CHEBI:30314 - (R)-lipoic acid

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ChEBI Name (R)-lipoic acid
ChEBI ID CHEBI:30314
ChEBI ASCII Name (R)-lipoic acid
Definition The (R)-enantiomer of lipoic acid. A vitamin-like, C8 thia fatty acid with anti-oxidant properties.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C8H14O2S2
Net Charge 0
Average Mass 206.32600
InChI InChI=1S/C8H14O2S2/c9-8(10)4-2-1-3-7-5-6-11-12-7/h7H,1-6H2,(H,9,10)/t7-/m1/s1
InChIKey AGBQKNBQESQNJD-SSDOTTSWSA-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): prosthetic group
A tightly bound, specific nonpolypeptide unit in a protein determining and involved in its biological activity.
fundamental metabolite
Any metabolite produced by all living cells.
(via lipoic acid )
Application(s): nutraceutical
A product in capsule, tablet or liquid form that provide essential nutrients, such as a vitamin, an essential mineral, a protein, an herb, or similar nutritional substance.
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ChEBI Ontology
Outgoing (R)-lipoic acid (CHEBI:30314) has functional parent caprylic acid (CHEBI:28837)
(R)-lipoic acid (CHEBI:30314) has role nutraceutical (CHEBI:50733)
(R)-lipoic acid (CHEBI:30314) has role prosthetic group (CHEBI:26348)
(R)-lipoic acid (CHEBI:30314) is a dithiolanes (CHEBI:39192)
(R)-lipoic acid (CHEBI:30314) is a heterocyclic fatty acid (CHEBI:48847)
(R)-lipoic acid (CHEBI:30314) is a lipoic acid (CHEBI:16494)
(R)-lipoic acid (CHEBI:30314) is a thia fatty acid (CHEBI:59643)
(R)-lipoic acid (CHEBI:30314) is conjugate acid of (R)-lipoate (CHEBI:83088)
(R)-lipoic acid (CHEBI:30314) is enantiomer of (S)-lipoic acid (CHEBI:43796)
Incoming (R)-lipoamide (CHEBI:83094) has functional parent (R)-lipoic acid (CHEBI:30314)
(R)-lipoyl-AMP (CHEBI:83864) has functional parent (R)-lipoic acid (CHEBI:30314)
(R)-lipoate (CHEBI:83088) is conjugate base of (R)-lipoic acid (CHEBI:30314)
(S)-lipoic acid (CHEBI:43796) is enantiomer of (R)-lipoic acid (CHEBI:30314)
(R)-lipoyl group (CHEBI:38232) is substituent group from (R)-lipoic acid (CHEBI:30314)
IUPAC Name
5-[(3R)-1,2-dithiolan-3-yl]pentanoic acid
Synonyms Sources
(+)-alpha-Lipoic acid ChemIDplus
(R)-(+)-Lipoate KEGG COMPOUND
(R)-(+)-lipoic acid ChEBI
(R)-1,2-Dithiolane-3-pentanoic acid ChemIDplus
(R)-1,2-dithiolane-3-valeric acid ChEBI
(R)-6,8-thioctic acid ChEBI
alpha-Lipoic acid KEGG COMPOUND
Lipoic acid KEGG COMPOUND
R-(+)-Lipoic acid KEGG COMPOUND
R-LA ChEBI
RLA ChEBI
Thioctic acid KEGG COMPOUND
Thioctic acid d-form ChemIDplus
Database Links Databases
C00000754 KNApSAcK
C00725 KEGG COMPOUND
C16241 KEGG COMPOUND
HMDB01451 HMDB
LIPOIC-ACID MetaCyc
Lipoic_acid Wikipedia
LMFA01130001 LIPID MAPS
MOL000161 COMe
View more database links
Registry Numbers Types Sources
1200-22-2 CAS Registry Number KEGG COMPOUND
1200-22-2 CAS Registry Number ChemIDplus
62-46-4 CAS Registry Number KEGG COMPOUND
81851 Beilstein Registry Number Beilstein
Citations Waiting for Citations Types Sources
10218658 PubMed citation CiteXplore
14991456 PubMed citation CiteXplore
15157071 PubMed citation CiteXplore
9252495 PubMed citation CiteXplore
Last Modified
24 November 2014