dihydrolipoic acid (CHEBI:18047)

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ChEBI Name	dihydrolipoic acid

ChEBI ID	CHEBI:18047

Definition	A 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.

Stars	This entity has been manually annotated by the ChEBI Team.

Secondary ChEBI IDs	CHEBI:4569, CHEBI:23752

Supplier Information	ChemicalBook:CB0180700, ChemicalBook:CB4302519, eMolecules:595156

Download	Molfile XML SDF

Wikipedia	License
Dihydrolipoic acid is an organic compound that is the reduced form of lipoic acid. This carboxylic acid features a pair of thiol groups, and therefore is a dithiol. 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.
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Formula

C8H16O2S2

Net Charge

Average Mass

208.34344

Monoisotopic Mass

208.05917

InChI

InChI=1S/C8H16O2S2/c9-8(10)4-2-1-3-7(12)5-6-11/h7,11-12H,1-6H2,(H,9,10)

InChIKey

IZFHEQBZOYJLPK-UHFFFAOYSA-N

SMILES

OC(=O)CCCCC(S)CCS

Roles Classification
Chemical Role(s):	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 (Bronsted base). (via oxoacid )

Biological Role(s):	human metabolite Any mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens).

Application(s):	neuroprotective agent Any compound that can be used for the treatment of neurodegenerative disorders.

ChEBI Ontology
Outgoing	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	(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

Last Modified

24 November 2014