1.0 2016-09-30 22:46:09 UTC 2020-05-21 16:28:29 UTC BMDB0001451 BMDB01451 Lipoic acid Lipoic acid, also known as RLA or a-lipoate, 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. Lipoic acid is a drug which is used for nutritional supplementation, also for treating dietary shortage or imbalance. Lipoic acid exists as a solid, very hydrophobic, practically insoluble (in water), and relatively neutral molecule. Lipoic acid exists in all living species, ranging from bacteria to humans. In cattle, lipoic acid is involved in the metabolic pathway called the glycine and serine metabolism pathway. (+)-alpha-Lipoic acid (R)-(+)-Lipoate (R)-(+)-Lipoic acid (R)-1,2-Dithiolane-3-pentanoic acid (R)-1,2-Dithiolane-3-valeric acid (R)-6,8-Thioctic acid alpha-Lipoic acid Lipoic acid R-(+)-Lipoic acid R-LA RLA Thioctic acid Thioctic acid D-form (+)-a-Lipoate (+)-a-Lipoic acid (+)-alpha-Lipoate (+)-α-lipoate (+)-α-lipoic acid (R)-Lipoate (R)-1,2-Dithiolane-3-pentanoate (R)-1,2-Dithiolane-3-valerate (R)-6,8-Thioctate a-Lipoate a-Lipoic acid alpha-Lipoate α-lipoate α-Lipoic acid Lipoate R-(+)-Lipoate Thioctate Thioctate D-form Acid, alpha-lipoic alpha Lipoic acid 1,2-Dithiolane-3R-pentanoic acid 1,2-Dithiolane-3R-pentanoate (R)-Lipoic acid (3R)-1,2-Dithiolane-3-pentanoic acid (R)-(+)-1,2-Dithiolane-3-pentanoic acid (R)-(+)-alpha-Lipoic acid (R)-(+)-α-Lipoic acid (R)-5-(1,2-Dithiolan-3-yl)pentanoicacid (R)-alpha-Lipoic acid (R)-α-Lipoic acid ALA alpha-(+)-Lipoic acid α-(+)-Lipoic acid 1,2-Dithiolane-3-valeric acid 5-(1,2-Dithiolan-3-yl)pentanoic acid 5-(1,2-Dithiolan-3-yl)valeric acid 6,8-Thioctic acid 6-Thioctic acid C8H14O2S2 206.326 206.043521072 5-[(3R)-1,2-dithiolan-3-yl]pentanoic acid lipoic acid 1200-22-2 OC(=O)CCCC[C@@H]1CCSS1 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 AGBQKNBQESQNJD-SSDOTTSWSA-N 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. Organic compounds Organoheterocyclic compounds Dithiolanes Lipoic acids and derivatives Lipoic acids and derivatives 1,2-dithiolanes Carbonyl compounds Carboxylic acids Heterocyclic fatty acids Hydrocarbon derivatives Medium-chain fatty acids Monocarboxylic acids and derivatives Organic disulfides Organic oxides Thia fatty acids 1,2-dithiolane Aliphatic heteromonocyclic compound Carbonyl group Carboxylic acid Carboxylic acid derivative Fatty acid Fatty acyl Heterocyclic fatty acid Hydrocarbon derivative Lipoic_acid_derivative Medium-chain fatty acid Monocarboxylic acid or derivatives Organic disulfide Organic oxide Organic oxygen compound Organooxygen compound Thia fatty acid Aliphatic heteromonocyclic compounds Thia fatty acids Thia fatty acids dithiolanes heterocyclic fatty acid lipoic acid thia fatty acid Solid logp 2.75 ALOGPS logs -2.96 ALOGPS logp 2.11 ChemAxon pka_strongest_acidic 4.52 ChemAxon iupac 5-[(3R)-1,2-dithiolan-3-yl]pentanoic acid ChemAxon average_mass 206.326 ChemAxon mono_mass 206.043521072 ChemAxon smiles OC(=O)CCCC[C@@H]1CCSS1 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-/m1/s1 ChemAxon inchikey AGBQKNBQESQNJD-SSDOTTSWSA-N ChemAxon polar_surface_area 37.3 ChemAxon refractivity 54.37 ChemAxon polarizability 21.74 ChemAxon rotatable_bond_count 5 ChemAxon acceptor_count 2 ChemAxon donor_count 1 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon number_of_rings 1 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon Ammonia Recycling SMP0087177 Glycine and Serine Metabolism SMP0087245 Specdb::CMs 3089 Specdb::CMs 31800 Specdb::CMs 38079 Specdb::CMs 99686 Specdb::CMs 100076 Specdb::CMs 100077 Specdb::CMs 155727 Specdb::NmrOneD 1710 Specdb::NmrTwoD 1651 Specdb::MsIr 1283 Specdb::MsIr 1284 Specdb::MsIr 1285 Specdb::MsMs 1580 Specdb::MsMs 1581 Specdb::MsMs 1582 Specdb::MsMs 179469 Specdb::MsMs 179470 Specdb::MsMs 179471 