CHEBI:16494 - lipoic acid

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ChEBI Name lipoic acid
ChEBI ID CHEBI:16494
Definition A heterocyclic thia fatty acid comprising pentanoic acid with a 1,2-dithiolan-3-yl group at the 5-position.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:146958, CHEBI:25058, CHEBI:6492
Supplier Information No supplier information found for this compound.
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Lipoic acid (LA), also known as α-lipoic acid, alpha-lipoic acid (ALA) and thioctic acid, is an organosulfur compound derived from caprylic acid (octanoic acid). ALA, which is made in animals normally, is essential for aerobic metabolism. It is also available as a dietary supplement or pharmaceutical drug in some countries. Lipoate is the conjugate base of lipoic acid, and the most prevalent form of LA under physiological conditions. Only the (R)-(+)-enantiomer (RLA) exists in nature. RLA is an essential cofactor of many processes.
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Formula C8H14O2S2
Net Charge 0
Average Mass 206.32756
Monoisotopic Mass 206.04352
InChI InChI=1S/C8H14O2S2/c9-8(10)4-2-1-3-7-5-6-11-12-7/h7H,1-6H2,(H,9,10)
InChIKey AGBQKNBQESQNJD-UHFFFAOYSA-N
SMILES OC(=O)CCCCC1CCSS1
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.
Application(s): geroprotector
Any compound that supports healthy aging, slows the biological aging process, or extends lifespan.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing lipoic acid (CHEBI:16494) has functional parent octanoic acid (CHEBI:28837)
lipoic acid (CHEBI:16494) has role fundamental metabolite (CHEBI:78675)
lipoic acid (CHEBI:16494) has role geroprotector (CHEBI:176497)
lipoic acid (CHEBI:16494) is a dithiolanes (CHEBI:39192)
lipoic acid (CHEBI:16494) is a heterocyclic fatty acid (CHEBI:48847)
lipoic acid (CHEBI:16494) is a thia fatty acid (CHEBI:59643)
lipoic acid (CHEBI:16494) is conjugate acid of lipoate (CHEBI:30313)
Incoming lipoamide (CHEBI:17460) has functional parent lipoic acid (CHEBI:16494)
lipoyl-AMP (CHEBI:55451) has functional parent lipoic acid (CHEBI:16494)
(R)-lipoic acid (CHEBI:30314) is a lipoic acid (CHEBI:16494)
(S)-lipoic acid (CHEBI:43796) is a lipoic acid (CHEBI:16494)
lipoate (CHEBI:30313) is conjugate base of lipoic acid (CHEBI:16494)
lipoyl group (CHEBI:25064) is substituent group from lipoic acid (CHEBI:16494)
IUPAC Name
5-(1,2-dithiolan-3-yl)pentanoic acid
Synonyms Sources
1,2-dithiolane-3-pentanoic acid ChEBI
1,2-dithiolane-3-valeric acid ChEBI
5-(1,2-dithiolan-3-yl)valeric acid ChEBI
5-(dithiolan-3-yl)valeric acid ChEBI
5-[3-(1,2-dithiolanyl)]pentanoic acid ChEBI
6,8-thioctic acid ChEBI
6,8-thiotic acid ChEBI
6-thioctic acid ChEBI
6-thiotic acid ChEBI
Acetate-replacing factor ChemIDplus
alpha-lipoic acid ChEBI
α-lipoic acid NIST Chemistry WebBook
alpha-Lipoic acid KEGG COMPOUND
α-Liponsäure ChemIDplus
Biletan ChemIDplus
Lipoic acid KEGG COMPOUND
liponic acid ChEBI
Thioctansäure ChEBI
Thioctic acid KEGG COMPOUND
Thioctsäure ChEBI
Thioktsäure ChEBI
Manual Xrefs Databases
4732 DrugCentral
C00725 KEGG COMPOUND
D00086 KEGG DRUG
DB00166 DrugBank
ECMDB01451 ECMDB
Lipoic_acid Wikipedia
YMDB00334 YMDB
View more database links
Registry Numbers Types Sources
122410 Beilstein Registry Number Beilstein
62-46-4 CAS Registry Number NIST Chemistry WebBook
62-46-4 CAS Registry Number ChemIDplus
720915 Gmelin Registry Number Gmelin
81853 Reaxys Registry Number Reaxys
Citations
Last Modified
28 October 2021