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Identification
YMDB IDYMDB14342
NamePGP(15:1(9Z)/16:1(11Z))
SpeciesSaccharomyces cerevisiae
StrainBrewer's yeast
DescriptionPGP(15:1(9Z)/16:1(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(15:1(9Z)/16:1(11Z)), in particular, consists of one 9Z-pentadecenoyl chain to the C-1 atom, and one 11Z-hexadecenoyl 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: 784.902
Monoisotopic: 784.42916631
InChI KeyCOJHLBUXVSVSKI-OSNMRKJZSA-N
InChIInChI=1S/C37H70O13P2/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/h9,11-12,14,34-35,38H,3-8,10,13,15-33H2,1-2H3,(H,44,45)(H2,41,42,43)/b11-9-,14-12-/t34-,35+/m0/s1
IUPAC Name[(2S)-3-({[(2R)-2-[(11Z)-hexadec-11-enoyloxy]-3-[(9Z)-pentadec-9-enoyloxy]propoxy](hydroxy)phosphoryl}oxy)-2-hydroxypropoxy]phosphonic acid
Traditional IUPAC Name(2S)-3-{[(2R)-2-[(11Z)-hexadec-11-enoyloxy]-3-[(9Z)-pentadec-9-enoyloxy]propoxy(hydroxy)phosphoryl]oxy}-2-hydroxypropoxyphosphonic acid
Chemical FormulaC37H70O13P2
SMILES[H][C@](O)(COP(O)(O)=O)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCC\C=C/CCCCC)OC(=O)CCCCCCCCC\C=C/CCCC
Chemical Taxonomy
Physical Properties
StateSolid
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility0.0016 g/LALOGPS
logP6.25ALOGPS
logP9.65ChemAxon
logS-5.7ALOGPS
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 Count39ChemAxon
Refractivity203.81 m³·mol⁻¹ChemAxon
Polarizability87.91 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 Pathways
Cardiolipin Biosynthesis CL(15:1(9Z)/16:1(11Z)/15:1(11Z)/16:1(11Z))PW012339 ThumbThumb?image type=greyscaleThumb?image type=simple
Cardiolipin Biosynthesis CL(15:1(9Z)/16:1(11Z)/15:1(11Z)/16:1(9Z))PW012340 ThumbThumb?image type=greyscaleThumb?image type=simple
Cardiolipin Biosynthesis CL(15:1(9Z)/16:1(11Z)/15:1(9Z)/16:1(11Z))PW012341 ThumbThumb?image type=greyscaleThumb?image type=simple
Cardiolipin Biosynthesis CL(15:1(9Z)/16:1(11Z)/15:1(9Z)/16:1(9Z))PW012342 ThumbThumb?image type=greyscaleThumb?image type=simple
Cardiolipin Biosynthesis CL(15:1(9Z)/16:1(11Z)/16:1(11Z)/23:1(11Z))PW012343 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG PathwaysNot Available
SMPDB Reactions
CDP-DG(15:1(9Z)/16:1(11Z)) + Glycerol 3-phosphatePGP(15:1(9Z)/16:1(11Z)) + hydron + Cytidine monophosphate
PGP(15:1(9Z)/16:1(11Z)) + waterphosphate + PG(15:1(9Z)/16:1(11Z))
KEGG ReactionsNot Available
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-05nr-1290062500-3ed775a7c59235505a50JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05ub-2490033200-706adafa8a4263b1a7dbJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4j-6491042000-e1b77aee9969bd357c61JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0fh0-3090020200-10935c81c4036db7b9f7JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9050000000-4caa760fe83f75b7e5afJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9010000000-5cb613c821cb99c3c565JSpectraViewer
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.