1.0 2011-09-21 01:58:11 UTC 2015-07-21 06:59:46 UTC FDB029596 Lipoyl-GMP Lipoyl-GMP is an intermediate in lipoic acid metabolism.In mammals, the posttranslational modification of unlipoylated apoproteins by addition of lipoic acid is done in a two-step enzymatic reaction using free lipoic acid. The free lipoic acid in the cell is first activated by reacting it with adenosine triphosphate, using up two high energy phosphate bonds to form lipoyl-AMP (GMP), a process catalyzed by lipoate activating enzyme (LAE).41 The activated lipoyl moiety is subsequently used to form an amide bond with lysine residues of the unlipoylated apoprotein, which is catalyzed by lipoyl-AMP(GMP):N-lysine lipoyl transferase Interestingly, purified LAE from bovine liver mitochondria preferentially utilizes guanosine triphosphate, instead of adenosine triphosphate, for the activation of lipoic acid to form lipoyl-GMP.44 Furthermore, genetic analysis of LAE reveals that the enzyme is identical to xenobiotic-metabolizing/medium-chain fatty acid:CoA ligase-III (XL-III) (also from bovine liver mitochondria). 44 Hence, there appear to be two pathways in which LAE is capable of activating carboxylic acids: one that uses guanosine triphosphate to form acyl-GMP; the other is dependent on adenosine triphosphate for the activation of carboxylic acids to the CoA thioester (acyl-CoA) via an acyl-AMP intermediate [HMDB] C18H26N5O9PS2 551.531 551.090955347 {[(2R,3S,4R,5R)-5-{2-[5-(1,2-dithiolan-3-yl)pentanamido]-6-oxo-6,9-dihydro-1H-purin-9-yl}-3,4-dihydroxyoxolan-2-yl]methoxy}phosphonic acid [(2R,3S,4R,5R)-5-{2-[5-(1,2-dithiolan-3-yl)pentanamido]-6-oxo-1H-purin-9-yl}-3,4-dihydroxyoxolan-2-yl]methoxyphosphonic acid O[C@@H]1[C@@H](COP(O)(O)=O)O[C@H]([C@@H]1O)N1C=NC2=C1N=C(NC(=O)CCCCC1CCSS1)NC2=O InChI=1S/C18H26N5O9PS2/c24-11(4-2-1-3-9-5-6-34-35-9)20-18-21-15-12(16(27)22-18)19-8-23(15)17-14(26)13(25)10(32-17)7-31-33(28,29)30/h8-10,13-14,17,25-26H,1-7H2,(H2,28,29,30)(H2,20,21,22,24,27)/t9?,10-,13-,14-,17-/m1/s1 DVZGUOFXTLKZTJ-LQLSJNDNSA-N belongs to the class of organic compounds known as purine ribonucleoside monophosphates. These are nucleotides consisting of a purine base linked to a ribose to which one monophosphate group is attached. Purine ribonucleoside monophosphates Organic compounds Nucleosides, nucleotides, and analogues Purine nucleotides Purine ribonucleotides Aromatic heteropolycyclic compounds 1,2-diols 1,2-dithiolanes 6-oxopurines Azacyclic compounds Carbonyl compounds Fatty amides Glycosylamines Heteroaromatic compounds Hydrocarbon derivatives Hypoxanthines Lipoamides Monoalkyl phosphates Monosaccharide phosphates N-arylamides N-substituted imidazoles Organic disulfides Organic oxides Organopnictogen compounds Oxacyclic compounds Pentose phosphates Pyrimidones Secondary alcohols Secondary carboxylic acid amides Tetrahydrofurans Vinylogous amides 1,2-diol 1,2-dithiolane 6-oxopurine Alcohol Alkyl phosphate Aromatic heteropolycyclic compound Azacycle