1.0 2011-09-21 00:20:22 UTC 2015-10-09 22:31:51 UTC FDB022837 Adenosylcobalamin Adenosylcobalamin is one of two metabolically active forms synthesized upon ingestion of vitamin B12 and is the predominant form in the liver; it acts as a coenzyme in the reaction catalyzed by methylmalonyl-CoA mutase. A cobalamin (cbl) derivative in which the substituent is deoxyadenosyl. It is one of two metabolically active forms synthesized upon ingestion of vitamin B12 and is the predominant form in the liver; it acts as a coenzyme in the reaction catalyzed by methylmalonyl-CoA mutase (MCM; E.C. 5.4.99.2). Inborn errors of vitamin B12 metabolism are autosomal recessive disorders and have been classified into nine distinct complementation classes. Disorders affecting adenosylcobalamin cause methylmalonic acidemia and metabolic acidosis. Methylmalonyl-CoA mutase catalyzes the conversion of L-methylmalonyl-CoA to succinyl-CoA and uses adenosylcobalamin (AdoCbl) as a cofactor. Cbl must be transported into mitochondria, reduced and adenosylated before it can be utilized by MCM. (PMID: 17011224) [HMDB] (5,6-Dimethylbenzimidazolyl)cobamide coenzyme (5'-Deoxy-5'-adenosyl)cobamide coenzyme 5,6-Dimethylbenzimidazolyl-5-deoxyadenosyl-cobamide 5,6-Dimethylbenzimidazolyl-CO-5'-deoxy-5'-adenosylcobamide 5'-Deoxy-5'-adenosyl vitamin B12 5'-Deoxy-5'-adenosyl-5,6-dimethylbenzimidazolylcobamide 5'-Deoxy-5'-adenosylcobalamin a-(5,6-Dimethylbenzimidazolyl)cobamide coenzyme Adenosylcob(III)alamin Adenosylcobalamin 5'-ate Adenosylcobalamin 5'-phosphate alpha-(5,6-Dimethylbenzimidazolyl)cobamide coenzyme Calomide Cobalamin coenzyme Cobamamide Cobamamide 5'-ate Cobamamide 5'-phosphate Cobamide coenzyme Coenzyme B12 Deoxyadenosylcobalamin Dibencozide DMBC coenzyme Funacomide vitamin B12 coenzyme Vitamin B12 coenzymes α-(5,6-dimethylbenzimidazolyl)cobamide coenzyme C72H100CoN18O17P 1579.5818 1578.65834557 13870-90-1 C1(C)(C)[C@]([H])(CCC(N)=O)C2=[N]3[Co+]456([N]7=CN([C@]8(O[C@]([H])(CO)[C@@](OP(O[C@@](C)([H])CNC(=O)CC[C@]9(C)[C@@](C([C@@]%10([N]4=C(C(=C4[C@](C)([C@]([H])(CCC(N)=O)C(=[N]54)C=C13)CC(N)=O)C)[C@@]([C@]%10(C)CC(N)=O)([H])CCC(N)=O)C)N6C9=C2C)([H])CC(N)=O)(=O)[O-])([C@]8(O)[H])[H])[H])C1=C7C=C(C)C(=C1)C)C[C@]1(O[C@]([C@@]([C@@]1(O)[H])(O)[H])(N1C=NC2=C1N=CN=C2N)[H])[H] InChI=1S/C62H89N13O14P.C10H12N5O3.Co/c1-29-20-39-40(21-30(29)2)75(28-70-39)57-52(84)53(41(27-76)87-57)89-90(85,86)88-31(3)26-69-49(83)18-19-59(8)37(22-46(66)80)56-62(11)61(10,25-48(68)82)36(14-17-45(65)79)51(74-62)33(5)55-60(9,24-47(67)81)34(12-15-43(63)77)38(71-55)23-42-58(6,7)35(13-16-44(64)78)50(72-42)32(4)54(59)73-56;1-4-6(16)7(17)10(18-4)15-3-14-5-8(11)12-2-13-9(5)15;/h20-21,23,28,31,34-37,41,52-53,56-57,76,84H,12-19,22,24-27H2,1-11H3,(H2,63,77)(H2,64,78)(H2,65,79)(H2,66,80)(H2,67,81)(H2,68,82)(H,69,83)(H,85,86);2-4,6-7,10,16-17H,1H2,(H2,11,12,13);/q-1;;+2/p-1/b54-32-;;/t31-,34-,35-,36-,37+,41-,52-,53-,56?,57+,59-,60+,61+,62+;4-,6-,7-,10-;/m11./s1 SWUYBPRJGLVABK-GONYIQIHSA-M belongs to the class of organic compounds known as cobalamin derivatives. These are organic compounds containing a corrin ring, a cobalt atom, an a nucleotide moiety. Cobalamin Derivatives are actually derived from vitamin B12. Cobalamin derivatives Organic compounds Organoheterocyclic compounds Tetrapyrroles and derivatives Corrinoids Aromatic heteropolycyclic compounds 5'-deoxyribonucleosides 6-aminopurines Amino acids and derivatives Aminopyrimidines and derivatives Azacyclic compounds Benzenoids Benzimidazoles