2.0 2012-05-31 14:10:15 -0600 2015-09-17 15:41:23 -0600 ECMDB06903 M2MDB000706 Adenosyl cobinamide Adenosyl cobinamide is an intermediate in Porphyrin and chlorophyll metabolism. It is the third to last step in the synthesis of vitamin B12 coenzyme and is converted from adenosyl cobyrinate hexaamide via the enzyme cobalamin biosynthetic protein CobC. It is then converted to adenosyl cobinamide phosphate via the enzyme adenosylcobinamide kinase / adenosylcobinamide-phosphate guanylyltransferase [EC:2.7.1.156 and EC 2.7.7.62]. 5'-Deoxy-5'-adenosylcobinamide Adenosylcobinamide C58H84CoN16O11 1240.3214 1239.583747804 (3R,4S,5S,9S,10S,15S,19R,20R,21R)-1-{[(2S,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl}-5,10,15-tris(2-carbamoylethyl)-4,9,20-tris(carbamoylmethyl)-19-(2-{[(2R)-2-hydroxypropyl]carbamoyl}ethyl)-3,4,7,9,14,14,17,19-octamethyl-2lambda5,22,23lambda5,24lambda5-tetraaza-1-cobaltaoctacyclo[11.9.1.1^{1,8}.0^{2,6}.0^{3,21}.0^{16,23}.0^{18,22}.0^{11,24}]tetracosa-2(6),7,11(24),12,16(23),17-hexaene-2,23,24-tris(ylium)-1,1-diuide (3R,4S,5S,9S,10S,15S,19R,20R,21R)-1-{[(2S,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl}-5,10,15-tris(2-carbamoylethyl)-4,9,20-tris(carbamoylmethyl)-19-(2-{[(2R)-2-hydroxypropyl]carbamoyl}ethyl)-3,4,7,9,14,14,17,19-octamethyl-2lambda5,22,23lambda5,24lambda5-tetraaza-1-cobaltaoctacyclo[11.9.1.1^{1,8}.0^{2,6}.0^{3,21}.0^{16,23}.0^{18,22}.0^{11,24}]tetracosa-2(6),7,11(24),12,16(23),17-hexaene-2,23,24-tris(ylium)-1,1-diuide C[C@@H](O)CNC(=O)CC[C@]1(C)[C@@H](CC(=O)N)[C@@]2([H])N([Co++]CC3OC(C(O)C3O)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(=O)N)[C@@H]4CCC(=O)N)\[C@@](C)(CC(=O)N)[C@@H]3CCC(=O)N)/C(C)(C)[C@@H]1CCC(=O)N InChI=1S/C48H73N11O8.C10H12N5O3.Co/c1-23(60)22-55-38(67)16-17-45(6)29(18-35(52)64)43-48(9)47(8,21-37(54)66)28(12-15-34(51)63)40(59-48)25(3)42-46(7,20-36(53)65)26(10-13-32(49)61)30(56-42)19-31-44(4,5)27(11-14-33(50)62)39(57-31)24(2)41(45)58-43;1-4-6(16)7(17)10(18-4)15-3-14-5-8(11)12-2-13-9(5)15;/h19,23,26-29,43,60H,10-18,20-22H2,1-9H3,(H14,49,50,51,52,53,54,55,56,57,58,59,61,62,63,64,65,66,67);2-4,6-7,10,16-17H,1H2,(H2,11,12,13);/q;;+3/p-1/t23-,26-,27-,28-,29+,43-,45-,46+,47+,48+;;/m1../s1 PAUPKJHCFVPREX-VUCSARQQSA-M Solid Cytosol logp -0.28 ALOGPS logs -5.33 ALOGPS solubility 6.44e-03 g/l ALOGPS logp -14 ChemAxon pka_strongest_acidic 12.49 ChemAxon pka_strongest_basic 3.92 ChemAxon iupac (3R,4S,5S,9S,10S,15S,19R,20R,21R)-1-{[(2S,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl}-5,10,15-tris(2-carbamoylethyl)-4,9,20-tris(carbamoylmethyl)-19-(2-{[(2R)-2-hydroxypropyl]carbamoyl}ethyl)-3,4,7,9,14,14,17,19-octamethyl-2lambda5,22,23lambda5,24lambda5-tetraaza-1-cobaltaoctacyclo[11.9.1.1^{1,8}.0^{2,6}.0^{3,21}.0^{16,23}.0^{18,22}.0^{11,24}]tetracosa-2(6),7,11(24),12,16(23),17-hexaene-2,23,24-tris(ylium)-1,1-diuide ChemAxon average_mass 1240.3214 ChemAxon mono_mass 1239.583747804 ChemAxon smiles C[C@@H](O)CNC(=O)CC[C@]1(C)[C@@H](CC(=O)N)[C@@]2([H])N([Co++]CC3OC(C(O)C3O)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(=O)N)[C@@H]4CCC(=O)N)\[C@@](C)(CC(=O)N)[C@@H]3CCC(=O)N)/C(C)(C)[C@@H]1CCC(=O)N ChemAxon formula C58H84CoN16O11 ChemAxon inchi InChI=1S/C48H73N11O8.C10H12N5O3.Co/c1-23(60)22-55-38(67)16-17-45(6)29(18-35(52)64)43-48(9)47(8,21-37(54)66)28(12-15-34(51)63)40(59-48)25(3)42-46(7,20-36(53)65)26(10-13-32(49)61)30(56-42)19-31-44(4,5)27(11-14-33(50)62)39(57-31)24(2)41(45)58-43;1-4-6(16)7(17)10(18-4)15-3-14-5-8(11)12-2-13-9(5)15;/h19,23,26-29,43,60H,10-18,20-22H2,1-9H3,(H14,49,50,51,52,53,54,55,56,57,58,59,61,62,63,64,65,66,67);2-4,6-7,10,16-17H,1H2,(H2,11,12,13);/q;;+3/p-1/t23-,26-,27-,28-,29+,43-,45-,46+,47+,48+;;/m1../s1 ChemAxon inchikey PAUPKJHCFVPREX-VUCSARQQSA-M ChemAxon polar_surface_area 439.45 ChemAxon refractivity 319.33 ChemAxon polarizability 127.45 ChemAxon rotatable_bond_count 23 ChemAxon acceptor_count 16 ChemAxon donor_count 11 ChemAxon physiological_charge 1 ChemAxon formal_charge 1 ChemAxon Porphyrin and chlorophyll metabolism