2.0 2012-05-31 13:02:53 -0600 2015-09-13 15:15:20 -0600 ECMDB00985 M2MDB000215 Dihydrolipoamide Dihydrolipoamide 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. Dihydrolipoamide is a molecule produced by the action of dihydrolipoyl dehydrogenase upon lipoamide. 6,8-bis-sulfanyloctanamide 6,8-Bis-sulphanyloctanamide 6,8-dimercapto-Octanamide 6,8-dimercaptooctanamide 6,8-disulfanyloctanamide 6,8-Disulphanyloctanamide Dihydrolipoamide Dihydrothioctamide C8H17NOS2 207.357 207.075155551 6,8-disulfanyloctanimidic acid dihydrothioctamide 3884-47-7 OC(=N)CCCCC(S)CCS InChI=1S/C8H17NOS2/c9-8(10)4-2-1-3-7(12)5-6-11/h7,11-12H,1-6H2,(H2,9,10) VLYUGYAKYZETRF-UHFFFAOYSA-N Outer membrane Inner membrane logp 2.22 ALOGPS logs -3.32 ALOGPS solubility 9.92e-02 g/l ALOGPS logp 1.44 ChemAxon pka_strongest_acidic 6.68 ChemAxon pka_strongest_basic 8.78 ChemAxon iupac 6,8-disulfanyloctanimidic acid ChemAxon average_mass 207.357 ChemAxon mono_mass 207.075155551 ChemAxon smiles OC(=N)CCCCC(S)CCS ChemAxon formula C8H17NOS2 ChemAxon inchi InChI=1S/C8H17NOS2/c9-8(10)4-2-1-3-7(12)5-6-11/h7,11-12H,1-6H2,(H2,9,10) ChemAxon inchikey VLYUGYAKYZETRF-UHFFFAOYSA-N ChemAxon polar_surface_area 44.08 ChemAxon refractivity 68.7 ChemAxon polarizability 23.77 ChemAxon rotatable_bond_count 7 ChemAxon acceptor_count 2 ChemAxon donor_count 4 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 3275 Specdb::CMs 37877 Specdb::CMs 157098 Specdb::CMs 1083092 Specdb::CMs 1083093 Specdb::CMs 1083094 Specdb::CMs 1083095 Specdb::CMs 1083096 Specdb::CMs 1083097 Specdb::CMs 1083098 Specdb::NmrOneD 293955 Specdb::NmrOneD 293956 Specdb::NmrOneD 293957 Specdb::NmrOneD 293958 Specdb::NmrOneD 293959 Specdb::NmrOneD 293960 Specdb::NmrOneD 293961 Specdb::NmrOneD 293962 Specdb::NmrOneD 293963 Specdb::NmrOneD 293964 Specdb::NmrOneD 293965 Specdb::NmrOneD 293966 Specdb::NmrOneD 293967 Specdb::NmrOneD 293968 Specdb::NmrOneD 293969 Specdb::NmrOneD 293970 Specdb::NmrOneD 293971 Specdb::NmrOneD 293972 Specdb::NmrOneD 293973 Specdb::NmrOneD 293974 Specdb::MsMs 23009 Specdb::MsMs 23010 Specdb::MsMs 23011 Specdb::MsMs 29807 Specdb::MsMs 29808 Specdb::MsMs 29809 Specdb::MsMs 2712296 Specdb::MsMs 2712297 Specdb::MsMs 2712298 Specdb::MsMs 2996966 Specdb::MsMs 2996967 Specdb::MsMs 2996968 HMDB00985 643 C00579 17694 DIHYDROLIPOAMIDE Dihydrolipoamide Keseler, I. 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"Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. 18331064 Brautigam CA, Chuang JL, Tomchick DR, Machius M, Chuang DT: Crystal structure of human dihydrolipoamide dehydrogenase: NAD+/NADH binding and the structural basis of disease-causing mutations. J Mol Biol. 2005 Jul 15;350(3):543-52. 15946682 Kim H: Asparagine-473 residue is important to the efficient function of human dihydrolipoamide dehydrogenase. J Biochem Mol Biol. 2005 Mar 31;38(2):248-52. 15826505 McMillan PJ, Stimmler LM, Foth BJ, McFadden GI, Muller S: The human malaria parasite Plasmodium falciparum possesses two distinct dihydrolipoamide dehydrogenases. Mol Microbiol. 2005 Jan;55(1):27-38. 15612914 Li XJ, Grunwald D, Mathieu J, Morel F, Stasia MJ: Crucial role of two potential cytosolic regions of Nox2, 191TSSTKTIRRS200 and 484DESQANHFAVHHDEEKD500, on NADPH oxidase activation. J Biol Chem. 2005 Apr 15;280(15):14962-73. Epub 2005 Jan 31. 15684431 Deres P, Halmosi R, Toth A, Kovacs K, Palfi A, Habon T, Czopf L, Kalai T, Hideg K, Sumegi B, Toth K: Prevention of doxorubicin-induced acute cardiotoxicity by an experimental antioxidant compound. J Cardiovasc Pharmacol. 2005 Jan;45(1):36-43. 15613977 Weitzman, P. D. J.; Hewson, Janet K.; Parker, M. G. Preparation of dihydrolipoamide by electrolytic reduction. FEBS Letters (1974), 43(1), 101-3. Dihydrolipoyllysine-residue acetyltransferase component of pyruvate dehydrogenase complex P06959 ODP2_ECOLI aceF http://ecmdb.ca/proteins/P06959.xml Dihydrolipoyl dehydrogenase P0A9P0 DLDH_ECOLI lpdA http://ecmdb.ca/proteins/P0A9P0.xml Dihydrolipoamide + NAD <> Lipoamide + NADH + Hydrogen ion R01698 Acetyl-CoA + Dihydrolipoamide Coenzyme A + S-Acetyldihydrolipoamide DIHYDLIPACETRANS-RXN Acetyl-CoA + Dihydrolipoamide + Dihydrolipoamide <> Coenzyme A + S-Acetyldihydrolipoamide PW_R005172 Succinyl-CoA + Dihydrolipoamide + Succinyl-CoA + Dihydrolipoamide > Coenzyme A + (S)-Succinyldihydrolipoamide PW_R005173