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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2008-09-25 13:34:34 UTC
Update Date2022-03-07 02:51:00 UTC
HMDB IDHMDB0010618
Secondary Accession Numbers
  • HMDB10618
Metabolite Identification
Common NamePG(18:1(11Z)/18:1(11Z))
DescriptionPG(18:1(11Z)/18:1(11Z)) 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(18:1(11Z)/18:1(11Z)), in particular, consists of one chain of vaccenic acid at the C-1 position and one chain of vaccenic acid at the C-2 position. The vaccenic acid moiety is derived from butter fat and animal fat, while the vaccenic acid moiety is derived from butter fat and animal fat. 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
Data?1582752852
Synonyms
ValueSource
1,2-Di(11Z-octadecenoyl)-rac-glycero-3-phospho-(1'-glycerol)HMDB
1,2-Divaccenoyl-rac-glycero-3-phosphoglycerolHMDB
GPG(18:1/18:1)HMDB
GPG(18:1N7/18:1N7)HMDB
GPG(18:1W7/18:1W7)HMDB
GPG(36:2)HMDB
PG(18:1/18:1)HMDB
PG(18:1N7/18:1N7)HMDB
PG(18:1W7/18:1W7)HMDB
PG(36:2)HMDB
Phosphatidylglycerol(18:1/18:1)HMDB
Phosphatidylglycerol(18:1n7/18:1n7)HMDB
Phosphatidylglycerol(18:1W7/18:1W7)HMDB
Phosphatidylglycerol(36:2)HMDB
1,2-Di(11Z-octadecenoyl)-rac-glycero-3-phosphoglycerolHMDB
PG(18:1(11Z)/18:1(11Z))Lipid Annotator
Chemical FormulaC42H79O10P
Average Molecular Weight775.058
Monoisotopic Molecular Weight774.541085742
IUPAC Name[(2R)-2,3-bis[(11Z)-octadec-11-enoyloxy]propoxy][(2S)-2,3-dihydroxypropoxy]phosphinic acid
Traditional Name(2R)-2,3-bis[(11Z)-octadec-11-enoyloxy]propoxy((2S)-2,3-dihydroxypropoxy)phosphinic acid
CAS Registry NumberNot Available
SMILES
[H][C@](O)(CO)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCCC\C=C/CCCCCC)OC(=O)CCCCCCCCC\C=C/CCCCCC
InChI Identifier
InChI=1S/C42H79O10P/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31-33-41(45)49-37-40(38-51-53(47,48)50-36-39(44)35-43)52-42(46)34-32-30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h13-16,39-40,43-44H,3-12,17-38H2,1-2H3,(H,47,48)/b15-13-,16-14-/t39-,40+/m0/s1
InChI KeySOLXJHKVRWSNJX-HKFASTTNSA-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. 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.
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 DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
Biological locationSource
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
Water Solubility8.5e-05 g/LALOGPS
logP8.46ALOGPS
logP11.99ChemAxon
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
Refractivity215.95 m³·mol⁻¹ChemAxon
Polarizability92.96 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]+291.15831661259
DarkChem[M-H]-275.14731661259
DeepCCS[M+H]+288.90330932474
DeepCCS[M-H]-286.92630932474
DeepCCS[M-2H]-320.16830932474
DeepCCS[M+Na]+294.81630932474
AllCCS[M+H]+288.632859911
AllCCS[M+H-H2O]+288.632859911
AllCCS[M+NH4]+288.632859911
AllCCS[M+Na]+288.532859911
AllCCS[M-H]-277.132859911
AllCCS[M+Na-2H]-283.632859911
AllCCS[M+HCOO]-290.732859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
PG(18:1(11Z)/18:1(11Z))[H][C@](O)(CO)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCCC\C=C/CCCCCC)OC(=O)CCCCCCCCC\C=C/CCCCCC4829.8Standard polar33892256
PG(18:1(11Z)/18:1(11Z))[H][C@](O)(CO)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCCC\C=C/CCCCCC)OC(=O)CCCCCCCCC\C=C/CCCCCC4655.6Standard non polar33892256
PG(18:1(11Z)/18:1(11Z))[H][C@](O)(CO)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCCC\C=C/CCCCCC)OC(=O)CCCCCCCCC\C=C/CCCCCC5461.8Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - PG(18:1(11Z)/18:1(11Z)) GC-MS (TMS_1_1) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - PG(18:1(11Z)/18:1(11Z)) GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - PG(18:1(11Z)/18:1(11Z)) GC-MS (TMS_1_3) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - PG(18:1(11Z)/18:1(11Z)) GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - PG(18:1(11Z)/18:1(11Z)) GC-MS (TBDMS_1_2) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - PG(18:1(11Z)/18:1(11Z)) GC-MS (TBDMS_1_3) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - PG(18:1(11Z)/18:1(11Z)) 10V, Positive-QTOFsplash10-056u-4161713900-aa8267363ecc2159da9c2015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - PG(18:1(11Z)/18:1(11Z)) 20V, Positive-QTOFsplash10-05xu-8294605300-633be60513fbf15f389c2015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - PG(18:1(11Z)/18:1(11Z)) 40V, Positive-QTOFsplash10-05i9-9045323000-1abb23a1728841f94f072015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - PG(18:1(11Z)/18:1(11Z)) 10V, Negative-QTOFsplash10-01x0-0190311400-9053237cfd3ab85807832015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - PG(18:1(11Z)/18:1(11Z)) 20V, Negative-QTOFsplash10-003r-5390300000-584d168169663f386c1b2015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - PG(18:1(11Z)/18:1(11Z)) 40V, Negative-QTOFsplash10-004i-9020100000-b962597174cbf3c00e0d2015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - PG(18:1(11Z)/18:1(11Z)) 10V, Negative-QTOFsplash10-00di-0000000900-4be40cd8142c638661cb2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - PG(18:1(11Z)/18:1(11Z)) 20V, Negative-QTOFsplash10-00f0-0190310900-bea2c111bfc5e8ef26412021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - PG(18:1(11Z)/18:1(11Z)) 40V, Negative-QTOFsplash10-00e9-0390310900-b557bf36898428bf0f082021-09-22Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
  • Feces
Tissue Locations
  • All Tissues
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.194 +/- 0.010 uMAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedNewborn (0-30 days old)Not Specified
Premature neonates
details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB027768
KNApSAcK IDNot Available
Chemspider ID24768117
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound53480617
PDB IDNot Available
ChEBI ID89273
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.

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