Specdb::MsMs 181797 Specdb::MsMs 181798 Specdb::MsMs 181799 Specdb::MsMs 2236189 Specdb::MsMs 2237205 Specdb::MsMs 2238327 Specdb::MsMs 2239242 Specdb::MsMs 2308539 Specdb::MsMs 2308540 Specdb::MsMs 2308541 Specdb::MsMs 2654048 Specdb::MsMs 2654049 Specdb::MsMs 2654050 Kidney Wishart DS, Feunang YD, Marcu A, Guo AC, Liang K, Vazquez-Fresno R, Sajed T, Johnson D, Li C, Karu N, Sayeeda Z, Lo E, Assempour N, Berjanskii M, Singhal S, Arndt D, Liang Y, Badran H, Grant J, Serra-Cayuela A, Liu Y, Mandal R, Neveu V, Pon A, Knox C, Wilson M, Manach C, Scalbert A: HMDB 4.0: the human metabolome database for 2018. Nucleic Acids Res. 2018 Jan 4;46(D1):D608-D617. doi: 10.1093/nar/gkx1089. 29140435 Liver Wishart DS, Feunang YD, Marcu A, Guo AC, Liang K, Vazquez-Fresno R, Sajed T, Johnson D, Li C, Karu N, Sayeeda Z, Lo E, Assempour N, Berjanskii M, Singhal S, Arndt D, Liang Y, Badran H, Grant J, Serra-Cayuela A, Liu Y, Mandal R, Neveu V, Pon A, Knox C, Wilson M, Manach C, Scalbert A: HMDB 4.0: the human metabolome database for 2018. Nucleic Acids Res. 2018 Jan 4;46(D1):D608-D617. doi: 10.1093/nar/gkx1089. 29140435 Milk By GC-TOFMS and UPLC-QTOFMS Qian L, Zhao A, Zhang Y, Chen T, Zeisel SH, Jia W, Cai W: Metabolomic Approaches to Explore Chemical Diversity of Human Breast-Milk, Formula Milk and Bovine Milk. Int J Mol Sci. 2016 Dec 17;17(12). pii: ijms17122128. doi: 10.3390/ijms17122128. 27999311 Neuron Wishart DS, Feunang YD, Marcu A, Guo AC, Liang K, Vazquez-Fresno R, Sajed T, Johnson D, Li C, Karu N, Sayeeda Z, Lo E, Assempour N, Berjanskii M, Singhal S, Arndt D, Liang Y, Badran H, Grant J, Serra-Cayuela A, Liu Y, Mandal R, Neveu V, Pon A, Knox C, Wilson M, Manach C, Scalbert A: HMDB 4.0: the human metabolome database for 2018. Nucleic Acids Res. 2018 Jan 4;46(D1):D608-D617. doi: 10.1093/nar/gkx1089. 29140435 Placenta Wishart DS, Feunang YD, Marcu A, Guo AC, Liang K, Vazquez-Fresno R, Sajed T, Johnson D, Li C, Karu N, Sayeeda Z, Lo E, Assempour N, Berjanskii M, Singhal S, Arndt D, Liang Y, Badran H, Grant J, Serra-Cayuela A, Liu Y, Mandal R, Neveu V, Pon A, Knox C, Wilson M, Manach C, Scalbert A: HMDB 4.0: the human metabolome database for 2018. Nucleic Acids Res. 2018 Jan 4;46(D1):D608-D617. doi: 10.1093/nar/gkx1089. 29140435 Skeletal Muscle Wishart DS, Feunang YD, Marcu A, Guo AC, Liang K, Vazquez-Fresno R, Sajed T, Johnson D, Li C, Karu N, Sayeeda Z, Lo E, Assempour N, Berjanskii M, Singhal S, Arndt D, Liang Y, Badran H, Grant J, Serra-Cayuela A, Liu Y, Mandal R, Neveu V, Pon A, Knox C, Wilson M, Manach C, Scalbert A: HMDB 4.0: the human metabolome database for 2018. Nucleic Acids Res. 2018 Jan 4;46(D1):D608-D617. doi: 10.1093/nar/gkx1089. 29140435 DB00166 FDB022631 5886 6112 30314 C16241 C00000754 LIPOIC-ACID 35801 Lipoic_acid 126 Qian L, Zhao A, Zhang Y, Chen T, Zeisel SH, Jia W, Cai W: Metabolomic Approaches to Explore Chemical Diversity of Human Breast-Milk, Formula Milk and Bovine Milk. Int J Mol Sci. 2016 Dec 17;17(12). pii: ijms17122128. doi: 10.3390/ijms17122128. 27999311 BMDBP00363 Dihydrolipoyllysine-residue acetyltransferase component of pyruvate dehydrogenase complex P11180 DLAT Enzyme BMDBP00509 Acyl-coenzyme A synthetase ACSM1, mitochondrial Q9BEA2 ACSM1 Enzyme BMDBP00628 Dihydrolipoyllysine-residue succinyltransferase component of 2-oxoglutarate dehydrogenase complex, mitochondrial P11179 DLST Enzyme BMDBP00785 Pyruvate dehydrogenase protein X component P22439 PDHX Enzyme BMDBP00786 Lipoamide acyltransferase component of branched-chain alpha-keto acid dehydrogenase complex, mitochondrial P11181 DBT Enzyme BMDBP00787 Aminomethyltransferase, mitochondrial P25285 AMT Enzyme BMDBP01981 Glycine cleavage system H protein, mitochondrial P20821 GCSH Enzyme BMDBP02870 Dihydrolipoyl dehydrogenase F1N206 DLD Enzyme