MiMeDB: Showing metabocard for (R)-Lipoic acid (MMDBc0000197)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2020-10-27 23:39:25 UTC

Update Date

2024-09-27 20:39:42 UTC

Metabolite ID

MMDBc0000197

Metabolite Identification

Common Name

(R)-Lipoic acid

Description

Lipoic acid is a vitamin-like antioxidant that acts as a free-radical scavenger. Alpha-lipoic acid is also known as thioctic acid. It is a naturally occurring compound that is synthesized by both plants and animals. Lipoic acid contains two thiol groups which may be either oxidized or reduced. The reduced form is known as dihydrolipoic acid (DHLA). Lipoic acid (Delta E= -0.288) is therefore capable of thiol-disulfide exchange, giving it antioxidant activity. Lipoate is a critical cofactor for aerobic metabolism, participating in the transfer of acyl or methylamine groups via the 2-Oxoacid dehydrogenase (2-OADH) or alpha-ketoglutarate dehydrogenase complex. This enzyme catalyzes the conversion of alpha-ketoglutarate to succinyl CoA. This activity results in the catabolism of the branched chain amino acids (leucine, isoleucine and valine). Lipoic acid also participates in the glycine cleavage system(GCV). The glycine cleavage system is a multi-enzyme complex that catalyzes the oxidation of glycine to form 5,10 methylene tetrahydrofolate, an important cofactor in nucleic acid synthesis. Since Lipoic acid is an essential cofactor for many enzyme complexes, it is essential for aerobic life as we know it. This system is used by many organisms and plays a crucial role in the photosynthetic carbon cycle. Lipoic acid was first postulated to be an effective antioxidant when it was found it prevented vitamin C and vitamin E deficiency. It is able to scavenge reactive oxygen species and reduce other metabolites, such as glutathione or vitamins, maintaining a healthy cellular redox state. Lipoic acid has been shown in cell culture experiments to increase cellular uptake of glucose by recruiting the glucose transporter GLUT4 to the cell membrane, suggesting its use in diabetes. Studies of rat aging have suggested that the use of L-carnitine and lipoic acid results in improved memory performance and delayed structural mitochondrial decay. As a result, it may be helpful for people with Alzheimer's disease or Parkinson's disease. -- Wikipedia .

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(+)-alpha-Lipoic acid	ChEBI, HMDB
(R)-(+)-Lipoate	ChEBI, KEGG
(R)-(+)-Lipoic acid	ChEBI, Generator
(R)-1,2-Dithiolane-3-pentanoic acid	ChEBI, HMDB
(R)-1,2-Dithiolane-3-valeric acid	ChEBI, HMDB
(R)-6,8-Thioctic acid	ChEBI, HMDB
alpha-Lipoic acid	ChEBI, HMDB
Lipoic acid	ChEBI, HMDB
R-(+)-Lipoic acid	ChEBI, KEGG
R-LA	ChEBI, HMDB
RLA	ChEBI, HMDB
Thioctic acid	ChEBI, HMDB
Thioctic acid D-form	ChEBI, HMDB
(+)-a-Lipoate	Generator, HMDB
(+)-a-Lipoic acid	Generator, HMDB
(+)-alpha-Lipoate	Generator, HMDB
(+)-α-lipoate	Generator, HMDB
(+)-α-lipoic acid	Generator, HMDB
(R)-Lipoate	Generator
(R)-1,2-Dithiolane-3-pentanoate	Generator, HMDB
(R)-1,2-Dithiolane-3-valerate	Generator, HMDB
(R)-6,8-Thioctate	Generator, HMDB
a-Lipoate	Generator, HMDB
a-Lipoic acid	Generator, HMDB
alpha-Lipoate	Generator, HMDB
α-lipoate	Generator, HMDB
α-Lipoic acid	Generator, HMDB
Lipoate	Generator, HMDB
R-(+)-Lipoate	Generator
Thioctate	Generator, HMDB
Thioctate D-form	Generator, HMDB
Acid, alpha-lipoic	MeSH, HMDB
alpha Lipoic acid	MeSH, HMDB
1,2-Dithiolane-3R-pentanoic acid	KEGG
1,2-Dithiolane-3R-pentanoate	Generator
(R)-Lipoic acid	KEGG
(3R)-1,2-Dithiolane-3-pentanoic acid	HMDB
(R)-(+)-1,2-Dithiolane-3-pentanoic acid	HMDB
(R)-(+)-alpha-Lipoic acid	HMDB
(R)-(+)-α-Lipoic acid	HMDB
(R)-5-(1,2-Dithiolan-3-yl)pentanoicacid	HMDB
(R)-alpha-Lipoic acid	HMDB
(R)-α-Lipoic acid	HMDB
ALA	HMDB
alpha-(+)-Lipoic acid	HMDB
α-(+)-Lipoic acid	HMDB
1,2-Dithiolane-3-valeric acid	HMDB
5-(1,2-Dithiolan-3-yl)pentanoic acid	HMDB
5-(1,2-Dithiolan-3-yl)valeric acid	HMDB
6,8-Thioctic acid	HMDB
6-Thioctic acid	HMDB

