Glycerophosphoglycerol (PAMDB001631)
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Version | 1.0 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Update Date | 1/22/2018 12:54:54 PM | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Metabolite ID | PAMDB001631 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Identification | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Name: | Glycerophosphoglycerol | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Description: | Glycerophosphoglycerol is a substrate for glycerol and phosphate salvage in Pseudomonas aeruginosa. Pseudomonas aeruginosa 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 Pseudomonas aeruginosa 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 | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Synonyms: |
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Chemical Formula: | C6H14O8P | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Average Molecular Weight: | 245.1443 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Monoisotopic Molecular Weight: | 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 | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Taxonomy Description | This compound belongs to the class of organic compounds known as glycerophosphoglycerols. These are glycerophosphoglycerols are lipids that contain two glycerol moeities that are linked to each other through the only phosphate group. | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Kingdom | Organic compounds | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Super Class | Lipids and lipid-like molecules | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Class | Glycerophospholipids | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Sub Class | Glycerophosphoglycerols | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Direct Parent | Glycerophosphoglycerols | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Alternative Parents | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Substituents |
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Molecular Framework | Aliphatic acyclic compounds | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
External Descriptors |
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Physical Properties | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
State: | Not Available | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Charge: | -1 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Melting point: | Not Available | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Experimental Properties: |
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Predicted Properties |
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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-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 2-Acyl-sn-glycero-3-phosphoglycerol (n-C12:0) + Water > Dodecanoate (N-C12:0) + Glycerophosphoglycerol + Hydrogen ion 2-Acyl-sn-glycero-3-phosphoglycerol (N-C14:0) + Water > Glycerophosphoglycerol + Hydrogen ion + tetradecanoate (n-C14:0) 2-Acyl-sn-glycero-3-phosphoglycerol (N-C14:1) + 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-C16:1) + 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-C18:1) + 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 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Pathways: | Not Available | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Spectra | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Spectra: |
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References | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
References: | Not Available | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Synthesis Reference: | Not Available | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Material Safety Data Sheet (MSDS) | Not Available | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Links | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
External Links: |
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Enzymes
- General function:
- Lipid transport and metabolism
- Specific function:
- 2-lysophosphatidylcholine + H(2)O = glycerophosphocholine + a carboxylate
- Gene Name:
- pldB
- Locus Tag:
- PA5089
- Molecular weight:
- 83.4 kDa
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
- Locus Tag:
- PA0347
- Molecular weight:
- 42 kDa
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
- Locus Tag:
- PA2856
- Molecular weight:
- 21 kDa
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
- Locus Tag:
- PA3187
- Molecular weight:
- 42.2 kDa
Reactions
ATP + H(2)O + glycerol-3-phosphate(Out) = ADP + phosphate + glycerol-3-phosphate(In). |
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
- Locus Tag:
- PA3187
- Molecular weight:
- 42.2 kDa
Reactions
ATP + H(2)O + glycerol-3-phosphate(Out) = ADP + phosphate + glycerol-3-phosphate(In). |