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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2017-09-09 08:44:23 UTC
Update Date2022-11-30 19:26:41 UTC
HMDB IDHMDB0116613
Secondary Accession NumbersNone
Metabolite Identification
Common NamePG(20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))
DescriptionPG(20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) is a phosphatidylglycerol - 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(20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)), in particular, consists of one chain of arachidonic acid at the C-1 position and one chain of docosahexaenoic acid at the C-2 position. 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 (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 cardiolipin synthesis.
Structure
Data?1563873737
Synonyms
ValueSource
1-arachidonoyl-2-docosahexaenoyl-sn-glycero-3-phospho-(1'-glycerol) SMPDB, HMDB
1-arachidonoyl-2-docosahexaenoyl-sn-glycero-3-phosphoglycerol SMPDB, HMDB
PG(20:4/22:6) SMPDB, HMDB
PG(20:4n6/22:6n3) SMPDB, HMDB
PG(20:4w6/22:6w3) SMPDB, HMDB
PG(42:10) SMPDB, HMDB
Phosphatidylglycerol(20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) SMPDB, HMDB
Phosphatidylglycerol(20:4/22:6) SMPDB, HMDB
Phosphatidylglycerol(20:4n6/22:6n3) SMPDB, HMDB
Phosphatidylglycerol(20:4w6/22:6w3) SMPDB, HMDB
Phosphatidylglycerol(42:10)SMPDB, HMDB
PG(20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))SMPDB
GPG(42:10)Lipid Annotator, HMDB
PG(20:4/22:6)Lipid Annotator
1-arachidonoyl-2-docosahexaenoyl-sn-glycero-3-phosphoglycerolLipid Annotator
PG(42:10)Lipid Annotator
1-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-2-(4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenoyl)-sn-glycero-3-phospho-(1'-glycerol)Lipid Annotator, HMDB
Phosphatidylglycerol(20:4/22:6)Lipid Annotator
1-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-2-(4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenoyl)-sn-glycero-3-phosphoglycerolLipid Annotator, HMDB
GPG(20:4/22:6)Lipid Annotator, HMDB
Chemical FormulaC48H75O10P
Average Molecular Weight843.092
Monoisotopic Molecular Weight842.509785613
IUPAC Name[(2S)-2,3-dihydroxypropoxy][(2R)-2-[(4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoyloxy]-3-[(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoyloxy]propoxy]phosphinic acid
Traditional Name(2S)-2,3-dihydroxypropoxy((2R)-2-[(4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoyloxy]-3-[(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoyloxy]propoxy)phosphinic acid
CAS Registry NumberNot Available
SMILES
[H][C@](O)(CO)COP(O)(=O)OC[C@@]([H])(COC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC)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/C48H75O10P/c1-3-5-7-9-11-13-15-17-19-21-22-24-26-28-30-32-34-36-38-40-48(52)58-46(44-57-59(53,54)56-42-45(50)41-49)43-55-47(51)39-37-35-33-31-29-27-25-23-20-18-16-14-12-10-8-6-4-2/h5,7,11-14,17-20,22,24-25,27-28,30-31,33-34,36,45-46,49-50H,3-4,6,8-10,15-16,21,23,26,29,32,35,37-44H2,1-2H3,(H,53,54)/b7-5-,13-11-,14-12-,19-17-,20-18-,24-22-,27-25-,30-28-,33-31-,36-34-/t45-,46+/m0/s1
InChI KeyOJQXZYUQNOHGMR-DTAASTIRSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as phosphatidylglycerols. These are glycerophosphoglycerols in which two fatty acids are bonded to the 1-glycerol moiety through ester linkages.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassGlycerophospholipids
Sub ClassGlycerophosphoglycerols
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
Physiological effectNot Available
DispositionNot Available
Process
Naturally occurring process
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
logP7.67ALOGPS
logP11.76ChemAxon
logS-6.8ALOGPS
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 Count40ChemAxon
Refractivity252.48 m³·mol⁻¹ChemAxon
Polarizability95.09 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+272.20830932474
DeepCCS[M-H]-269.81230932474
DeepCCS[M-2H]-302.69630932474
DeepCCS[M+Na]+278.1230932474
AllCCS[M+H]+296.132859911
AllCCS[M+H-H2O]+296.032859911
AllCCS[M+NH4]+296.232859911
AllCCS[M+Na]+296.232859911
AllCCS[M-H]-300.732859911
AllCCS[M+Na-2H]-307.832859911
AllCCS[M+HCOO]-315.632859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
PG(20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))[H][C@](O)(CO)COP(O)(=O)OC[C@@]([H])(COC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC)OC(=O)CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CC6303.9Standard polar33892256
PG(20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))[H][C@](O)(CO)COP(O)(=O)OC[C@@]([H])(COC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC)OC(=O)CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CC4999.8Standard non polar33892256
PG(20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))[H][C@](O)(CO)COP(O)(=O)OC[C@@]([H])(COC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC)OC(=O)CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CC6011.7Semi standard non polar33892256
Spectra

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - PG(20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) 10V, Positive-QTOFsplash10-004r-4177082190-ab616315e08649ad41a92019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - PG(20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) 20V, Positive-QTOFsplash10-02di-5195032320-89ae7a4cb559a554456e2019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - PG(20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) 40V, Positive-QTOFsplash10-0bvj-9077101200-e1cc119a4cc0f69ac2a02019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - PG(20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) 10V, Negative-QTOFsplash10-0udr-1149030140-aa01a526b1eb10957f062019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - PG(20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) 20V, Negative-QTOFsplash10-0ufr-7359110100-dd6d81cb4957eb26e99c2019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - PG(20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) 40V, Negative-QTOFsplash10-004i-9002000000-b6110ebfb66edd7c4b912019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - PG(20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) 10V, Negative-QTOFsplash10-0006-0000000090-33b7ed85c058fd5ce6c72021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - PG(20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) 20V, Negative-QTOFsplash10-0ufu-0009130040-31f49b7eeea52524adad2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - PG(20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) 40V, Negative-QTOFsplash10-0ufu-0109130040-993c3c7f9ff03e7127be2021-09-22Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound52926309
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents 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.