. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  3. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  4. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  5. Divecha N, Irvine RF: Phospholipid signaling. Cell. 1995 Jan 27;80(2):269-78. [PubMed:7834746 ]
  6. Cevc, Gregor (1993). Phospholipids Handbook. Marcel Dekker.
  7. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Enzymes

General function:
Involved in acyltransferase activity
Specific function:
Lysophoshatidylglycerol (LPG) specific acyltransferase that recognizes various acyl-CoAs and LPGs as substrates but demonstrates a clear preference for long chain saturated fatty acyl-CoAs and oleoyl-CoA as acyl donors. Prefers oleoyl-LPG over palmitoyl-LPG as an acyl receptor and oleoyl-CoA over lauroyl-CoA as an acyl donor
Gene Name:
LPGAT1
Uniprot ID:
Q92604
Molecular weight:
43089.1