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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2010-05-13 16:10:09 UTC
Update Date2022-11-30 19:04:14 UTC
HMDB IDHMDB0013564
Secondary Accession Numbers
  • HMDB13564
Metabolite Identification
Common NamePGP(18:3(6Z,9Z,12Z)/18:0)
DescriptionPGP(18:3(6Z,9Z,12Z)/18:0) is a phosphatidylglycerolphosphate or glycerophospholipid (PGP or GP). It is a glycerophospholipid in which a phosphoglycerol moiety occupies a glycerol substitution site followed by another phosphate moiety. 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. PGP(18:3(6Z,9Z,12Z)/18:0), in particular, consists of one chain of g-linolenic acid at the C-1 position and one chain of stearic acid at the C-2 position. The g-linolenic acid moiety is derived from animal fats, while the stearic acid moiety is derived from animal fats, coco butter and sesame oil. Phosphatidylglycerolphosphate 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 Phosphatidylglycerolphosphate increases during fetal development. Phosphatidylglycerolphosphate 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. PGPs have a net charge of -1 at physiological pH and are found in high concentration in mitochondrial membranes and as components of pulmonary surfactant. PGP also serves as a precursor for the synthesis of cardiolipin. PGP is synthesized from CDP-diacylglycerol and glycerol-3-phosphate.
Structure
Data?1582753133
Synonyms
ValueSource
PGP(18:3(6Z,9Z,12Z)/18:0)Lipid Annotator
3-sn-phosphatidyl-1'-sn-glycerol 3'-phosphoric acidLipid Annotator, HMDB
PGP(36:3)Lipid Annotator, HMDB
1-g-linolenoyl-2-stearoyl-sn-glycero-3-phospho-(1'-sn-glycerol-3'-phosphate)Lipid Annotator, HMDB
1-(6Z,9Z,12Z-octadecatrienoyl)-2-octadecanoyl-sn-glycero-3-phospho-(1'-sn-glycerol-3'-phosphate)Lipid Annotator, HMDB
PGP(18:3/18:0)Lipid Annotator, HMDB
1-gamma-Linolenoyl-2-stearoyl-sn-glycero-3-phospho-(1'-sn-glycerol-3'-phosphate)HMDB
PGP(18:3n6/18:0)HMDB
PGP(18:3W6/18:0)HMDB
[(2S)-2-Hydroxy-3-({hydroxy[(2R)-3-[(6Z,9Z,12Z)-octadeca-6,9,12-trienoyloxy]-2-(octadecanoyloxy)propoxy]phosphoryl}oxy)propoxy]phosphonateGenerator
Chemical FormulaC42H78O13P2
Average Molecular Weight853.0084
Monoisotopic Molecular Weight852.491765606
IUPAC Name[(2S)-2-hydroxy-3-({hydroxy[(2R)-3-[(6Z,9Z,12Z)-octadeca-6,9,12-trienoyloxy]-2-(octadecanoyloxy)propoxy]phosphoryl}oxy)propoxy]phosphonic acid
Traditional Name(2S)-2-hydroxy-3-{[hydroxy((2R)-3-[(6Z,9Z,12Z)-octadeca-6,9,12-trienoyloxy]-2-(octadecanoyloxy)propoxy)phosphoryl]oxy}propoxyphosphonic acid
CAS Registry NumberNot Available
SMILES
CCCCCCCCCCCCCCCCCC(=O)O[C@]([H])(COC(=O)CCCC\C=C/C\C=C/C\C=C/CCCCC)COP(=O)(O)OC[C@@]([H])(O)COP(=O)(O)O
InChI Identifier
InChI=1S/C42H78O13P2/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31-33-41(44)51-37-40(38-54-57(49,50)53-36-39(43)35-52-56(46,47)48)55-42(45)34-32-30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h11,13,17,19,23,25,39-40,43H,3-10,12,14-16,18,20-22,24,26-38H2,1-2H3,(H,49,50)(H2,46,47,48)/b13-11-,19-17-,25-23-/t39-,40+/m0/s1
InChI KeyBUTGJPALEJEZBL-VLJMGXKQSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as phosphatidylglycerophosphates. These are glycerophosphoglycerophosphates 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 ClassGlycerophosphoglycerophosphates
Direct ParentPhosphatidylglycerophosphates
Alternative Parents
Substituents
  • Diacylglycerophosphoglycerophosphate
  • Sn-glycerol-3-phosphate
  • Fatty acid ester
  • Monoalkyl phosphate
  • Dialkyl phosphate
  • Dicarboxylic acid or derivatives
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Alkyl phosphate
  • Fatty acyl
  • Secondary alcohol