Molecular Formula

C₈H₁₄O₂S₂

Average Mass

206.326

Monoisotopic Mass

206.043521072

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

1200-22-2

SMILES

Not Available

InChI Identifier

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

InChI Key

AGBQKNBQESQNJD-SSDOTTSWSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as lipoic acids and derivatives. Lipoic acids and derivatives are compounds containing a lipoic acid moiety (or a derivative thereof), which consists of a pentanoic acid (or derivative) attached to the C3 carbon atom of a 1,2-dithiolane ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Dithiolanes

Sub Class

Lipoic acids and derivatives

Direct Parent

Lipoic acids and derivatives

Alternative Parents

Substituents

Lipoic_acid_derivative
Medium-chain fatty acid
Heterocyclic fatty acid
Thia fatty acid
Fatty acyl
Fatty acid
1,2-dithiolane
Organic disulfide
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Hydrocarbon derivative
Organooxygen compound
Organic oxide
Organic oxygen compound
Carbonyl group
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

dithiolanes (CHEBI:30314 )
thia fatty acid (CHEBI:30314 )
heterocyclic fatty acid (CHEBI:30314 )
lipoic acid (CHEBI:30314 )
Thia fatty acids (C16241 )
Thia fatty acids (LMFA01130001 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Not Available

Spectra

Not Available

Biological Properties

Cellular Locations

Cytoplasm
Extracellular
Membrane

Biospecimen Locations

Blood
Feces
Kidney
Liver
Neuron
Placenta
Skeletal Muscle
Urine

Tissue Locations

Kidney
Liver
Neuron
Placenta
Skeletal Muscle

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species
MMDBp0191715	Pyruvate dehydrogenase protein X component, mitochondrial	Enzyme	O00330	Homo sapiens
MMDBp0191729	Dihydrolipoyllysine-residue acetyltransferase component of pyruvate dehydrogenase complex, mitochondrial	Enzyme	P10515	Homo sapiens
MMDBp0191854	NADPH--cytochrome P450 reductase	Unknown	P16435	Homo sapiens
MMDBp0192557	Dihydrolipoyllysine-residue succinyltransferase component of 2-oxoglutarate dehydrogenase complex, mitochondrial	Enzyme	P36957	Homo sapiens
MMDBp0193789	Glycine cleavage system H protein, mitochondrial	Enzyme	P23434	Homo sapiens
MMDBp0193802	Lipoamide acyltransferase component of branched-chain alpha-keto acid dehydrogenase complex, mitochondrial	Enzyme	P11182	Homo sapiens
MMDBp0195915	3-oxoacyl-[acyl-carrier-protein] synthase, mitochondrial	Enzyme	Q9NWU1	Homo sapiens
MMDBp0196268	Lipoyltransferase 1, mitochondrial	Enzyme	Q9Y234	Homo sapiens

Human Pathways

Pathways

Name	SMPDB/PathBank
Arsenate Detoxification

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Data Source	Reference
MMDBr0004274	Lipoyllysine	(R)-Lipoic acid	Not Available	VMH	2502979
MMDBr0004387	Dihydrolipoate	Ascorbic acid	Not Available	VMH	11160563
MMDBr0007955	(R)-Lipoic acid	Lipoyl-AMP	Not Available	VMH	30371894
MMDBr0008182	5-Aminopentanoic acid	Dihydrolipoate	Not Available	VMH	30371894
MMDBr0010336	(R)-Lipoic acid	Dihydrolipoamide	dihydrolipoamide dehydrogenase	VMH	30371894

