2.02012-05-31 14:10:15 -06002015-09-17 15:41:23 -0600ECMDB06903M2MDB000706Adenosyl cobinamideAdenosyl 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'-adenosylcobinamideAdenosylcobinamideC58H84CoN16O111240.32141239.583747804(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-diuideC[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)NInChI=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../s1PAUPKJHCFVPREX-VUCSARQQSA-MSolidCytosollogp-0.28logs-5.33solubility6.44e-03 g/llogp-14pka_strongest_acidic12.49pka_strongest_basic3.92iupac(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-diuideaverage_mass1240.3214mono_mass1239.583747804smilesC[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)NformulaC58H84CoN16O11inchiInChI=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../s1inchikeyPAUPKJHCFVPREX-VUCSARQQSA-Mpolar_surface_area439.45refractivity319.33polarizability127.45rotatable_bond_count23acceptor_count16donor_count11physiological_charge1formal_charge1Porphyrin 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-1Specdb::NmrOneD92112Specdb::NmrOneD92113Specdb::NmrOneD92114Specdb::NmrOneD92115Specdb::NmrOneD92116Specdb::NmrOneD92117Specdb::NmrOneD92118Specdb::NmrOneD92119Specdb::NmrOneD92120Specdb::NmrOneD92121Specdb::NmrOneD92122Specdb::NmrOneD92123Specdb::NmrOneD92124Specdb::NmrOneD92125Specdb::NmrOneD92126Specdb::NmrOneD92127Specdb::NmrOneD92128Specdb::NmrOneD92129Specdb::NmrOneD92130Specdb::NmrOneD92131Specdb::MsMs1238611Specdb::MsMs1238612Specdb::MsMs1238613Specdb::MsMs2422413Specdb::MsMs2422414Specdb::MsMs2422415HMDB0690323657884C065082480ADENOSYLCOBINAMIDEKeseler, 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 80:2939-2948.18331064Cob(I)yrinic acid a,c-diamide adenosyltransferaseP0A9H5BTUR_ECOLIbtuRhttp://ecmdb.ca/proteins/P0A9H5.xmlBifunctional adenosylcobalamin biosynthesis protein cobUP0AE76COBU_ECOLIcobUhttp://ecmdb.ca/proteins/P0AE76.xmlEthanolamine utilization cobalamin adenosyltransferaseP65643EUTT_ECOLIeutThttp://ecmdb.ca/proteins/P65643.xmlAdenosine triphosphate + Cobinamide + Hydrogen ion <> Adenosyl cobinamide + TriphosphateR07268Adenosyl cobinamide + Adenosine triphosphate > Adenosyl cobinamide phosphate + ADP + Hydrogen ionR05221COBINAMIDEKIN-RXNAdenosyl cobinamide + Adenosine triphosphate <> Adenosyl cobinamide phosphate + ADPR05221Adenosyl cobinamide + Guanosine triphosphate <> Adenosyl cobinamide phosphate + Guanosine diphosphateR06558Adenosine triphosphate + Cobinamide <> Triphosphate + Adenosyl cobinamideR07268Cob(I)yrinate a,c diamide + Adenosine triphosphate > Adenosyl cobinamide + TriphosphateBTUR2-RXNAdenosine triphosphate + Cobinamide > Triphosphate + Adenosyl cobinamideATP or GTP + Adenosyl cobinamide > adenosylcobinamide phosphate + ADP or GDPAdenosine triphosphate + Cob(I)yrinate a,c diamide + Cobinamide <> Triphosphate + Adenosyl cobyrinate a,c diamide + Adenosyl cobinamideR05220 Adenosine triphosphate + Guanosine triphosphate + Adenosyl cobinamide <> Adenosyl cobinamide phosphate + ADP + Guanosine diphosphateR05221 R06558 Cobinamide + Adenosine triphosphate + Cobinamide > Adenosyl cobinamide + Triphosphate + Adenosyl cobinamide + TriphosphatePW_R005139Adenosyl cobinamide + Adenosine triphosphate + Adenosyl cobinamide > Adenosine diphosphate + Hydrogen ion + adenosylcobinamide phosphate + ADPPW_R005140Adenosyl cobinamide + Adenosine triphosphate > Adenosyl cobinamide phosphate + ADP + Hydrogen ion