| Record Information |
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| Version | 1.0 |
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| Creation Date | 2016-09-30 22:43:17 UTC |
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| Update Date | 2020-06-04 19:55:18 UTC |
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| BMDB ID | BMDB0001264 |
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| Secondary Accession Numbers | |
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| Metabolite Identification |
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| Common Name | Dehydroascorbic acid |
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| Description | Dehydroascorbic acid, also known as dehydroascorbate or dhaa, belongs to the class of organic compounds known as gamma butyrolactones. Gamma butyrolactones are compounds containing a gamma butyrolactone moiety, which consists of an aliphatic five-member ring with four carbon atoms, one oxygen atom, and bears a ketone group on the carbon adjacent to the oxygen atom. Dehydroascorbic acid is possibly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). Dehydroascorbic acid exists in all living organisms, ranging from bacteria to humans. Norepinephrine and dehydroascorbic acid can be biosynthesized from dopamine and ascorbic acid through its interaction with the enzyme dopamine beta-hydroxylase. In cattle, dehydroascorbic acid is involved in the metabolic pathway called the tyrosine metabolism pathway. |
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| Structure | |
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| Synonyms | | Value | Source |
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| Dehydroascorbate | Generator | | 1-Dehydroascorbate | HMDB | | 1-Dehydroascorbic acid | HMDB | | Dehydro-L-ascorbate | HMDB | | Dehydro-L-ascorbic acid | HMDB | | DHAA | HMDB | | L-Dehydroascorbate | HMDB | | L-Dehydroascorbic acid | HMDB | | L-Threo-2,3-hexodiulosonic acid gamma-lactone | HMDB | | L-Threo-hexo-2,3-diulosono-1,4-lactone | HMDB | | Oxidized ascorbate | HMDB | | Oxidized ascorbic acid | HMDB | | Oxidized vitamin C | HMDB | | Dehydroerythorbic acid | HMDB |
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| Chemical Formula | C6H6O6 |
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| Average Molecular Weight | 174.1082 |
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| Monoisotopic Molecular Weight | 174.016437924 |
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| IUPAC Name | (5R)-5-[(1R)-1,2-dihydroxyethyl]oxolane-2,3,4-trione |
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| Traditional Name | (5R)-5-[(1R)-1,2-dihydroxyethyl]oxolane-2,3,4-trione |
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| CAS Registry Number | 490-83-5 |
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| SMILES | [H][C@@]1(OC(=O)C(=O)C1=O)[C@H](O)CO |
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| InChI Identifier | InChI=1S/C6H6O6/c7-1-2(8)5-3(9)4(10)6(11)12-5/h2,5,7-8H,1H2/t2-,5-/m1/s1 |
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| InChI Key | SBJKKFFYIZUCET-DUZGATOHSA-N |
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| Chemical Taxonomy |
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| Description | belongs to the class of organic compounds known as gamma butyrolactones. Gamma butyrolactones are compounds containing a gamma butyrolactone moiety, which consists of an aliphatic five-member ring with four carbon atoms, one oxygen atom, and bears a ketone group on the carbon adjacent to the oxygen atom. |
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| Kingdom | Organic compounds |
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| Super Class | Organoheterocyclic compounds |
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| Class | Lactones |
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| Sub Class | Gamma butyrolactones |
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| Direct Parent | Gamma butyrolactones |
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| Alternative Parents | |
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| Substituents | - 3-furanone
- Gamma butyrolactone
- Tetrahydrofuran
- 1,2-diol
- Carboxylic acid ester
- Cyclic ketone
- Secondary alcohol
- Ketone
- Carboxylic acid derivative
- Oxacycle
- Monocarboxylic acid or derivatives
- Alcohol
- Hydrocarbon derivative
- Organic oxide
- Organic oxygen compound
- Carbonyl group
- Primary alcohol
- Organooxygen compound
- Aliphatic heteromonocyclic compound
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| Molecular Framework | Aliphatic heteromonocyclic compounds |
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| External Descriptors | Not Available |
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| Ontology |
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| Status | Detected and Quantified |
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| Origin | |
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| Biofunction | Not Available |
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| Application | Not Available |
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| Cellular locations | |
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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 | | Spectrum Type | Description | Splash Key | |
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| Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-001i-9200000000-0a414c4d59046ece51c1 | View in MoNA |
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| Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive | splash10-0fki-9831000000-c4b46024e1624e983ac3 | View in MoNA |
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| LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated) | splash10-004i-4900000000-25a652482451303b3ca4 | View in MoNA |
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| Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-056r-1900000000-f1d23791c8a7b59576a3 | View in MoNA |
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| Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0a4r-2900000000-5ebc67e43b07167f34cb | View in MoNA |
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| Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0abc-9000000000-27ae8f5e1795d4f732a8 | View in MoNA |
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| Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0229-0900000000-ee719ada45193fc650a0 | View in MoNA |
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| Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0mbc-1900000000-d54b8e72e08e6ea1f7c0 | View in MoNA |
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| Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0btc-9200000000-d07ff0053ddc28ce1915 | View in MoNA |
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| 1D NMR | 1H NMR Spectrum (1D, 600 MHz, H2O, experimental) | Not Available | View in JSpectraViewer |
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| 2D NMR | [1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental) | Not Available | View in JSpectraViewer |
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