EMBL-EBI | Chemical Biology | ChEBI

Example searches: iron*, InChI=1S/CH4O/c1-2/h2H,1H3, caffeine | Advanced Search

CHEBI:30314 - (R)-lipoic acid

Default Structure
ChEBI IDCHEBI:30314
ChEBI Name(R)-lipoic acid
Stars
ASCII Name(R)-lipoic acid
DefinitionThe (R)-enantiomer of lipoic acid. A vitamin-like, C8 thia fatty acid with anti-oxidant properties.
Last Modified25 July 2019
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-/m1/s1
InChIKeyAGBQKNBQESQNJD-SSDOTTSWSA-N
Wikipedia
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 Roles:
cofactor  An organic molecule or ion (usually a metal ion) that is required by an enzyme for its activity. It may be attached either loosely (coenzyme) or tightly (prosthetic group).
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.
Applications:
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.
geroprotector  Any compound that supports healthy aging, slows the biological aging process, or extends lifespan.
ChEBI Ontology
Outgoing Relation(s)
(R)-lipoic acid (CHEBI:30314) has functional parent octanoic acid (CHEBI:28837)
(R)-lipoic acid (CHEBI:30314) has role cofactor (CHEBI:23357)
(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 Relation(s)
(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)-lipoyl-GMP (CHEBI:86459) 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  Source
(+)-alpha-Lipoic acidChemIDplus
alpha-Lipoic acidKEGG COMPOUND
(R)-1,2-dithiolane-3-valeric acidChEBI
(R)-6,8-thioctic acidChEBI
(R)-(+)-lipoic acidChEBI
Lipoic acidKEGG COMPOUND
Manual XrefsDatabases
C00000754KNApSAcK
C00725KEGG COMPOUND
C16241KEGG COMPOUND
HMDB0001451HMDB
Lipoic_acidWikipedia
LIPOIC-ACIDMetaCyc
LMFA01130001LIPID MAPS
Registry NumbersSources
Beilstein:81851Beilstein
CAS:1200-22-2ChemIDplus
CAS:1200-22-2KEGG COMPOUND
CAS:62-46-4KEGG COMPOUND
Citations