| Record Information |
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| Version | 4.0 |
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| Status | Detected and Quantified |
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| Creation Date | 2006-08-12 22:34:16 UTC |
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| Update Date | 2017-12-20 20:30:08 UTC |
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| HMDB ID | HMDB0003514 |
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| Secondary Accession Numbers | |
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| Metabolite Identification |
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| Common Name | Alpha-D-Glucose 1,6-bisphosphate |
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| Description | Glucose 1,6-diphosphate (G-1,6-P2) is considered to be a major regulator of carbohydrate metabolism. It has been demonstrated that G-1,6-P2 is a potent activator (deinhibitor) of skeletal muscle phosphofructokinase (PFK) and phosphoglucomutase, while being an inhibitor of hexokinase (see Ref. 2). In addition, G-1,6-P2 has been shown to inhibit 6-phosphogluconate dehydrogenase in various rat tissues and fructose 1,6-bisphosphatase in bovine liver. Various factors and conditions affect the tissue content of G-1,6-P2. Specifically, anoxia induce a rapid fall in the content of G-l,6-P2 in brain. Glucose 1,6-diphosphate have been recognized as a regulatory signal implicated in the control of metabolism, oxygen affinity of red cells and other cellular functions. The levels of G 1,6-P2 are reduced in the liver and in the muscle of rats with experimentally induced diabetes. In muscle of genetically dystrophic mice a decrease in the levels of G 1,6-P2 has been found, probably resulting from enhancement of glucose 1,6-P2 phosphatase activity. G 1,6-P2 is an inhibitor of hexokinase and its level is increased significantly after 5 min of exercise (~ 25%) and then decreased continuously. G 1,6-P2 is a potent allosteric activator of phosphofructokinase, and is markedly decreased in muscles of patients with glycogenosis type VII (muscle phosphofructokinase deficiency) and type V (muscle phosphorylase deficiency). Chronic alcohol intake produces an increase in the concentration of G 1,6-P2 in human muscle before the first sign of myopathy appears. When myopathy is present the level decreases to be similar of healthy humans. These changes could contribute to the decline in skeletal muscle performance. (PMID: 1449560 , 2018547 , 2003594 , 3407759 ). |
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| Structure | |
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| Synonyms | | Value | Source |
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| alpha-D-Glucose 1,6-biphosphate | ChEBI | | D-Glucose 1,6-biphosphate | ChEBI | | a-D-Glucose 1,6-biphosphate | Generator | | a-D-Glucose 1,6-biphosphoric acid | Generator | | alpha-D-Glucose 1,6-biphosphoric acid | Generator | | α-D-glucose 1,6-biphosphate | Generator | | α-D-glucose 1,6-biphosphoric acid | Generator | | a-D-Glucose 1,6-bisphosphate | Generator | | a-D-Glucose 1,6-bisphosphoric acid | Generator | | alpha-D-Glucose 1,6-bisphosphoric acid | Generator | | α-D-glucose 1,6-bisphosphate | Generator | | α-D-glucose 1,6-bisphosphoric acid | Generator | | D-Glucose 1,6-biphosphoric acid | Generator | | a-D-Glucose 1,6-bis(dihydrogen phosphate) | HMDB | | a-D-Glucose 1,6-diphosphate | HMDB | | alpha-D-1,6-Bis(dihydrogen phosphate) glucopyranose | HMDB | | alpha-D-Glucose 1,6-bis(dihydrogen phosphate) | HMDB | | alpha-D-Glucose 1,6-diphosphate | HMDB | | alpha-delta-1,6-Bis(dihydrogen phosphate) glucopyranose | HMDB | | alpha-delta-Glucose 1,6-bis(dihydrogen phosphate) | HMDB | | alpha-delta-Glucose 1,6-bisphosphate | HMDB | | alpha-delta-Glucose 1,6-diphosphate | HMDB | | D-Glucose 1,6-diphosphate | HMDB | | delta-Glucose 1,6-diphosphate | HMDB | | Glucose 1,6-bisphosphate | HMDB | | Glucose 1,6-diphosphate | HMDB | | beta-D-Glucose 1,6-(bis)phosphate | MeSH | | Glucose-1,6-diphosphate | MeSH | | Glucose-1,6-bisphosphate | MeSH |
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| Chemical Formula | C6H14O12P2 |
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| Average Molecular Weight | 340.1157 |
