Record Information
Version2.0
Creation Date2012-07-30 14:55:00 -0600
Update Date2015-06-03 17:20:55 -0600
Secondary Accession Numbers
  • ECMDB21223
Identification
Name:Glycerophosphoglycerol
Description:Glycerophosphoglycerol is a substrate for glycerol and phosphate salvage in E. coli. E. coli K12 possesses two systems the salvage of glycerophosphoryl diesters, the Glp system and the Ugp system. In the Glp system, the glpQ gene encodes a periplasmic glycerophosphoryl diester phosphodiesterase (periplasmic GDP) which hydrolyzes deacylated phospholipids to an alcohol and sn-glycerol-3-phosphate. The latter is then transported into the cell by the GlpT transporter. Periplasmic GDP is specific for the glycerophospho- moiety of the substrate, while the alcohol can be any one of several alcohols. This provides the cell with the capability of channeling a wide variety of glycerophosphodiesters into the glpQT-encoded dissimilatory system. In the Ugp system the diesters are hydrolyzed during transport at the cytoplasmic side of the inner membrane to sn-glycerol-3-phosphate and an alcohol by a cytoplasmic GDP, an enzyme encoded by the ugpQ gene. The Ugp system is induced when the cells are starved for inorganic phospate, which is generates phosphate by the system. In E. coli sn-glycerol-3-phosphate can be further metabolized to dihydroxyacetone phosphate by either of two membrane-bound enzymes, depending on the growth conditions. The presumed role of this process is the salvage of glycerol and glycerol phosphates generated by the breakdown of phospholipids and triacylglycerol.
Structure
Thumb
Synonyms:
  • Bis(2,3-dihydroxypropyl) hydrogen phosphate
  • Bis(2,3-dihydroxypropyl) hydrogen phosphoric acid
  • Glycerophosphoglycerol
Chemical Formula:C6H14O8P
Weight:Average: 245.1443
Monoisotopic: 245.042628936
InChI Key:LLCSXHMJULHSJN-UHFFFAOYSA-M
InChI:InChI=1S/C6H15O8P/c7-1-5(9)3-13-15(11,12)14-4-6(10)2-8/h5-10H,1-4H2,(H,11,12)/p-1
CAS number:Not Available
IUPAC Name:3-[(2,3-dihydroxypropyl phosphonato)oxy]propane-1,2-diol
Traditional IUPAC Name:glycerophosphoglycerol(1-)
SMILES:OCC(O)COP([O-])(=O)OCC(O)CO
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as glycerophosphoglycerols. These are glycerophosphoglycerols are lipids that contain two glycerol moieties that are linked to each other through the only phosphate group.
KingdomChemical entities
Super ClassOrganic compounds
ClassLipids and lipid-like molecules
Sub ClassGlycerophospholipids
Direct ParentGlycerophosphoglycerols
Alternative Parents
Substituents
  • Glycero-3-phospho-1p-glycerol
  • Dialkyl phosphate
  • Alkyl phosphate
  • Phosphoric acid ester
  • Organic phosphoric acid derivative
  • Secondary alcohol
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Alcohol
  • Organic anion
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
State:Not Available
Charge:-1
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility43.2 mg/mLALOGPS
logP-2.2ALOGPS
logP-2.9ChemAxon
logS-0.78ALOGPS
pKa (Strongest Acidic)1.89ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area139.51 Å2ChemAxon
