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Record Information |
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Version | 4.0 |
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Status | Expected but not Quantified |
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Creation Date | 2005-11-16 15:48:42 UTC |
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Update Date | 2020-02-26 21:22:49 UTC |
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HMDB ID | HMDB0000985 |
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Secondary Accession Numbers | - HMDB0006948
- HMDB00985
- HMDB06948
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Metabolite Identification |
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Common Name | Dihydrolipoamide |
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Description | Dihydrolipoamide is an intermediate in glycolysis/gluconeogenesis, citrate cycle (TCA cycle), alanine, aspartate and pyruvate metabolism, and valine, leucine and isoleucine degradation (KEGG ID C00579). It is converted to lipoamide via the enzyme dihydrolipoamide dehydrogenase [EC:1.8.1.4]. Dihydrolipoamide is also a substrate of enzyme Acyltransferases [EC 2.3.1.-]. (KEGG). |
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Structure | |
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Synonyms | Value | Source |
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6,8-Dimercaptooctanamide | ChEBI | Dihydrothioctamide | ChEBI | 6,8-Bis-sulfanyloctanamide | HMDB | 6,8-Dimercapto-octanamide | HMDB | 6,8-Disulfanyloctanamide | HMDB | Dihydrolipoamide, (+-)-isomer | HMDB |
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Chemical Formula | C8H17NOS2 |
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Average Molecular Weight | 207.357 |
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Monoisotopic Molecular Weight | 207.075155551 |
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IUPAC Name | 6,8-disulfanyloctanimidic acid |
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Traditional Name | dihydrothioctamide |
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CAS Registry Number | 3884-47-7 |
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SMILES | OC(=N)CCCCC(S)CCS |
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InChI Identifier | InChI=1S/C8H17NOS2/c9-8(10)4-2-1-3-7(12)5-6-11/h7,11-12H,1-6H2,(H2,9,10) |
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InChI Key | VLYUGYAKYZETRF-UHFFFAOYSA-N |
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Chemical Taxonomy |
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Description | belongs to the class of organic compounds known as fatty amides. These are carboxylic acid amide derivatives of fatty acids, that are formed from a fatty acid and an amine. |
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Kingdom | Organic compounds |
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Super Class | Lipids and lipid-like molecules |
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Class | Fatty Acyls |
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Sub Class | Fatty amides |
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Direct Parent | Fatty amides |
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Alternative Parents | |
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Substituents | - Fatty amide
- Primary carboxylic acid amide
- Carboxamide group
- Carboxylic acid derivative
- Alkylthiol
- Organic nitrogen compound
- Organic oxygen compound
- Organopnictogen compound
- Organic oxide
- Hydrocarbon derivative
- Organosulfur compound
- Organooxygen compound
- Organonitrogen compound
- Carbonyl group
- Aliphatic acyclic compound
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Molecular Framework | Aliphatic acyclic 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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Role | Biological role: |
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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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| Spectrum Type | Description | Splash Key | View |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-0006-9700000000-936a7170a2da09aecf11 | Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive | splash10-00di-9410000000-9f1410bc40e59db39d21 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0ab9-1960000000-1e45a79f64407fb4dea8 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0ab9-5930000000-297b157da8ed63567faa | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0006-9000000000-82e7dacb48c8cab103d4 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0a4l-0940000000-f34746a5ea022152ba75 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-052f-1900000000-99beaa28d55837788743 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0m2i-9400000000-53152f2f29c03cd0cbcd | Spectrum |
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Biological Properties |
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Cellular Locations | |
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Biospecimen Locations | Not Available |
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Tissue Locations | Not Available |
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Pathways | |
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Normal Concentrations |
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| Not Available |
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Abnormal Concentrations |
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| Not Available |
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Associated Disorders and Diseases |
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Disease References | None |
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Associated OMIM IDs | None |
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External Links |
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DrugBank ID | Not Available |
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Phenol Explorer Compound ID | Not Available |
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FooDB ID | FDB022352 |
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KNApSAcK ID | Not Available |
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Chemspider ID | 643 |
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KEGG Compound ID | C00579 |
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BioCyc ID | Not Available |
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BiGG ID | 35406 |
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Wikipedia Link | Dihydrolipoamide |
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METLIN ID | 5920 |
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PubChem Compound | 663 |
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PDB ID | Not Available |
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ChEBI ID | 17694 |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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MarkerDB ID | |
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References |
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Synthesis Reference | Weitzman, P. D. J.; Hewson, Janet K.; Parker, M. G. Preparation of dihydrolipoamide by electrolytic reduction. FEBS Letters (1974), 43(1), 101-3. |
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Material Safety Data Sheet (MSDS) | Not Available |
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General References | - Brautigam CA, Chuang JL, Tomchick DR, Machius M, Chuang DT: Crystal structure of human dihydrolipoamide dehydrogenase: NAD+/NADH binding and the structural basis of disease-causing mutations. J Mol Biol. 2005 Jul 15;350(3):543-52. [PubMed:15946682 ]
- Kim H: Asparagine-473 residue is important to the efficient function of human dihydrolipoamide dehydrogenase. J Biochem Mol Biol. 2005 Mar 31;38(2):248-52. [PubMed:15826505 ]
- McMillan PJ, Stimmler LM, Foth BJ, McFadden GI, Muller S: The human malaria parasite Plasmodium falciparum possesses two distinct dihydrolipoamide dehydrogenases. Mol Microbiol. 2005 Jan;55(1):27-38. [PubMed:15612914 ]
- Li XJ, Grunwald D, Mathieu J, Morel F, Stasia MJ: Crucial role of two potential cytosolic regions of Nox2, 191TSSTKTIRRS200 and 484DESQANHFAVHHDEEKD500, on NADPH oxidase activation. J Biol Chem. 2005 Apr 15;280(15):14962-73. Epub 2005 Jan 31. [PubMed:15684431 ]
- Deres P, Halmosi R, Toth A, Kovacs K, Palfi A, Habon T, Czopf L, Kalai T, Hideg K, Sumegi B, Toth K: Prevention of doxorubicin-induced acute cardiotoxicity by an experimental antioxidant compound. J Cardiovasc Pharmacol. 2005 Jan;45(1):36-43. [PubMed:15613977 ]
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