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Organooxygen compound
  • Organic oxide
  • Organic oxygen compound
  • Alcohol
  • Carbonyl group
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
Physiological effect
Disposition
Process
Role
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
Water Solubility0.00064 g/LALOGPS
logP7.43ALOGPS
logP11.51ChemAxon
logS-6.1ALOGPS
pKa (Strongest Acidic)1.35ChemAxon
pKa (Strongest Basic)-3.4ChemAxon
Physiological Charge-3ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area195.35 ŲChemAxon
Rotatable Bond Count43ChemAxon
Refractivity227.94 m³·mol⁻¹ChemAxon
Polarizability95.5 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
DarkChem[M+H]+310.52231661259
DarkChem[M-H]-296.35131661259
DeepCCS[M+H]+274.06730932474
DeepCCS[M-H]-272.24230932474
DeepCCS[M-2H]-305.48130932474
DeepCCS[M+Na]+279.79230932474
AllCCS[M+H]+296.732859911
AllCCS[M+H-H2O]+296.832859911
AllCCS[M+NH4]+296.532859911
AllCCS[M+Na]+296.532859911
AllCCS[M-H]-288.732859911
AllCCS[M+Na-2H]-295.532859911
AllCCS[M+HCOO]-302.932859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
PGP(18:3(6Z,9Z,12Z)/18:0)CCCCCCCCCCCCCCCCCC(=O)O[C@]([H])(COC(=O)CCCC\C=C/C\C=C/C\C=C/CCCCC)COP(=O)(O)OC[C@@]([H])(O)COP(=O)(O)O5399.5Standard polar33892256
PGP(18:3(6Z,9Z,12Z)/18:0)CCCCCCCCCCCCCCCCCC(=O)O[C@]([H])(COC(=O)CCCC\C=C/C\C=C/C\C=C/CCCCC)COP(=O)(O)OC[C@@]([H])(O)COP(=O)(O)O4835.0Standard non polar33892256
PGP(18:3(6Z,9Z,12Z)/18:0)CCCCCCCCCCCCCCCCCC(=O)O[C@]([H])(COC(=O)CCCC\C=C/C\C=C/C\C=C/CCCCC)COP(=O)(O)OC[C@@]([H])(O)COP(=O)(O)O5882.4Semi standard non polar33892256
Spectra

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - PGP(18:3(6Z,9Z,12Z)/18:0) 10V, Positive-QTOFsplash10-0ldr-1290062150-45457accc616ed6cf2102017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - PGP(18:3(6Z,9Z,12Z)/18:0) 20V, Positive-QTOFsplash10-014i-2292022110-96c41ab3789558bca7312017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - PGP(18:3(6Z,9Z,12Z)/18:0) 40V, Positive-QTOFsplash10-0aor-9485133300-8e263f10b4a11beea7f62017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - PGP(18:3(6Z,9Z,12Z)/18:0) 10V, Negative-QTOFsplash10-004i-3090020020-9b067dab4ffdfd21b8db2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - PGP(18:3(6Z,9Z,12Z)/18:0) 20V, Negative-QTOFsplash10-004i-9050000000-add0af5aeb5e5f1c27572017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - PGP(18:3(6Z,9Z,12Z)/18:0) 40V, Negative-QTOFsplash10-004i-9010000000-66115fd2c27315098ce32017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - PGP(18:3(6Z,9Z,12Z)/18:0) 10V, Positive-QTOFsplash10-0udi-3112009880-35327b13987a0bac56be2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - PGP(18:3(6Z,9Z,12Z)/18:0) 20V, Positive-QTOFsplash10-0a4i-1401009800-d1248054642c87508cbc2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - PGP(18:3(6Z,9Z,12Z)/18:0) 40V, Positive-QTOFsplash10-0079-0431900000-06505615cf451e02f53c2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - PGP(18:3(6Z,9Z,12Z)/18:0) 10V, Negative-QTOFsplash10-0udi-0000000090-7c6ca3412dafd58f3fd02021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - PGP(18:3(6Z,9Z,12Z)/18:0) 20V, Negative-QTOFsplash10-0ugj-9080171050-e9cdfb16f7a1a231a09b2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - PGP(18:3(6Z,9Z,12Z)/18:0) 40V, Negative-QTOFsplash10-004i-7093110000-f56b42274ccd37678abd2021-09-25Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen LocationsNot Available
Tissue Locations
  • All Tissues
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 IDFDB029564
KNApSAcK IDNot Available
Chemspider ID35032741
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound53481882
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.