Metabolite Card
Formula: C8H14O2S2 (206.0435)
SMILES: OC(=O)CCCC[C@@H]1CCSS1
Synonyms [en]
(R)-lipoic acid; lipoic acid; R-(+)-Lipoic acid; (R)-(+)-Lipoate; Thioctic acid d-form; alpha-Lipoic Acid
Last reviewed on 2024-06-28.
Cite this Page
(R)-Lipoate. 数据之源,洞见之始. SMRUCC genomics institute, a synthetic life researcher from China.
https://biocad_registry.innovation.ac.cn/s/(-)-arctiin
(retrieved
2026-01-03) (CAD Registry RN: BioCAD00000000871). Licensed
under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).
Note
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.
DBLinks
- CAS Registry Number: 1200-22-2
- PubChem CID: 6112
- ChEBI: 30314
- HMDB: HMDB0001451
- LipidMaps: LMFA01130001
- KEGG: C16241
- BioCyc: LIPOIC-ACID
- NCBI MeSH: Thioctic Acid
- Wikipedia: Lipoic_acid
Other DBLinks
- CAS Registry Number: 1200-22-2
- CAS Registry Number: 62-46-4
- PubChem: 445125
- PubChem: 6112
- PubChem: 864
- ChEBI: ChEBI:16494
- ChEBI: ChEBI:30314
- ChEBI: ChEBI:43796
- HMDB: HMDB0001451
- HMDB: HMDB0014312
- LipidMaps: LMFA01130001
- KEGG: C16241
- KEGG: D00086
- BioCyc: LIPOIC-ACID
- NCBI MeSH: Thioctic Acid
- Wikipedia: Lipoic_acid
- DrugBank: DB00166
- RefMet: RM0118061
- RefMet: RM0153264
- MoNA: EMBL_MCF_2_0_HRMS_Library000494
- MoNA: EMBL_MCF_2_0_HRMS_Library000495
- MoNA: FiehnHILIC001300
- MoNA: FiehnHILIC002802
- MoNA: HMDB0001451_c_ms_100076
- MoNA: HMDB0001451_c_ms_100077
- MoNA: HMDB0001451_c_ms_99686
- MoNA: HMDB0001451_ms_ms_1580
- MoNA: HMDB0001451_ms_ms_1581
- MoNA: HMDB0001451_ms_ms_1582
- MoNA: LU101551
- MoNA: LU101552
- MoNA: LU101553
- MoNA: LU101554
- MoNA: LU101555
- MoNA: LU101556
- MoNA: MoNA035148
- MoNA: MoNA035149
- MoNA: MoNA035151
- MoNA: MoNA038210
- Coconut NaturalProduct: CNP0120491.1
Class / Ontology
- WishartLab ClassyFire: [Lipoic acids and derivatives] Lipoic acids and derivatives
- RefMet: [Thia FA] Thia FA
- RefMet: [Lipoic acids] Lipoic acids
- LipidMaps: [Thia fatty acids [FA0113]] Thia fatty acids [FA0113]
- ChEBI: [CHEBI:30314] (R)-lipoic acid
- Coconut NaturalProduct: [Thia fatty acids] Thia fatty acids
| ID | EC Number | Name |
|---|---|---|
| KEGG:R07770 | 6.3.1.20 | C00002 + C16241<=>C00013 + C16238 |
| KEGG:R11143 | 6.3.1.20 | [lipoyl-carrier protein]-L-lysine:lipoate ligase (AMP-forming) |
| KEGG:R12433 | 6.3.1.20 | [glycine cleavage system H]-L-lysine:(R)-lipoate ligase (AMP-forming) |
| KEGG:R12449 | 6.3.1.20 | [lipoyl-carrier protein E2]-L-lysine:(R)-lipoate ligase (AMP-forming) |
| BioCyc:RXN0-1141 | 6.3.1.20 | lipoate--GcvH protein ligase |
| BioCyc:RXN0-1139 | 6.3.1.20 | ATP + E2P-MONOMER + LIPOIC-ACID --> AMP + PPI + ACEF-LIPOATE |
| BioCyc:TRANS-RXN0-278 | LIPOIC-ACID --> LIPOIC-ACID | |
| BioCyc:RXN-17127 | 6.3.1.20 | Lipoyl-Protein-L-Lysine + LIPOIC-ACID + ATP --> Lipoyl-Protein-N6-lipoyllysine + AMP + PPI + PROTON |
| BioCyc:RXN-8654 | PROTON + LIPOIC-ACID + ATP --> LIPOYL-AMP + PPI | |
| BioCyc:RXN0-1140 | 6.3.1.20 | LIPOIC-ACID + E2O-MONOMER + ATP --> SUCB-LIPOATE + AMP + PPI |
| BioCyc:RXN-13031 | 3.5.1.138 | Lipoyl-Protein-N6-lipoyllysine + WATER --> Lipoyl-Protein-L-Lysine + LIPOIC-ACID |
| BioCyc:RXN-7002 | RIBOSE-1-ARSENATE + CPD-296 + 2 PROTON --> D-Ribofuranose + CPD0-2040 + LIPOIC-ACID | |
| BioCyc:RXN-18330 | 1.8.1.- | CPD-296 + NAD<=>LIPOIC-ACID + NADH + PROTON |
| BioCyc:RXN-18328 | 1.8.1.- | CPD-296 + NADP<=>LIPOIC-ACID + NADPH + PROTON |
Taxonomy Source
- Escherichia coli [ncbi taxid: 562]
- Homo sapiens [ncbi taxid: 9606]
- Liriodendron tulipifera [ncbi taxid: 3415]
- Porphyra tenera [ncbi taxid: ]
- Pyropia tenera [ncbi taxid: 2785]
Pathway Synthetic
| pathway id | name |
|---|---|
| PathBank:SMP0000793 | Lipoic Acid Metabolism |
| WikiPathways:WP1311 | Folic acid network |
| WikiPathways:WP1272 | Selenium micronutrient network |
| WikiPathways:WP15 | Selenium micronutrient network |
| WikiPathways:WP1310 | Selenium micronutrient network |
| WikiPathways:WP5355 | Metabolic Epileptic Disorders |
| WikiPathways:WP1273 | Folic acid network |
| WikiPathways:WP3257 | Selenium micronutrient network |
| PathBank:SMP0120694 | Dihydropyrimidine Dehydrogenase Deficiency (DHPD) |
| PathBank:SMP0120754 | Non-Ketotic Hyperglycinemia |
| PathBank:SMP0120770 | Hyperglycinemia, Non-Ketotic |
| PathBank:SMP0000009 | Ammonia Recycling |
| PathBank:SMP0000242 | Dimethylglycine Dehydrogenase Deficiency |
| PathBank:SMP0000223 | Non-Ketotic Hyperglycinemia |
| PathBank:SMP0000484 | Dimethylglycine Dehydrogenase Deficiency |
| PathBank:SMP0087177 | Ammonia Recycling |
| PathBank:SMP0087282 | Ammonia Recycling |
| PathBank:SMP0087338 | Glycine and Serine Metabolism |
| PathBank:SMP0087466 | Glycine and Serine Metabolism |
| PathBank:SMP0063579 | Ammonia Recycling |