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PG(18:1(9Z)/18:1(9Z)) (YMDB01214)

Identification
YMDB IDYMDB01214
NamePG(18:1(9Z)/18:1(9Z))
SpeciesSaccharomyces cerevisiae
StrainBrewer's yeast
DescriptionPG(18:1(9Z)/18:1(9Z)) 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)/18:1(9Z)), in particular, consists of two 9Z-octadecenoyl chains at positions C-1 and C-2. 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
  • 1,2-di(9Z-octadecenoyl)-rac-glycero-3-phospho-(1'-glycerol)
  • 1,2-dioleoyl-rac-glycero-3-phosphoglycerol
  • GPG(18:1/18:1)
  • GPG(18:1n9/18:1n9)
  • GPG(18:1w9/18:1w9)
  • GPG(36:2)
  • PG(18:1/18:1)
  • PG(18:1n9/18:1n9)
  • PG(18:1w9/18:1w9)
  • PG(36:2)
  • Phosphatidylglycerol(18:1/18:1)
  • Phosphatidylglycerol(18:1n9/18:1n9)
  • Phosphatidylglycerol(18:1w9/18:1w9)
  • Phosphatidylglycerol(36:2)
  • 1,2-Di-(9Z-octadecenoyl)-sn-glycero-3-phospho-(1'-sn-glycerol)
  • 1,2-Di-[(9Z)-octadecenoyl]-sn-glycero-3-phospho-(1'-sn-glycerol)
  • 1,2-Dioleoyl-sn-3-phosphatidylglycerol
  • 1,2-Dioleoyl-sn-glycero-3-phosphoglycerol
  • PG(18:1OMEGA9/18:1OMEGA9)
  • Phosphatidylglycerol(18:1omega9/18:1omega9)
  • 1,2-Dioleoyl-sn-glycero-3-phosphoglycerol, (Z)-isomer
  • 1,2-Dioleoylphosphatidylglycerol
  • 1,2-Dioleoyl-sn-glycero-3-phospho(1-rac-glycerol)
  • 1,2-Dioleoyl-sn-glycero-3-phosphoglycerol, (R-(r*,s*))-(Z)-isomer
  • DOPG
  • Di-C18-1(C)-PG
  • PG(18:1(9Z)/18:1(9Z))
  • 1,2-di(9Z-octadecenoyl)-rac-glycero-3-phosphoglycerol
CAS number66322-31-4
WeightAverage: 775.058
Monoisotopic: 774.541085742
InChI KeyDSNRWDQKZIEDDB-SQYFZQSCSA-N
InChIInChI=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/h17-20,39-40,43-44H,3-16,21-38H2,1-2H3,(H,47,48)/b19-17-,20-18-/t39-,40+/m0/s1
IUPAC Name[(2R)-2,3-bis[(9Z)-octadec-9-enoyloxy]propoxy][(2S)-2,3-dihydroxypropoxy]phosphinic acid
Traditional IUPAC Name(2R)-2,3-bis[(9Z)-octadec-9-enoyloxy]propoxy((2S)-2,3-dihydroxypropoxy)phosphinic acid
Chemical FormulaC42H79O10P
SMILES[H][C@](O)(CO)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCC\C=C/CCCCCCCC)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
StateSolid
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility8.4e-05 g/LALOGPS
logP8.47ALOGPS
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
Polarizability93.13 ųChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular LocationsNot Available
Organoleptic PropertiesNot Available
SMPDB Pathways
Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/18:1(9Z)/18:1(11Z))PW007898 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG PathwaysNot Available
SMPDB Reactions
PGP(18:1(9Z)/18:1(9Z)) + water → phosphate + PG(18:1(9Z)/18:1(9Z))
PG(18:1(9Z)/18:1(9Z)) + CDP-DG(18:1(9Z)/18:1(11Z)) → Cytidine monophosphate + hydron + CL(18:1(9Z)/18:1(9Z)/18:1(9Z)/18:1(11Z))
KEGG ReactionsNot Available
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_3) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-056u-4161713900-0edb6e993315b6b70d87JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05xu-8294705300-166f0e559fd290f8a699JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05i9-9046322000-971789173e215398bfb5JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-01x0-0190311400-9053237cfd3ab8580783JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-003r-5390300000-584d168169663f386c1bJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9020100000-b962597174cbf3c00e0dJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0000000900-4be40cd8142c638661cbJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00f0-0190310900-bea2c111bfc5e8ef2641JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00e9-0390310900-b557bf36898428bf0f08JSpectraViewer
References
References:
  • Ejsing, C. S., Sampaio, J. L., Surendranath, V., Duchoslav, E., Ekroos, K., Klemm, R. W., Simons, K., Shevchenko, A. (2009). "Global analysis of the yeast lipidome by quantitative shotgun mass spectrometry." Proc Natl Acad Sci U S A 106:2136-2141.19174513
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID75385
HMDB IDHMDB10634
Pubchem Compound ID119120
Kegg IDNot Available
ChemSpider ID24768133
FOODB IDFDB027784
Wikipedia IDNot Available
BioCyc IDNot Available

Enzymes

Protein Details
1. Cardiolipin synthase
General function:
Involved in phosphotransferase activity, for other substituted phosphate groups
Specific function:
Catalyzes the reversible phosphatidyl group transfer from one phosphatidylglycerol molecule to another to form cardiolipin (CL) (diphosphatidylglycerol) and glycerol
Gene Name:
CRD1
Uniprot ID:
Q07560
Molecular weight:
32019.30078
Reactions
2 Phosphatidylglycerol → diphosphatidylglycerol + glycerol.
Protein Details
2. Phosphatidylglycerophosphatase GEP4, mitochondrial
General function:
Involved in phosphatidylglycerophosphatase activity
Specific function:
Phosphatidylglycerophosphatase involved in the biosynthesis of cardiolipin (CL), a unique dimeric phosphoglycerolipid predominantly present in mitochondrial membranes and which has important functions for cellular energy metabolism, mitochondrial dynamics and the initiation of apoptotic pathways. Required for the stability of respiratory chain supercomplexes and for growth at elevated temperature, in presence of ethidium bromide or in absence of prohibitins
Gene Name:
GEP4
Uniprot ID:
P38812
Molecular weight:
20944.90039
Reactions
Phosphatidylglycerophosphate + H(2)O → phosphatidylglycerol + phosphate.