Carbonyl compounds Carboxamidines Fatty amides Heteroaromatic compounds Hydrocarbon derivatives Imidolactams Lactams Metalloheterocyclic compounds Metallotetrapyrroles N-substituted imidazoles Organic cobalt salts Organic oxides Organic phosphoric acids and derivatives Organic zwitterions Organopnictogen compounds Organotransition metal compounds Oxacyclic compounds Pentose phosphates Primary alcohols Primary amines Primary carboxylic acid amides Propargyl-type 1,3-dipolar organic compounds Pyrrolidines Pyrrolines Secondary alcohols Secondary carboxylic acid amides Tetrahydrofurans Transition metal alkyls 5'-deoxyribonucleoside 6-aminopurine Alcohol Amidine Amine Amino acid or derivatives Aminopyrimidine Aromatic heteropolycyclic compound Azacycle Azole Benzenoid Benzimidazole Carbonyl group Carboxamide group Carboxylic acid amidine Carboxylic acid derivative Cobalamin Fatty acyl Fatty amide Heteroaromatic compound Hydrocarbon derivative Imidazole Imidazopyrimidine Imidolactam Lactam Metalloheterocycle Metallotetrapyrrole skeleton Monosaccharide N-substituted imidazole Organic 1,3-dipolar compound Organic cobalt salt Organic metal salt Organic nitrogen compound Organic oxide Organic oxygen compound Organic phosphoric acid derivative Organic salt Organic transition metal moeity Organic transition metal salt Organic zwitterion Organometallic compound Organonitrogen compound Organooxygen compound Organopnictogen compound Oxacycle Pentose phosphate Primary alcohol Primary amine Primary carboxylic acid amide Propargyl-type 1,3-dipolar organic compound Purine Pyrimidine Pyrrolidine Pyrroline Secondary alcohol Secondary carboxylic acid amide Tetrahydrofuran Transition metal alkyl Solid logp 0.37 ALOGPS logs -4.38 ALOGPS solubility 6.85e-02 g/l ALOGPS average_mass 1579.5818 ChemAxon mono_mass 1578.65834557 ChemAxon smiles C1(C)(C)[C@]([H])(CCC(N)=O)C2=[N]3[Co+]456([N]7=CN([C@]8(O[C@]([H])(CO)[C@@](OP(O[C@@](C)([H])CNC(=O)CC[C@]9(C)[C@@](C([C@@]%10([N]4=C(C(=C4[C@](C)([C@]([H])(CCC(N)=O)C(=[N]54)C=C13)CC(N)=O)C)[C@@]([C@]%10(C)CC(N)=O)([H])CCC(N)=O)C)N6C9=C2C)([H])CC(N)=O)(=O)[O-])([C@]8(O)[H])[H])[H])C1=C7C=C(C)C(=C1)C)C[C@]1(O[C@]([C@@]([C@@]1(O)[H])(O)[H])(N1C=NC2=C1N=CN=C2N)[H])[H] ChemAxon formula C72H100CoN18O17P ChemAxon inchi InChI=1S/C62H89N13O14P.C10H12N5O3.Co/c1-29-20-39-40(21-30(29)2)75(28-70-39)57-52(84)53(41(27-76)87-57)89-90(85,86)88-31(3)26-69-49(83)18-19-59(8)37(22-46(66)80)56-62(11)61(10,25-48(68)82)36(14-17-45(65)79)51(74-62)33(5)55-60(9,24-47(67)81)34(12-15-43(63)77)38(71-55)23-42-58(6,7)35(13-16-44(64)78)50(72-42)32(4)54(59)73-56;1-4-6(16)7(17)10(18-4)15-3-14-5-8(11)12-2-13-9(5)15;/h20-21,23,28,31,34-37,41,52-53,56-57,76,84H,12-19,22,24-27H2,1-11H3,(H2,63,77)(H2,64,78)(H2,65,79)(H2,66,80)(H2,67,81)(H2,68,82)(H,69,83)(H,85,86);2-4,6-7,10,16-17H,1H2,(H2,11,12,13);/q-1;;+2/p-1/b54-32-;;/t31-,34-,35-,36-,37+,41-,52-,53-,56?,57+,59-,60+,61+,62+;4-,6-,7-,10-;/m11./s1 ChemAxon inchikey SWUYBPRJGLVABK-GONYIQIHSA-M ChemAxon polar_surface_area 598.55 ChemAxon refractivity 408.83 ChemAxon polarizability 158.25 ChemAxon rotatable_bond_count 19 ChemAxon acceptor_count 0 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon HMDB02086 18408 #<Reference:0x000055ce32097418> 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 Cob(I)yrinic acid a,c-diamide adenosyltransferase, mitochondrial Q96EY8 MMAB Methylmalonic aciduria type A protein, mitochondrial Q8IVH4 MMAA Methylmalonyl-CoA mutase, mitochondrial P22033 MUT