2.0 2012-05-31 14:19:49 -0600 2015-06-03 17:19:00 -0600 ECMDB11112 M2MDB000805 N1-(alpha-D-ribosyl)-5,6-dimethyl-benzimidazole N1-(alpha-D-ribosyl)-5,6-dimethyl-benzimidazole is also known as alpha-ribazole. It is converted from N1-(5-Phospho-alpha-D-ribosyl)-5,6-dimethylbenzimidazole via dephosphorylation by the enzyme alpha-ribazole phosphatase (EC 3.1.3.73). It can subsequently be used to synthesize Vitamin B12 coenzyme. (KEGG) (2S,5R)-2-(5,6 dimethylbenzimidazol-1-yl)-5 (hydroxymethyl)oxolane-3,4-diol 5,6-Dimethyl-1-a-D-ribofuranosyl-1H-benzimidazole 5,6-Dimethyl-1-a-delta-ribofuranosyl-1H-benzimidazole 5,6-Dimethyl-1-a-δ-ribofuranosyl-1H-benzimidazole 5,6-Dimethyl-1-alpha-delta-ribofuranosyl-1H-benzimidazole 5,6-Dimethyl-1-α-δ-ribofuranosyl-1H-benzimidazole A-Ribazole Alpha-Ribazole N1-(&alpha;-D-ribosyl)-5,6-dimethylbenzimidazole N1-(a-D-Ribosyl)-5,6-dimethyl-benzimidazole N1-(a-D-Ribosyl)-5,6-dimethylbenzimidazole N1-(a-delta-Ribosyl)-5,6-dimethylbenzimidazole N1-(a-δ-Ribosyl)-5,6-dimethylbenzimidazole N1-(alpha-D-ribosyl)-5,6-dimethylbenzimidazole N1-(alpha-delta-ribosyl)-5,6-dimethylbenzimidazole N1-(α-D-Ribosyl)-5,6-dimethyl-benzimidazole N1-(α-D-Ribosyl)-5,6-dimethylbenzimidazole N1-(α-δ-Ribosyl)-5,6-dimethylbenzimidazole α-Ribazole C14H18N2O4 278.3037 278.126657074 (2S,5R)-2-(5,6-dimethyl-1H-1,3-benzodiazol-1-yl)-5-(hydroxymethyl)oxolane-3,4-diol (2S,5R)-2-(5,6-dimethyl-1,3-benzodiazol-1-yl)-5-(hydroxymethyl)oxolane-3,4-diol CC1=CC2=C(C=C1C)N(C=N2)[C@H]1O[C@H](CO)C(O)C1O InChI=1S/C14H18N2O4/c1-7-3-9-10(4-8(7)2)16(6-15-9)14-13(19)12(18)11(5-17)20-14/h3-4,6,11-14,17-19H,5H2,1-2H3/t11-,12?,13?,14+/m1/s1 HLRUKOJSWOKCPP-RYSNWHEDSA-N Solid Cytosol logp 0.35 ALOGPS logs -1.84 ALOGPS solubility 4.03e+00 g/l ALOGPS logp 0.73 ChemAxon pka_strongest_acidic 12.46 ChemAxon pka_strongest_basic 6 ChemAxon iupac (2S,5R)-2-(5,6-dimethyl-1H-1,3-benzodiazol-1-yl)-5-(hydroxymethyl)oxolane-3,4-diol ChemAxon average_mass 278.3037 ChemAxon mono_mass 278.126657074 ChemAxon smiles CC1=CC2=C(C=C1C)N(C=N2)[C@H]1O[C@H](CO)C(O)C1O ChemAxon formula C14H18N2O4 ChemAxon inchi InChI=1S/C14H18N2O4/c1-7-3-9-10(4-8(7)2)16(6-15-9)14-13(19)12(18)11(5-17)20-14/h3-4,6,11-14,17-19H,5H2,1-2H3/t11-,12?,13?,14+/m1/s1 ChemAxon inchikey HLRUKOJSWOKCPP-RYSNWHEDSA-N ChemAxon polar_surface_area 87.74 ChemAxon refractivity 71.65 ChemAxon polarizability 29.38 ChemAxon rotatable_bond_count 2 ChemAxon acceptor_count 5 ChemAxon donor_count 3 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Porphyrin and chlorophyll metabolism ec00860 Metabolic pathways eco01100 Specdb::CMs 24233 Specdb::CMs 39549 Specdb::CMs 131416 Specdb::CMs 139150 Specdb::NmrOneD 92712 Specdb::NmrOneD 92713 Specdb::NmrOneD 92714 Specdb::NmrOneD 92715 Specdb::NmrOneD 92716 Specdb::NmrOneD 92717 Specdb::NmrOneD 92718 Specdb::NmrOneD 92719 Specdb::NmrOneD 92720 Specdb::NmrOneD 92721 Specdb::NmrOneD 92722 Specdb::NmrOneD 92723 Specdb::NmrOneD 92724 Specdb::NmrOneD 92725 Specdb::NmrOneD 92726 Specdb::NmrOneD 92727 Specdb::NmrOneD 92728 Specdb::NmrOneD 92729 Specdb::NmrOneD 92730 Specdb::NmrOneD 92731 Specdb::MsMs 25490 Specdb::MsMs 25491 Specdb::MsMs 25492 Specdb::MsMs 32048 Specdb::MsMs 32049 Specdb::MsMs 32050 Specdb::MsMs 2795597 Specdb::MsMs 2795598 Specdb::MsMs 2795599 Specdb::MsMs 2886938 Specdb::MsMs 2886939 Specdb::MsMs 2886940 HMDB11112 440780 389646 C05775 10329 ALPHA-RIBAZOLE 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 Cobalamin synthase P36561 COBS_ECOLI cobS http://ecmdb.ca/proteins/P36561.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 Adenosylcobinamide-GDP + N1-(alpha-D-ribosyl)-5,6-dimethyl-benzimidazole > Adenosylcobalamin + Guanosine monophosphate + Hydrogen ion R05223 COBALAMINSYN-RXN N1-(5-Phospho-a-D-ribosyl)-5,6-dimethylbenzimidazole + Water <> N1-(alpha-D-ribosyl)-5,6-dimethyl-benzimidazole + Phosphate R04594 Adenosylcobalamin + Guanosine monophosphate <> Adenosylcobinamide-GDP + N1-(alpha-D-ribosyl)-5,6-dimethyl-benzimidazole R05223 Adenosylcobinamide-GDP + N1-(alpha-D-ribosyl)-5,6-dimethyl-benzimidazole Hydrogen ion + Adenosylcobalamin + Guanosine monophosphate COBALAMINSYN-RXN 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 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