2.02012-05-31 14:10:12 -06002015-09-17 15:41:21 -0600ECMDB06902M2MDB000705CobinamideCobinamide 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. CbiCobinamideCobinamide dihydrateCobinamide dihydric acidCobyrinate a,c-diamideCobyrinic acid a,c-diamideDiaquocobinamideC48H72CoN11O8990.0874989.48973352913497-85-3C[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)NInChI=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./s1FEESAGIUMZGLMF-JFYQDRLCSA-MSolidCytosolExtra-organismPeriplasmlogp0.93logs-5.55solubility3.02e-03 g/laverage_mass990.0874mono_mass989.489733529smilesC[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)NformulaC48H72CoN11O8inchiInChI=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./s1inchikeyFEESAGIUMZGLMF-JFYQDRLCSA-Mpolar_surface_area368.74refractivity258.94polarizability104.11rotatable_bond_count20acceptor_count0donor_count0physiological_charge2formal_charge2Porphyrin and chlorophyll metabolismec00860Metabolic pathwayseco01100adenosylcobalamin salvage from cobinamideCobinamide 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 B12PW001884Metabolicadenosylcobalamin salvage from cobinamide ICOBALSYN-PWY-1HMDB0690254867099702912C0577428956COBINAMIDEKeseler, 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-D590.21097882Kanehisa, 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-D114.22080510van 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 370:17-25.17765195Winder, 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 80:2939-2948.18331064Vitamin B12 import ATP-binding protein BtuDP06611BTUD_ECOLIbtuDhttp://ecmdb.ca/proteins/P06611.xmlCob(I)yrinic acid a,c-diamide adenosyltransferaseP0A9H5BTUR_ECOLIbtuRhttp://ecmdb.ca/proteins/P0A9H5.xmlEthanolamine utilization cobalamin adenosyltransferaseP65643EUTT_ECOLIeutThttp://ecmdb.ca/proteins/P65643.xmlVitamin B12 import system permease protein BtuCP06609BTUC_ECOLIbtuChttp://ecmdb.ca/proteins/P06609.xmlVitamin B12-binding proteinP37028BTUF_ECOLIbtuFhttp://ecmdb.ca/proteins/P37028.xmlVitamin B12 import ATP-binding protein BtuDP06611BTUD_ECOLIbtuDhttp://ecmdb.ca/proteins/P06611.xmlVitamin B12 import system permease protein BtuCB1XG18BTUC_ECODHbtuChttp://ecmdb.ca/proteins/B1XG18.xmlVitamin B12 transporter BtuBP06129BTUB_ECOLIbtuBhttp://ecmdb.ca/proteins/P06129.xmlVitamin B12 import system permease protein BtuCP06609BTUC_ECOLIbtuChttp://ecmdb.ca/proteins/P06609.xmlVitamin B12-binding proteinP37028BTUF_ECOLIbtuFhttp://ecmdb.ca/proteins/P37028.xmlBiopolymer transport protein exbBP0ABU7EXBB_ECOLIexbBhttp://ecmdb.ca/proteins/P0ABU7.xmlBiopolymer transport protein exbDP0ABV2EXBD_ECOLIexbDhttp://ecmdb.ca/proteins/P0ABV2.xmlProtein tonBP02929TONB_ECOLItonBhttp://ecmdb.ca/proteins/P02929.xmlAdenosine triphosphate + Water + Cobinamide > ADP + Cobinamide + Hydrogen ion + PhosphateAdenosine triphosphate + Water + Cobinamide > ADP + Cobinamide + Hydrogen ion + PhosphateAdenosine triphosphate + Cobinamide + Hydrogen ion <> Adenosyl cobinamide + TriphosphateR07268Adenosine triphosphate + Cobinamide <> Triphosphate + Adenosyl cobinamideR07268Adenosine triphosphate + Cobinamide > Triphosphate + Adenosyl cobinamideAdenosine triphosphate + Cob(I)yrinate a,c diamide + Cobinamide <> Triphosphate + Adenosyl cobyrinate a,c diamide + Adenosyl cobinamideR05220 Cobinamide + Adenosine triphosphate + Cobinamide > Adenosyl cobinamide + Triphosphate + Adenosyl cobinamide + TriphosphatePW_R005139Cobinamide + Adenosine triphosphate + Water + Cobinamide > Adenosine diphosphate + Phosphate + Hydrogen ion + Cobinamide + ADPPW_RCT000169