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| Monoisotopic Molecular Weight | 339.996048936 |
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| IUPAC Name | {[(2R,3S,4S,5R,6R)-3,4,5-trihydroxy-6-(phosphonooxy)oxan-2-yl]methoxy}phosphonic acid |
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| Traditional Name | glucose 1,6-bisphosphate |
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| CAS Registry Number | 10139-18-1 |
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| SMILES | O[C@H]1[C@H](O)[C@@H](COP(O)(O)=O)O[C@H](OP(O)(O)=O)[C@@H]1O |
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| InChI Identifier | InChI=1S/C6H14O12P2/c7-3-2(1-16-19(10,11)12)17-6(5(9)4(3)8)18-20(13,14)15/h2-9H,1H2,(H2,10,11,12)(H2,13,14,15)/t2-,3-,4+,5-,6-/m1/s1 |
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| InChI Key | RWHOZGRAXYWRNX-VFUOTHLCSA-N |
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| Chemical Taxonomy |
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| Description | This compound belongs to the class of organic compounds known as hexose phosphates. These are carbohydrate derivatives containing a hexose substituted by one or more phosphate groups. |
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| Kingdom | Organic compounds |
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| Super Class | Organic oxygen compounds |
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| Class | Organooxygen compounds |
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| Sub Class | Carbohydrates and carbohydrate conjugates |
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| Direct Parent | Hexose phosphates |
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| Alternative Parents | |
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| Substituents | - Hexose phosphate
- Monosaccharide phosphate
- Monoalkyl phosphate
- Alkyl phosphate
- Phosphoric acid ester
- Oxane
- Organic phosphoric acid derivative
- Secondary alcohol
- Oxacycle
- Organoheterocyclic compound
- Polyol
- Organic oxide
- Hydrocarbon derivative
- Alcohol
- Aliphatic heteromonocyclic compound
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| Molecular Framework | Aliphatic heteromonocyclic compounds |
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| External Descriptors | |
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| Ontology |
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| Disposition | Biological location: Source: |
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| Process | Naturally occurring process: |
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| Role | Industrial application: |
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| Physical Properties |
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| State | Solid |
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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 | -4.374 | Not Available |
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| Predicted Properties | |
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| Spectra |
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| Spectra | |
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| General References | - Yamada Y, Kono N, Nakajima H, Shimizu T, Kiyokawa H, Kawachi M, Ono A, Nishimura T, Kuwajima M, Tarui S: Low glucose-1, 6-bisphosphate and high fructose-2, 6-bisphosphate concentrations in muscles of patients with glycogenosis types VII and V. Biochem Biophys Res Commun. 1991 Apr 15;176(1):7-10. [PubMed:2018547 ]
- Cadefau JA, Andres V, Carreras J, Vernet M, Grau JM, Urbano-Marquez A, Cusso R: Glucose 1,6-bisphosphate and fructose 2,6-bisphosphate in muscle from healthy humans and chronic alcoholic patients. Alcohol Alcohol. 1992 May;27(3):253-6. [PubMed:1449560 ]
- Katz A, Sahlin K, Broberg S: Regulation of glucose utilization in human skeletal muscle during moderate dynamic exercise. Am J Physiol. 1991 Mar;260(3 Pt 1):E411-5. [PubMed:2003594 ]
- Katz A: G-1,6-P2, glycolysis, and energy metabolism during circulatory occlusion in human skeletal muscle. Am J Physiol. 1988 Aug;255(2 Pt 1):C140-4. [PubMed:3407759 ]
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