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Identification
YMDB IDYMDB01211
NamePG(16:1(9Z)/16:1(9Z))
SpeciesSaccharomyces cerevisiae
StrainBrewer's yeast
DescriptionPG(16:1(9Z)/16:1(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(16:1(9Z)/16:1(9Z)), in particular, consists of two 9Z-hexadecenoyl 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
Synonyms
  • 1,2-di(9Z-hexadecenoyl)-rac-glycero-3-phospho-(1'-glycerol)
  • 1,2-dipalmitoleoyl-rac-glycero-3-phosphoglycerol
  • GPG(16:1/16:1)
  • GPG(16:1n7/16:1n7)
  • GPG(16:1w7/16:1w7)
  • GPG(32:2)
  • PG(16:1/16:1)
  • PG(16:1n7/16:1n7)
  • PG(16:1w7/16:1w7)
  • PG(32:2)
  • Phosphatidylglycerol(16:1/16:1)
  • Phosphatidylglycerol(16:1n7/16:1n7)
  • Phosphatidylglycerol(16:1w7/16:1w7)
  • Phosphatidylglycerol(32:2)
  • 1,2-Di(9Z-hexadecenoyl)-rac-glycero-3-phosphoglycerol
  • PG(16:1(9Z)/16:1(9Z))
CAS number66322-31-4
WeightAverage: 718.95
Monoisotopic: 718.478485484
InChI KeyGHQNERCMPIDAAU-NWHZUZAFSA-N
InChIInChI=1S/C38H71O10P/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-37(41)45-33-36(34-47-49(43,44)46-32-35(40)31-39)48-38(42)30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h13-16,35-36,39-40H,3-12,17-34H2,1-2H3,(H,43,44)/b15-13-,16-14-/t35-,36+/m0/s1
IUPAC Name[(2R)-2,3-bis[(9Z)-hexadec-9-enoyloxy]propoxy][(2S)-2,3-dihydroxypropoxy]phosphinic acid
Traditional IUPAC Name(2R)-2,3-bis[(9Z)-hexadec-9-enoyloxy]propoxy((2S)-2,3-dihydroxypropoxy)phosphinic acid
Chemical FormulaC38H71O10P
SMILES[H][C@](O)(CO)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCC\C=C/CCCCCC)OC(=O)CCCCCCC\C=C/CCCCCC
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 Solubility0.00015 g/LALOGPS
logP7.53ALOGPS
logP10.21ChemAxon
logS-6.7ALOGPS
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 Count38ChemAxon
Refractivity197.54 m³·mol⁻¹ChemAxon
Polarizability84.58 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(16:1(9Z)/16:1(9Z)/16:1(11Z)/16:1(11Z))PW012836 ThumbThumb?image type=greyscaleThumb?image type=simple
Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/16:1(11Z)/16:1(9Z))PW012837 ThumbThumb?image type=greyscaleThumb?image type=simple
Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/16:1(11Z)/18:0)PW012838 ThumbThumb?image type=greyscaleThumb?image type=simple
Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/16:1(11Z)/18:1(11Z))PW012839 ThumbThumb?image type=greyscaleThumb?image type=simple
Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/16:1(11Z)/18:1(9Z))PW012840 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG PathwaysNot Available
SMPDB Reactions
PGP(16:1(9Z)/16:1(9Z)) + waterphosphate + PG(16:1(9Z)/16:1(9Z))
PG(16:1(9Z)/16:1(9Z)) + CDP-DG(16:1(11Z)/16:1(11Z))Cytidine monophosphate + hydron + CL(16:1(9Z)/16:1(9Z)/16:1(11Z)/16:1(11Z))
PG(16:1(9Z)/16:1(9Z)) + CDP-DG(16:1(11Z)/16:1(9Z))Cytidine monophosphate + hydron + CL(16:1(9Z)/16:1(9Z)/16:1(11Z)/16:1(9Z))
PG(16:1(9Z)/16:1(9Z)) + CDP-DG(16:1(11Z)/18:0)Cytidine monophosphate + hydron + CL(16:1(9Z)/16:1(9Z)/16:1(11Z)/18:0)
PG(16:1(9Z)/16:1(9Z)) + CDP-DG(16:1(11Z)/18:1(11Z))Cytidine monophosphate + hydron + CL(16:1(9Z)/16:1(9Z)/16:1(11Z)/18:1(11Z))
KEGG ReactionsNot Available
Concentrations
Intracellular Concentrations
Intracellular ConcentrationSubstrateGrowth ConditionsStrainCitation
14250 ± 4300 umol/L SD media with 2% raffinose37 oCBY4741PMID: 19174513
Conversion Details Here
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0gb9-5270921800-f4e2b38856bc1e6f4706JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0fvs-7391522200-c7937fce4dd0c2ae2a96JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a6s-9153231000-f6cd56307ab34ea34152JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udr-0190402200-1ed8e688ab88aec28e41JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0ug0-5291201000-59b06416b6afbd41045eJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9020100000-93f22c469a98f24b9da2JSpectraViewer
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 IDNot Available
HMDB IDHMDB10586
Pubchem Compound ID119120
Kegg IDNot Available
ChemSpider ID24768085
FOODB IDFDB027736
Wikipedia IDNot Available
BioCyc IDNot Available

Enzymes

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.
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.