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Identification
YMDB IDYMDB14372
NamePGP(16:0/16:0)
SpeciesSaccharomyces cerevisiae
StrainBrewer's yeast
DescriptionPGP(16:0/16:0) 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(16:0/16:0), in particular, consists of two hexadecanoyl 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
Synonyms
  • 1,2-Dihexadecanoylphosphatidylglycerol phosphate
  • 1,2-Dipalmitoyl-sn-glycero-3-phospho-(1'-sn-glycerol-3'-phosphate)
  • 1,2-Dipalmitoylphosphatidylglycerol phosphate
  • Phosphatidylglycerol phosphate 16:0/16:0
  • 1,2-Dihexadecanoylphosphatidylglycerol phosphoric acid
  • 1,2-Dipalmitoyl-sn-glycero-3-phospho-(1'-sn-glycerol-3'-phosphoric acid)
  • 1,2-Dipalmitoylphosphatidylglycerol phosphoric acid
  • Phosphatidylglycerol phosphoric acid 16:0/16:0
  • 1,2-Dipalmitoyl-rac-glycero-3-phospho-(1'-sn-glycerol-3'-phosphate)
  • 3-sn-Phosphatidyl-1'-sn-glycerol 3'-phosphoric acid
  • PGP(32:0)
  • 1,2-Dihexadecanoyl-rac-glycero-3-phospho-(1'-sn-glycerol-3'-phosphate)
  • PGP(16:0/16:0)
CAS numberNot Available
WeightAverage: 802.961
Monoisotopic: 802.476116503
InChI KeyONJBJMDJKLHMEK-MPQUPPDSSA-N
InChIInChI=1S/C38H76O13P2/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-37(40)47-33-36(34-50-53(45,46)49-32-35(39)31-48-52(42,43)44)51-38(41)30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h35-36,39H,3-34H2,1-2H3,(H,45,46)(H2,42,43,44)/t35-,36+/m0/s1
IUPAC Name[(2S)-3-({[(2R)-2,3-bis(hexadecanoyloxy)propoxy](hydroxy)phosphoryl}oxy)-2-hydroxypropoxy]phosphonic acid
Traditional IUPAC Name(2S)-3-{[(2R)-2,3-bis(hexadecanoyloxy)propoxy(hydroxy)phosphoryl]oxy}-2-hydroxypropoxyphosphonic acid
Chemical FormulaC38H76O13P2
SMILES[H][C@](O)(COP(O)(O)=O)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCCC
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 DescriptorsNot Available
Physical Properties
StateSolid
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility0.00088 g/LALOGPS
logP6.51ALOGPS
logP10.81ChemAxon
logS-6ALOGPS
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 Count42ChemAxon
Refractivity206.18 m³·mol⁻¹ChemAxon
Polarizability91.8 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 BiosynthesisPW002431 ThumbThumb?image type=greyscaleThumb?image type=simple
Cardiolipin Biosynthesis CL(10:0/12:0/12:0/24:0)PW003741 ThumbThumb?image type=greyscaleThumb?image type=simple
Cardiolipin Biosynthesis CL(10:0/12:0/12:0/26:0)PW003742 ThumbThumb?image type=greyscaleThumb?image type=simple
Cardiolipin Biosynthesis CL(10:0/12:0/12:0/26:1(11Z))PW003743 ThumbThumb?image type=greyscaleThumb?image type=simple
Cardiolipin Biosynthesis CL(10:0/12:0/12:0/26:1(9Z))PW003744 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG PathwaysNot Available
SMPDB Reactions
CDP-DG(16:0/16:0) + Glycerol 3-phosphatePGP(16:0/16:0) + hydron + Cytidine monophosphate
CDP-DG(10:0/12:0) + Glycerol 3-phosphatePGP(16:0/16:0) + hydron + Cytidine monophosphate
CDP-DG(10:0/14:0) + Glycerol 3-phosphatePGP(16:0/16:0) + hydron + Cytidine monophosphate
CDP-DG(10:0/14:1(11Z)) + Glycerol 3-phosphatePGP(16:0/16:0) + hydron + Cytidine monophosphate
CDP-DG(10:0/14:1(9Z)) + Glycerol 3-phosphatePGP(16:0/16:0) + hydron + Cytidine monophosphate
KEGG ReactionsNot Available
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
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 ID136773
HMDB IDHMDB0013472
Pubchem Compound ID49859598
Kegg IDNot Available
ChemSpider IDNot Available
FOODB IDFDB029472
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.