2.0 2012-05-31 13:02:40 -0600 2015-09-13 15:15:20 -0600 ECMDB00962 M2MDB000211 Lipoamide Lipoamide is a trivial name for 6,8-dithiooctanoic amide. It is 6,8-dithiooctanoic acid's functional form where the carboxyl group is attached to protein (or any other amine) by an amide linkage (containing -NH2) to an amino group. -- Wikipedia 1,2-Dithiolane-3-pentanamide 5-(1,2-Dithiolan-3-yl)-pentanamide 5-(1,2-dithiolan-3-yl)pentanamide 5-(1,2-Dithiolan-3-yl)valeramide 5-(Dithiolan-3-yl)valeramide 6,8-Dithiooctanoic amide a-Lipoate a-Lipoate amide a-Lipoic acid a-Lipoic acid amide Alpha-lipoate alpha-Lipoate amide Alpha-lipoic acid Alpha-lipoic acid amide Dl-6-Thioctic amide DL-lipoamide Lipamide Lipoacin Lipoamid Lipoicin Lipozyme Lypoaran Pathoclon Thioami Thioctamid Thioctamide Thioctate amide Thioctate amide (jan) Thioctic acid amide Thioctic acid amide (jan) Thiotomin Ticolin Vitamin n α-Lipoate α-Lipoate amide α-Lipoic acid α-Lipoic acid amide C8H15NOS2 205.341 205.059505487 5-(1,2-dithiolan-3-yl)pentanamide lipoamide 940-69-2 NC(=O)CCCCC1CCSS1 InChI=1S/C8H15NOS2/c9-8(10)4-2-1-3-7-5-6-11-12-7/h7H,1-6H2,(H2,9,10) FCCDDURTIIUXBY-UHFFFAOYSA-N Solid Outer membrane Inner membrane logp 2.30 ALOGPS logs -3.31 ALOGPS solubility 1.01e-01 g/l ALOGPS melting_point 126.0-129.0oC logp 1.31 ChemAxon pka_strongest_acidic 16.45 ChemAxon pka_strongest_basic -1.4 ChemAxon iupac 5-(1,2-dithiolan-3-yl)pentanamide ChemAxon average_mass 205.341 ChemAxon mono_mass 205.059505487 ChemAxon smiles NC(=O)CCCCC1CCSS1 ChemAxon formula C8H15NOS2 ChemAxon inchi InChI=1S/C8H15NOS2/c9-8(10)4-2-1-3-7-5-6-11-12-7/h7H,1-6H2,(H2,9,10) ChemAxon inchikey FCCDDURTIIUXBY-UHFFFAOYSA-N ChemAxon polar_surface_area 43.09 ChemAxon refractivity 56.19 ChemAxon polarizability 22.38 ChemAxon rotatable_bond_count 5 ChemAxon acceptor_count 1 ChemAxon donor_count 1 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Specdb::CMs 1777 Specdb::CMs 1855 Specdb::CMs 3400 Specdb::CMs 31270 Specdb::CMs 31271 Specdb::CMs 32171 Specdb::CMs 32172 Specdb::CMs 166223 Specdb::NmrOneD 1625 Specdb::NmrOneD 4945 Specdb::NmrOneD 4946 Specdb::NmrOneD 301925 Specdb::NmrOneD 301926 Specdb::NmrOneD 301927 Specdb::NmrOneD 301928 Specdb::NmrOneD 301929 Specdb::NmrOneD 301930 Specdb::NmrOneD 301931 Specdb::NmrOneD 301932 Specdb::NmrOneD 301933 Specdb::NmrOneD 301934 Specdb::NmrOneD 301935 Specdb::NmrOneD 301936 Specdb::NmrOneD 301937 Specdb::NmrOneD 301938 Specdb::NmrOneD 301939 Specdb::NmrOneD 301940 Specdb::NmrOneD 301941 Specdb::NmrOneD 301942 Specdb::NmrOneD 301943 Specdb::NmrOneD 301944 Specdb::MsMs 1366 Specdb::MsMs 1367 Specdb::MsMs 1368 Specdb::MsMs 4983 Specdb::MsMs 4984 Specdb::MsMs 4985 Specdb::MsMs 4986 Specdb::MsMs 4987 Specdb::MsMs 4988 Specdb::MsMs 4989 Specdb::MsMs 4990 Specdb::MsMs 180099 Specdb::MsMs 180100 Specdb::MsMs 180101 Specdb::MsMs 182433 Specdb::MsMs 182434 Specdb::MsMs 182435 Specdb::MsMs 446435 Specdb::MsMs 446436 Specdb::MsMs 446437 Specdb::MsMs 446438 Specdb::MsMs 446439 Specdb::MsMs 447238 Specdb::MsMs 451974 Specdb::MsMs 2235967 Specdb::NmrTwoD 1566 HMDB00962 840 C00248 17460 LIPOAMIDE Lipoamide Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. 21097882 Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. 22080510 van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. 17765195 Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. 18331064 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. 8769129 Nordman T, Xia L, Bjorkhem-Bergman L, Damdimopoulos A, Nalvarte I, Arner ES, Spyrou G, Eriksson LC, Bjornstedt M, Olsson JM: Regeneration of the antioxidant ubiquinol by lipoamide dehydrogenase, thioredoxin reductase and glutathione reductase. Biofactors. 2003;18(1-4):45-50. 14695919 Oizumi J, Hayakawa K: Liberation of lipoate by human serum lipoamidase from bovine heart pyruvate dehydrogenase. 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Faming Zhuanli Shenqing Gongkai Shuomingshu (1997), 5 pp. http://hmdb.ca/system/metabolites/msds/000/000/866/original/HMDB00962.pdf?1358461284 Dihydrolipoyl dehydrogenase P0A9P0 DLDH_ECOLI lpdA http://ecmdb.ca/proteins/P0A9P0.xml Dihydrolipoamide + NAD <> Lipoamide + NADH + Hydrogen ion R01698 Hydrogen ion + Pyruvic acid + Lipoamide S-Acetyldihydrolipoamide + Carbon dioxide PYRUVATEDECARB-RXN