2.0 2012-05-31 14:00:30 -0600 2015-06-03 15:54:32 -0600 ECMDB03882 M2MDB000527 N1-(5-Phospho-a-D-ribosyl)-5,6-dimethylbenzimidazole N1-(5-Phospho-alpha-D-ribosyl)-5,6-dimethylbenzimidazole (or alpha-ribazole-5'-Phosphate) is an intermediate in Riboflavin metabolism. In particular, alpha-Ribazole 5'-phosphate is converted from Dimethylbenzimidazole via the enzyme nicotinate-nucleotide-dimethylbenzimidazole &alpha;-ribazole-5'-P a-Ribazole 5'-phosphate a-Ribazole 5'-phosphoric acid a-Ribazole-5'-P a-Ribazole-5'-PO4 Alpha-Ribazole 5'-phosphate alpha-Ribazole 5'-phosphoric acid Alpha-Ribazole-5'-P Alpha-Ribazole-5'-PO4 DMB-ribose-5'-P N1-(5'-phospho-&alpha;-D-ribosyl)-5,6-dimethylbenzimidazole N1-(5'-phospho-a-D-Ribosyl)-5,6-dimethylbenzimidazole N1-(5'-phospho-alpha-D-ribosyl)-5,6-dimethylbenzimidazole N1-(5'-phospho-α-D-Ribosyl)-5,6-dimethylbenzimidazole N1-(5-phospho-a-delta-Ribosyl)-5,6-dimethylbenzimidazole N1-(5-phospho-a-δ-Ribosyl)-5,6-dimethylbenzimidazole N1-(5-Phospho-alpha-D-ribosyl)-5,6-dimethylbenzimidazole N1-(5-Phospho-alpha-delta-ribosyl)-5,6-dimethylbenzimidazole N1-(5-phospho-α-D-Ribosyl)-5,6-dimethylbenzimidazole N1-(5-phospho-α-δ-Ribosyl)-5,6-dimethylbenzimidazole Ribazole5'P α-Ribazole 5'-phosphate α-Ribazole 5'-phosphoric acid α-Ribazole-5'-P α-Ribazole-5'-PO4 C14H19N2O7P 358.2836 358.092987484 {[(2R,3S,4R,5S)-5-(5,6-dimethyl-1H-1,3-benzodiazol-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}phosphonic acid α-ribazole-5'-P CC1=CC2=C(C=C1C)N(C=N2)[C@H]1O[C@H](COP(O)(O)=O)[C@@H](O)[C@H]1O InChI=1S/C14H19N2O7P/c1-7-3-9-10(4-8(7)2)16(6-15-9)14-13(18)12(17)11(23-14)5-22-24(19,20)21/h3-4,6,11-14,17-18H,5H2,1-2H3,(H2,19,20,21)/t11-,12-,13-,14+/m1/s1 ZMRGXEJKZPRBPJ-SYQHCUMBSA-N Solid Cytosol logp -0.32 ALOGPS logs -2.37 ALOGPS solubility 1.53e+00 g/l ALOGPS logp -1.5 ChemAxon pka_strongest_acidic 1.22 ChemAxon pka_strongest_basic 5.81 ChemAxon iupac {[(2R,3S,4R,5S)-5-(5,6-dimethyl-1H-1,3-benzodiazol-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}phosphonic acid ChemAxon average_mass 358.2836 ChemAxon mono_mass 358.092987484 ChemAxon smiles CC1=CC2=C(C=C1C)N(C=N2)[C@H]1O[C@H](COP(O)(O)=O)[C@@H](O)[C@H]1O ChemAxon formula C14H19N2O7P ChemAxon inchi InChI=1S/C14H19N2O7P/c1-7-3-9-10(4-8(7)2)16(6-15-9)14-13(18)12(17)11(23-14)5-22-24(19,20)21/h3-4,6,11-14,17-18H,5H2,1-2H3,(H2,19,20,21)/t11-,12-,13-,14+/m1/s1 ChemAxon inchikey ZMRGXEJKZPRBPJ-SYQHCUMBSA-N ChemAxon polar_surface_area 134.27 ChemAxon refractivity 82.52 ChemAxon polarizability 34.13 ChemAxon rotatable_bond_count 4 ChemAxon acceptor_count 7 ChemAxon donor_count 4 ChemAxon physiological_charge -2 ChemAxon formal_charge 0 ChemAxon Porphyrin and chlorophyll metabolism ec00860 Riboflavin metabolism ec00740 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::CMs 