| Record Information |
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| Version | 4.0 |
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| Status | Detected and Quantified |
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| Creation Date | 2005-11-16 15:48:42 UTC |
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| Update Date | 2019-07-23 05:44:44 UTC |
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| HMDB ID | HMDB0001127 |
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| Secondary Accession Numbers | |
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| Metabolite Identification |
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| Common Name | 6-Phosphonoglucono-D-lactone |
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| Description | 6-Phosphonoglucono-D-lactone, also known as D-glucono-1,5-lactone 6-phosphate or 6-PGDL, 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. 6-Phosphonoglucono-D-lactone (d-6PGL) is the immediate product of the Glucose-6-phosphate dehydrogenase (G-6-PD), the first enzyme of the hexose monophosphate pathway. 6-Phosphonoglucono-D-lactone is an extremely weak basic (essentially neutral) compound (based on its pKa). 6-Phosphonoglucono-D-lactone exists in all living species, ranging from bacteria to humans. Within humans, 6-phosphonoglucono-D-lactone participates in a number of enzymatic reactions. In particular, 6-phosphonoglucono-D-lactone can be converted into 6-phosphogluconic acid through the action of the enzyme 6-phosphogluconolactonase. In addition, 6-phosphonoglucono-D-lactone can be biosynthesized from Beta-D-glucose 6-phosphate through its interaction with the enzyme glucose-6-phosphate 1-dehydrogenase. In humans, 6-phosphonoglucono-D-lactone is involved in the metabolic disorder called the warburg effect pathway. Outside of the human body, 6-phosphonoglucono-D-lactone has been detected, but not quantified in, several different foods, such as oxheart cabbages, green zucchinis, radish, lima beans, and lingonberries. This could make 6-phosphonoglucono-D-lactone a potential biomarker for the consumption of these foods. By efficiently catalyzing the hydrolysis of d-6PGL, 6-phosphogluconolactonase prevents the reaction between d-6PGL and intracellular nucleophiles; such a reaction would interrupt the functioning of the pentose-phosphate pathway. The pentose-phosphate pathway provides reductive power and nucleotide precursors to the cell through oxidative and nonoxidative branches. 6-Phosphogluconolactonase is the second enzyme of the oxidative branch and catalyzes the hydrolysis of 6-phosphogluconolactones, the products of glucose 6-phosphate oxidation by glucose-6-phosphate dehydrogenase. |
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| Structure | |
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| Synonyms | | Value | Source |
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| 6-Phospho-D-glucono-1,5-lactone | ChEBI | | 6-Phosphonoglucono-delta-lactone | ChEBI | | [(2R,3S,4S,5R)-3,4,5-Trihydroxy-6-oxotetrahydro-2H-pyran-2-yl]methyl dihydrogen phosphate | ChEBI | | D-Gluconic acid, delta-lactone, 6-(dihydrogen phosphate) | ChEBI | | D-Glucono-1,5-lactone 6-phosphate | ChEBI | | 6-Phosphonoglucono-δ-lactone | Generator | | [(2R,3S,4S,5R)-3,4,5-Trihydroxy-6-oxotetrahydro-2H-pyran-2-yl]methyl dihydrogen phosphoric acid | Generator | | D-Gluconate, delta-lactone, 6-(dihydrogen phosphate) | Generator | | D-Gluconate, δ-lactone, 6-(dihydrogen phosphate) | Generator | | D-Gluconic acid, delta-lactone, 6-(dihydrogen phosphoric acid) | Generator | | D-Gluconic acid, δ-lactone, 6-(dihydrogen phosphoric acid) | Generator | | D-Glucono-1,5-lactone 6-phosphoric acid | Generator | | 6-(Dihydrogen phosphate)-(8ci)-D-gluconic acid delta-lactone | HMDB | | 6-(Dihydrogen phosphate)-(9ci)-D-gluconic acid delta-lactone | HMDB | | 6-(Dihydrogen phosphate)-D-gluconic acid delta-lactone | HMDB | | 6-PGDL | HMDB | | 6-Phosphoglucono-delta-lactone | HMDB | | 6-Phosphogluconolactone | HMDB | | D-6-Phospho-glucono-delta-lactone | HMDB | | D-6-Phosphoglucono-delta-lactone | HMDB | | D-Glucono-delta-lactone-6-phosphate | HMDB | | delta-Gluconolactone 6-phosphate | HMDB | | p-Gluconolactone | HMDB |