Azole Carbonyl group Carboxamide group Carboxylic acid derivative Dithiolane Fatty acyl Fatty amide Glycosyl compound Heteroaromatic compound Hydrocarbon derivative Hypoxanthine Imidazole Imidazopyrimidine Lipoamide Monoalkyl phosphate Monosaccharide Monosaccharide phosphate N-arylamide N-glycosyl compound N-substituted imidazole Organic disulfide Organic nitrogen compound Organic oxide Organic oxygen compound Organic phosphoric acid derivative Organoheterocyclic compound Organonitrogen compound Organooxygen compound Organopnictogen compound Oxacycle Pentose monosaccharide Pentose phosphate Pentose-5-phosphate Phosphoric acid ester Purine Purine ribonucleoside monophosphate Pyrimidine Pyrimidone Secondary alcohol Secondary carboxylic acid amide Tetrahydrofuran Vinylogous amide Solid logp 0.55 ALOGPS logs -2.69 ALOGPS solubility 1.12e+00 g/l ALOGPS logp -0.86 ChemAxon pka_strongest_acidic 1.29 ChemAxon pka_strongest_basic 0.36 ChemAxon iupac {[(2R,3S,4R,5R)-5-{2-[5-(1,2-dithiolan-3-yl)pentanamido]-6-oxo-6,9-dihydro-1H-purin-9-yl}-3,4-dihydroxyoxolan-2-yl]methoxy}phosphonic acid ChemAxon average_mass 551.531 ChemAxon mono_mass 551.090955347 ChemAxon smiles O[C@@H]1[C@@H](COP(O)(O)=O)O[C@H]([C@@H]1O)N1C=NC2=C1N=C(NC(=O)CCCCC1CCSS1)NC2=O ChemAxon formula C18H26N5O9PS2 ChemAxon inchi InChI=1S/C18H26N5O9PS2/c24-11(4-2-1-3-9-5-6-34-35-9)20-18-21-15-12(16(27)22-18)19-8-23(15)17-14(26)13(25)10(32-17)7-31-33(28,29)30/h8-10,13-14,17,25-26H,1-7H2,(H2,28,29,30)(H2,20,21,22,24,27)/t9?,10-,13-,14-,17-/m1/s1 ChemAxon inchikey DVZGUOFXTLKZTJ-LQLSJNDNSA-N ChemAxon polar_surface_area 204.83 ChemAxon refractivity 126.67 ChemAxon polarizability 52.23 ChemAxon rotatable_bond_count 10 ChemAxon acceptor_count 10 ChemAxon donor_count 6 ChemAxon physiological_charge -2 ChemAxon formal_charge 0 ChemAxon Specdb::NmrOneD 11982 Specdb::NmrOneD 11983 Specdb::NmrOneD 11984 Specdb::NmrOneD 11985 Specdb::NmrOneD 11986 Specdb::NmrOneD 11987 Specdb::NmrOneD 11988 Specdb::NmrOneD 11989 Specdb::NmrOneD 11990 Specdb::NmrOneD 11991 Specdb::NmrOneD 11992 Specdb::NmrOneD 11993 Specdb::NmrOneD 11994 Specdb::NmrOneD 11995 Specdb::NmrOneD 11996 Specdb::NmrOneD 11997 Specdb::NmrOneD 11998 Specdb::NmrOneD 11999 Specdb::NmrOneD 12000 Specdb::NmrOneD 12001 Specdb::MsMs 317383 Specdb::MsMs 317384 Specdb::MsMs 317385 Specdb::MsMs 363838 Specdb::MsMs 363839 Specdb::MsMs 363840 Specdb::MsMs 2371834 Specdb::MsMs 2371835 Specdb::MsMs 2371836 Specdb::MsMs 2562978 Specdb::MsMs 2562979 Specdb::MsMs 2562980 Specdb::CMs 23152 Specdb::CMs 40130 Specdb::CMs 281761 Specdb::CMs 333282 Specdb::CMs 333283 Specdb::CMs 333284 Specdb::CMs 333285 Specdb::CMs 333286 Specdb::CMs 333287 Specdb::CMs 333288 Specdb::CMs 333289 Specdb::CMs 333290 Specdb::CMs 333291 Specdb::CMs 333292 Specdb::CMs 333293 Specdb::CMs 333294 Specdb::CMs 333295 Specdb::CMs 333296 Specdb::CMs 333297 Specdb::CMs 333298 Specdb::CMs 333299 Specdb::CMs 333300 Specdb::CMs 333301 Specdb::CMs 333302 Specdb::CMs 333303 HMDB13617