2.0 2012-05-31 13:55:35 -0600 2015-10-23 17:32:54 -0600 ECMDB02086 M2MDB000439 Adenosylcobalamin Adenosylcobalamin is one of two metabolically active forms of vitamin B12. it acts as a coenzyme in the reaction catalyzed by methylmalonyl-CoA mutase. A cobalamin (cbl) derivative in which the substituent is deoxyadenosyl. (E.C. 5.4.99.2). (5'-Deoxy-5'-adenosyl)cobamide coenzyme (5,6-dimethylbenzimidazolyl)cobamide coenzyme 5'-Deoxy-5'-adenosyl vitamin B12 5'-Deoxy-5'-adenosylcobalamin 5'-Deoxyadenosyl vitamin B12 5'-Deoxyadenosyl-5,6-dimethylbenzimidazolylcobamide 5'-Deoxyadenosylcobalamin 5,6-Dimethylbenzimidazolyl-5-deoxyadenosyl-cobamide 5,6-Dimethylbenzimidazolyl-Co-5'-deoxyadenosylcobamide Adenosylcobalamin Adenosylcobalamin 5'-phosphate Adenosylcobalamin 5'-phosphoric acid Calomide CoB12 Cobalamin coenzyme Cobamamid Cobamamide Cobamamide 5'-phosphate Cobamamide 5'-phosphoric acid Cobamide coenzyme Coenzyme B12 Deoxyadenosylcobalamin Dibencozide Funacomide Vitamin B12 Vitamin B12 coenzyme Vitamin B12 coenzymes Vitamin B₁₂ C72H101CoN18O17P 1580.5897 1579.666170602 {[(2S,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl}[(2R,3S,4S,8S,9S,14S,18R,19R)-4,9,14-tris(2-carbamoylethyl)-3,8,19-tris(carbamoylmethyl)-18-(2-{[(2R)-2-[({[(2R,3S,4R,5S)-5-(5,6-dimethyl-1H-1,3-benzodiazol-1-yl)-4-hydroxy-2-(hydroxymethyl)oxolan-3-yl]oxy}(hydroxy)phosphoryl)oxy]propyl]carbamoyl}ethyl)-2,3,6,8,13,13,16,18-octamethyl-20,21,22,23-tetraazapentacyclo[15.2.1.1²,⁵.1⁷,¹⁰.1¹²,¹⁵]tricosa-5(23),6,10(22),11,15(21),16-hexaen-20-yl]cobaltylium {[(2S,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl}[(2R,3S,4S,8S,9S,14S,18R,19R)-4,9,14-tris(2-carbamoylethyl)-3,8,19-tris(carbamoylmethyl)-18-(2-{[(2R)-2-({[(2R,3S,4R,5S)-5-(5,6-dimethyl-1,3-benzodiazol-1-yl)-4-hydroxy-2-(hydroxymethyl)oxolan-3-yl]oxy(hydroxy)phosphoryl}oxy)propyl]carbamoyl}ethyl)-2,3,6,8,13,13,16,18-octamethyl-20,21,22,23-tetraazapentacyclo[15.2.1.1²,⁵.1⁷,¹⁰.1¹²,¹⁵]tricosa-5(23),6,10(22),11,15(21),16-hexaen-20-yl]cobaltylium 13870-90-1 OC[C@H]1O[C@@H]([C@H](O)[C@@H]1OP(O)(=O)O[C@H](C)CNC(=O)CC[C@]1(C)[C@@H](CC(N)=O)C2N([Co+]C[C@H]3O[C@H]([C@H](O)[C@@H]3O)N3C=NC4=C3N=CN=C4N)\C1=C(C)/C1=N/C(=C\C3=N\C(=C(C)/C4=N[C@]2(C)[C@@](C)(CC(N)=O)[C@@H]4CCC(N)=O)\[C@@](C)(CC(N)=O)[C@@H]3CCC(N)=O)/C(C)(C)[C@@H]1CCC(N)=O)N1C=NC2=C1C=C(C)C(C)=C2 InChI=1S/C62H90N13O14P.