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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:
prosthetic group  A tightly bound, specific nonpolypeptide unit in a protein determining and involved in its biological activity.
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).
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