2.0 2012-05-31 13:54:03 -0600 2015-06-03 15:54:11 -0600 ECMDB01526 M2MDB000411 S-Acetyldihydrolipoamide S-acetyldihydrolipoamide is a member of the chemical class known as N-acyl Amines. These are compounds containing a fatty acid moiety linked to an amine group through an ester linkage. In E. coli the dihydrolipoyl transacetylase component (E2) of the pyruvate dehydrogenase complex catalyzes the reaction of acetyl coenzyme A (acetyl-CoA) with dihydrolipoamide, producing coenzyme A and S-acetyldihydrolipoamide. [PMID: 3101735] 6-acetylsulfanyl-8-sulfanyl-octanamide 6-Acetylsulphanyl-8-sulphanyl-octanamide 6-S-Acetyldihydrolipoamide S-Acetyldihydrolipoamide S-[6-amino-6-oxo-1-(2-sulfanylethyl)hexyl] ethanethioate S-[6-amino-6-oxo-1-(2-sulfanylethyl)hexyl] ethanethioic acid S-[6-amino-6-oxo-1-(2-Sulphanylethyl)hexyl] ethanethioate S-[6-amino-6-oxo-1-(2-Sulphanylethyl)hexyl] ethanethioic acid C10H19NO2S2 249.393 249.085720237 6-(acetylsulfanyl)-8-sulfanyloctanamide S(6)-acetyldihydrolipoamide CC(=O)SC(CCS)CCCCC(N)=O InChI=1S/C10H19NO2S2/c1-8(12)15-9(6-7-14)4-2-3-5-10(11)13/h9,14H,2-7H2,1H3,(H2,11,13) ARGXEXVCHMNAQU-UHFFFAOYSA-N Outer membrane Inner membrane logp 2.46 ALOGPS logs -3.85 ALOGPS solubility 3.55e-02 g/l ALOGPS logp 1.24 ChemAxon pka_strongest_acidic 10.19 ChemAxon pka_strongest_basic -0.58 ChemAxon iupac 6-(acetylsulfanyl)-8-sulfanyloctanamide ChemAxon average_mass 249.393 ChemAxon mono_mass 249.085720237 ChemAxon smiles CC(=O)SC(CCS)CCCCC(N)=O ChemAxon formula C10H19NO2S2 ChemAxon inchi InChI=1S/C10H19NO2S2/c1-8(12)15-9(6-7-14)4-2-3-5-10(11)13/h9,14H,2-7H2,1H3,(H2,11,13) ChemAxon inchikey ARGXEXVCHMNAQU-UHFFFAOYSA-N ChemAxon polar_surface_area 60.16 ChemAxon refractivity 67.23 ChemAxon polarizability 27.66 ChemAxon rotatable_bond_count 9 ChemAxon acceptor_count 2 ChemAxon donor_count 2 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon glycolysis and pyruvate dehydrogenase Fructose metabolism begins with the transport of Beta-D-glucose 6-phosphate through a glucose PTS permease, resulting in a Beta-D-glucose 6-phosphate. This compound is isomerized by a glucose-6-phosphate isomerase resulting in a fructose 6-phosphate. This compound can be phosphorylated by two different enzymes, a pyridoxal phosphatase/fructose 1,6-bisphosphatase or a ATP driven-6-phosphofructokinase-1 resulting in a fructose 1,6-biphosphate. This compound can either react with a fructose bisphosphate aldolase class 1 resulting in D-glyceraldehyde 3-phosphate and a dihydroxyacetone phosphate or through a fructose biphosphate aldolase class 2 resulting in a D-glyceraldehyde 3-phosphate. This compound can then either react in a reversible triosephosphate isomerase resulting in a dihydroxyacetone phosphate or react with a phosphate through a NAD dependent Glyceraldehyde 3-phosphate dehydrogenase resulting in a glyceric acid 1,3-biphosphate. This compound is desphosphorylated by a phosphoglycerate kinase resulting in a 3-phosphoglyceric acid.This compound in turn can either react with a 2,3-bisphosphoglycerate-independent phosphoglycerate mutase or a 2,3-bisphosphoglycerate-independent phosphoglycerate mutase resulting in a 2-phospho-D-glyceric acid. This compound interacts with an enolase resulting in a phosphoenolpyruvic acid and water. Phosphoenolpyruvic acid can react either through a AMP driven phosphoenoylpyruvate synthase or a ADP driven pyruvate kinase protein complex resulting in a pyruvic acid. Pyruvic acid reacts with CoA through a NAD driven pyruvate dehydrogenase complex resulting in a carbon dioxide and a Acetyl-CoA which gets incorporated into the TCA cycle pathway. PW000785 Metabolic Specdb::CMs 10907 Specdb::CMs 164262 Specdb::NmrOneD 336598 Specdb::NmrOneD 336599 Specdb::NmrOneD 336600 Specdb::NmrOneD 336601 Specdb::NmrOneD 336602 Specdb::NmrOneD 336603 Specdb::NmrOneD 336604 Specdb::NmrOneD 336605 Specdb::NmrOneD 336606 Specdb::NmrOneD 336607 Specdb::NmrOneD 336608 Specdb::NmrOneD 336609 Specdb::NmrOneD 336610 Specdb::NmrOneD 336611 Specdb::NmrOneD 336612 Specdb::NmrOneD 336613 Specdb::NmrOneD 336614 Specdb::NmrOneD 336615 Specdb::NmrOneD 336616 Specdb::NmrOneD 336617 Specdb::MsMs 29732 Specdb::MsMs 29733 Specdb::MsMs 29734 Specdb::MsMs 36290 Specdb::MsMs 36291 Specdb::MsMs 36292 Specdb::MsMs 2770016 Specdb::MsMs 2770017 Specdb::MsMs 2770018 Specdb::MsMs 2908179 Specdb::MsMs 2908180 Specdb::MsMs 2908181 HMDB01526 1046 C01136 16807 S-ACETYLDIHYDROLIPOAMIDE 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 Yang, Y. S., Frey, P. A. (1986). "Dihydrolipoyl transacetylase of Escherichia coli. Formation of 8-S-acetyldihydrolipoamide." Biochemistry 25:8173-8178. 3101735 Butterworth PJ, Tsai CS, Eley MH, Roche TE, Reed LJ: A kinetic study of dihydrolipoyl transacetylase from bovine kidney. J Biol Chem. 1975 Mar 10;250(5):1921-5. 1089667 O'Connor TP, Roche TE, Paukstelis JV: 13C nuclear magnetic resonance study of the pyruvate dehydrogenase-catalyzed acetylation of dihydrolipoamide. J Biol Chem. 1982 Mar 25;257(6):3110-2. 6801041 Dihydrolipoyllysine-residue acetyltransferase component of pyruvate dehydrogenase complex P06959 ODP2_ECOLI aceF http://ecmdb.ca/proteins/P06959.xml Acetyl-CoA + Dihydrolipoamide Coenzyme A + S-Acetyldihydrolipoamide DIHYDLIPACETRANS-RXN Hydrogen ion + Pyruvic acid + Lipoamide S-Acetyldihydrolipoamide + Carbon dioxide PYRUVATEDECARB-RXN Acetyl-CoA + Dihydrolipoamide + Dihydrolipoamide <> Coenzyme A + S-Acetyldihydrolipoamide PW_R005172