2.0 2012-10-10 12:13:10 -0600 2015-08-05 16:22:03 -0600 ECMDB23028 M2MDB003418 lipoate A thia fatty acid anion that is the conjugate base of lipoic acid; major species at pH 7.3. 1,2-Dithiolane-3-pentanoate 1,2-Dithiolane-3-pentanoic acid 1,2-Dithiolane-3-valerate 1,2-Dithiolane-3-valeric acid 5-(1,2-Dithiolan-3-yl)valerate 5-(1,2-Dithiolan-3-yl)valeric acid 5-(Dithiolan-3-yl)valerate 5-(Dithiolan-3-yl)valeric acid 5-[3-(1,2-Dithiolanyl)]pentanoate 5-[3-(1,2-Dithiolanyl)]pentanoic acid 6,8-Thioctate 6,8-Thioctic acid 6,8-Thiotate 6,8-Thiotic acid 6-Thioctate 6-Thioctic acid 6-Thiotate 6-Thiotic acid a-Lipoate a-Lipoic acid a-Liponsaeure Acetate-replacing factor Acetic acid-replacing factor alpha-Lipoate alpha-Lipoic acid alpha-Liponsaeure Biletan Lipoic acid Liponate Liponic acid Thioctansaeure Thioctate Thioctic acid Thioctsaeure Thioktsaeure α-Lipoate α-Lipoic acid α-Liponsaeure C8H14O2S2 206.326 206.043521072 5-(1,2-dithiolan-3-yl)pentanoic acid 6,8-thioctic acid 62-46-4 OC(=O)CCCCC1CCSS1 InChI=1S/C8H14O2S2/c9-8(10)4-2-1-3-7-5-6-11-12-7/h7H,1-6H2,(H,9,10) AGBQKNBQESQNJD-UHFFFAOYSA-N Solid Membrane Cytoplasm Membrane 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-(1,2-dithiolan-3-yl)pentanoic acid ChemAxon average_mass 206.326 ChemAxon mono_mass 206.043521072 ChemAxon smiles OC(=O)CCCCC1CCSS1 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) ChemAxon inchikey AGBQKNBQESQNJD-UHFFFAOYSA-N ChemAxon polar_surface_area 37.3 ChemAxon refractivity 54.37 ChemAxon polarizability 22 ChemAxon rotatable_bond_count 5 ChemAxon acceptor_count 2 ChemAxon donor_count 1 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon Lipoic acid metabolism Lipoic acid metabolism starts with caprylic acid being introduced into the cytoplasm however no transporter has been identified yet. Once caprylic acid is in the cytoplasm, it can either reacts with a holo-acp, through an ATP driven 2-acylglycerophosphoethanolamine acyltransferase / acyl-ACP synthetase resulting in pyrophosphate, AMP and octanoyl-[acp]. The latter compound can also be obtained from palmitate biosynthesis. Octanoyl-acp interacts with a lipoyl-carrier protein L-lysine through a Octanoyltransferase resulting in a hydrogen ion, a holo-acyl-acp, and a protein N6-0octanoyl) lysine. The latter compound reacts with an S-adenosylmethionine, a sulfurated[sulfur carrier] and a reduced ferredoxin through a lipoate-protein ligase A, resulting in a 5-deoxyadenosine, a L-methionine, an unsulfurated [sulfur carrier], oxidized ferredoxin, and a Protein N6-(lipoyl) lysine. Caprylic acid can also interact with ATP and a lipoyl-carrier protein-L-lysine through a lipoate-protein ligase A resulting in a amp, pyrophosphate, hydrogen ion, protein N6-(octanoyl)lysine. The latter compound reacts with an S-adenosylmethionine, a sulfurated[sulfur carrier] and a reduced ferredoxin through a lipoate-protein ligase A, resulting in a 5-deoxyadenosine, a L-methionine, an unsulfurated [sulfur carrier], oxidized ferredoxin, and a Protein N6-(lipoyl) lysine. R-lipoic acid can be absorbed from the environment, as seen in studies by Morris TW. In this pathway the lipoyl-protein ligase LplA utilizes pre-existing lipoate that has been imported from outside the cell, and thus catalyzes a salvage pathway. Lipoic acid interacts with ATP and hydrogen ion through a lipoyl-protein ligase A, resulting in a pyrophosphate and a Lipoyl-AMP (lipoyl-adenylate). This compound then interacts with a lipoyl-carrier protein-L-lysine through a lipoate-protein ligase A resulting a AMP, a hydrogen ion and a Protein N6-(lipoyl) lysine. It has been suggested that the conversion of octanoylated-domains to lipoylated ones described in this pathway may be a type of a repair pathway, activated only if the other lipoate biosynthetic pathways are malfunctioning . PW000770 ec00785 Metabolic Metabolic pathways eco01100 Specdb::CMs 112144 Specdb::CMs 125546 Specdb::CMs 875443 Specdb::CMs 875444 Specdb::NmrOneD 4668 Specdb::NmrOneD 4690 Specdb::MsMs 24557 Specdb::MsMs 24558 Specdb::MsMs 24559 Specdb::MsMs 31115 Specdb::MsMs 31116 Specdb::MsMs 31117 Specdb::MsMs 2245284 Specdb::MsMs 2251448 Specdb::MsMs 2252848 Specdb::MsMs 2253635 Specdb::MsMs 2254865 Specdb::MsMs 2255698 Specdb::MsMs 2258825 Specdb::MsMs 2259740 Specdb::MsMs 3430437 Specdb::MsMs 3430438 Specdb::MsMs 3430439 Specdb::MsMs 3430440 Specdb::MsMs 3430441 Specdb::MsMs 3430442 HMDB14312 864 C00725 16494 Lipoic_Acid Lipoate-protein ligase A P32099 LPLA_ECOLI lplA http://ecmdb.ca/proteins/P32099.xml Adenosine triphosphate + lipoate > Pyrophosphate + Lipoyl-AMP Adenosine triphosphate + lipoate + Lipoyl-AMP + Apoprotein <> Pyrophosphate + Protein N6-(lipoyl)lysine + Adenosine monophosphate R07770 lipoate + Adenosine triphosphate > Lipoyl-AMP + Pyrophosphate + Lipoyl-AMP PW_R002523