14437 Specdb::CMs 38668 Specdb::CMs 133626 Specdb::CMs 141360 Specdb::NmrOneD 149680 Specdb::NmrOneD 149681 Specdb::NmrOneD 149682 Specdb::NmrOneD 149683 Specdb::NmrOneD 149684 Specdb::NmrOneD 149685 Specdb::NmrOneD 149686 Specdb::NmrOneD 149687 Specdb::NmrOneD 149688 Specdb::NmrOneD 149689 Specdb::NmrOneD 149690 Specdb::NmrOneD 149691 Specdb::NmrOneD 149692 Specdb::NmrOneD 149693 Specdb::NmrOneD 149694 Specdb::NmrOneD 149695 Specdb::NmrOneD 149696 Specdb::NmrOneD 149697 Specdb::NmrOneD 149698 Specdb::NmrOneD 149699 Specdb::MsMs 29537 Specdb::MsMs 29538 Specdb::MsMs 29539 Specdb::MsMs 36095 Specdb::MsMs 36096 Specdb::MsMs 36097 Specdb::MsMs 2662855 Specdb::MsMs 2662856 Specdb::MsMs 2662857 Specdb::MsMs 3016104 Specdb::MsMs 3016105 Specdb::MsMs 3016106 HMDB03882 444941 392720 C04778 16837 ALPHA-RIBAZOLE-5-P RIC 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 Cobalamin synthase P36561 COBS_ECOLI cobS http://ecmdb.ca/proteins/P36561.xml Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase P36562 COBT_ECOLI cobT http://ecmdb.ca/proteins/P36562.xml Alpha-ribazole phosphatase P52086 COBC_ECOLI cobC http://ecmdb.ca/proteins/P52086.xml N1-(5-Phospho-a-D-ribosyl)-5,6-dimethylbenzimidazole + Water > Phosphate + N1-(alpha-D-ribosyl)-5,6-dimethyl-benzimidazole R04594 RIBAZOLEPHOSPHAT-RXN Dimethylbenzimidazole + Nicotinamide ribotide <> N1-(5-Phospho-a-D-ribosyl)-5,6-dimethylbenzimidazole + Hydrogen ion + Nicotinic acid R04148 DMBPPRIBOSYLTRANS-RXN N1-(5-Phospho-a-D-ribosyl)-5,6-dimethylbenzimidazole + Water <> N1-(alpha-D-ribosyl)-5,6-dimethyl-benzimidazole + Phosphate R04594 Adenosylcobinamide-GDP + N1-(5-Phospho-a-D-ribosyl)-5,6-dimethylbenzimidazole > adenosylcobalamin 5'-phosphate + Guanosine monophosphate + Hydrogen ion COBALAMIN5PSYN-RXN Nicotinamide ribotide + Dimethylbenzimidazole > Hydrogen ion + Nicotinic acid + N1-(5-Phospho-a-D-ribosyl)-5,6-dimethylbenzimidazole DMBPPRIBOSYLTRANS-RXN N1-(5-Phospho-a-D-ribosyl)-5,6-dimethylbenzimidazole + Water > alpha-ribazole + Inorganic phosphate Nicotinamide ribotide + Dimethylbenzimidazole > Nicotinic acid + N1-(5-Phospho-a-D-ribosyl)-5,6-dimethylbenzimidazole 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 Dimethylbenzimidazole + nicotinate beta-D-ribonucleotide + Nicotinamide ribotide > Hydrogen ion + Nicotinic acid + N1-(5-Phospho-a-D-ribosyl)-5,6-dimethylbenzimidazole PW_R005142 N1-(5-Phospho-a-D-ribosyl)-5,6-dimethylbenzimidazole + Adenosylcobinamide-GDP + Adenosylcobinamide-GDP > Hydrogen ion + GMP + Adenosylcobalamin 5'-phosphate PW_R005143 N1-(5-Phospho-a-D-ribosyl)-5,6-dimethylbenzimidazole + Water > Phosphate + N1-(alpha-D-ribosyl)-5,6-dimethyl-benzimidazole N1-(5-Phospho-a-D-ribosyl)-5,6-dimethylbenzimidazole + Water > Phosphate + N1-(alpha-D-ribosyl)-5,6-dimethyl-benzimidazole