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Firmicutes	234	Human ; Human feces; Human sputum; Human saliva; Human urine; Human supragingival plaque; Cattle ; Human subgingival plaque	Microbial culture; Metabolic reconstruction
Bacteria	Actinobacteria	80	Human feces; Human ; Human supragingival plaque; Human mucosa; Human subgingival plaque	Metabolic reconstruction
Bacteria	Proteobacteria	97	Human feces; Human ; Human pleural fluid plaque; Human dental plaque; Human nasal swab; Human sputum; Human stool; Human feces; pleural fluid plaque; bal	Metabolic reconstruction
Bacteria	Verrucomicrobia	1	Human ; Human feces	Metabolic reconstruction
Bacteria	Bacteroidetes	64	Human feces; Human ; Human stool; Human saliva	Metabolic reconstruction
Bacteria	Synergistetes	4	Human feces	Metabolic reconstruction
Archaea	Euryarchaeota	2		Metabolic reconstruction
Bacteria	Fusobacteria	1	Human ; Human feces	Metabolic reconstruction
Bacteria	Candidatus melainabacteria	1	Human feces	Metabolic reconstruction
Bacteria	Tenericutes	1	Human feces	Metabolic reconstruction
Bacteria	Planctomycetes	1	Human feces	Metabolic reconstruction
Archaea	Crenarchaeota	1		Metabolic reconstruction
Eukaryota/Fungi	Ascomycota	1	Human feces; Human saliva	Unknown

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference
Animal	Milk	Bos taurus	FooDB	31437929

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Units	Age	Sex	Health Condition	Data Source	Reference
Human Feces	Detected but not Quantified							HMDB
Human Blood	Detected and Quantified	0.077	0.017	uM	Adult (>18 years old)	Both	Normal	HMDB	Geigy Scientific Tables, 8th Rev edition, pp. 130. Edited by C. Lentner, West Cadwell, N.J.: Medical education Div., Ciba-Geigy Corp. Basel, Switzerland c1981-1992.
Human Kidney	Detected but not Quantified				Not Specified	Not Specified	Normal	HMDB	34986597
Human Liver	Detected but not Quantified				Not Specified	Not Specified	Normal	HMDB	34986597
Human Neuron	Detected but not Quantified				Not Specified	Not Specified	Normal	HMDB	34986597
Human Placenta	Detected but not Quantified				Not Specified	Not Specified	Normal	HMDB	34986597
Human Skeletal muscle	Detected but not Quantified				Not Specified	Not Specified	Normal	HMDB	34986597
Human Urine	Detected but not Quantified				Adult (>18 years old)	Both	Normal	HMDB	32966057
Human Blood	Detected but not Quantified				Adult (>18 years old)	Both	Normal	HMDB	32966057

