2.0 2012-05-31 14:31:13 -0600 2015-06-03 17:19:27 -0600 ECMDB20170 M2MDB001017 Lipoyl-AMP Lipoyl-amp belongs to the class of Purine Ribonucleoside Monophosphates. These are nucleotides consisting of a purine base linked to a ribose to which one monophosphate group is attached. (inferred from compound structure) (2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-ylmethoxy-hydroxyphosphoryl 5-(dithiolan-3-yl)pentanoate (2R,3S,4R,5R)-5-(6-Aminopurin-9-yl)-3,4-dihydroxyoxolan-2-ylmethoxy-hydroxyphosphoryl 5-(dithiolan-3-yl)pentanoic acid 5'-O-{5-(1,2-Dithiolan-3-yl)pentanoyloxy}(hydroxy)phosphoryladenosine Lipoyl-AMP C18H26N5O8PS2 535.532 535.096040725 {[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}({[5-(1,2-dithiolan-3-yl)pentanoyl]oxy})phosphinic acid Lipoyl-AMP NC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](COP(O)(=O)OC(=O)CCCCC2CCSS2)[C@@H](O)[C@H]1O InChI=1S/C18H26N5O8PS2/c19-16-13-17(21-8-20-16)23(9-22-13)18-15(26)14(25)11(30-18)7-29-32(27,28)31-12(24)4-2-1-3-10-5-6-33-34-10/h8-11,14-15,18,25-26H,1-7H2,(H,27,28)(H2,19,20,21)/t10?,11-,14-,15-,18-/m1/s1 QWEGOCJRZOKSOE-NLJBGGCZSA-N Cytosol logp 0.25 ALOGPS logs -2.68 ALOGPS solubility 1.12e+00 g/l ALOGPS logp -2.3 ChemAxon pka_strongest_acidic 0.83 ChemAxon pka_strongest_basic 4.99 ChemAxon iupac {[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}({[5-(1,2-dithiolan-3-yl)pentanoyl]oxy})phosphinic acid ChemAxon average_mass 535.532 ChemAxon mono_mass 535.096040725 ChemAxon smiles NC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](COP(O)(=O)OC(=O)CCCCC2CCSS2)[C@@H](O)[C@H]1O ChemAxon formula C18H26N5O8PS2 ChemAxon inchi InChI=1S/C18H26N5O8PS2/c19-16-13-17(21-8-20-16)23(9-22-13)18-15(26)14(25)11(30-18)7-29-32(27,28)31-12(24)4-2-1-3-10-5-6-33-34-10/h8-11,14-15,18,25-26H,1-7H2,(H,27,28)(H2,19,20,21)/t10?,11-,14-,15-,18-/m1/s1 ChemAxon inchikey QWEGOCJRZOKSOE-NLJBGGCZSA-N ChemAxon polar_surface_area 192.14 ChemAxon refractivity 124.95 ChemAxon polarizability 50.71 ChemAxon rotatable_bond_count 11 ChemAxon acceptor_count 10 ChemAxon donor_count 4 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 lipoate salvage I PWY0-522 Specdb::CMs 35084 Specdb::CMs 47827 Specdb::CMs 249788 Specdb::CMs 249789 Specdb::CMs 249790 Specdb::CMs 249791 Specdb::CMs 249792 Specdb::CMs 249793 Specdb::CMs 249794 Specdb::CMs 249795 Specdb::CMs 249796 Specdb::CMs 249797 Specdb::CMs 249798 Specdb::CMs 249799 Specdb::CMs 249800 Specdb::CMs 249801 Specdb::CMs 249802 Specdb::CMs 249803 Specdb::CMs 249804 Specdb::CMs 249805 Specdb::CMs 249806 Specdb::CMs 249807 Specdb::CMs 249808 Specdb::CMs 281191 Specdb::NmrOneD 51702 Specdb::NmrOneD 51703 Specdb::NmrOneD 51704 Specdb::NmrOneD 51705 Specdb::NmrOneD 51706 Specdb::NmrOneD 51707 Specdb::NmrOneD 51708 Specdb::NmrOneD 51709 Specdb::NmrOneD 51710 Specdb::NmrOneD 51711 Specdb::NmrOneD 51712 Specdb::NmrOneD 51713 Specdb::NmrOneD 51714 Specdb::NmrOneD 51715 Specdb::NmrOneD 51716 Specdb::NmrOneD 51717 Specdb::NmrOneD 51718 Specdb::NmrOneD 51719 Specdb::NmrOneD 51720 Specdb::NmrOneD 51721 Specdb::MsMs 29690 Specdb::MsMs 29691 Specdb::MsMs 29692 Specdb::MsMs 36248 Specdb::MsMs 36249 Specdb::MsMs 36250 Specdb::MsMs 2669851 Specdb::MsMs 2669852 Specdb::MsMs 2669853 Specdb::MsMs 3009385 Specdb::MsMs 3009386 Specdb::MsMs 3009387 23724672 26330628 C16238 LIPOYL-AMP 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 Lipoate-protein ligase A P32099 LPLA_ECOLI lplA http://ecmdb.ca/proteins/P32099.xml Adenosine triphosphate + Lipoic acid > Lipoyl-AMP + Pyrophosphate R07770 RXN-8654 Lipoyl-AMP > Adenosine monophosphate + lipoate (protein bound) Adenosine triphosphate + Lipoic acid <> Pyrophosphate + Lipoyl-AMP R07770 Lipoyl-AMP + Apoprotein <> Protein N6-(lipoyl)lysine + Adenosine monophosphate R07771 Hydrogen ion + Lipoic acid + Adenosine triphosphate > Lipoyl-AMP + Pyrophosphate RXN-8654 Adenosine triphosphate + lipoate > Pyrophosphate + Lipoyl-AMP Lipoyl-AMP + protein > protein N(6)-(lipoyl)lysine + Adenosine monophosphate Adenosine triphosphate + lipoate + Lipoyl-AMP + Apoprotein <> Pyrophosphate + Protein N6-(lipoyl)lysine + Adenosine monophosphate R07770 lipoate + Adenosine triphosphate > Lipoyl-AMP + Pyrophosphate + Lipoyl-AMP PW_R002523 Lipoyl-AMP + apoprotein + Lipoyl-AMP > Protein N6-(lipoyl)lysine + Adenosine monophosphate PW_R002524 (R)-lipoic acid + Adenosine triphosphate + Hydrogen ion + Lipoic acid > Pyrophosphate + Lipoyl-AMP + Lipoyl-AMP PW_R003559 Lipoyl-AMP + a [lipoyl-carrier protein]-L-lysine + Lipoyl-AMP > Adenosine monophosphate + Hydrogen ion + Protein N6-(lipoyl)lysine PW_R003560