2.0 2012-05-31 14:03:03 -0600 2015-09-17 16:24:10 -0600 ECMDB04040 M2MDB000574 Cob(I)alamin Cob(I)alamin is the substrate of the enzyme ATP:cob(I)alamin adenosyltransferase (EC 2.5.1.17), that converts reduced cob(I)alamin to the adenosylcobalamin co-factor required for the functional activity of methylmalonyl-CoA mutase (EC 5.4.99.2). Vitamin B12 (cobalamin) is a complex cobalt-containing molecule. It is synthesized in bacteria where it catalyzes numerous methyl transfer and intramolecular rearrangement reactions. B12 Cbl Cob(I)alamin Cobalamin Coenzyme B12 Cyanocobalamin Hydrido-Cobalamin Hydridocobalamin Vitamin B12 Vitamin B12s Vitamin B<SUB>12</SUB> C62H88CoN13O14P 1329.3478 1328.564331295 18534-66-2 [H][C@]12[C@H](CC(N)=O)[C@@]3(C)CCC(=O)NC[C@@]([H])(C)OP([O-])(=O)O[C@H]4[C@@H](O)[C@H](O[C@@H]4CO)N4C=[N](C5=CC(C)=C(C)C=C45)[Co]456N1C3=C(C)C1=[N]4C(=CC3=[N]5C(=C(C)C4=[N]6[C@]2(C)[C@@](C)(CC(N)=O)[C@@H]4CCC(N)=O)[C@@](C)(CC(N)=O)[C@@H]3CCC(N)=O)C(C)(C)[C@@H]1CCC(N)=O InChI=1S/C62H90N13O14P.Co/c1-29-20-39-40(21-30(29)2)75(28-70-39)57-52(84)53(41(27-76)87-57)89-90(85,86)88-31(3)26-69-49(83)18-19-59(8)37(22-46(66)80)56-62(11)61(10,25-48(68)82)36(14-17-45(65)79)51(74-62)33(5)55-60(9,24-47(67)81)34(12-15-43(63)77)38(71-55)23-42-58(6,7)35(13-16-44(64)78)50(72-42)32(4)54(59)73-56;/h20-21,23,28,31,34-37,41,52-53,56-57,76,84H,12-19,22,24-27H2,1-11H3,(H15,63,64,65,66,67,68,69,71,72,73,74,77,78,79,80,81,82,83,85,86);/q;+1/p-2/t31-,34-,35-,36-,37+,41-,52-,53-,56-,57+,59-,60+,61+,62+;/m1./s1 OMAOKVYASDIYQG-DSRCUDDDSA-L Solid Cytosol Extra-organism Periplasm logp 0.79 ALOGPS logs -4.61 ALOGPS solubility 3.34e-02 g/l ALOGPS average_mass 1329.3478 ChemAxon mono_mass 1328.564331295 ChemAxon smiles [H][C@]12[C@H](CC(N)=O)[C@@]3(C)CCC(=O)NC[C@@]([H])(C)OP([O-])(=O)O[C@H]4[C@@H](O)[C@H](O[C@@H]4CO)N4C=[N](C5=CC(C)=C(C)C=C45)[Co]456N1C3=C(C)C1=[N]4C(=CC3=[N]5C(=C(C)C4=[N]6[C@]2(C)[C@@](C)(CC(N)=O)[C@@H]4CCC(N)=O)[C@@](C)(CC(N)=O)[C@@H]3CCC(N)=O)C(C)(C)[C@@H]1CCC(N)=O ChemAxon formula C62H88CoN13O14P ChemAxon inchi InChI=1S/C62H90N13O14P.Co/c1-29-20-39-40(21-30(29)2)75(28-70-39)57-52(84)53(41(27-76)87-57)89-90(85,86)88-31(3)26-69-49(83)18-19-59(8)37(22-46(66)80)56-62(11)61(10,25-48(68)82)36(14-17-45(65)79)51(74-62)33(5)55-60(9,24-47(67)81)34(12-15-43(63)77)38(71-55)23-42-58(6,7)35(13-16-44(64)78)50(72-42)32(4)54(59)73-56;/h20-21,23,28,31,34-37,41,52-53,56-57,76,84H,12-19,22,24-27H2,1-11H3,(H15,63,64,65,66,67,68,69,71,72,73,74,77,78,79,80,81,82,83,85,86);/q;+1/p-2/t31-,34-,35-,36-,37+,41-,52-,53-,56-,57+,59-,60+,61+,62+;/m1./s1 ChemAxon inchikey OMAOKVYASDIYQG-DSRCUDDDSA-L ChemAxon polar_surface_area 479.24 ChemAxon refractivity 348.45 ChemAxon polarizability 136.34 ChemAxon rotatable_bond_count 16 ChemAxon acceptor_count 0 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge -1 ChemAxon Porphyrin and chlorophyll metabolism ec00860 HMDB03429 5462228 C00853 15982 COB-I-ALAMIN Cyanocobalamin 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 Cobalamin synthase P36561 COBS_ECOLI cobS http://ecmdb.ca/proteins/P36561.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 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 + Cob(I)alamin > ADP + Cob(I)alamin + Hydrogen ion + Phosphate ABC-5-RXN Adenosine triphosphate + Water + Cob(I)alamin > ADP + Cob(I)alamin + Hydrogen ion + Phosphate ABC-5-RXN Adenosine triphosphate + Cob(I)alamin + Hydrogen ion <> Adenosylcobalamin + Triphosphate R01492 COBALADENOSYLTRANS-RXN Adenosine triphosphate + Cob(I)alamin <> Triphosphate + Adenosylcobalamin R01492 Adenosine triphosphate + Cob(I)alamin + Water > ADP + Phosphate + Cob(I)alamin + Hydrogen ion ABC-5-RXN Adenosine triphosphate + Cob(I)alamin + Water > ADP + Phosphate + Cob(I)alamin + Hydrogen ion ABC-5-RXN Adenosine triphosphate + Cob(I)alamin > Adenosylcobalamin + Triphosphate COBALADENOSYLTRANS-RXN GDP-cobinamide + alpha-ribazole > Cob(I)alamin + Guanosine monophosphate