Rotatable Bond Count8ChemAxon
Refractivity47 m3·mol-1ChemAxon
Polarizability20.7 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
Adenosine triphosphate + Water + Glycerophosphoglycerol > ADP + Glycerophosphoglycerol + Hydrogen ion + Phosphate
Adenosine triphosphate + Water + Glycerophosphoglycerol > ADP + Glycerophosphoglycerol + Hydrogen ion + Phosphate
1-Acyl-sn-glycero-3-phosphoglycerol (N-C12:0) + Water > Dodecanoate (N-C12:0) + Glycerophosphoglycerol + Hydrogen ion
1-Acyl-sn-glycero-3-phosphoglycerol (N-C14:0) + Water > Glycerophosphoglycerol + Hydrogen ion + tetradecanoate (n-C14:0)
1-Acyl-sn-glycero-3-phosphoglycerol (N-C14:1) + Water > Glycerophosphoglycerol + Hydrogen ion + Tetradecenoate (N-C14:1)
1-Acyl-sn-glycero-3-phosphoglycerol (N-C16:0) + Water > Glycerophosphoglycerol + Hydrogen ion + Palmitic acid
1-Acyl-sn-glycero-3-phosphoglycerol (N-C16:1) + Water > Glycerophosphoglycerol + Hydrogen ion + Hexadecenoate (n-C16:1)
1-Acyl-sn-glycero-3-phosphoglycerol (N-C18:0) + Water > Glycerophosphoglycerol + Hydrogen ion + Octadecanoate (N-C18:0)
1-Acyl-sn-glycero-3-phosphoglycerol (N-C18:1) + Water > Glycerophosphoglycerol + Hydrogen ion + Octadecenoate (N-C18:1)
Glycerophosphoglycerol + Water > Glycerol + Glycerol 3-phosphate + Hydrogen ion
Glycerophosphoglycerol + Water > Glycerol + Glycerol 3-phosphate + Hydrogen ion
2-Acyl-sn-glycero-3-phosphoglycerol (n-C12:0) + Water > Dodecanoate (N-C12:0) + Glycerophosphoglycerol + Hydrogen ion
2-Acyl-sn-glycero-3-phosphoglycerol (n-C12:0) + PG(12:0/12:0) > Acyl phosphatidylglycerol (N-C12:0) + Glycerophosphoglycerol
2-Acyl-sn-glycero-3-phosphoglycerol (N-C14:0) + Water > Glycerophosphoglycerol + Hydrogen ion + tetradecanoate (n-C14:0)
2-Acyl-sn-glycero-3-phosphoglycerol (N-C14:0) + PG(14:0/14:0) > Acyl phosphatidylglycerol (N-C14:0) + Glycerophosphoglycerol
2-Acyl-sn-glycero-3-phosphoglycerol (N-C14:1) + Water > Glycerophosphoglycerol + Hydrogen ion + Tetradecenoate (N-C14:1)
2-Acyl-sn-glycero-3-phosphoglycerol (N-C14:1) + PG(14:1(7Z)/14:1(7Z)) > Acyl phosphatidylglycerol (N-C14:1) + Glycerophosphoglycerol
2-Acyl-sn-glycero-3-phosphoglycerol (N-C16:0) + Water > Glycerophosphoglycerol + Hydrogen ion + Palmitic acid
2-Acyl-sn-glycero-3-phosphoglycerol (N-C16:0) + PG(16:0/16:0) > Acyl phosphatidylglycerol (N-C16:0) + Glycerophosphoglycerol
2-Acyl-sn-glycero-3-phosphoglycerol (N-C16:1) + Water > Glycerophosphoglycerol + Hydrogen ion + Hexadecenoate (n-C16:1)
2-Acyl-sn-glycero-3-phosphoglycerol (N-C16:1) + PG(16:1(9Z)/16:1(9Z)) > Acyl phosphatidylglycerol (N-C16:1) + Glycerophosphoglycerol
2-Acyl-sn-glycero-3-phosphoglycerol (N-C18:0) + Water > Glycerophosphoglycerol + Hydrogen ion + Octadecanoate (N-C18:0)
2-Acyl-sn-glycero-3-phosphoglycerol (N-C18:0) + PG(18:0/18:0) > Acyl phosphatidylglycerol (N-C18:0) + Glycerophosphoglycerol
2-Acyl-sn-glycero-3-phosphoglycerol (N-C18:1) + Water > Glycerophosphoglycerol + Hydrogen ion + Octadecenoate (N-C18:1)
2-Acyl-sn-glycero-3-phosphoglycerol (N-C18:1) + PG(18:1(11Z)/18:1(11Z)) > Acyl phosphatidylglycerol (N-C18:1) + Glycerophosphoglycerol

