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PG(18:1(9Z)/18:0) (M2MDB006396)

Record Information
Version2.0
Creation Date2015-09-08 18:59:55 -0600
Update Date2015-12-09 12:08:17 -0700
Secondary Accession Numbers
  • ECMDB24279
Identification
Name:PG(18:1(9Z)/18:0)
DescriptionPG(18:1(9Z)/18:0) is a phosphatidylglycerol. Phosphatidylglycerols consist of a glycerol 3-phosphate backbone esterified to either saturated or unsaturated fatty acids on carbons 1 and 2. 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. PG(18:1(9Z)/18:0), in particular, consists of one 9Z-octadecenoyl chain to the C-1 atom, and one octadecanoyl to the C-2 atom. In E. coli glycerophospholipid metabolism, phosphatidylglycerol is formed from phosphatidic acid (1,2-diacyl-sn-glycerol 3-phosphate) by a sequence of enzymatic reactions that proceeds via two intermediates, cytidine diphosphate diacylglycerol (CDP-diacylglycerol) and phosphatidylglycerophosphate (PGP, a phosphorylated phosphatidylglycerol). Phosphatidylglycerols, along with CDP-diacylglycerol, also serve as precursor molecules for the synthesis of cardiolipin, a phospholipid found in membranes.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms:
ValueSource
1-Stearoyl-2-oleoyl-sn-glycero-3-phospho-(1'-sn-glycerol)ChEBI
1-Stearoyl-2-oleoyl-sn-glycero-3-phosphoglycerolChEBI
2-Oleoyl-1-stearoyl-sn-glycero-3-phospho-(1'-sn-glycerol)ChEBI
GPG(18:0/18:1)ChEBI
GPG(18:0/18:1OMEGA9)ChEBI
GPG(36:1)ChEBI
PG(18:0/18:1)ChEBI
PG(18:0/18:1OMEGA9)ChEBI
PG(36:1)ChEBI
Phosphatidylglycerol(18:0/18:1)ChEBI
Phosphatidylglycerol(18:0/18:1omega9)ChEBI
Phosphatidylglycerol(36:1)ChEBI
1-Octadecanoyl-2-(9Z-octadecenoyl)-sn-glycero-3-phospho-(1'-glycerol)HMDB
GPG(18:0/18:1N9)HMDB
GPG(18:0/18:1W9)HMDB
PG(18:0/18:1N9)HMDB
PG(18:0/18:1W9)HMDB
Phosphatidylglycerol(18:0/18:1n9)HMDB
Phosphatidylglycerol(18:0/18:1W9)HMDB
1-Octadecanoyl-2-(9Z-octadecenoyl)-sn-glycero-3-phosphoglycerolHMDB
PG(18:0/18:1(9Z))Lipid Annotator
Chemical Formula:C42H81O10P
Weight:Average: 777.0603
Monoisotopic: 776.556735324
InChI Key:ZEFGRNLJASLRBZ-QIJYXWHJSA-N
InChI:InChI=1S/C42H81O10P/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/h18,20,39-40,43-44H,3-17,19,21-38H2,1-2H3,(H,47,48)/b20-18-/t39-,40+/m0/s1
CAS number:Not Available
IUPAC Name:[(2S)-2,3-dihydroxypropoxy][(2R)-2-[(9Z)-octadec-9-enoyloxy]-3-(octadecanoyloxy)propoxy]phosphinic acid
Traditional IUPAC Name:(2S)-2,3-dihydroxypropoxy((2R)-2-[(9Z)-octadec-9-enoyloxy]-3-(octadecanoyloxy)propoxy)phosphinic acid
SMILES:[H][C@](O)(CO)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCCCCCCCCCCC)OC(=O)CCCCCCC\C=C/CCCCCCCC
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 Descriptors
Physical Properties
State:Not Available
Charge:-1
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility8.5e-05 g/LALOGPS
logP8.58ALOGPS
logP12.35ChemAxon
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 Count43ChemAxon
Refractivity214.83 m³·mol⁻¹ChemAxon
Polarizability94.62 ųChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Membrane
Reactions:
SMPDB Pathways:Not Available
KEGG Pathways:Not Available
EcoCyc Pathways:Not Available
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_3) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-056r-4162702900-15fabc4779f8137ffd9eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ar0-8294504300-a977932ef4abea0301deView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a6r-9045312000-a32d542c90aafda93703View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00o0-0190310400-f5df4a1930de90b74930View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00o0-5290200100-5036a9dc7e3c656ea737View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0059-9020100000-ec1b29db666a398da987View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0000000900-1a681c2a3ed3bb343905View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-003r-0090310400-9b147c90eeab5c860848View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-003r-0190310400-8f6a1bac7e3458bae88dView in MoNA
References
References:
  • Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
  • Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
  • Uniprot Consortium (2012). "Reorganizing the protein space at the Universal Protein Resource (UniProt)." Nucleic Acids Res 40:D71-D75. Pubmed: 22102590
  • Yurtsever D. (2007). Fatty acid methyl ester profiling of Enterococcus and Esherichia coli for microbial source tracking. M.sc. Thesis. Villanova University: U.S.A
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI ID73242
HMDB IDHMDB0010604
Pubchem Compound ID24779551
Kegg IDNot Available
ChemSpider ID24768103
Wikipedia IDNot Available
BioCyc IDNot Available