1.0 2011-09-21 00:28:17 UTC 2015-07-21 06:57:38 UTC FDB023336 Biotinyl-5'-AMP 5'-biotinyl-AMP (B-AMP) is the active form of biotin in mammals. In human cells, biotin is essential to maintain metabolic homeostasis and as regulator of gene expression. The vitamin biotin plays an essential role in gluconeogenesis, fatty acid synthesis, and carbohydrate metabolism because of its role as cofactor of five carboxylases; pyruvate carboxylase (PC), propionyl-CoA carboxylase (PCC), methylcrotonyl-CoA carboxylase, and two forms of acetyl-CoA carboxylase (ACC-1 and ACC-2). Carboxylase biotinylation is catalyzed by the enzyme holocarboxylase synthetase (HCS) through a reaction that involves the transformation of biotin into B-AMP and its subsequent attachment to a specific lysine residue in the carboxylases. B-AMP is also required to activate a signal transduction cascade that includes a soluble guanylate cyclase (sGC) and cGMP-dependent protein kinase (PKG). The regulatory role of biotin in the biotin cycle seems to be limited to the expression of proteins involved in the transport and utilization of exogenous vitamin while having no effect on biotinidase mRNA levels, enzyme responsible for biotin recycling during carboxylase turnover. Multiple carboxylase deficiency (MCD) is a life-threatening disease characterized by the lack of carboxylase activities because of deficiency of HCS activity. (PMID: 15905112, 11959985) [HMDB] (+)-Biotinyl 5'-adenylate [3aS-(3aa,4b,6aa)]-5'-Adenylic acid monoanhydride with hexahydro-2-oxo-1H-thieno[3,4-d]imidazole-4-pentanoate [3aS-(3aa,4b,6aa)]-5'-Adenylic acid monoanhydride with hexahydro-2-oxo-1H-thieno[3,4-d]imidazole-4-pentanoic acid 5'-Adenylic acid anhydride with biotin 5'-Adenylic acid monoanhydride with biotin B-AMP beta-AMP bio-5-AMP Biotin anhydride with 5'-adenylic acid Biotinoyl 5'-adenylate Biotinyl 5'-AMP C20H28N7O9PS 573.517 573.140682731 {[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}({5-[(4S)-2-oxo-hexahydro-1H-thieno[3,4-d]imidazolidin-4-yl]pentanoyl}oxy)phosphinic acid [(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy({5-[(4S)-2-oxo-hexahydrothieno[3,4-d]imidazolidin-4-yl]pentanoyl}oxy)phosphinic acid 4130-20-5 NC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](COP(O)(=O)OC(=O)CCCC[C@@H]2SCC3NC(=O)NC23)[C@@H](O)[C@H]1O InChI=1S/C20H28N7O9PS/c21-17-14-18(23-7-22-17)27(8-24-14)19-16(30)15(29)10(35-19)5-34-37(32,33)36-12(28)4-2-1-3-11-13-9(6-38-11)25-20(31)26-13/h7-11,13,15-16,19,29-30H,1-6H2,(H,32,33)(H2,21,22,23)(H2,25,26,31)/t9?,10-,11+,13?,15-,16-,19-/m1/s1 UTQCSTJVMLODHM-CFYKWCKVSA-N belongs to the class of organic compounds known as 5'-acylphosphoadenosines. These are ribonucleoside derivatives containing an adenoside moiety, where the phosphate group is acylated. 5'-acylphosphoadenosines Organic compounds Nucleosides, nucleotides, and analogues Purine nucleotides Purine ribonucleotides Aromatic heteropolycyclic compounds 1,2-diols 6-aminopurines Acyl phosphates Amino acids and derivatives Aminopyrimidines and derivatives Azacyclic compounds Biotin and derivatives Carbonyl compounds Carboxylic acid salts Dialkylthioethers Glycosylamines Heteroaromatic compounds Hydrocarbon derivatives Imidazolidinones Imidolactams Monoalkyl phosphates Monocarboxylic acids and derivatives Monosaccharide phosphates N-substituted imidazoles Organic oxides Organic salts Organopnictogen compounds Oxacyclic compounds Pentose phosphates Primary amines Secondary alcohols Tetrahydrofurans Thienoimidazolidines Thiolanes Thiophenes Ureas 1,2-diol 5'-acylphosphoadenosine 6-aminopurine Acyl phosphate Alcohol Alkyl phosphate Amine Amino acid or derivatives Aminopyrimidine Aromatic heteropolycyclic compound Azacycle Azole Biotin Biotin_derivative Carbonic acid derivative Carbonyl group Carboxylic acid derivative Carboxylic acid salt Dialkylthioether Glycosyl compound Heteroaromatic compound Hydrocarbon derivative Imidazole Imidazolidine Imidazolidinone Imidazopyrimidine Imidolactam Monoalkyl phosphate Monocarboxylic acid or derivatives Monosaccharide Monosaccharide phosphate N-glycosyl