2.0 2012-05-31 14:10:12 -0600 2015-09-17 15:41:21 -0600 ECMDB06902 M2MDB000705 Cobinamide Cobinamide is an intermediate in porphyrin and chlorophyll metabolism. It is converted to adenosyl cobinamide via the enzyme cob(I)alamin adenosyltransferase [EC:2.5.1.17]. Adenosyl cobinamide is the third to last step in the synthesis of vitamin B12 coenzyme. Cbi Cobinamide Cobinamide dihydrate Cobinamide dihydric acid Cobyrinate a,c-diamide Cobyrinic acid a,c-diamide Diaquocobinamide C48H72CoN11O8 990.0874 989.489733529 13497-85-3 C[C@@H](O)CNC(=O)CC[C@]1(C)[C@@H](CC(=O)N)[C@@]2([H])N([Co++])\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.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;/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);/q;+3/p-1/t23-,26-,27-,28-,29+,43-,45-,46+,47+,48+;/m1./s1 FEESAGIUMZGLMF-JFYQDRLCSA-M Solid Cytosol Extra-organism Periplasm logp 0.93 ALOGPS logs -5.55 ALOGPS solubility 3.02e-03 g/l ALOGPS average_mass 990.0874 ChemAxon mono_mass 989.489733529 ChemAxon smiles C[C@@H](O)CNC(=O)CC[C@]1(C)[C@@H](CC(=O)N)[C@@]2([H])N([Co++])\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 C48H72CoN11O8 ChemAxon inchi InChI=1S/C48H73N11O8.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;/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);/q;+3/p-1/t23-,26-,27-,28-,29+,43-,45-,46+,47+,48+;/m1./s1 ChemAxon inchikey FEESAGIUMZGLMF-JFYQDRLCSA-M ChemAxon polar_surface_area 368.74 ChemAxon refractivity 258.94 ChemAxon polarizability 104.11 ChemAxon rotatable_bond_count 20 ChemAxon acceptor_count 0 ChemAxon donor_count 0 ChemAxon physiological_charge 2 ChemAxon formal_charge 2 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 HMDB06902 5486709 9702912 C05774 28956 COBINAMIDE 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 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 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 import system permease protein BtuC B1XG18 BTUC_ECODH btuC http://ecmdb.ca/proteins/B1XG18.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 + Cobinamide > ADP + Cobinamide + Hydrogen ion + Phosphate Adenosine triphosphate + Water + Cobinamide > ADP + Cobinamide + Hydrogen ion + Phosphate Adenosine triphosphate + Cobinamide + Hydrogen ion <> Adenosyl cobinamide + Triphosphate R07268 Adenosine triphosphate + Cobinamide <> Triphosphate + Adenosyl cobinamide R07268 Adenosine triphosphate + Cobinamide > Triphosphate + Adenosyl cobinamide Adenosine triphosphate + Cob(I)yrinate a,c diamide + Cobinamide <> Triphosphate + Adenosyl cobyrinate a,c diamide + Adenosyl cobinamide R05220 Cobinamide + Adenosine triphosphate + Cobinamide > Adenosyl cobinamide + Triphosphate + Adenosyl cobinamide + Triphosphate PW_R005139 Cobinamide + Adenosine triphosphate + Water + Cobinamide > Adenosine diphosphate + Phosphate + Hydrogen ion + Cobinamide + ADP PW_RCT000169