Record Information |
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Version | 1.0 |
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Creation Date | 2016-10-03 18:34:12 UTC |
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Update Date | 2020-05-21 16:28:29 UTC |
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BMDB ID | BMDB0012210 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Dihydrolipoate |
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Description | Dihydrolipoate, also known as dihydrolipoate or dihydrolipoate, belongs to the class of organic compounds known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms. Dihydrolipoate is possibly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). Dihydrolipoate exists in all living organisms, ranging from bacteria to humans. Dihydrolipoate participates in a number of enzymatic reactions, within cattle. In particular, Dihydrolipoate and 5,10-methylene-THF can be biosynthesized from tetrahydrofolic acid and 8-[(aminomethyl)sulfanyl]-6-sulfanyloctanoic acid through its interaction with the enzyme aminomethyltransferase, mitochondrial. In addition, Dihydrolipoate can be converted into (R)-lipoic acid; which is mediated by the enzyme dihydrolipoyl dehydrogenase, mitochondrial. In cattle, dihydrolipoate is involved in the metabolic pathway called the glycine and serine metabolism pathway. |
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Structure | |
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Synonyms | Value | Source |
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6,8-Bis-sulfanyloctanoic acid | ChEBI | 6,8-Dihydrothioctic acid | ChEBI | 6,8-Dimercapto-octanoic acid | ChEBI | 6,8-Dimercaptooctanoic acid | ChEBI | DHLA | ChEBI | Dihydro-alpha-lipoic acid | ChEBI | Dihydro-lipoic acid | ChEBI | Dihydrothioctic acid | ChEBI | Dihydrolipoic acid | Kegg | 6,8-Bis-sulfanyloctanoate | Generator | 6,8-Bis-sulphanyloctanoate | Generator | 6,8-Bis-sulphanyloctanoic acid | Generator | 6,8-Dihydrothioctate | Generator | 6,8-Dimercapto-octanoate | Generator | 6,8-Dimercaptooctanoate | Generator | Dihydro-a-lipoate | Generator | Dihydro-a-lipoic acid | Generator | Dihydro-alpha-lipoate | Generator | Dihydro-α-lipoate | Generator | Dihydro-α-lipoic acid | Generator | Dihydro-lipoate | Generator | Dihydrothioctate | Generator | 6,8-Disulfanyloctanoate | HMDB | 6,8-Disulfanyloctanoic acid | HMDB | D,L-Dihydrolipoate | HMDB | D,L-Dihydrolipoic acid | HMDB | dihydro-DL-alpha-Lipoate | HMDB | dihydro-DL-alpha-Lipoic acid | HMDB | dihydro-Thioctic acid | HMDB | dihydro-Thiocytic acid | HMDB | DL-dihydro-a-6-Thioctic acid | HMDB | DL-dihydro-alpha-6-Thioctic acid | HMDB | Reduced DL-6,8-thioctic acid | HMDB | Reduced lipoate | HMDB | Reduced lipoic acid | HMDB | Reduced thioctic acid | HMDB | Dihydrolipoic acid, (+-)-isomer | MeSH, HMDB | Dihydrolipoic acid, sodium salt | MeSH, HMDB |
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Chemical Formula | C8H16O2S2 |
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Average Molecular Weight | 208.341 |
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Monoisotopic Molecular Weight | 208.059171136 |
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IUPAC Name | 6,8-disulfanyloctanoic acid |
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Traditional Name | dihydrolipoic acid |
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CAS Registry Number | 462-20-4 |
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SMILES | OC(=O)CCCCC(S)CCS |
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InChI Identifier | InChI=1S/C8H16O2S2/c9-8(10)4-2-1-3-7(12)5-6-11/h7,11-12H,1-6H2,(H,9,10) |
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InChI Key | IZFHEQBZOYJLPK-UHFFFAOYSA-N |
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Chemical Taxonomy |
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Description | belongs to the class of organic compounds known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms. |
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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 acids and conjugates |
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Direct Parent | Medium-chain fatty acids |
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Alternative Parents | |
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Substituents | - Medium-chain fatty acid
- Thia fatty acid
- Monocarboxylic acid or derivatives
- Carboxylic acid
- Carboxylic acid derivative
- Alkylthiol
- Organic oxygen compound
- Organic oxide
- Hydrocarbon derivative
- Organosulfur compound
- Organooxygen 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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Status | Expected but not 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 | - Adiposome
- Cell membrane
- Cytoplasm
- Membrane
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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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GC-MS | GC-MS Spectrum - GC-EI-TOF (Non-derivatized) | splash10-0007-5920000000-99648df42c67f7327a1d | View in MoNA |
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GC-MS | GC-MS Spectrum - GC-EI-TOF (Non-derivatized) | splash10-0007-5920000000-99648df42c67f7327a1d | View in MoNA |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-0kij-5900000000-7564ff734a37b263a7ac | View in MoNA |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive | splash10-00di-9520000000-35f52ace937d40f6ba6e | View in MoNA |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | Not Available | View in JSpectraViewer |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | Not Available | View in JSpectraViewer |
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LC-MS/MS | LC-MS/MS Spectrum - 20V, Positive | splash10-00di-0900000000-832657635f2c81515eac | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - 20V, Negative | splash10-00di-1900000000-832657635f2c81515eac | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - 10V, Negative | splash10-0ab9-0690000000-bb3d2691ed5ceb749b8c | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0a4l-0920000000-203769a6e5514dfdacce | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0bvl-0900000000-e0d6ca4b105aaeae3f10 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-06vi-9500000000-30fa7bade921a70952d5 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0ab9-0960000000-352daa80c3d73329d4b8 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0a4i-1930000000-dee930722526f680e10d | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-053r-9300000000-c53948709f447f46266c | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0a4i-0930000000-266230745999efddf6dd | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0ufr-2900000000-24ea3b6c12cfdd8e2cac | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0006-9300000000-a87ea4acfc88c77960a6 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0a4i-0190000000-212b987ce9dfd82aaeb6 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0a4r-3920000000-1948f3bf848db6d6ef45 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-001l-9400000000-39e9224d6c07b378fb5a | View in MoNA |
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