compound N-substituted imidazole Organic nitrogen compound Organic oxide Organic oxygen compound Organic phosphoric acid derivative Organic salt Organoheterocyclic compound Organonitrogen compound Organooxygen compound Organopnictogen compound Oxacycle Pentose monosaccharide Pentose phosphate Pentose-5-phosphate Phosphoric acid ester Primary amine Purine Pyrimidine Secondary alcohol Tetrahydrofuran Thienoimidazolidine Thioether Thiolane Thiophene Urea Solid logp -1.24 ALOGPS logs -2.41 ALOGPS solubility 2.24e+00 g/l ALOGPS logp -4.1 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-[(4S)-2-oxo-hexahydro-1H-thieno[3,4-d]imidazolidin-4-yl]pentanoyl}oxy)phosphinic acid ChemAxon average_mass 573.517 ChemAxon mono_mass 573.140682731 ChemAxon smiles NC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](COP(O)(=O)OC(=O)CCCC[C@@H]2SCC3NC(=O)NC23)[C@@H](O)[C@H]1O ChemAxon formula C20H28N7O9PS ChemAxon inchi InChI=1S/C20H28N7O9PS/c21-17-14-18(23-7-22-17)27(8-24-14)19-16(30)15(29)10(35-19)5-34-37(32,33)36-12(28)4-2-1-3-11-13-9(6-38-11)25-20(31)26-13/h7-11,13,15-16,19,29-30H,1-6H2,(H,32,33)(H2,21,22,23)(H2,25,26,31)/t9?,10-,11+,13?,15-,16-,19-/m1/s1 ChemAxon inchikey UTQCSTJVMLODHM-CFYKWCKVSA-N ChemAxon polar_surface_area 233.27 ChemAxon refractivity 130.63 ChemAxon polarizability 53.92 ChemAxon rotatable_bond_count 11 ChemAxon acceptor_count 11 ChemAxon donor_count 6 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon Biotin Metabolism SMP00066 map00780 Specdb::CMs 26041 Specdb::CMs 38732 Specdb::CMs 282399 Specdb::CMs 371015 Specdb::CMs 371016 Specdb::CMs 371017 Specdb::CMs 371018 Specdb::CMs 371019 Specdb::CMs 371020 Specdb::CMs 371021 Specdb::CMs 371022 Specdb::CMs 371023 Specdb::CMs 371024 Specdb::CMs 371025 Specdb::CMs 371026 Specdb::CMs 371027 Specdb::CMs 371028 Specdb::CMs 371029 Specdb::CMs 371030 Specdb::CMs 371031 Specdb::CMs 371032 Specdb::CMs 371033 Specdb::CMs 371034 Specdb::CMs 371035 Specdb::CMs 371036 Specdb::NmrOneD 47902 Specdb::NmrOneD 47903 Specdb::NmrOneD 47904 Specdb::NmrOneD 47905 Specdb::NmrOneD 47906 Specdb::NmrOneD 47907 Specdb::NmrOneD 47908 Specdb::NmrOneD 47909 Specdb::NmrOneD 47910 Specdb::NmrOneD 47911 Specdb::NmrOneD 47912 Specdb::NmrOneD 47913 Specdb::NmrOneD 47914 Specdb::NmrOneD 47915 Specdb::NmrOneD 47916 Specdb::NmrOneD 47917 Specdb::NmrOneD 47918 Specdb::NmrOneD 47919 Specdb::NmrOneD 47920 Specdb::NmrOneD 47921 Specdb::MsMs 27284 Specdb::MsMs 27285 Specdb::MsMs 27286 Specdb::MsMs 33842 Specdb::MsMs 33843 Specdb::MsMs 33844 Specdb::MsMs 2709473 Specdb::MsMs 2709474 Specdb::MsMs 2709475 Specdb::MsMs 2995838 Specdb::MsMs 2995839 Specdb::MsMs 2995840 HMDB04220 #<Reference:0x000055ce32dd0fd0> #<Reference:0x000055ce32dd0df0> Anatidae Type 1 specific Anatidae 8830 Beefalo Type 1 specific Bos taurus X Bison bison 297284 Bison Type 1 specific Bison bison 9901 Buffalo Type 1 specific Bubalus bubalis 89462 Cattle (Beef, Veal) Type 1 specific Bos taurus 9913 Chicken Type 1 specific Gallus gallus 9031 Columbidae (Dove, Pigeon) Type 1 specific Columbidae 8930 Deer Type 1 specific Cervidae 9850 Domestic goat Type 1 specific Capra aegagrus hircus 9925 Domestic pig Type 1 specific Sus scrofa domestica 9825 Elk Type 1 specific Cervus canadensis 1574408 Emu Type 1 specific Dromaius novaehollandiae 8790 European rabbit Type 1 specific Oryctolagus 9984 Greylag goose Type 1 specific Anser anser 8843 Guinea hen Type 1 specific Numida meleagris 8996 Horse Type 1 specific Equus caballus 9796 Mallard duck Type 1 specific Anas platyrhynchos 8839 Mountain hare Type 1 specific Lepus timidus 62621 Mule deer Type 1 specific Odocoileus 9871 Ostrich Type 1 specific Struthio camelus 8801 Pheasant Type 1 specific Phasianus colchicus 9054 Quail Type 1 specific Phasianidae 9005 Rabbit Type 1 specific Leporidae 9979 Rock ptarmigan Type 1 specific Lagopus muta 64668 Sheep (Mutton, Lamb) Type 1 specific Ovis aries 9940 Squab Type 1 specific Columba 8931 Turkey Type 1 specific Meleagris gallopavo 9103 Velvet duck Type 1 specific Melanitta fusca 371864 Wild boar Type 1 specific Sus scrofa 9823 Biotin--protein ligase P50747 HLCS