Record Information |
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Version | 1.0 |
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Created at | 2005-11-16 15:48:42 UTC |
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Updated at | 2021-08-09 22:32:56 UTC |
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NP-MRD ID | NP0001399 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | 3-Deoxyarabinohexonic acid |
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Description | 3-Deoxyarabinohexonic acid, also known as arabino-3-deoxyhexonate or D-2-keto-3-deoxygluconate, belongs to the class of organic compounds known as medium-chain hydroxy acids and derivatives. These are hydroxy acids with a 6 to 12 carbon atoms. 3-Deoxyarabinohexonic acid is a thermal decomposition product of plant-derived sugars such as nigerose (3-O-α-D-glucopyranosyl-D-glucose), turanose and 3-O-methyl glucose. 3-Deoxyarabinohexonic acid is found in plants and plant products that have been heated. As a consequence, it can be detected in the biofluids of animals that have consumed plant foods (including humans). |
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Structure | OC[C@@H](O)[C@@H](O)C[C@H](O)C(O)=O InChI=1S/C6H12O6/c7-2-5(10)3(8)1-4(9)6(11)12/h3-5,7-10H,1-2H2,(H,11,12)/t3-,4-,5+/m0/s1 |
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Synonyms | Value | Source |
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(2S,4S,5R)-2,4,5,6-Tetrahydroxyhexanoic acid | ChEBI | 3-Deoxy-arabino-hexonic acid | ChEBI | 3-Deoxyarabino-hexonic acid | ChEBI | (2S,4S,5R)-2,4,5,6-Tetrahydroxyhexanoate | Generator | 3-Deoxy-arabino-hexonate | Generator | 3-Deoxyarabino-hexonate | Generator | 3-Deoxyarabinohexonate | Generator | 3-Deoxy-D-arabino-hexonic acid | HMDB | Arabino-3-deoxyhexonate | HMDB | Arabino-3-deoxyhexonic acid | HMDB | D-2-Keto-3-deoxygluconate | HMDB | 3-Deoxy-arabino-hexonic acid, monosodium salt, (D)-isomer | HMDB | 3-Deoxy-arabino-hexonic acid, (D)-isomer | HMDB | 3-Deoxy-D-arabino-hexonate | HMDB |
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Chemical Formula | C6H12O6 |
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Average Mass | 180.1559 Da |
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Monoisotopic Mass | 180.06339 Da |
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IUPAC Name | (2S,4S,5R)-2,4,5,6-tetrahydroxyhexanoic acid |
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Traditional Name | 3-deoxy-arabinohexonic acid |
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CAS Registry Number | 29625-79-4 |
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SMILES | OC[C@@H](O)[C@@H](O)C[C@H](O)C(O)=O |
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InChI Identifier | InChI=1S/C6H12O6/c7-2-5(10)3(8)1-4(9)6(11)12/h3-5,7-10H,1-2H2,(H,11,12)/t3-,4-,5+/m0/s1 |
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InChI Key | YGMNHEPVTNXLLS-VAYJURFESA-N |
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Experimental Spectra |
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| Spectrum Type | Description | Depositor Email | Depositor Organization | Depositor | Deposition Date | View |
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2D NMR | [1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum |
| Predicted Spectra |
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| Not Available | Chemical Shift Submissions |
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| Spectrum Type | Description | Depositor ID | Depositor Organization | Depositor | Deposition Date | View |
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1D NMR | 1H NMR Spectrum (1D, 600 MHz, CDCl3, simulated) | Varshavi.d26 | | | 2021-08-10 | View Spectrum |
| Species |
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Species of Origin | |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as medium-chain hydroxy acids and derivatives. These are hydroxy acids with a 6 to 12 carbon atoms long side chain. |
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Kingdom | Organic compounds |
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Super Class | Organic acids and derivatives |
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Class | Hydroxy acids and derivatives |
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Sub Class | Medium-chain hydroxy acids and derivatives |
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Direct Parent | Medium-chain hydroxy acids and derivatives |
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Alternative Parents | |
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Substituents | - Medium-chain hydroxy acid
- Medium-chain fatty acid
- Hydroxy fatty acid
- Alpha-hydroxy acid
- Fatty acyl
- Fatty acid
- Secondary alcohol
- Carboxylic acid derivative
- Carboxylic acid
- Monocarboxylic acid or derivatives
- Polyol
- Hydrocarbon derivative
- Organic oxide
- Alcohol
- Organic oxygen compound
- Organooxygen compound
- Carbonyl group
- Primary 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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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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General References | - Schoots AC, Mikkers FE, Cramers CA, Ringoir S: Profiling of uremic serum by high-resolution gas chromatography-electron-impact, chemical ionization mass spectrometry. J Chromatogr. 1979 Sep 11;164(1):1-8. [PubMed:541389 ]
- Schoots AC, Leclercq PA: Chemical ionization mass spectrometry of trimethylsilylated carbohydrates and organic acids retained in uremic serum. Biomed Mass Spectrom. 1979 Nov;6(11):502-7. [PubMed:534687 ]
- Theodossis A, Walden H, Westwick EJ, Connaris H, Lamble HJ, Hough DW, Danson MJ, Taylor GL: The structural basis for substrate promiscuity in 2-keto-3-deoxygluconate aldolase from the Entner-Doudoroff pathway in Sulfolobus solfataricus. J Biol Chem. 2004 Oct 15;279(42):43886-92. doi: 10.1074/jbc.M407702200. Epub 2004 Jul 20. [PubMed:15265860 ]
- Zhang W, Carmichael I, Serianni AS: Rearrangement of 3-deoxy-D-erythro-hexos-2-ulose in aqueous solution: NMR evidence of intramolecular 1,2-hydrogen transfer. J Org Chem. 2011 Oct 21;76(20):8151-8. doi: 10.1021/jo200288t. Epub 2011 Sep 20. [PubMed:21793547 ]
- Liu X, Ser Z, Cluntun AA, Mentch SJ, Locasale JW: A strategy for sensitive, large scale quantitative metabolomics. J Vis Exp. 2014 May 27;(87). doi: 10.3791/51358. [PubMed:24894601 ]
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