PGP(18:1(9Z)/18:1(9Z)) (YMDB14519)

Identification
YMDB IDYMDB14519
NamePGP(18:1(9Z)/18:1(9Z))
SpeciesSaccharomyces cerevisiae
StrainBrewer's yeast
DescriptionPGP(18:1(9Z)/18:1(9Z)) 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(18:1(9Z)/18:1(9Z)), in particular, consists of two 9Z-octadecenoyl chains at positions C-1 and C-2. 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
  • 1,2-Di-(9Z-octadecenoyl)-sn-glycero-3-phospho-(1'-sn-glycerol-3'-phosphate)
  • PGP(18:1/18:1)
  • PGP(18:1n9/18:1n9)
  • PGP(18:1W9/18:1W9)
  • PGP(36:2)
  • 1,2-Di-(9Z-octadecenoyl)-sn-glycero-3-phospho-(1'-sn-glycerol-3'-phosphoric acid)
  • 3-sn-phosphatidyl-1'-sn-glycerol 3'-phosphoric acid
  • 1,2-dioleoyl-rac-glycero-3-phospho-(1'-sn-glycerol-3'-phosphate)
  • PGP(18:1(9Z)/18:1(9Z))
  • 1,2-di(9Z-octadecenoyl)-rac-glycero-3-phospho-(1'-sn-glycerol-3'-phosphate)
CAS numberNot Available
WeightAverage: 855.037
Monoisotopic: 854.507416632
InChI KeyFRKGQUQUVYQCIV-SQYFZQSCSA-N
InChIInChI=1S/C42H80O13P2/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31-33-41(44)51-37-40(38-54-57(49,50)53-36-39(43)35-52-56(46,47)48)55-42(45)34-32-30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h17-20,39-40,43H,3-16,21-38H2,1-2H3,(H,49,50)(H2,46,47,48)/b19-17-,20-18-/t39-,40+/m0/s1
IUPAC Name[(2S)-3-({[(2R)-2,3-bis[(9Z)-octadec-9-enoyloxy]propoxy](hydroxy)phosphoryl}oxy)-2-hydroxypropoxy]phosphonic acid
Traditional IUPAC Name(2S)-3-{[(2R)-2,3-bis[(9Z)-octadec-9-enoyloxy]propoxy(hydroxy)phosphoryl]oxy}-2-hydroxypropoxyphosphonic acid
Chemical FormulaC42H80O13P2
SMILES[H][C@](O)(COP(O)(O)=O)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 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
  • Fatty acid ester
  • Monoalkyl phosphate
  • Dialkyl phosphate
  • Dicarboxylic acid or derivatives
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Alkyl phosphate
  • Fatty acyl
  • Secondary alcohol
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Organooxygen compound
  • Organic oxide
  • Organic oxygen compound
  • Alcohol
  • Carbonyl group
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
  • 3-(3-sn-phosphatidyl)-sn-glycerol 1-phosphate (CHEBI:82848 )
Physical Properties
StateSolid
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility0.0006 g/LALOGPS
logP7.48ALOGPS
logP11.87ChemAxon
logS-6.2ALOGPS
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 Count44ChemAxon
Refractivity226.82 m³·mol⁻¹ChemAxon
Polarizability96.68 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(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
CDP-DG(18:1(9Z)/18:1(9Z)) + Glycerol 3-phosphate → PGP(18:1(9Z)/18:1(9Z)) + hydron + Cytidine monophosphate
PGP(18:1(9Z)/18:1(9Z)) + water → phosphate + PG(18:1(9Z)/18:1(9Z))
KEGG ReactionsNot Available
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0ab9-0491083480-def259306a016c480fb8JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0awi-2593134110-7bc2f232d49a2eaf6a22JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0abl-6977432300-8ec89ad4d2e235908fd5JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0gz9-3090030020-c186e3bd63bf0b2122ecJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9050000000-246f8e2232f19c9d072aJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9010000000-d1f9da01c178a98406b9JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0010000090-0e1fc7ebef97ef8fefb2JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0uk9-2090160030-f1e901a25f5cb17bfea8JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0pba-3090261000-7c08b741f2d72ca4b6faJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-2101015690-e604d2ee5a448f07b4a2JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0pb9-1400009400-a18f9772b3bc4f441031JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ufu-3472911000-c546776a4bd3eeb91751JSpectraViewer
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 ID82848
HMDB IDHMDB0013536
Pubchem Compound ID53481854
Kegg IDNot Available
ChemSpider ID34448616
FOODB IDFDB029536
Wikipedia IDNot Available
BioCyc IDNot Available

Enzymes

Protein Details
1. CDP-diacylglycerol--glycerol-3-phosphate 3-phosphatidyltransferase
General function:
Involved in phosphotransferase activity, for other substituted phosphate groups
Specific function:
Essential for the viability of mitochondrial petite mutant. Catalyzes the committed step to the synthesis of the acidic phospholipids
Gene Name:
PGS1
Uniprot ID:
P25578
Molecular weight:
59369.69922
Reactions
CDP-diacylglycerol + sn-glycerol 3-phosphate → CMP + 3(3-sn-phosphatidyl)-sn-glycerol 1-phosphate.
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.