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PG(16:1(11Z)/16:1(11Z)) (YMDB14970)

Identification
YMDB IDYMDB14970
NamePG(16:1(11Z)/16:1(11Z))
SpeciesSaccharomyces cerevisiae
StrainBrewer's yeast
DescriptionPG(16:1(11Z)/16:1(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(16:1(11Z)/16:1(11Z)), in particular, consists of two 11Z-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
MOLSDFPDBSMILESInChI
SynonymsNot Available
CAS numberNot Available
WeightAverage: 718.95
Monoisotopic: 718.478485484
InChI KeyVQPXLARVQGVXLS-RCISCIBQSA-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/h9-12,35-36,39-40H,3-8,13-34H2,1-2H3,(H,43,44)/b11-9-,12-10-/t35-,36+/m0/s1
IUPAC Name[(2R)-2,3-bis[(11Z)-hexadec-11-enoyloxy]propoxy][(2S)-2,3-dihydroxypropoxy]phosphinic acid
Traditional IUPAC Name(2R)-2,3-bis[(11Z)-hexadec-11-enoyloxy]propoxy((2S)-2,3-dihydroxypropoxy)phosphinic acid
Chemical FormulaC38H71O10P
SMILES[H][C@](O)(CO)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCCC\C=C/CCCC)OC(=O)CCCCCCCCC\C=C/CCCC
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
  • Dialkyl phosphate
  • Fatty acid ester
  • Fatty acyl
  • Alkyl phosphate
  • Phosphoric acid ester
  • Organic phosphoric acid derivative
  • Dicarboxylic acid or derivatives
  • Secondary alcohol
  • Carboxylic acid ester
  • 1,2-diol
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Physical Properties
StateSolid
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility0.00015 g/LALOGPS
logP7.52ALOGPS
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
Polarizability84.86 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(16:1(11Z)/16:1(11Z)/16:1(11Z)/16:1(11Z))PW012630 ThumbThumb?image type=greyscaleThumb?image type=simple
Cardiolipin Biosynthesis CL(16:1(11Z)/16:1(11Z)/16:1(11Z)/16:1(9Z))PW012631 ThumbThumb?image type=greyscaleThumb?image type=simple
Cardiolipin Biosynthesis CL(16:1(11Z)/16:1(11Z)/16:1(11Z)/18:0)PW012632 ThumbThumb?image type=greyscaleThumb?image type=simple
Cardiolipin Biosynthesis CL(16:1(11Z)/16:1(11Z)/16:1(11Z)/18:1(11Z))PW012633 ThumbThumb?image type=greyscaleThumb?image type=simple
Cardiolipin Biosynthesis CL(16:1(11Z)/16:1(11Z)/16:1(11Z)/18:1(9Z))PW012634 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG PathwaysNot Available
SMPDB Reactions
PG(16:1(11Z)/16:1(11Z)) + CDP-DG(18:1(9Z)/20:1(13Z)) → Cytidine monophosphate + hydron + CL(16:1(11Z)/16:1(11Z)/18:1(9Z)/20:1(13Z))
PG(16:1(11Z)/16:1(11Z)) + CDP-DG(18:1(9Z)/22:0) → Cytidine monophosphate + hydron + CL(16:1(11Z)/16:1(11Z)/18:1(9Z)/22:0)
PG(16:1(11Z)/16:1(11Z)) + CDP-DG(16:0/16:0) → Cytidine monophosphate + hydron + CL(16:1(11Z)/16:1(11Z)/18:1(9Z)/22:1(11Z))
PG(16:1(11Z)/16:1(11Z)) + CDP-DG(18:1(9Z)/22:1(9Z)) → Cytidine monophosphate + hydron + CL(16:1(11Z)/16:1(11Z)/18:1(9Z)/22:1(9Z))
PG(16:1(11Z)/16:1(11Z)) + CDP-DG(20:0/20:1(11Z)) → Cytidine monophosphate + hydron + CL(16:1(11Z)/16:1(11Z)/20:0/20:1(11Z))
KEGG ReactionsNot Available
Concentrations
Intracellular Concentrations
Intracellular ConcentrationSubstrateGrowth ConditionsStrainCitation
14750 ± 2150 umol/L SD media with 2% raffinose24 oCBY4741PMID: 19174513
14250 ± 4300 umol/L SD media with 2% raffinose37 oCBY4741PMID: 19174513
Conversion Details Here
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0091300000-0e87f1da18ebe82b5c1fJSpectraViewer
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 IDNot Available
HMDB IDNot Available
Pubchem Compound IDNot Available
Kegg IDNot Available
ChemSpider IDNot Available
FOODB IDNot Available
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.