| Record Information |
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| Version | 2.0 |
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| Creation Date | 2015-09-08 17:49:56 -0600 |
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| Update Date | 2015-09-14 16:46:07 -0600 |
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| Secondary Accession Numbers | |
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| Identification |
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| Name: | 3-deoxy-D-arabino-heptulosonate-7-phosphate |
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| Description | 3-Deoxy-D-arabino-heptulosonate-7-phosphate is a member of the chemical class known as Medium-chain Keto Acids and Derivatives. These are keto acids with a 6 to 12 carbon atoms long side chain. DAHPS is involved in the biosynthesis of aromatic amino acids. Maritima DAHP synthase is a metalloenzyme. This report is the first description of a thermophilic eubacterial DAHP synthase. (PMID 12743122) DAHPS(Phe) is a metal-catalyzed oxidation system wherein bound substrate protects active-site residues from oxidative attack catalyzed by bound redox metal cofactor. (PMID 10049398) The first regulatory step in the synthesis of aromatic amino acids is catalyzed by 3-deoxy-D-arabino-heptulosonate 7-phosphate synthase (DAHPS). (PMID 15378531) While several similarities exist between the two enzymatic reactions, classic studies on the Escherichia coli enzymes have established that DAHPS is a metalloenzyme, whereas KDO8PS has no metal requirement. aeolicus KDO8PS is a metalloenzyme in vivo and point to a previously unrecognized relationship between the KDO8PS and DAHPS families. (PMID 10811802) |
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| Structure | |
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| Synonyms: | - 3-Deoxy-D-arabino-heptulosonic acid-7-phosphoric acid
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| Chemical Formula: | C7H10O10P |
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| Weight: | Average: 285.122
Monoisotopic: 285.00280426 |
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| InChI Key: | PJWIPEXIFFQAQZ-PUFIMZNGSA-K |
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| InChI: | InChI=1S/C7H13O10P/c8-3(1-4(9)7(12)13)6(11)5(10)2-17-18(14,15)16/h3,5-6,8,10-11H,1-2H2,(H,12,13)(H2,14,15,16)/p-3/t3-,5-,6+/m1/s1 |
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| CAS number: | Not Available |
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| IUPAC Name: | (4R,5S,6R)-4,5,6-trihydroxy-2-oxo-7-(phosphonatooxy)heptanoate |
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| Traditional IUPAC Name: | (4R,5S,6R)-4,5,6-trihydroxy-2-oxo-7-(phosphonatooxy)heptanoate |
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| SMILES: | [H][C@@](O)(COP([O-])([O-])=O)[C@@]([H])(O)[C@]([H])(O)CC(=O)C([O-])=O |
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| Chemical Taxonomy |
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| Description | belongs to the class of organic compounds known as monosaccharide phosphates. These are monosaccharides comprising a phosphated group linked to the carbohydrate unit. |
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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 | Monosaccharide phosphates |
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| Alternative Parents | |
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| Substituents | - Heptose monosaccharide
- Monosaccharide phosphate
- Medium-chain keto acid
- Sugar acid
- Alpha-keto acid
- Beta-hydroxy ketone
- Alkyl phosphate
- Keto acid
- Phosphoric acid ester
- Organic phosphoric acid derivative
- Secondary alcohol
- Ketone
- Carboxylic acid derivative
- Carboxylic acid
- Polyol
- Monocarboxylic acid or derivatives
- Alcohol
- Carbonyl group
- Organic oxide
- Hydrocarbon derivative
- Organic anion
- Aliphatic acyclic compound
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| Molecular Framework | Aliphatic acyclic compounds |
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| External Descriptors | |
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| Physical Properties |
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| State: | Not Available |
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| Charge: | -3 |
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| Melting point: | Not Available |
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| Experimental Properties: | |
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| Predicted Properties | |
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| Biological Properties |
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| Cellular Locations: | Cytoplasm |
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| Reactions: | |
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| SMPDB Pathways: | | Chorismate biosynthesis | PW000816 |    | | Secondary Metabolites: Shikimate Pathway | PW000985 |    |
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| KEGG Pathways: | Not Available |
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| EcoCyc Pathways: | Not Available |
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| Concentrations |
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| Not Available |
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| Spectra |
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| Spectra: | |
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| References |
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| References: | Not Available |
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| Synthesis Reference: | Not Available |
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| Material Safety Data Sheet (MSDS) | Not Available |
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| Links |
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| External Links: | |
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