Dihydrolipoate (CHEM040711)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-27 00:26:04 UTC
Update Date2016-11-09 01:22:19 UTC
Accession NumberCHEM040711
Identification
Common NameDihydrolipoate
ClassSmall Molecule
DescriptionA thio-fatty acid that is reduced form of lipoic acid. A potent antioxidant shown to directly destroy superoxide, hydroperoxy and hydroxyl radicals; also has neuroprotective and anti-tumour effects.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
6,8-Bis-sulfanyloctanoic acidChEBI
6,8-Dihydrothioctic acidChEBI
6,8-Dimercapto-octanoic acidChEBI
6,8-Dimercaptooctanoic acidChEBI
DHLAChEBI
Dihydro-alpha-lipoic acidChEBI
Dihydro-lipoic acidChEBI
Dihydrothioctic acidChEBI
Dihydrolipoic acidKegg
6,8-Bis-sulfanyloctanoateGenerator
6,8-Bis-sulphanyloctanoateGenerator
6,8-Bis-sulphanyloctanoic acidGenerator
6,8-DihydrothioctateGenerator
6,8-Dimercapto-octanoateGenerator
6,8-DimercaptooctanoateGenerator
Dihydro-a-lipoateGenerator
Dihydro-a-lipoic acidGenerator
Dihydro-alpha-lipoateGenerator
Dihydro-α-lipoateGenerator
Dihydro-α-lipoic acidGenerator
Dihydro-lipoateGenerator
DihydrothioctateGenerator
6,8-DisulfanyloctanoateHMDB
6,8-Disulfanyloctanoic acidHMDB
D,L-DihydrolipoateHMDB
D,L-Dihydrolipoic acidHMDB
dihydro-DL-alpha-LipoateHMDB
dihydro-DL-alpha-Lipoic acidHMDB
dihydro-Thioctic acidHMDB
dihydro-Thiocytic acidHMDB
DL-dihydro-a-6-Thioctic acidHMDB
DL-dihydro-alpha-6-Thioctic acidHMDB
Reduced DL-6,8-thioctic acidHMDB
Reduced lipoateHMDB
Reduced lipoic acidHMDB
Reduced thioctic acidHMDB
Dihydrolipoic acid, (+-)-isomerMeSH, HMDB
Dihydrolipoic acid, sodium saltMeSH, HMDB
Chemical FormulaC8H16O2S2
Average Molecular Mass208.341 g/mol
Monoisotopic Mass208.059 g/mol
CAS Registry Number462-20-4
IUPAC Name6,8-disulfanyloctanoic acid
Traditional Namedihydrolipoic acid
SMILESOC(=O)CCCCC(S)CCS
InChI IdentifierInChI=1S/C8H16O2S2/c9-8(10)4-2-1-3-7(12)5-6-11/h7,11-12H,1-6H2,(H,9,10)
InChI KeyIZFHEQBZOYJLPK-UHFFFAOYSA-N
Chemical Taxonomy
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.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acids and conjugates
Direct ParentMedium-chain fatty acids
Alternative Parents
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
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.1 g/LALOGPS
logP2.24ALOGPS
logP2.2ChemAxon
logS-3.3ALOGPS
pKa (Strongest Acidic)4.91ChemAxon
pKa (Strongest Basic)-9.6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity55.94 m³·mol⁻¹ChemAxon
Polarizability23.3 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0007-5920000000-99648df42c67f7327a1dSpectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0007-5920000000-99648df42c67f7327a1dSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0kij-5900000000-7564ff734a37b263a7acSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00di-9520000000-35f52ace937d40f6ba6eSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-00di-0900000000-832657635f2c81515eacSpectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-00di-1900000000-832657635f2c81515eacSpectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-0ab9-0690000000-bb3d2691ed5ceb749b8cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4l-0920000000-203769a6e5514dfdacceSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0bvl-0900000000-e0d6ca4b105aaeae3f10Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-06vi-9500000000-30fa7bade921a70952d5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0ab9-0960000000-352daa80c3d73329d4b8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-1930000000-dee930722526f680e10dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-053r-9300000000-c53948709f447f46266cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0930000000-266230745999efddf6ddSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ufr-2900000000-24ea3b6c12cfdd8e2cacSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9300000000-a87ea4acfc88c77960a6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0190000000-212b987ce9dfd82aaeb6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4r-3920000000-1948f3bf848db6d6ef45Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001l-9400000000-39e9224d6c07b378fb5aSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0012210
FooDB IDFDB028855
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc ID6-S-ACETYL-DIHYDROLIPOATE
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkDihydrolipoic_acid
Chemspider ID408
ChEBI ID18047
PubChem Compound ID421
Kegg Compound IDC02147
YMDB IDNot Available
ECMDB IDECMDB21458
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=12127266
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=1345759
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=17403519
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=18951944
5. Prehn JH, Karkoutly C, Nuglisch J, Peruche B, Krieglstein J: Dihydrolipoate reduces neuronal injury after cerebral ischemia. J Cereb Blood Flow Metab. 1992 Jan;12(1):78-87.
6. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9.
7. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10.
8. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20.
9. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621.
10. The lipid handbook with CD-ROM