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Identification
YMDB IDYMDB14308
NamePGP(15:1(11Z)/16:0)
SpeciesSaccharomyces cerevisiae
StrainBrewer's yeast
DescriptionPGP(15:1(11Z)/16:0) 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(15:1(11Z)/16:0), in particular, consists of one 11Z-pentadecenoyl chain to the C-1 atom, and one hexadecanoyl 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
SynonymsNot Available
CAS numberNot Available
WeightAverage: 786.918
Monoisotopic: 786.444816374
InChI KeyCNUPEXDFZYFIDI-KKTGDPMLSA-N
InChIInChI=1S/C37H72O13P2/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-37(40)50-35(33-49-52(44,45)48-31-34(38)30-47-51(41,42)43)32-46-36(39)28-26-24-22-20-18-16-14-12-10-8-6-4-2/h8,10,34-35,38H,3-7,9,11-33H2,1-2H3,(H,44,45)(H2,41,42,43)/b10-8-/t34-,35+/m0/s1
IUPAC Name[(2S)-3-({[(2R)-2-(hexadecanoyloxy)-3-[(11Z)-pentadec-11-enoyloxy]propoxy](hydroxy)phosphoryl}oxy)-2-hydroxypropoxy]phosphonic acid
Traditional IUPAC Name(2S)-3-{[(2R)-2-(hexadecanoyloxy)-3-[(11Z)-pentadec-11-enoyloxy]propoxy(hydroxy)phosphoryl]oxy}-2-hydroxypropoxyphosphonic acid
Chemical FormulaC37H72O13P2
SMILES[H][C@](O)(COP(O)(O)=O)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCCC\C=C/CCC)OC(=O)CCCCCCCCCCCCCCC
Chemical Taxonomy
Physical Properties
StateSolid
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility0.0014 g/LALOGPS
logP6.34ALOGPS
logP10.01ChemAxon
logS-5.8ALOGPS
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 Count40ChemAxon
Refractivity202.7 m³·mol⁻¹ChemAxon
Polarizability89.29 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(15:1(11Z)/16:0/15:1(11Z)/16:0)PW012019 ThumbThumb?image type=greyscaleThumb?image type=simple
Cardiolipin Biosynthesis CL(15:1(11Z)/16:0/15:1(9Z)/16:0)PW012020 ThumbThumb?image type=greyscaleThumb?image type=simple
Cardiolipin Biosynthesis CL(15:1(11Z)/16:0/16:0/23:1(11Z))PW012021 ThumbThumb?image type=greyscaleThumb?image type=simple
Cardiolipin Biosynthesis CL(15:1(11Z)/16:0/16:0/23:1(9Z))PW012022 ThumbThumb?image type=greyscaleThumb?image type=simple
Cardiolipin Biosynthesis CL(15:1(11Z)/16:0/16:0/25:0)PW012023 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG PathwaysNot Available
SMPDB Reactions
CDP-DG(15:1(11Z)/16:0) + Glycerol 3-phosphatePGP(15:1(11Z)/16:0) + hydron + Cytidine monophosphate
PGP(15:1(11Z)/16:0) + waterphosphate + PG(15:1(11Z)/16:0)
KEGG ReactionsNot Available
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-1290062500-1db7f515689165439121JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05ts-3490023200-d52e62993d707691a3ffJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4j-7591142000-47e80da3b180efe4a3e9JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-002r-3090020200-872f7653673b6c47eb21JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9050000000-72c4351a6640bba3a9a2JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9010000000-6bbec0f8737eeabe2be5JSpectraViewer
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

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.
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.