External Links

HMDB ID

HMDB0001451

DrugBank ID

DB00166

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Wikipedia Link

METLIN ID

PubChem Compound

PDB ID

Not Available

ChEBI ID

30314

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Steinmann B, Gitzelmann R: Strychnine treatment attempted in newborn twins with severe nonketotic hyperglycinemia. Helv Paediatr Acta. 1979;34(6):589-99. [PubMed:541222 ]
Loginov AS, Nilova TV, Bendikov EA, Petrakov AV: [Pharmacokinetics of preparations of lipoic acid and their effect on ATP synthesis, processes of microsomal and cytosol oxidation in hepatocytes in liver damage in man]. Farmakol Toksikol. 1989 Jul-Aug;52(4):78-82. [PubMed:2509239 ]
Nagamatsu M, Nickander KK, Schmelzer JD, Raya A, Wittrock DA, Tritschler H, Low PA: Lipoic acid improves nerve blood flow, reduces oxidative stress, and improves distal nerve conduction in experimental diabetic neuropathy. Diabetes Care. 1995 Aug;18(8):1160-7. doi: 10.2337/diacare.18.8.1160. [PubMed:7587852 ]
Barbiroli B, Medori R, Tritschler HJ, Klopstock T, Seibel P, Reichmann H, Iotti S, Lodi R, Zaniol P: Lipoic (thioctic) acid increases brain energy availability and skeletal muscle performance as shown by in vivo 31P-MRS in a patient with mitochondrial cytopathy. J Neurol. 1995 Jul;242(7):472-7. doi: 10.1007/BF00873552. [PubMed:7595680 ]
Semenova TV, Azhitskii GIu, Sarnatskaia VV, Nikolaev VG: [Effect of various specific agents on the heat stability of human serum albumin]. Ukr Biokhim Zh (1978). 1993 Sep-Oct;65(5):26-30. [PubMed:8160293 ]
Arner ES, Nordberg J, Holmgren A: Efficient reduction of lipoamide and lipoic acid by mammalian thioredoxin reductase. Biochem Biophys Res Commun. 1996 Aug 5;225(1):268-74. doi: 10.1006/bbrc.1996.1165. [PubMed:8769129 ]
Chevion S, Hofmann M, Ziegler R, Chevion M, Nawroth PP: The antioxidant properties of thioctic acid: characterization by cyclic voltammetry. Biochem Mol Biol Int. 1997 Feb;41(2):317-27. doi: 10.1080/15216549700201331. [PubMed:9063572 ]
Baker H, Deangelis B, Baker ER, Hutner SH: A practical assay of lipoate in biologic fluids and liver in health and disease. Free Radic Biol Med. 1998 Sep;25(4-5):473-9. doi: 10.1016/s0891-5849(98)00087-2. [PubMed:9741583 ]
Redden PR, Melanson RL, Douglas JA, Dick AJ: Acyloxymethyl acidic drug derivatives: in vitro hydrolytic reactivity. Int J Pharm. 1999 Apr 15;180(2):151-60. doi: 10.1016/s0378-5173(98)00372-x. [PubMed:10370185 ]
McCormick DB: A trail of research on cofactors: an odyssey with friends. J Nutr. 2000 Feb;130(2S Suppl):323S-330S. doi: 10.1093/jn/130.2.323S. [PubMed:10721897 ]
Haj-Yehia AI, Assaf P, Nassar T, Katzhendler J: Determination of lipoic acid and dihydrolipoic acid in human plasma and urine by high-performance liquid chromatography with fluorimetric detection. J Chromatogr A. 2000 Feb 18;870(1-2):381-8. doi: 10.1016/s0021-9673(99)00857-2. [PubMed:10722093 ]
Henriksen EJ, Saengsirisuwan V: Exercise training and antioxidants: relief from oxidative stress and insulin resistance. Exerc Sport Sci Rev. 2003 Apr;31(2):79-84. doi: 10.1097/00003677-200304000-00005. [PubMed:12715971 ]
Burke DG, Chilibeck PD, Parise G, Tarnopolsky MA, Candow DG: Effect of alpha-lipoic acid combined with creatine monohydrate on human skeletal muscle creatine and phosphagen concentration. Int J Sport Nutr Exerc Metab. 2003 Sep;13(3):294-302. doi: 10.1123/ijsnem.13.3.294. [PubMed:14669930 ]
Bruggraber SF, Leung PS, Amano K, Quan C, Kurth MJ, Nantz MH, Benson GD, Van de Water J, Luketic V, Roche TE, Ansari AA, Coppel RL, Gershwin ME: Autoreactivity to lipoate and a conjugated form of lipoate in primary biliary cirrhosis. Gastroenterology. 2003 Dec;125(6):1705-13. doi: 10.1053/j.gastro.2003.09.034. [PubMed:14724823 ]
Teichert J, Tuemmers T, Achenbach H, Preiss C, Hermann R, Ruus P, Preiss R: Pharmacokinetics of alpha-lipoic acid in subjects with severe kidney damage and end-stage renal disease. J Clin Pharmacol. 2005 Mar;45(3):313-28. doi: 10.1177/0091270004270792. [PubMed:15703366 ]
Tankova T, Cherninkova S, Koev D: Treatment for diabetic mononeuropathy with alpha-lipoic acid. Int J Clin Pract. 2005 Jun;59(6):645-50. doi: 10.1111/j.1742-1241.2005.00452.x. [PubMed:15924591 ]
Konrad D: Utilization of the insulin-signaling network in the metabolic actions of alpha-lipoic acid-reduction or oxidation? Antioxid Redox Signal. 2005 Jul-Aug;7(7-8):1032-9. doi: 10.1089/ars.2005.7.1032. [PubMed:15998258 ]
Lee WJ, Lee IK, Kim HS, Kim YM, Koh EH, Won JC, Han SM, Kim MS, Jo I, Oh GT, Park IS, Youn JH, Park SW, Lee KU, Park JY: Alpha-lipoic acid prevents endothelial dysfunction in obese rats via activation of AMP-activated protein kinase. Arterioscler Thromb Vasc Biol. 2005 Dec;25(12):2488-94. doi: 10.1161/01.ATV.0000190667.33224.4c. Epub 2005 Oct 13. [PubMed:16224049 ]

Showing metabocard for (R)-Lipoic acid (MMDBc0000197)

MOL for #<Metabolite:0x0000559d0532eec8>

3D MOL for #<Metabolite:0x0000559d0532eec8>

3D SDF for #<Metabolite:0x0000559d0532eec8>

3D-SDF for #<Metabolite:0x0000559d0532eec8>

PDB for #<Metabolite:0x0000559d0532eec8>

3D PDB for #<Metabolite:0x0000559d0532eec8>

SMILES for #<Metabolite:0x0000559d0532eec8>

INCHI for #<Metabolite:0x0000559d0532eec8>

Structure for #<Metabolite:0x0000559d0532eec8>

3D Structure for #<Metabolite:0x0000559d0532eec8>