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Ontology Browser

Term:
Parent Terms Term With Siblings Child Terms
cofactor +   
dithiolanes +     
lipoic acid +     
thia fatty acid +     
(+)-alpha-tocopherol +   
(+)-pentacycloanammoxic acid +  
(2S,3R,4S)-4-[(2S,7S,8R,9S)-2-[(5S)-5-ethyl-5-[(3S,5R)-5-[(3S,5R,6R)-6-hydroxy-6-(hydroxymethyl)-3,5-dimethyl-2-oxanyl]-3-methyl-2-oxolanyl]-2-oxolanyl]-7-hydroxy-2,8-dimethyl-1,10-dioxaspiro[4.5]decan-9-yl]-3-methoxy-2-methylpentanoic acid 
(3S,4S)-3-hydroxy-4-methyloctanoic acid +  
(6R)-5,10-methylenetetrahydrofolate(2-) +  
(6R)-5,10-methylenetetrahydrofolic acid +  
(6S)-5,6,7,8-tetrahydrofolate(2-) 
(6S)-5,6,7,8-tetrahydrofolic acid 
(7R)-7-hydroxyoctanoic acid +  
(\{[(2R,3S,4R,5R)-3,4-dihydroxy-5-(9H-purin-9-yl)oxolan-2-yl]methyl phosphonato\}oxy)(phosphonatooxy)phosphinate +   
(R)-carnitine +   
(R)-lipoate 
(R)-lipoic acid +   
The (R)-enantiomer of lipoic acid. A vitamin-like, C8 thia fatty acid with anti-oxidant properties.
(R)-lipoyl-GMP 
(S)-lipoic acid +  
1,2-dioctanoyl-3-beta-D-galactosyl-sn-glycerol 
1,3-dioctanoylglycerol 
1,4-benzoquinone +   
1-O-(alpha-D-galactopyranosyl)-N-octanoylphytosphingosine 
1-octadecanoyl-2-octanoyl-sn-glycero-3-phosphocholine 
1alpha,25-dihydroxyvitamin D2 
2-(pentylsulfanyl)acetic acid +  
2-cyano-N-(2,4-dichlorophenyl)-3-[5-(2-methylcyclopropyl)-2-furanyl]-2-propenamide 
2-hydroxy-4-(methylthio)butanoic acid 
2-hydroxyoctanoic acid +  
2-O-[6-O-octanoyl-alpha-D-glucosyl-(1->6)-alpha-D-glucosyl]-D-glyceric acid 
2-octanoyl-sn-glycero-3-phosphocholine 
25-hydroxyvitamin D2 
3'-hydroxyechinenone 
3-(methylthio)propionic acid +  
3-aminooctanoic acid 
3-hydroxyoctanoic acid +  
3-methylbutyl octanoate 
3-oxooctanoic acid +  
4,7-dioxooctanoic acid 
4-(4-chlorophenyl)-1-\{3-[2-(4-fluorophenyl)-1,3-dithiolan-2-yl]propyl\}piperidin-4-ol 
4-(4-ethyl-1-piperazinyl)-4-oxo-2-butenoic acid 
5,6,7,8-tetrahydrobiopterin +   
5,6,7,8-tetrahydropteridine 
5-hydroxybenzimidazolylcob(I)amide 
5-hydroxybenzimidazolylcob(I)amide(1-) 
6,7-dimethyl-8-(1-D-ribityl)lumazine 
6,7-dimethyl-8-(1-D-ribityl)lumazine(1-) 
6-decylubiquinone  
6-hydroxy-3,7-dimethyloctanoic acid +  
6-hydroxy-FAD 
6-hydroxy-FAD(3-) 
7,8-didemethyl-8-hydroxy-5-deazariboflavin +  
8-(5-hexylfuran-2-yl)octanoic acid 
8-[(1R,2R)-3-oxo-2-\{(Z)-pent-2-en-1-yl\}cyclopentyl]octanoic acid 
8-hydroxyoctanoic acid +   
adenosine 5'-monophosphate +   
adenosine 5'-monophosphate(2-) +  
all-cis-5,8,11,14,17-icosapentaenoic acid +  
all-cis-docosa-4,7,10,13,16,19-hexaenoic acid +   
all-cis-icosa-8,11,14-trienoic acid +  
all-trans-retinyl octanoate 
alpha-linolenic acid +   
ammonium +   
asparagusate 
asparagusic acid 
aspartame  
ATP +   
ATP(3-) 
ATP(4-) +  
B vitamin +   
bacillithiol 
barium(2+)  
benfotiamine 
beta-carotene +   
biotin +   
biotinate +  
bis(molybdopterin)tungsten cofactor 
Bisnorbiotin 
