PGP(18:2(9Z,12Z)/18:2(9Z,12Z)) (PAMDB006287)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 11:54:54 AM
Metabolite IDPAMDB006287
Identification
Name: PGP(18:2(9Z,12Z)/18:2(9Z,12Z))
Description:PGP(18:2(9Z,12Z)/18:2(9Z,12Z)) 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(18:2(9Z,12Z)/18:2(9Z,12Z)), in particular, consists of two 9Z,12Z-octadecadienoyl chains at positions C-1 and C-2. In Pseudomonas aeruginosa, 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
🔍MOLSDFPDBSMILESInChIView Structure
Synonyms:Not Available
Chemical Formula: C44H80O13P2
Average Molecular Weight: 879.059
Monoisotopic Molecular Weight: 878.507416632
InChI Key: LTCGYYIQFPFMIB-NHPPMFAOSA-N
InChI:InChI=1S/C44H80O13P2/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31-33-35-43(46)53-39-42(40-56-59(51,52)55-38-41(45)37-54-58(48,49)50)57-44(47)36-34-32-30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h13-16,19-22,41-42,45H,3-12,17-18,23-40H2,1-2H3,(H,51,52)(H2,48,49,50)/b15-13-,16-14-,21-19-,22-20-/t41-,42+/m0/s1
CAS number: Not Available
IUPAC Name:[(2S)-3-({[(2R)-2,3-bis[(9Z,12Z)-nonadeca-9,12-dienoyloxy]propoxy](hydroxy)phosphoryl}oxy)-2-hydroxypropoxy]phosphonic acid
Traditional IUPAC Name: (2S)-3-{[(2R)-2,3-bis[(9Z,12Z)-nonadeca-9,12-dienoyloxy]propoxy(hydroxy)phosphoryl]oxy}-2-hydroxypropoxyphosphonic acid
SMILES:[H][C@](O)(COP(O)(O)=O)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCC\C=C/C\C=C/CCCCCC)OC(=O)CCCCCCC\C=C/C\C=C/CCCCCC
Chemical Taxonomy
Taxonomy DescriptionThis compound 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.
Kingdom Organic compounds
Super ClassLipids and lipid-like molecules
Class Glycerophospholipids
Sub ClassGlycerophosphoglycerophosphates
Direct Parent Phosphatidylglycerophosphates
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 Framework Aliphatic acyclic compounds
External Descriptors Not Available
Physical Properties
State: Not Available
Charge:-3
Melting point: Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility0.000518 mg/mLALOGPS
logP7.66ALOGPS
logP12.03ChemAxon
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 Å2ChemAxon
Rotatable Bond Count44ChemAxon
Refractivity238.25 m3·mol-1ChemAxon
Polarizability99.55 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Membrane
Reactions:
CDP-DG(18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) + Glycerol 3-phosphate + CDP-DG(18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) > PGP(18:2(9Z,12Z)/18:2(9Z,12Z)) + Hydrogen ion + Cytidine monophosphate + Cytidine monophosphate
PGP(18:2(9Z,12Z)/18:2(9Z,12Z)) + Water > Phosphate + PG(18:2(9Z,12Z)/18:2(9Z,12Z))
Pathways: Not Available
Spectra
Spectra:
References
References:
  • Yurtsever D. (2007). Fatty acid methyl ester profiling of Enterococcus and Esherichia coli for microbial source tracking. M.sc. Thesis. Villanova University: U.S.A
Synthesis Reference: Not Available
Material Safety Data Sheet (MSDS) Not Available
External Links:
ResourceLink
CHEBI IDNot Available
HMDB IDNot Available
Pubchem Compound IDNot Available
Kegg IDNot Available
ChemSpider IDNot Available
Wikipedia IDNot Available
BioCyc IDNot Available