SMPDB Pathways:
glycerol metabolism IV (glycerophosphoglycerol)PW000917 Pw000917Pw000917 greyscalePw000917 simple
KEGG Pathways:Not Available
EcoCyc Pathways:Not Available
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-4290000000-97a1907e1243b94a60f0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-08ir-7390000000-a9dad17140d8232468a2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a6r-9000000000-2c7ec6b3808cb3772b99View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004l-0190000000-334e7aee7826d0f38c1cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0fml-2970000000-fcf81ffea44475383ab5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0fai-9300000000-0f6ec8985ffb971bba92View in MoNA
References
References:Not Available
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI ID5457
HMDB IDNot Available
Pubchem Compound ID25202983
Kegg IDC03274
ChemSpider ID26332446
Wikipedia IDNot Available
BioCyc IDGLYCEROPHOSPHOGLYCEROL
EcoCyc IDGLYCEROPHOSPHOGLYCEROL

Enzymes

General function:
Lipid transport and metabolism
Specific function:
2-lysophosphatidylcholine + H(2)O = glycerophosphocholine + a carboxylate
Gene Name:
pldB
Uniprot ID:
P07000
Molecular weight:
38978
Reactions
2-lysophosphatidylcholine + H(2)O = glycerophosphocholine + a carboxylate.
General function:
Involved in glycerophosphodiester phosphodiesterase activity
Specific function:
Glycerophosphoryl diester phosphodiesterase hydrolyzes deacylated phospholipids to G3P and the corresponding alcohols
Gene Name:
glpQ
Uniprot ID:
P09394
Molecular weight:
40843
Reactions
A glycerophosphodiester + H(2)O = an alcohol + sn-glycerol 3-phosphate.
General function:
Involved in hydrolase activity
Specific function:
Hydrolyzes only long chain acyl thioesters (C12-C18). Specificity similar to chymotrypsin
Gene Name:
tesA
Uniprot ID:
P0ADA1
Molecular weight:
23622
Reactions
2-lysophosphatidylcholine + H(2)O = glycerophosphocholine + a carboxylate.
General function:
Involved in nucleotide binding
Specific function:
Part of the ABC transporter complex UgpABCE involved in sn-glycerol-3-phosphate import. Responsible for energy coupling to the transport system (Probable). Can also transport glycerophosphoryl diesters
Gene Name:
ugpC
Uniprot ID:
P10907
Molecular weight:
39524
Reactions
ATP + H(2)O + glycerol-3-phosphate(Out) = ADP + phosphate + glycerol-3-phosphate(In).
General function:
Involved in glycerophosphodiester phosphodiesterase activity
Specific function:
Glycerophosphoryl diester phosphodiesterase hydrolyzes deacylated phospholipids to G3P and the corresponding alcohols
Gene Name:
ugpQ
Uniprot ID:
P10908
Molecular weight:
27409
Reactions
A glycerophosphodiester + H(2)O = an alcohol + sn-glycerol 3-phosphate.
General function:
Involved in transporter activity
Specific function:
Part of the binding-protein-dependent transport system for sn-glycerol-3-phosphate; probably responsible for the translocation of the substrate across the membrane
Gene Name:
ugpA
Uniprot ID:
P10905
Molecular weight:
33264
General function:
Involved in transporter activity
Specific function:
Part of the binding-protein-dependent transport system for sn-glycerol-3-phosphate; probably responsible for the translocation of the substrate across the membrane
Gene Name:
ugpE
Uniprot ID:
P10906
Molecular weight:
31499
General function:
Involved in transporter activity
Specific function:
sn-glycerol-3-phosphate and glycerophosphoryl diester- binding protein interacts with the binding protein-dependent transport system ugpACE
Gene Name:
ugpB
Uniprot ID:
P0AG80
Molecular weight:
48448

Transporters

General function:
Involved in nucleotide binding
Specific function:
Part of the ABC transporter complex UgpABCE involved in sn-glycerol-3-phosphate import. Responsible for energy coupling to the transport system (Probable). Can also transport glycerophosphoryl diesters
Gene Name:
ugpC
Uniprot ID:
P10907
Molecular weight:
39524
Reactions
ATP + H(2)O + glycerol-3-phosphate(Out) = ADP + phosphate + glycerol-3-phosphate(In).
General function:
Involved in transporter activity
Specific function:
Part of the binding-protein-dependent transport system for sn-glycerol-3-phosphate; probably responsible for the translocation of the substrate across the membrane
Gene Name:
ugpA
Uniprot ID:
P10905
Molecular weight:
33264
General function:
Involved in transporter activity
Specific function:
Part of the binding-protein-dependent transport system for sn-glycerol-3-phosphate; probably responsible for the translocation of the substrate across the membrane
Gene Name:
ugpE
Uniprot ID:
P10906
Molecular weight:
31499
General function:
Involved in transporter activity
Specific function:
Non-specific porin
Gene Name:
ompN
Uniprot ID:
P77747
Molecular weight:
41220
General function:
Involved in transporter activity
Specific function:
Uptake of inorganic phosphate, phosphorylated compounds, and some other negatively charged solutes
Gene Name:
phoE
Uniprot ID:
P02932
Molecular weight:
38922
General function:
Involved in transporter activity
Specific function:
OmpF is a porin that forms passive diffusion pores which allow small molecular weight hydrophilic materials across the outer membrane. It is also a receptor for the bacteriophage T2
Gene Name:
ompF
Uniprot ID:
P02931
Molecular weight:
39333
General function:
Involved in transporter activity
Specific function:
sn-glycerol-3-phosphate and glycerophosphoryl diester- binding protein interacts with the binding protein-dependent transport system ugpACE
Gene Name:
ugpB
Uniprot ID:
P0AG80
Molecular weight:
48448
General function:
Involved in transporter activity
Specific function:
Forms passive diffusion pores which allow small molecular weight hydrophilic materials across the outer membrane
Gene Name:
ompC
Uniprot ID:
P06996
Molecular weight:
40368