cadmium(2+) +   
calcidiol +   
calcitriol +   
calcium(2+) +   
cerium(3+) 
chloride +   
chlorophyll a +  
chlorophyll a(1-) +  
chlorophyll b 
chlorophyll b(1-) 
ciliatamide B 
cob(I)alamin 
cob(I)alamin(1-) 
cob(II)alamin 
cobalamin +  
cobalt(2+) +   
cobalt(3+) 
cobamamide +   
coenzyme +   
coenzyme F430 
coenzyme F430(5-) 
copper cation +   
copper(1+) +   
copper(2+) +   
corrin 
corrinoid +   
creatine +   
crocetin +   
curcumin +   
D-pantetheine 4'-phosphate +  
D-pantetheine 4'-phosphate(2-) 
decylplastoquinone 
dehydro-D-arabinono-1,4-lactone 
dihydrogenvanadate 
dihydrolipoamide +   
dihydrolipoic acid +   
dipyrromethane cofactor 
dipyrromethane cofactor(4-) 
disodium selenite +   
disodium selenite pentahydrate 
dithiolane +   
dithiolanecarboxylic acid +  
divinyl chlorophyll a 
divinyl chlorophyll a(1-) 
divinyl chlorophyll b 
divinyl chlorophyll b(1-) 
echinenone +  
epoxy fatty acid +   
FAD  
FAD(3-) 
Fe-coproporphyrin III 
Fe-coproporphyrin III(4-) 
Fe4S2O2 iron-sulfur-oxygen cluster 
ferriheme a +  
ferriheme a(1-) 
ferroheme b +   
ferroheme b(2-) 
ferroheme c 
ferroheme c(2-) 
flavin adenine dinucleotide +   
flavin mononucleotide +   
FMN +   
FMN(3-) +  
FMNH2 +  
FMNH2(2-) 
glucomannan 
glutathionate(1-) +  
glutathione +   
glycine +   
guanidinoacetic acid 
GW 0791 
heme +   
heme d cis-diol +  
heme d cis-diol(2-) 
heme o +  
hydrogen peroxide +   
hydrogencarbonate +   
hydrogenphosphate +  
hydroquinone +   
iron cation +   
iron(2+) +   
iron(2+) sulfate heptahydrate 
iron(2+) sulfate monohydrate 
iron(3+) +   
iron(III) citrate +  
iron-sulfur-iron cofactor 
iron-sulfur-molybdenum cofactor 
iron-sulfur-vanadium cofactor 
isoprothiolane +   
L-arginine +   
L-ascorbate +  
L-ascorbic acid +   
L-asparagine +   
L-citrulline +  
L-glutamic acid +   
L-glutamine +  
L-histidine +   
L-lysine +   
L-methionine +   
L-phenylalanine +   
L-proline +   
L-threonine +  
L-tryptophan +   
L-tyrosine +   
L-valine +   
lanthanum(3+) 
lead(2+) +   
Leinamycin 
lipoamide +   
lipoic acid +   
lipoyl group +  
lipoyl-AMP +  
magnesium(2+) +  
manganese(2+) +   
manganese(II) chloride +   
manganese(II) chloride dihydrate 
manganese(II) chloride tetrahydrate 
manganese(II) sulfate +   
manganese(II) sulfate dihydrate 
manganese(II) sulfate hexahydrate 
manganese(II) sulfate monohydrate 
manganese(II) sulfate pentahydrate 
manganese(II) sulfate tetrahydrate 
menadione +   
metal-sulfur cluster +  
methyl (+)-pentacycloanammoxate 
methylcobalamin  
molybdopterin cofactor +  
mycothiol +  
myo-inositol hexakisphosphate  
myo-inositol hexakisphosphate(12-) 
N-(octanoyl)-L-homoserine 
N-(octanoyl)ethanolamine 
N-acetyl-L-aspartic acid +   
N-acetyl-L-methionine +  
N-capryloyl-1-palmitoyl-2-linoleoyl-sn-glycero-3-phosphoethanolamine 
N-octanoyl-(2S)-hydroxyglycine 
N-octanoylanthranilate 
N-octanoylanthranilic acid 