ec00860 Metabolic pathways eco01100 adenosylcobalamin salvage from cobinamide Cobinamide is incorporated from the extracellular space through a transport system into the cytosol. Once inside the cytosol, cobinamide interacts with ATP through a cobinamide adenosyl transferase resulting in the release of a triphosphate and an adenosylcobinamide. The latter compound is then phosphorylated through an ATP-dependent cobinamide kinase resulting in the release of ADP, a hydrogen ion and adenosyl-cobinamide phosphate. This last compound then interacts with GTP and a hydrogen ion through a cobinamide-P guanylyltransferase resulting in the release of a pyrophosphate and an adenosylcobinamide-GDP. A dimethylbenzimidazole interacts with a nicotinate D-ribonucleotide through a nicotinate-nucleotide dimethylbenzumidazole phosphoribosyltransferase resulting in the release of a nicotinate, a hydrogen ion and an alpha-ribazole 5' phosphate. The adenosylcobinamide-GDP and the alpha-ribazole 5' phosphate interact together through a cobalamin 5' phosphate synthase resulting in the release of a hydrogen ion, a GMP and Adenosylcobalamin 5'-phosphate. The latter compound then interacts with a water molecule through an adenosylcbalamin 5' phosphate phosphatase resulting in the release of a phosphate and a coenzyme B12. Likewise a cobalamin molecule can interact with ATP through a cobalamin adenosyltransferase resulting in the release of a triphosphate and a coenzyme B12 PW001884 Metabolic adenosylcobalamin salvage from cobinamide I COBALSYN-PWY-1 Specdb::NmrOneD 92112 Specdb::NmrOneD 92113 Specdb::NmrOneD 92114 Specdb::NmrOneD 92115 Specdb::NmrOneD 92116 Specdb::NmrOneD 92117 Specdb::NmrOneD 92118 Specdb::NmrOneD 92119 Specdb::NmrOneD 92120 Specdb::NmrOneD 92121 Specdb::NmrOneD 92122 Specdb::NmrOneD 92123 Specdb::NmrOneD 92124 Specdb::NmrOneD 92125 Specdb::NmrOneD 92126 Specdb::NmrOneD 92127 Specdb::NmrOneD 92128 Specdb::NmrOneD 92129 Specdb::NmrOneD 92130 Specdb::NmrOneD 92131 Specdb::MsMs 1238611 Specdb::MsMs 1238612 Specdb::MsMs 1238613 Specdb::MsMs 2422413 Specdb::MsMs 2422414 Specdb::MsMs 2422415 HMDB06903 23657884 C06508 2480 ADENOSYLCOBINAMIDE 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 Cob(I)yrinic acid a,c-diamide adenosyltransferase P0A9H5 BTUR_ECOLI btuR http://ecmdb.ca/proteins/P0A9H5.xml Bifunctional adenosylcobalamin biosynthesis protein cobU P0AE76 COBU_ECOLI cobU http://ecmdb.ca/proteins/P0AE76.xml Ethanolamine utilization cobalamin adenosyltransferase P65643 EUTT_ECOLI eutT http://ecmdb.ca/proteins/P65643.xml Adenosine triphosphate + Cobinamide + Hydrogen ion <> Adenosyl cobinamide + Triphosphate R07268 Adenosyl cobinamide + Adenosine triphosphate > Adenosyl cobinamide phosphate + ADP + Hydrogen ion R05221 COBINAMIDEKIN-RXN Adenosyl cobinamide + Adenosine triphosphate <> Adenosyl cobinamide phosphate + ADP R05221 Adenosyl cobinamide + Guanosine triphosphate <> Adenosyl cobinamide phosphate + Guanosine diphosphate R06558 Adenosine triphosphate + Cobinamide <> Triphosphate + Adenosyl cobinamide R07268 Cob(I)yrinate a,c diamide + Adenosine triphosphate > Adenosyl cobinamide + Triphosphate BTUR2-RXN Adenosine triphosphate + Cobinamide > Triphosphate + Adenosyl cobinamide ATP or GTP + Adenosyl cobinamide > adenosylcobinamide phosphate + ADP or GDP Adenosine triphosphate + Cob(I)yrinate a,c diamide + Cobinamide <> Triphosphate + Adenosyl cobyrinate a,c diamide + Adenosyl cobinamide R05220 Adenosine triphosphate + Guanosine triphosphate + Adenosyl cobinamide <> Adenosyl cobinamide phosphate + ADP + Guanosine diphosphate R05221 R06558 Cobinamide + Adenosine triphosphate + Cobinamide > Adenosyl cobinamide + Triphosphate + Adenosyl cobinamide + Triphosphate PW_R005139 Adenosyl cobinamide + Adenosine triphosphate + Adenosyl cobinamide > Adenosine diphosphate + Hydrogen ion + adenosylcobinamide phosphate + ADP PW_R005140 Adenosyl cobinamide + Adenosine triphosphate > Adenosyl cobinamide phosphate + ADP + Hydrogen ion