| 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 | 2018-05-19 21:24:39 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-phosphoglucono-delta-lactone (d-6PGL) is the immediate product of the Glucose-6-phosphate dehydrogenase (G-6-PD), the first enzyme of the hexose monophosphate pathway. (PMID 3711719 ). 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. 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. (PMID 11457850 ). |
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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 | MeSH |
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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 | 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
- 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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| Spectra |
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| Spectra | |
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| General References | - 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 ]
- 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 ]
- 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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