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Glycerophosphocholine (ECMDB00086) (M2MDB000032)
Record Information | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
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Version | 2.0 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Creation Date | 2012-05-31 09:57:00 -0600 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Update Date | 2015-09-13 12:56:06 -0600 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Secondary Accession Numbers |
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Identification | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Name: | Glycerophosphocholine | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Description | Glycerophosphorylcholine (GPC) is a choline derivative and one of the two major forms of choline storage (along with phosphocholine) in the cytosol. Glycerophosphorylcholine is also osmolyte. GPC is an intermediate of glycerophospholipid metabolism. It is converted from both 2-acyl-sn-glycero-3-phosphocholine and 1-acyl-sn-glycero-3-phosphocholine by lysophospholipase L2 (EC:3.1.1.5). It is converted to choline and sn-glycerol 3-phosphate by glycerophosphodiester phosphodiesterase (EC:3.1.4.46). (KEGG) | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Structure | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Synonyms: |
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Chemical Formula: | C8H21NO6P | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Weight: | Average: 258.2292 Monoisotopic: 258.110648921 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
InChI Key: | SUHOQUVVVLNYQR-MRVPVSSYSA-O | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
InChI: | InChI=1S/C8H20NO6P/c1-9(2,3)4-5-14-16(12,13)15-7-8(11)6-10/h8,10-11H,4-7H2,1-3H3/p+1/t8-/m1/s1 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
CAS number: | 28319-77-9 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
IUPAC Name: | [(2R)-2,3-dihydroxypropoxy][2-(trimethylazaniumyl)ethoxy]phosphinic acid | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Traditional IUPAC Name: | glycerylphosphorylcholine | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
SMILES: | C[N+](C)(C)CCO[P@](O)(=O)OC[C@H](O)CO | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Chemical Taxonomy | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Description | belongs to the class of organic compounds known as glycerophosphocholines. These are lipids containing a glycerol moiety carrying a phosphocholine at the 3-position. | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Kingdom | Organic compounds | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Super Class | Lipids and lipid-like molecules | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Class | Glycerophospholipids | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Sub Class | Glycerophosphocholines | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Direct Parent | Glycerophosphocholines | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Alternative Parents | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Substituents |
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Molecular Framework | Aliphatic acyclic compounds | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
External Descriptors | Not Available | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Physical Properties | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
State: | Solid | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Charge: | 0 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Melting point: | 142.5 °C | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Experimental Properties: |
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Predicted Properties |
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Biological Properties | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Cellular Locations: | Cytoplasm | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Reactions: | Adenosine triphosphate + Water + Glycerophosphocholine > ADP + Glycerophosphocholine + Hydrogen ion + Phosphate Adenosine triphosphate + Water + Glycerophosphocholine > ADP + Glycerophosphocholine + Hydrogen ion + Phosphate Glycerophosphocholine + Water > Choline + Glycerol 3-phosphate + Hydrogen ion Glycerophosphocholine + Water <> Choline + Glycerol 3-phosphate 2-Acylglycerophosphocholine + Water a carboxylate + Glycerophosphocholine + Hydrogen ion 2-lysophosphatidylcholine + Water > Glycerophosphocholine + a carboxylate 1-Acyl-sn-glycero-3-phosphocholine + Water <> Glycerophosphocholine + Carboxylate Glycerophosphocholine + Water > Choline + Glycerol 3-phosphate + Hydrogen ion 1-Acyl-sn-glycero-3-phosphocholine + Water <> Glycerophosphocholine + Carboxylate Glycerophosphocholine + Water > Choline + Glycerol 3-phosphate + Hydrogen ion 1-Acyl-sn-glycero-3-phosphocholine + Water <> Glycerophosphocholine + Carboxylate | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
SMPDB Pathways: | Not Available | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
KEGG Pathways: | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
EcoCyc Pathways: |
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Concentrations | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Not Available | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Spectra | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Spectra: |
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References | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
References: |
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Synthesis Reference: | Evans, Christopher Thomas; McCague, Raymond; Tyrrell, Nicholas David. Preparation of phospholipid-intermediate glycerophosphocholine by a crystallization process. PCT Int. Appl. (1993), 8 pp. | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Material Safety Data Sheet (MSDS) | Download (PDF) | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
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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