PGP(23:1(9Z)/25:1(11Z)) (YMDB14685)

Identification
YMDB IDYMDB14685
NamePGP(23:1(9Z)/25:1(11Z))
SpeciesSaccharomyces cerevisiae
StrainBrewer's yeast
DescriptionPGP(23:1(9Z)/25:1(11Z)) belongs to the class of glycerophosphoglycerophosphates, also called phosphatidylglycerophosphates (PGPs). These lipids contain a common glycerophosphate skeleton linked to at least one fatty acyl chain and a glycero-3-phosphate moiety. As is the case with diacylglycerols, phosphatidylglycerophosphates can have many different combinations of fatty acids of varying lengths and saturation attached to the C-1 and C-2 positions. PGP(23:1(9Z)/25:1(11Z)), in particular, consists of one 9Z-tricosanoyl chain to the C-1 atom, and one 11Z-pentacosanoyl to the C-2 atom. In E. coli, PGPs can be found in the cytoplasmic membrane. The are synthesized by the addition of glycerol 3-phosphate to a CDP-diacylglycerol. In turn, PGPs are dephosphorylated to Phosphatidylglycerols (PGs) by the enzyme Phosphatidylglycerophosphatase.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
  • [(2S)-2-Hydroxy-3-({hydroxy[(2R)-2-[(11Z)-pentacos-11-enoyloxy]-3-[(9Z)-tricos-9-enoyloxy]propoxy]phosphoryl}oxy)propoxy]phosphonate
CAS numberNot Available
WeightAverage: 1023.361
Monoisotopic: 1022.695217405
InChI KeyXNROHJJJRDBNKU-IOUDBUSZSA-N
InChIInChI=1S/C54H104O13P2/c1-3-5-7-9-11-13-15-17-19-21-23-25-26-28-30-32-34-36-38-40-42-44-46-54(57)67-52(50-66-69(61,62)65-48-51(55)47-64-68(58,59)60)49-63-53(56)45-43-41-39-37-35-33-31-29-27-24-22-20-18-16-14-12-10-8-6-4-2/h26,28-29,31,51-52,55H,3-25,27,30,32-50H2,1-2H3,(H,61,62)(H2,58,59,60)/b28-26-,31-29-/t51-,52+/m0/s1
IUPAC Name[(2S)-2-hydroxy-3-({hydroxy[(2R)-2-[(11Z)-pentacos-11-enoyloxy]-3-[(9Z)-tricos-9-enoyloxy]propoxy]phosphoryl}oxy)propoxy]phosphonic acid
Traditional IUPAC Name(2S)-2-hydroxy-3-{[hydroxy((2R)-2-[(11Z)-pentacos-11-enoyloxy]-3-[(9Z)-tricos-9-enoyloxy]propoxy)phosphoryl]oxy}propoxyphosphonic acid
Chemical FormulaC54H104O13P2
SMILES[H][C@](O)(COP(O)(O)=O)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCC\C=C/CCCCCCCCCCCCC)OC(=O)CCCCCCCCC\C=C/CCCCCCCCCCCCC
Chemical Taxonomy
Description belongs to the class of organic compounds known as phosphatidylglycerophosphates. These are glycerophosphoglycerophosphates in which two fatty acids are bonded to the 1-glycerol moiety through ester linkages.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassGlycerophospholipids
Sub ClassGlycerophosphoglycerophosphates
Direct ParentPhosphatidylglycerophosphates
Alternative Parents
Substituents
  • Diacylglycerophosphoglycerophosphate
  • Sn-glycerol-3-phosphate
  • Dialkyl phosphate
  • Monoalkyl phosphate
  • Fatty acid ester
  • Fatty acyl
  • Alkyl phosphate
  • Phosphoric acid ester
  • Organic phosphoric acid derivative
  • Dicarboxylic acid or derivatives
  • Secondary alcohol
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • 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
logP9.19ALOGPS
logP17.2ChemAxon
logS-6.8ALOGPS
pKa (Strongest Acidic)1.35ChemAxon
pKa (Strongest Basic)-3.4ChemAxon
Physiological Charge-3ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area195.35 ŲChemAxon
Rotatable Bond Count56ChemAxon
Refractivity282.03 m³·mol⁻¹ChemAxon
Polarizability123.91 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 PathwaysNot Available
KEGG PathwaysNot Available
SMPDB ReactionsNot Available
KEGG ReactionsNot Available
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0c00-7219004111-775839e09f89aa43c957JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0bti-4219002111-3a586eefdd9a44607388JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-7219200312-045b50cf26a3a0068f60JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0fc0-5019002000-b330763cdd844608d30fJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0fb9-9014000000-2f45e72bcf5c3c9aed22JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9001000000-53737b3b7797da8dc867JSpectraViewer
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