CHEBI:43796 - (S)-lipoic acid

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ChEBI Name (S)-lipoic acid
ChEBI ID CHEBI:43796
ChEBI ASCII Name (S)-lipoic acid
Definition The (S)-enantiomer of lipoic acid. Not found in nature, it may exert detrimental effects on biosystems.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:43790, CHEBI:30315
Supplier Information
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Formula C8H14O2S2
Net Charge 0
Average Mass 206.32756
Monoisotopic Mass 206.044
InChI InChI=1S/C8H14O2S2/c9-8(10)4-2-1-3-7-5-6-11-12-7/h7H,1-6H2,(H,9,10)/t7-/m0/s1
InChIKey AGBQKNBQESQNJD-ZETCQYMHSA-N
SMILES OC(=O)CCCC[C@H]1CCSS1
Roles Classification
Chemical Role(s): Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
(via oxoacid )
Biological Role(s): fundamental metabolite
Any metabolite produced by all living cells.
(via lipoic acid )
View more via ChEBI Ontology
ChEBI Ontology
Outgoing (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 (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 Sources
(S)-(−)-lipoic acid ChEBI
(S)-1,2-dithiolane-3-pentanoic acid ChemIDplus
(S)-alpha-lipoic acid ChEBI
L-1,2-dithiolane 3-valeric acid ChEBI
L-6,8-thioctic acid ChEBI
L-6-thioctic acid ChEBI
LIPOIC ACID PDBeChem
S-LA ChEBI
SLA ChEBI
thioctic acid l-form ChemIDplus
Manual Xrefs Databases
HMDB0014312 HMDB
LPA PDBeChem
View more database links
Registry Numbers Types Sources
1077-27-6 CAS Registry Number ChemIDplus
81852 Beilstein Registry Number Beilstein
Citations Waiting for Citations Types Sources
10218658 PubMed citation Europe PMC
14991456 PubMed citation Europe PMC
15157071 PubMed citation Europe PMC
9252495 PubMed citation Europe PMC
Last Modified
26 August 2014