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CHEBI:18047 - dihydrolipoic acid

ChEBI IDCHEBI:18047
ChEBI Namedihydrolipoic acid
Stars
DefinitionA 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.
Secondary ChEBI IDsCHEBI:4569, CHEBI:23752
Last Modified24 November 2014
DownloadsMolfile
FormulaC8H16O2S2
Net Charge0
Average Mass208.348
Monoisotopic Mass208.05917
SMILESO=C(O)CCCCC(S)CCS
InChIInChI=1S/C8H16O2S2/c9-8(10)4-2-1-3-7(12)5-6-11/h7,11-12H,1-6H2,(H,9,10)
InChIKeyIZFHEQBZOYJLPK-UHFFFAOYSA-N
Wikipedia
Roles Classification
Chemical Roles:
antioxidant  A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides.
Bronsted acid  A molecular entity capable of donating a hydron to an acceptor (Brønsted base).
Biological Role:
human metabolite  Any mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens).
Application:
neuroprotective agent  Any compound that can be used for the treatment of neurodegenerative disorders.
ChEBI Ontology
Outgoing Relation(s)
dihydrolipoic acid (CHEBI:18047) has functional parent octanoic acid (CHEBI:28837)
dihydrolipoic acid (CHEBI:18047) has role antioxidant (CHEBI:22586)
dihydrolipoic acid (CHEBI:18047) has role human metabolite (CHEBI:77746)
dihydrolipoic acid (CHEBI:18047) has role neuroprotective agent (CHEBI:63726)
dihydrolipoic acid (CHEBI:18047) is a thio-fatty acid (CHEBI:59913)
dihydrolipoic acid (CHEBI:18047) is conjugate acid of dihydrolipoate (CHEBI:30316)
Incoming Relation(s)
(R)-dihydrolipoic acid (CHEBI:45230) is a dihydrolipoic acid (CHEBI:18047)
(S)-dihydrolipoic acid (CHEBI:30318) is a dihydrolipoic acid (CHEBI:18047)
dihydrolipoate (CHEBI:30316) is conjugate base of dihydrolipoic acid (CHEBI:18047)
IUPAC Name 
6,8-disulfanyloctanoic acid
Synonyms  Source
Dihydrolipoic acidKEGG COMPOUND
Dihydrothioctic acidKEGG COMPOUND
6,8-dimercaptooctanoic acidChemIDplus
DHLAChEBI
6,8-Dihydrothioctic acidChemIDplus
dihydro-α-lipoic acidNIST Chemistry WebBook
Manual XrefsDatabases
C02147KEGG COMPOUND
DB03760DrugBank
HMDB0012210HMDB
Dihydrolipoic_acidWikipedia
Registry NumbersSources
Gmelin:675796Gmelin
Reaxys:1722777Reaxys
CAS:462-20-4KEGG COMPOUND
CAS:462-20-4NIST Chemistry WebBook
CAS:462-20-4ChemIDplus
Citations