2.0 2015-09-08 17:48:56 -0600 2015-09-14 16:46:05 -0600 ECMDB24069 M2MDB006186 (R)-lipoic acid Lipoic acid is a vitamin-like antioxidant that acts as a free-radical scavenger. Alpha-lipoic acid is also known as thioctic acid. 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. 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. (Wikipedia) (R)-Lipoate C8H14O2S2 206.326 206.043521072 5-[(3S)-1,2-dithiolan-3-yl]pentanoic acid S-LA [H][C@]1(CCCCC(O)=O)CCSS1 InChI=1S/C8H14O2S2/c9-8(10)4-2-1-3-7-5-6-11-12-7/h7H,1-6H2,(H,9,10)/t7-/m0/s1 AGBQKNBQESQNJD-ZETCQYMHSA-N logp 2.75 ALOGPS logs -2.96 ALOGPS solubility 2.24e-01 g/l ALOGPS logp 2.11 ChemAxon pka_strongest_acidic 4.52 ChemAxon iupac 5-[(3S)-1,2-dithiolan-3-yl]pentanoic acid ChemAxon average_mass 206.326 ChemAxon mono_mass 206.043521072 ChemAxon smiles [H][C@]1(CCCCC(O)=O)CCSS1 ChemAxon formula C8H14O2S2 ChemAxon inchi InChI=1S/C8H14O2S2/c9-8(10)4-2-1-3-7-5-6-11-12-7/h7H,1-6H2,(H,9,10)/t7-/m0/s1 ChemAxon inchikey AGBQKNBQESQNJD-ZETCQYMHSA-N ChemAxon polar_surface_area 37.3 ChemAxon refractivity 54.37 ChemAxon polarizability 21.91 ChemAxon rotatable_bond_count 5 ChemAxon acceptor_count 2 ChemAxon donor_count 1 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon Specdb::CMs 132092 Specdb::CMs 139826 Specdb::MsMs 26138 Specdb::MsMs 26139 Specdb::MsMs 26140 Specdb::MsMs 32696 Specdb::MsMs 32697 Specdb::MsMs 32698 Specdb::MsMs 2802049 Specdb::MsMs 2802050 Specdb::MsMs 2802051 Specdb::MsMs 2879837 Specdb::MsMs 2879838 Specdb::MsMs 2879839