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,(H15,63,64,65,66,67,68,69,71,72,73,74,77,78,79,80,81,82,83,85,86);2-4,6-7,10,16-17H,1H2,(H2,11,12,13);/q;;+2/p-1/t31-,34-,35-,36-,37+,41-,52-,53-,56?,57+,59-,60+,61+,62+;4-,6-,7-,10-;/m11./s1 ZIHHMGTYZOSFRC-QRVZQHAISA-M Solid Cytosol Extra-organism Membrane Periplasm logp 2.10 ALOGPS logs -4.80 ALOGPS solubility 2.56e-02 g/l ALOGPS logp -5.9 ChemAxon pka_strongest_acidic 1.82 ChemAxon pka_strongest_basic 8.76 ChemAxon iupac {[(2S,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl}[(2R,3S,4S,8S,9S,14S,18R,19R)-4,9,14-tris(2-carbamoylethyl)-3,8,19-tris(carbamoylmethyl)-18-(2-{[(2R)-2-[({[(2R,3S,4R,5S)-5-(5,6-dimethyl-1H-1,3-benzodiazol-1-yl)-4-hydroxy-2-(hydroxymethyl)oxolan-3-yl]oxy}(hydroxy)phosphoryl)oxy]propyl]carbamoyl}ethyl)-2,3,6,8,13,13,16,18-octamethyl-20,21,22,23-tetraazapentacyclo[15.2.1.1²,⁵.1⁷,¹⁰.1¹²,¹⁵]tricosa-5(23),6,10(22),11,15(21),16-hexaen-20-yl]cobaltylium ChemAxon average_mass 1580.5897 ChemAxon mono_mass 1579.666170602 ChemAxon smiles OC[C@H]1O[C@@H]([C@H](O)[C@@H]1OP(O)(=O)O[C@H](C)CNC(=O)CC[C@]1(C)[C@@H](CC(N)=O)C2N([Co+]C[C@H]3O[C@H]([C@H](O)[C@@H]3O)N3C=NC4=C3N=CN=C4N)\C1=C(C)/C1=N/C(=C\C3=N\C(=C(C)/C4=N[C@]2(C)[C@@](C)(CC(N)=O)[C@@H]4CCC(N)=O)\[C@@](C)(CC(N)=O)[C@@H]3CCC(N)=O)/C(C)(C)[C@@H]1CCC(N)=O)N1C=NC2=C1C=C(C)C(C)=C2 ChemAxon formula C72H101CoN18O17P ChemAxon inchi InChI=1S/C62H90N13O14P.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,(H15,63,64,65,66,67,68,69,71,72,73,74,77,78,79,80,81,82,83,85,86);2-4,6-7,10,16-17H,1H2,(H2,11,12,13);/q;;+2/p-1/t31-,34-,35-,36-,37+,41-,52-,53-,56?,57+,59-,60+,61+,62+;4-,6-,7-,10-;/m11./s1 ChemAxon inchikey ZIHHMGTYZOSFRC-QRVZQHAISA-M ChemAxon polar_surface_area 570.54 ChemAxon refractivity 392.44 ChemAxon polarizability 160.65 ChemAxon rotatable_bond_count 30 ChemAxon acceptor_count 24 ChemAxon donor_count 13 ChemAxon physiological_charge 3 ChemAxon formal_charge 1 ChemAxon Porphyrin and chlorophyll metabolism ec00860 Metabolic pathways eco01100 adenosylcobalamin salvage from cobinamide I COBALSYN-PWY-1 HMDB02086 6436143 C00194 18408 ADENOSYLCOBALAMIN Adenosylcobalamin 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 Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. 