N-octanoyldihydrosphingosine 
N-octanoylglycine 
N-octanoylphytosphingosine 
N-octanoylsphingosine 
N-octanoylsphingosine 1-phosphate 
NAD(+)  
NAD(1-) +  
NADH +  
NADH(2-) +  
NADP(+) +   
NADP(3-) 
NADPH +  
NADPH(4-) +  
nereistoxin 
Ni(II)-pyridinium-3,5-bisthiocarboxylate mononucleotide(1-) 
Ni(II)-pyridinium-3,5-bisthiocarboxylic acid mononucleotide 
nickel cation +   
nickel(2+) +   
nicotinamide +   
NiFe4S4 cluster 
octanamide 
octanoate ester +   
octanoyl group +  
octanoyl-CoA +  
oleocanthal 
oleuropein +   
pantetheine 4'-phosphate +  
pantetheine 4'-phosphate(2-) +  
pantethine 
pantothenic acids +   
perfluorooctanoic acid  
pescaprein XXX 
phylloquinone +   
phytochromobilin +  
polypeptide-derived cofactor +  
porphyrins +   
potassium(1+) +   
prenyl-FMN 
prenyl-FMN(2-) 
prenyl-FMNH2 
prosthetic group +   
pyridoxal +   
pyridoxal 5'-phosphate +   
pyridoxal 5'-phosphate(2-) 
pyridoxal hydrochloride 
pyridoxine +   
pyrroloquinoline cofactor +   
pyrroloquinoline quinone  
pyrroloquinoline quinone(3-) 
pyruvate +  
pyruvic acid +   
riboflavin +   
riboflavin(1-) 
S-adenosyl-L-homocysteine  
S-adenosyl-L-methionine +   
S-adenosyl-L-methionine zwitterion +  
S-octanoyl-4'-phosphopantetheine 
S-octanoyl-L-cysteine 
sapropterin +   
siderophore +   
siroheme 
siroheme(8-) 
sirohydrochlorin +  
sirohydrochlorin(8-) 
sodium succinate hexahydrate 
sodium(1+) +   
strontium(2+)  
succinic acid +   
sulfate +   
Technetium Tc 99m succimer 
tetra-mu3-sulfido-tetrairon +  
tetrahydrodictyopterin 
tetrahydromonapterin 
thiamine(1+) diphosphate +  
thiamine(1+) diphosphate(3-) 
TTQ cofactor 
vanadium cation +   
vitamin B complex 
vitamin B6 phosphate +   
vitamin D2 +   
Wyerone 
Wyerone acid 
zeaxanthin +  
zinc(2+) +   

Synonyms
Exact Synonyms: 5-[(3R)-1,2-dithiolan-3-yl]pentanoic acid
Related Synonyms: (R)-(+)-Lipoate ;   (R)-1,2-Dithiolane-3-pentanoic acid ;   (R)-1,2-dithiolane-3-valeric acid ;   (R)-6,8-thioctic acid ;   Formula=C8H14O2S2 ;   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 ;   Lipoic acid ;   R-LA ;   RLA ;   SMILES=OC(=O)CCCC[C@@H]1CCSS1 ;   Thioctic acid ;   Thioctic acid d-form ;   alpha-Lipoic acid
Xrefs: Beilstein:81851 "Beilstein" ;   CAS:1200-22-2 "ChemIDplus" ;   CAS:1200-22-2 "KEGG COMPOUND" ;   CAS:62-46-4 "KEGG COMPOUND" ;   COMe:MOL000161 ;   HMDB:HMDB0001451 ;   KEGG:C00725 ;   KEGG:C16241 ;   KNApSAcK:C00000754 ;   LIPID_MAPS_instance:LMFA01130001 "LIPID MAPS"
Xref Mesh: MESH:D008063
Xrefs: MetaCyc:LIPOIC-ACID ;   PMID:10218658 "Europe PMC" ;   PMID:14991456 "Europe PMC" ;   PMID:15157071 "Europe PMC" ;   PMID:9252495 "Europe PMC" ;   Wikipedia:Lipoic_acid
Cyclic Relationships: is_conjugate_acid_of CHEBI:83088 ;   is_enantiomer_of CHEBI:43796

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RGD is funded by grant HL64541 from the National Heart, Lung, and Blood Institute on behalf of the NIH.