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Record Information
Version1.0
Creation Date2016-10-03 18:34:12 UTC
Update Date2020-05-21 16:28:29 UTC
BMDB IDBMDB0012210
Secondary Accession Numbers
  • BMDB12210
Metabolite Identification
Common NameDihydrolipoate
DescriptionDihydrolipoate, 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.
Structure
Thumb
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 Weight208.341
Monoisotopic Molecular Weight208.059171136
IUPAC NameNot Available
Traditional NameNot Available
CAS Registry Number462-20-4
SMILESNot Available
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)
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
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Adiposome
  • Cell membrane
  • Cytoplasm
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted PropertiesNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Biological Properties
Cellular Locations
  • Adiposome
  • Cell membrane
  • Cytoplasm
  • Membrane
Biospecimen LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
HMDB IDHMDB0012210
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB028855
KNApSAcK IDNot Available
Chemspider ID408
KEGG Compound IDC02147
BioCyc ID6-S-ACETYL-DIHYDROLIPOATE
BiGG IDNot Available
Wikipedia LinkDihydrolipoic_acid
METLIN IDNot Available
PubChem Compound421
PDB IDNot Available
ChEBI ID18047
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Involved in prostaglandin-E synthase activity
Specific function:
Isomerase that catalyzes the conversion of PGH2 into the more stable prostaglandin E2 (PGE2).
Gene Name:
PTGES2
Uniprot ID:
Q66LN0
Molecular weight:
41738.0
General function:
Not Available
Specific function:
Not Available
Gene Name:
DLD
Uniprot ID:
F1N206
Molecular weight:
54187.0
Reactions
Dihydrolipoate + NAD → Lipoic acid + NADHdetails