2.02012-05-31 14:03:03 -06002015-09-17 16:24:10 -0600ECMDB04040M2MDB000574Cob(I)alaminCob(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.B12CblCob(I)alaminCobalaminCoenzyme B12CyanocobalaminHydrido-CobalaminHydridocobalaminVitamin B12Vitamin B12sVitamin B<SUB>12</SUB>C62H88CoN13O14P1329.34781328.56433129518534-66-2[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)=OInChI=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./s1OMAOKVYASDIYQG-DSRCUDDDSA-LSolidCytosolExtra-organismPeriplasmlogp0.79logs-4.61solubility3.34e-02 g/laverage_mass1329.3478mono_mass1328.564331295smiles[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)=OformulaC62H88CoN13O14PinchiInChI=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./s1inchikeyOMAOKVYASDIYQG-DSRCUDDDSA-Lpolar_surface_area479.24refractivity348.45polarizability136.34rotatable_bond_count16acceptor_count0donor_count0physiological_charge0formal_charge-1Porphyrin and chlorophyll metabolismec00860HMDB034295462228C0085315982COB-I-ALAMINCyanocobalaminKeseler, 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.xmlCobalamin synthaseP36561COBS_ECOLIcobShttp://ecmdb.ca/proteins/P36561.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 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 + Cob(I)alamin > ADP + Cob(I)alamin + Hydrogen ion + PhosphateABC-5-RXNAdenosine triphosphate + Water + Cob(I)alamin > ADP + Cob(I)alamin + Hydrogen ion + PhosphateABC-5-RXNAdenosine triphosphate + Cob(I)alamin + Hydrogen ion <> Adenosylcobalamin + TriphosphateR01492COBALADENOSYLTRANS-RXNAdenosine triphosphate + Cob(I)alamin <> Triphosphate + AdenosylcobalaminR01492Adenosine triphosphate + Cob(I)alamin + Water > ADP + Phosphate + Cob(I)alamin + Hydrogen ionABC-5-RXNAdenosine triphosphate + Cob(I)alamin + Water > ADP + Phosphate + Cob(I)alamin + Hydrogen ionABC-5-RXNAdenosine triphosphate + Cob(I)alamin > Adenosylcobalamin + TriphosphateCOBALADENOSYLTRANS-RXNGDP-cobinamide + alpha-ribazole > Cob(I)alamin + Guanosine monophosphate