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Glycerophosphoglycerol (M2MDB001631)
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| Version | 2.0 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Creation Date | 2012-07-30 14:55:00 -0600 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Update Date | 2015-06-03 17:20:55 -0600 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Secondary Accession Numbers |
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| 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 |  | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Synonyms: |
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| 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 | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Description | belongs to the class of organic compounds known as glycerophosphoglycerols. These are glycerophosphoglycerols are lipids that contain two glycerol moieties 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-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 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 Glycerophosphoglycerol + Water > Benzyl alcohol + Hydrogen ion + Glycerol 3-phosphate | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| SMPDB Pathways: |
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| KEGG Pathways: | Not Available | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| EcoCyc Pathways: | Not Available | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Concentrations | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| 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
- 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