| Record Information |
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| Version | 1.0 |
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| Creation Date | 2016-07-13 19:40:58 UTC |
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| Update Date | 2016-07-20 20:48:55 UTC |
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| Lmdb | LMDB00036 |
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| Secondary Accession Numbers | None |
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| Metabolite Identification |
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| Common Name | Glycerophosphocholine |
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| 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 one of the four major organic osmolytes in renal medullary cells, changing their intracellular osmolyte concentration in parallel with extracellular tonicity during cellular osmoadaptation. As an osmolyte, Glycerophosphorylcholine counteracts the effects of urea on enzymes and other macromolecules. Kidneys (especially medullar cells), which are exposed under normal physiological conditions to widely fluctuating extracellular solute concentrations, respond to hypertonic stress by accumulating the organic osmolytes glycerophosphorylcholine (GPC), betaine, myo-inositol, sorbitol and free amino acids. Increased intracellular contents of these osmolytes are achieved by a combination of increased uptake (myo-inositol and betaine) and synthesis (sorbitol, GPC), decreased degradation (GPC) and reduced osmolyte release. GPC is formed in the breakdown of phosphatidylcholine (PtC). This pathway is active in many body tissues, including mammary tissue. |
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| Structure | |
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| Synonyms | | Value | Source |
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| 2-[[(2,3-Dihydroxypropoxy)hydroxyphosphinyl]oxy]-N,N,N-trimethyl-ethanaminium inner salt | HMDB | | a-Glycerophosphorylcholine | HMDB | | a-Glycerylphosphorylcholine | HMDB | | alpha-Glycerophosphorylcholine | HMDB | | alpha-Glycerylphosphorylcholine | HMDB | | Choline alfoscerate | HMDB, MeSH | | Choline glycerophosphate | HMDB | | Glycerol 3-phosphocholine | HMDB, MeSH | | Glycerol phosphorylcholine | HMDB | | Glycerol-3-phosphatidylcholine | HMDB | | Glycerophosphatidylcholine | HMDB | | Glycerophosphorylcholine | HMDB, MeSH | | GPC | HMDB | | GPCho | HMDB | | Hydrogen glycerophosphate choline | HMDB | | L-alpha-Glycerophosphocholine | HMDB | | L-alpha-Glycerophosphorylcholine | HMDB | | L-alpha-Glycerylphosphorylcholine | HMDB, MeSH | | L-Choline hydroxide 2,3-dihydroxypropyl hydrogen phosphate inner salt | HMDB | | sn-glycero-3-Phosphocholine | HMDB | | Alfoscerate, choline | MeSH, HMDB | | Choline alphoscerate | MeSH, HMDB | | Glycerophosphate, choline | MeSH, HMDB | | Alphoscerate, choline | MeSH, HMDB | | L alpha Glycerylphosphorylcholine | MeSH, HMDB | | 3-Phosphocholine, glycerol | MeSH, HMDB | | Glycerol 3 phosphocholine | MeSH, HMDB | | Glycerylphosphorylcholine | MeSH, HMDB | | Cereton | HMDB | | Cholicerin | HMDB | | Cholitiline | HMDB | | Delecit | HMDB | | Gliatilin | HMDB | | Glycerol 3-phosphorylcholine | HMDB | | Glycerophosphocholine | HMDB | | Glycerophosphoric acid choline ester | HMDB | | Glyceryl 3-phosphorylcholine | HMDB | | Glycerylphosphocholine | HMDB | | L-alpha-GPC | HMDB | | L-α-GPC | HMDB | | L-α-Glycerophosphocholine | HMDB | | L-α-Glycerophosphorylcholine | HMDB | | L-α-Glycerylphosphorylcholine | HMDB | | O-(sn-glycero-3-Phosphoryl)-choline | HMDB | | sn-glycero-3-Phosphorylcholine | HMDB | | α-Glycerophosphorylcholine | HMDB | | α-Glycerylphosphorylcholine | HMDB |
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| Chemical Formula | C8H20NO6P |
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| Average Molecular Weight | 257.2213 |
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| Monoisotopic Molecular Weight | 257.102823889 |
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| IUPAC Name | (2-{[(2S)-2,3-dihydroxypropyl phosphonato]oxy}ethyl)trimethylazanium |
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| Traditional Name | Alpha-GPC |
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| CAS Registry Number | 28319-77-9 |
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| SMILES | C[N+](C)(C)CCOP([O-])(=O)OC[C@@H](O)CO |
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| InChI Identifier | 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/t8-/m0/s1 |
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| InChI Key | SUHOQUVVVLNYQR-QMMMGPOBSA-N |
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| Chemical Taxonomy |
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| 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. |
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| Kingdom | Organic compounds |
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| Super Class | Lipids and lipid-like molecules |
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| Class | Glycerophospholipids |
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| Sub Class | Glycerophosphocholines |
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| Direct Parent | Glycerophosphocholines |
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| Alternative Parents | |
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| Substituents | - Glycero-3-phosphocholine
- Phosphocholine
- Dialkyl phosphate
- Organic phosphoric acid derivative
- Phosphoric acid ester
- Alkyl phosphate
- Tetraalkylammonium salt
- Quaternary ammonium salt
- 1,2-diol
- Secondary alcohol
- Organic nitrogen compound
- Organic salt
- Hydrocarbon derivative
- Primary alcohol
- Organic oxide
- Organopnictogen compound
- Organooxygen compound
- Organonitrogen compound
- Organic oxygen compound
- Amine
- Alcohol
- Aliphatic acyclic compound
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| Molecular Framework | Aliphatic acyclic compounds |
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| External Descriptors | Not Available |
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| Ontology |
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| Status | Detected and Quantified |
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| Origin | Not Available |
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| Biofunction | Not Available |
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| Application | Not Available |
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| Cellular locations | Not Available |
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| Physical Properties |
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| State | Not Available |
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| Experimental Properties | | Property | Value | Reference |
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| Melting Point | Not Available | Not Available | | Boiling Point | Not Available | Not Available | | Water Solubility | Not Available | Not Available | | LogP | Not Available | Not Available |
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| Predicted Properties | |
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| Spectra |
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| Spectra | | Spectrum Type | Description | Splash Key | View |
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| Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-001j-7910000000-79a0f6ec434740d09410 | Spectrum | | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive | splash10-00ds-9324000000-3f77ad31e891fc64627e | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-052r-9140000000-dfaa66ba1da98fca7ee7 | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0a7r-9210000000-dd605c88980d8b4928bb | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0a4r-9000000000-5b8e226d6d1b7bba9ba2 | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0a4i-0390000000-4e2ca054587803166774 | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0kor-2920000000-8d45ca644a1b5ea88a2c | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-004i-9100000000-65a218b9f08d2ce2ed9c | Spectrum |
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