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CHEBI:43796 - (S)-lipoic acid

ChEBI IDCHEBI:43796
ChEBI Name(S)-lipoic acid
Stars
ASCII Name(S)-lipoic acid
DefinitionThe (S)-enantiomer of lipoic acid. Not found in nature, it may exert detrimental effects on biosystems.
Secondary ChEBI IDsCHEBI:30315, CHEBI:43790
Last Modified26 August 2014
SubmitterKirill Degtyarenko
DownloadsMolfile
FormulaC8H14O2S2
Net Charge0
Average Mass206.332
Monoisotopic Mass206.04352
SMILESO=C(O)CCCC[C@H]1CCSS1
InChIInChI=1S/C8H14O2S2/c9-8(10)4-2-1-3-7-5-6-11-12-7/h7H,1-6H2,(H,9,10)/t7-/m0/s1
InChIKeyAGBQKNBQESQNJD-ZETCQYMHSA-N
Roles Classification
Chemical Roles:
Bronsted acid  A molecular entity capable of donating a hydron to an acceptor (Brønsted base).
Bronsted acid  A molecular entity capable of donating a hydron to an acceptor (Brønsted base).
Biological Role:
fundamental metabolite  Any metabolite produced by all living cells.
Application:
geroprotector  Any compound that supports healthy aging, slows the biological aging process, or extends lifespan.
ChEBI Ontology
Outgoing Relation(s)
(S)-lipoic acid (CHEBI:43796) has functional parent octanoic acid (CHEBI:28837)
(S)-lipoic acid (CHEBI:43796) is a dithiolanes (CHEBI:39192)
(S)-lipoic acid (CHEBI:43796) is a heterocyclic fatty acid (CHEBI:48847)
(S)-lipoic acid (CHEBI:43796) is a lipoic acid (CHEBI:16494)
(S)-lipoic acid (CHEBI:43796) is a thia fatty acid (CHEBI:59643)
(S)-lipoic acid (CHEBI:43796) is enantiomer of (R)-lipoic acid (CHEBI:30314)
Incoming Relation(s)
(R)-lipoic acid (CHEBI:30314) is enantiomer of (S)-lipoic acid (CHEBI:43796)
(S)-lipoyl group (CHEBI:38233) is substituent group from (S)-lipoic acid (CHEBI:43796)
IUPAC Name 
5-[(3S)-1,2-dithiolan-3-yl]pentanoic acid
Synonyms  Source
thioctic acid l-formChemIDplus
(S)-1,2-dithiolane-3-pentanoic acidChemIDplus
LIPOIC ACIDPDBeChem
(S)-(−)-lipoic acidChEBI
SLAChEBI
L-6-thioctic acidChEBI
Manual XrefsDatabases
LPAPDBeChem
HMDB0014312HMDB
Registry NumbersSources
Beilstein:81852Beilstein
CAS:1077-27-6ChemIDplus
Citations