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Human Metabolome Database Version 2.5
Showing metabocard for Dihydrolipoate (HMDB12210)
Legend: enzyme field
| Version | 2.5 | ||||||||||||||||||
| Creation Date | 2009-04-06 17:21:04 | ||||||||||||||||||
| Update Date | 2009-06-01 14:34:09 | ||||||||||||||||||
| Accession Number | HMDB12210 | ||||||||||||||||||
| Secondary Accession Numbers | Not Available | ||||||||||||||||||
| Common Name | Dihydrolipoate | ||||||||||||||||||
| Description | Dihydrolipoic acid is an organic compound that is the reduced form of lipoic acid. This carboxylic acid features a pair of thiol groups. It is optically active but only the R-enantiomer is biochemically significant. The lipoic acid/dihydrolipoic acid pair participate in a variety of biochemical transformations.( from Wiki) Inside the cell, alpha lipoic acid is readily reduced or broken down to dihydrolipoic acid. Dihydrolipoic acid is even more potent than alpha lipoic acid, neutralizing free radicals, preventing them from causing harm. It directly destroys damaging superoxide radicals, hydroperoxy radicals and hydroxyl radicals. It has been shown in vitro that dihydrolipoate (DL-6,8-dithioloctanoic acid) has antioxidant activity against microsomal lipid peroxidation.Dihydrolipoate is tested for its neuroprotective activity using models of hypoxic and excitotoxic neuronal damage in vitro and rodent models of cerebral ischemia in vivo. Dihydrolipoate, similarly to dimethylthiourea, is able to protect neurons against ischemic damage by diminishing the accumulation of reactive oxygen species within the cerebral tissue.(PMID: 1345759) | ||||||||||||||||||
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| Chemical IUPAC Name | 6,8-bis-sulfanyloctanoic acid | ||||||||||||||||||
| Chemical Formula | C8H16O2S2 | ||||||||||||||||||
| Chemical Structure | |||||||||||||||||||
| Chemical Taxonomy |
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| Average Molecular Weight | 208.341 | ||||||||||||||||||
| Monoisotopic Molecular Weight | 208.059174 | ||||||||||||||||||
| Isomeric SMILES | OC(=O)CCCCC(S)CCS | ||||||||||||||||||
| Canonical SMILES | OC(=O)CCCCC(S)CCS | ||||||||||||||||||
| KEGG Compound ID | C02147  |
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| BioCyc ID | 6-S-ACETYL-DIHYDROLIPOATE |
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| BiGG ID | Not Available | ||||||||||||||||||
| Wikipedia Link | Not Available | ||||||||||||||||||
| NuGOwiki Link | HMDB12210 |
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| Metagene Link | HMDB12210 |
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| METLIN ID | Not Available | ||||||||||||||||||
| PubChem Compound | 421 |
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| PubChem Substance | 10523439 |
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| ChEBI ID | 18047 |
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| CAS Registry Number | 462-20-4 | ||||||||||||||||||
| InChI Identifier | InChI=1/C8H16O2S2/c9-8(10)4-2-1-3-7(12)5-6-11/h7,11-12H,1-6H2,(H,9,10) | ||||||||||||||||||
| Synthesis Reference | Not Available | ||||||||||||||||||
| Melting Point (Experimental) | Not Available | ||||||||||||||||||
| Experimental Water Solubility | Not Available Source: PhysProp | ||||||||||||||||||
| Predicted Water Solubility | 0.103 mg/mL [Predicted by ALOGPS] Calculated using ALOGPS | ||||||||||||||||||
| Physiological Charge | 0 | ||||||||||||||||||
| State | Solid | ||||||||||||||||||
| Experimental LogP/Hydrophobicity | Not Available Source: PhysProp | ||||||||||||||||||
| Predicted LogP/Hydrophobicity | 2.24 [Predicted by ALOGPS] Calculated using ALOGPS | ||||||||||||||||||
| Material Safety Data Sheet (MSDS) | Not Available | ||||||||||||||||||
| MOL File | Show | ||||||||||||||||||
| SDF File | Show | ||||||||||||||||||
| PDB File | Show | ||||||||||||||||||
| 2D Structure | |||||||||||||||||||
| 3D Structure | |||||||||||||||||||
| Experimental PDB ID | Not Available | ||||||||||||||||||
| Experimental 1H NMR Spectrum | Not Available | ||||||||||||||||||
| Experimental 13C NMR Spectrum | Not Available | ||||||||||||||||||
| Experimental 13C HSQC Spectrum | Not Available | ||||||||||||||||||
| Predicted 1H NMR Spectrum |
Not Available Not Available |
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| Predicted 13C NMR Spectrum |
Not Available Not Available |
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| Mass Spectrum | Not Available | ||||||||||||||||||
| Simplified TOCSY Spectrum | Not Available | ||||||||||||||||||
| BMRB Spectrum | Not Available | ||||||||||||||||||
| Cellular Location | Not Available | ||||||||||||||||||
| Biofluid Location | Not Available | ||||||||||||||||||
| Tissue Location | Not Available | ||||||||||||||||||
| Concentrations (Normal) | Not Available | ||||||||||||||||||
| Concentrations (Abnormal) | Not Available | ||||||||||||||||||
| Associated Disorders | Not Available | ||||||||||||||||||
| OMIM ID | Not Available | ||||||||||||||||||
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| General References | Not Available |
