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Identification
YMDB IDYMDB14944
NamePG(16:0/18:1(11Z))
SpeciesSaccharomyces cerevisiae
StrainBrewer's yeast
DescriptionPG(16:0/18:1(11Z)) 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(16:0/18:1(11Z)), in particular, consists of one hexadecanoyl chain to the C-1 atom, and one 11Z-octadecenoyl 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
Synonyms
  • 1-Hexadecanoyl-2-(11Z-octadecenoyl)-sn-glycero-3-phospho-(1'-glycerol)
  • 1-Palmitoyl-2-vaccenoyl-sn-glycero-3-phosphoglycerol
  • GPG(16:0/18:1)
  • GPG(16:0/18:1N7)
  • GPG(16:0/18:1W7)
  • GPG(34:1)
  • PG(16:0/18:1)
  • PG(16:0/18:1N7)
  • PG(16:0/18:1W7)
  • PG(34:1)
  • Phosphatidylglycerol(16:0/18:1)
  • Phosphatidylglycerol(16:0/18:1n7)
  • Phosphatidylglycerol(16:0/18:1W7)
  • Phosphatidylglycerol(34:1)
  • 1-Hexadecanoyl-2-(11Z-octadecenoyl)-sn-glycero-3-phosphoglycerol
  • 1-Palmitoyl-2-cis-vaccenoyl-sn-glycero-3-phospho-(1'-glycerol)
  • 1-Palmitoyl-2-cis-vaccenoyl-sn-glycero-3-phospho-(1’-glycerol)
  • 1-Palmitoyl-2-cis-vaccenoyl-sn-glycero-3-phosphoglycerol
  • 1-Palmitoyl-2-oleoyl-GPG
  • Phosphatidylglycerol(16:0/18:1(11Z))
  • 1-Palmitoyl-2-cis-vaccenoyl-GPG
  • GPG(16:0/18:1(11Z))
  • PG(16:0/18:1(11Z))
CAS numberNot Available
WeightAverage: 749.0071
Monoisotopic: 748.525435196
InChI KeyADYWCMPUNIVOEA-GPJPVTGXSA-N
InChIInChI=1S/C40H77O10P/c1-3-5-7-9-11-13-15-17-18-20-22-24-26-28-30-32-40(44)50-38(36-49-51(45,46)48-34-37(42)33-41)35-47-39(43)31-29-27-25-23-21-19-16-14-12-10-8-6-4-2/h13,15,37-38,41-42H,3-12,14,16-36H2,1-2H3,(H,45,46)/b15-13-/t37-,38+/m0/s1
IUPAC Name[(2S)-2,3-dihydroxypropoxy][(2R)-3-(hexadecanoyloxy)-2-[(11Z)-octadec-11-enoyloxy]propoxy]phosphinic acid
Traditional IUPAC Name(2S)-2,3-dihydroxypropoxy(2R)-3-(hexadecanoyloxy)-2-[(11Z)-octadec-11-enoyloxy]propoxyphosphinic acid
Chemical FormulaC40H77O10P
SMILES[H][C@](O)(CO)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCCCCCCCCC)OC(=O)CCCCCCCCC\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 Solubility0.0001 g/LALOGPS
logP8.16ALOGPS
logP11.46ChemAxon
logS-6.9ALOGPS
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 Count41ChemAxon
Refractivity205.63 m³·mol⁻¹ChemAxon
Polarizability90.5 ųChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • Mitochondrion membrane
Organoleptic PropertiesNot Available
SMPDB Pathways
Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/16:0/18:1(11Z))PW012601 ThumbThumb?image type=greyscaleThumb?image type=simple
Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/16:0/18:1(9Z))PW012602 ThumbThumb?image type=greyscaleThumb?image type=simple
Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/18:1(11Z)/18:1(11Z))PW012603 ThumbThumb?image type=greyscaleThumb?image type=simple
Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/18:1(11Z)/18:1(9Z))PW012604 ThumbThumb?image type=greyscaleThumb?image type=simple
Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/18:1(11Z)/20:0)PW012605 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG PathwaysNot Available
SMPDB Reactions
PG(16:0/18:1(11Z)) + CDP-DG(18:1(11Z)/20:0)Cytidine monophosphate + hydron + CL(16:0/18:1(11Z)/18:1(11Z)/20:0)
PG(16:0/18:1(11Z)) + CDP-DG(18:1(11Z)/20:1(11Z))Cytidine monophosphate + hydron + CL(16:0/18:1(11Z)/18:1(11Z)/20:1(11Z))
PG(16:0/18:1(11Z)) + CDP-DG(18:1(11Z)/20:1(13Z))Cytidine monophosphate + hydron + CL(16:0/18:1(11Z)/18:1(11Z)/20:1(13Z))
PG(16:0/18:1(11Z)) + CDP-DG(18:1(9Z)/18:1(11Z))Cytidine monophosphate + hydron + CL(16:0/18:1(11Z)/18:1(9Z)/18:1(11Z))
PG(16:0/18:1(11Z)) + CDP-DG(18:1(9Z)/18:1(9Z))Cytidine monophosphate + hydron + CL(16:0/18:1(11Z)/18:1(9Z)/18:1(9Z))
KEGG ReactionsNot Available
Concentrations
Intracellular Concentrations
Intracellular ConcentrationSubstrateGrowth ConditionsStrainCitation
5750 ± 8125 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, Positivesplash10-017s-3190510500-a232a0e6b31e206456a5JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00p0-3291211100-ce1f407ae16906efc250JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0bvi-8193120000-88875c045da848cb0c46JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a5j-0190200200-a2eadc8237be8cb5a4e6JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0adr-4290100000-2968fa6dd408cb021628JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9030100000-e323076807b814672f5eJSpectraViewer
References
References:
  • Rattray JB, Schibeci A, Kidby DK. (1975). "Lipids of yeasts." Bacteriol Rev. 1975 Sep;39(3):197-231.240350
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID44946
HMDB IDHMDB0010573
Pubchem Compound ID5289145
Kegg IDNot Available
ChemSpider ID4451166
FOODB IDFDB027723
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.