(R)-Lipoate (BioCAD00000000871)

blood urine kidney liver neuron placenta skeletal muscle

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

Reviewed

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.

Entity Information

DBLinks

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

Metabolic Network
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
View More
Organism Source

Taxonomy Source

  1. Escherichia coli [ncbi taxid: 562]
  2. Homo sapiens [ncbi taxid: 9606]
  3. Liriodendron tulipifera [ncbi taxid: 3415]
  4. Porphyra tenera [ncbi taxid: ]
  5. 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
View All Pathways