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| Chemical Formula | C6H11O9P |
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| Average Molecular Weight | 258.1199 |
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| Monoisotopic Molecular Weight | 258.014068462 |
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| IUPAC Name | {[(2R,3S,4S,5R)-3,4,5-trihydroxy-6-oxooxan-2-yl]methoxy}phosphonic acid |
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| Traditional Name | 6-phosphogluconolactone |
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| CAS Registry Number | 2641-81-8 |
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| SMILES | O[C@H]1[C@H](O)[C@@H](COP(O)(O)=O)OC(=O)[C@@H]1O |
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| InChI Identifier | InChI=1S/C6H11O9P/c7-3-2(1-14-16(11,12)13)15-6(10)5(9)4(3)8/h2-5,7-9H,1H2,(H2,11,12,13)/t2-,3-,4+,5-/m1/s1 |
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| InChI Key | IJOJIVNDFQSGAB-SQOUGZDYSA-N |
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| Chemical Taxonomy |
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| Description | 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
- Gluconolactone
- Monosaccharide phosphate
- Delta valerolactone
- Delta_valerolactone
- Monoalkyl phosphate
- Alkyl phosphate
- Organic phosphoric acid derivative
- Phosphoric acid ester
- Oxane
- Secondary alcohol
- Carboxylic acid ester
- Lactone
- Organoheterocyclic compound
- Carboxylic acid derivative
- Monocarboxylic acid or derivatives
- Oxacycle
- Polyol
- Hydrocarbon derivative
- Organic oxide
- Alcohol
- Carbonyl group
- 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 | Route of exposure: Source: Biological location: |
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| Process | Naturally occurring process: |
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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 | Not Available | Not Available |
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| Predicted Properties | |
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| | Spectrum Type | Description | Splash Key | View |
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| Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-0002-9410000000-eed74c30dd7f6e1f6308 | JSpectraViewer | | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positive | splash10-0gb9-4962700000-904ef84e4218dd793e1f | JSpectraViewer | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0a4l-0490000000-b7b9499f5fb3885d4a30 | JSpectraViewer | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-06r7-5940000000-effb433b86b6c959da1d | JSpectraViewer | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0ukc-7900000000-4009a042c78eba5dae17 | JSpectraViewer | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0a6r-7290000000-09bacc885b7c74c16ece | JSpectraViewer | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-004i-9000000000-5f41258b7bf2096e04fd | JSpectraViewer | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-004i-9000000000-82b3c16e1939174dae85 | JSpectraViewer |
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| General References | - Beutler E, Kuhl W: Characteristics and significance of the reverse glucose-6-phosphate dehydrogenase reaction. J Lab Clin Med. 1986 Jun;107(6):502-7. [PubMed:3711719 ]
- Nakayama Y, Kinoshita A, Tomita M: Dynamic simulation of red blood cell metabolism and its application to the analysis of a pathological condition. Theor Biol Med Model. 2005 May 9;2:18. [PubMed:15882454 ]
- Rakitzis ET, Papandreou P: Kinetic analysis of 6-phosphogluconolactone hydrolysis in hemolysates. Biochem Mol Biol Int. 1995 Nov;37(4):747-55. [PubMed:8589648 ]
- Miclet E, Stoven V, Michels PA, Opperdoes FR, Lallemand JY, Duffieux F: NMR spectroscopic analysis of the first two steps of the pentose-phosphate pathway elucidates the role of 6-phosphogluconolactonase. J Biol Chem. 2001 Sep 14;276(37):34840-6. Epub 2001 Jul 16. [PubMed:11457850 ]
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