18331064 http://hmdb.ca/system/metabolites/msds/000/001/669/original/HMDB02086.pdf?1358462453 Vitamin B12 import ATP-binding protein BtuD P06611 BTUD_ECOLI btuD http://ecmdb.ca/proteins/P06611.xml Cob(I)yrinic acid a,c-diamide adenosyltransferase P0A9H5 BTUR_ECOLI btuR http://ecmdb.ca/proteins/P0A9H5.xml Cobalamin synthase P36561 COBS_ECOLI cobS http://ecmdb.ca/proteins/P36561.xml Alpha-ribazole phosphatase P52086 COBC_ECOLI cobC http://ecmdb.ca/proteins/P52086.xml Ethanolamine utilization cobalamin adenosyltransferase P65643 EUTT_ECOLI eutT http://ecmdb.ca/proteins/P65643.xml Vitamin B12 import system permease protein BtuC P06609 BTUC_ECOLI btuC http://ecmdb.ca/proteins/P06609.xml Vitamin B12-binding protein P37028 BTUF_ECOLI btuF http://ecmdb.ca/proteins/P37028.xml Vitamin B12 import ATP-binding protein BtuD P06611 BTUD_ECOLI btuD http://ecmdb.ca/proteins/P06611.xml Vitamin B12 transporter BtuB P06129 BTUB_ECOLI btuB http://ecmdb.ca/proteins/P06129.xml Vitamin B12 import system permease protein BtuC P06609 BTUC_ECOLI btuC http://ecmdb.ca/proteins/P06609.xml Vitamin B12-binding protein P37028 BTUF_ECOLI btuF http://ecmdb.ca/proteins/P37028.xml Biopolymer transport protein exbB P0ABU7 EXBB_ECOLI exbB http://ecmdb.ca/proteins/P0ABU7.xml Biopolymer transport protein exbD P0ABV2 EXBD_ECOLI exbD http://ecmdb.ca/proteins/P0ABV2.xml Protein tonB P02929 TONB_ECOLI tonB http://ecmdb.ca/proteins/P02929.xml Adenosine triphosphate + Water + Adenosylcobalamin > Adenosylcobalamin + ADP + Hydrogen ion + Phosphate Adenosine triphosphate + Water + Adenosylcobalamin > Adenosylcobalamin + ADP + Hydrogen ion + Phosphate Adenosine triphosphate + Cob(I)alamin + Hydrogen ion <> Adenosylcobalamin + Triphosphate R01492 COBALADENOSYLTRANS-RXN Adenosylcobinamide-GDP + N1-(alpha-D-ribosyl)-5,6-dimethyl-benzimidazole > Adenosylcobalamin + Guanosine monophosphate + Hydrogen ion R05223 COBALAMINSYN-RXN Adenosine triphosphate + Cob(I)alamin <> Triphosphate + Adenosylcobalamin R01492 Adenosylcobalamin + Guanosine monophosphate <> Adenosylcobinamide-GDP + N1-(alpha-D-ribosyl)-5,6-dimethyl-benzimidazole R05223 Adenosine triphosphate + Cob(I)alamin > Adenosylcobalamin + Triphosphate COBALADENOSYLTRANS-RXN Adenosylcobinamide-GDP + N1-(alpha-D-ribosyl)-5,6-dimethyl-benzimidazole Hydrogen ion + Adenosylcobalamin + Guanosine monophosphate COBALAMINSYN-RXN adenosylcobalamin 5'-phosphate + Water > Adenosylcobalamin + Phosphate RXN-8770 Adenosylcobalamin + Water > Adenosylcobalamin + Inorganic phosphate Adenosylcobalamin + Water > Adenosylcobalamin + Inorganic phosphate Adenosylcobinamide-GDP + N1-(alpha-D-ribosyl)-5,6-dimethyl-benzimidazole + N1-(5-Phospho-a-D-ribosyl)-5,6-dimethylbenzimidazole <> Guanosine monophosphate + Adenosylcobalamin + Adenosylcobalamin 5'-phosphate R05223