2.02012-05-31 13:55:35 -06002015-10-23 17:32:54 -0600ECMDB02086M2MDB000439AdenosylcobalaminAdenosylcobalamin is one of two metabolically active forms of vitamin B12. it acts as a coenzyme in the reaction catalyzed by methylmalonyl-CoA mutase. A cobalamin (cbl) derivative in which the substituent is deoxyadenosyl. (E.C. 5.4.99.2).(5'-Deoxy-5'-adenosyl)cobamide coenzyme(5,6-dimethylbenzimidazolyl)cobamide coenzyme5'-Deoxy-5'-adenosyl vitamin B125'-Deoxy-5'-adenosylcobalamin5'-Deoxyadenosyl vitamin B125'-Deoxyadenosyl-5,6-dimethylbenzimidazolylcobamide5'-Deoxyadenosylcobalamin5,6-Dimethylbenzimidazolyl-5-deoxyadenosyl-cobamide5,6-Dimethylbenzimidazolyl-Co-5'-deoxyadenosylcobamideAdenosylcobalaminAdenosylcobalamin 5'-phosphateAdenosylcobalamin 5'-phosphoric acidCalomideCoB12Cobalamin coenzymeCobamamidCobamamideCobamamide 5'-phosphateCobamamide 5'-phosphoric acidCobamide coenzymeCoenzyme B12DeoxyadenosylcobalaminDibencozideFunacomideVitamin B12Vitamin B12 coenzymeVitamin B12 coenzymesVitamin B<sub>12</sub>C72H101CoN18O17P1580.58971579.666170602{[(2S,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl}[(2R,3S,4S,8S,9S,14S,18R,19R)-4,9,14-tris(2-carbamoylethyl)-3,8,19-tris(carbamoylmethyl)-18-(2-{[(2R)-2-[({[(2R,3S,4R,5S)-5-(5,6-dimethyl-1H-1,3-benzodiazol-1-yl)-4-hydroxy-2-(hydroxymethyl)oxolan-3-yl]oxy}(hydroxy)phosphoryl)oxy]propyl]carbamoyl}ethyl)-2,3,6,8,13,13,16,18-octamethyl-20,21,22,23-tetraazapentacyclo[15.2.1.1²,⁵.1⁷,¹⁰.1¹²,¹⁵]tricosa-5(23),6,10(22),11,15(21),16-hexaen-20-yl]cobaltylium{[(2S,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl}[(2R,3S,4S,8S,9S,14S,18R,19R)-4,9,14-tris(2-carbamoylethyl)-3,8,19-tris(carbamoylmethyl)-18-(2-{[(2R)-2-({[(2R,3S,4R,5S)-5-(5,6-dimethyl-1,3-benzodiazol-1-yl)-4-hydroxy-2-(hydroxymethyl)oxolan-3-yl]oxy(hydroxy)phosphoryl}oxy)propyl]carbamoyl}ethyl)-2,3,6,8,13,13,16,18-octamethyl-20,21,22,23-tetraazapentacyclo[15.2.1.1²,⁵.1⁷,¹⁰.1¹²,¹⁵]tricosa-5(23),6,10(22),11,15(21),16-hexaen-20-yl]cobaltylium13870-90-1OC[C@H]1O[C@@H]([C@H](O)[C@@H]1OP(O)(=O)O[C@H](C)CNC(=O)CC[C@]1(C)[C@@H](CC(N)=O)C2N([Co+]C[C@H]3O[C@H]([C@H](O)[C@@H]3O)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(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)N1C=NC2=C1C=C(C)C(C)=C2InChI=1S/C62H90N13O14P.C10H12N5O3.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;1-4-6(16)7(17)10(18-4)15-3-14-5-8(11)12-2-13-9(5)15;/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);2-4,6-7,10,16-17H,1H2,(H2,11,12,13);/q;;+2/p-1/t31-,34-,35-,36-,37+,41-,52-,53-,56?,57+,59-,60+,61+,62+;4-,6-,7-,10-;/m11./s1ZIHHMGTYZOSFRC-QRVZQHAISA-MSolidCytosolExtra-organismMembranePeriplasmlogp2.10logs-4.80solubility2.56e-02 g/llogp-5.9pka_strongest_acidic1.82pka_strongest_basic8.76iupac{[(2S,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl}[(2R,3S,4S,8S,9S,14S,18R,19R)-4,9,14-tris(2-carbamoylethyl)-3,8,19-tris(carbamoylmethyl)-18-(2-{[(2R)-2-[({[(2R,3S,4R,5S)-5-(5,6-dimethyl-1H-1,3-benzodiazol-1-yl)-4-hydroxy-2-(hydroxymethyl)oxolan-3-yl]oxy}(hydroxy)phosphoryl)oxy]propyl]carbamoyl}ethyl)-2,3,6,8,13,13,16,18-octamethyl-20,21,22,23-tetraazapentacyclo[15.2.1.1²,⁵.1⁷,¹⁰.1¹²,¹⁵]tricosa-5(23),6,10(22),11,15(21),16-hexaen-20-yl]cobaltyliumaverage_mass1580.5897mono_mass1579.666170602smilesOC[C@H]1O[C@@H]([C@H](O)[C@@H]1OP(O)(=O)O[C@H](C)CNC(=O)CC[C@]1(C)[C@@H](CC(N)=O)C2N([Co+]C[C@H]3O[C@H]([C@H](O)[C@@H]3O)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(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)N1C=NC2=C1C=C(C)C(C)=C2formulaC72H101CoN18O17PinchiInChI=1S/C62H90N13O14P.C10H12N5O3.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;1-4-6(16)7(17)10(18-4)15-3-14-5-8(11)12-2-13-9(5)15;/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);2-4,6-7,10,16-17H,1H2,(H2,11,12,13);/q;;+2/p-1/t31-,34-,35-,36-,37+,41-,52-,53-,56?,57+,59-,60+,61+,62+;4-,6-,7-,10-;/m11./s1inchikeyZIHHMGTYZOSFRC-QRVZQHAISA-Mpolar_surface_area570.54refractivity392.44polarizability160.65rotatable_bond_count30acceptor_count24donor_count13physiological_charge3formal_charge1Porphyrin and chlorophyll metabolismec00860Metabolic pathwayseco01100adenosylcobalamin salvage from cobinamide ICOBALSYN-PWY-1HMDB020866436143C0019418408ADENOSYLCOBALAMINAdenosylcobalaminKeseler, 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 80:2939-2948.18331064http://hmdb.ca/system/metabolites/msds/000/001/669/original/HMDB02086.pdf?1358462453Vitamin 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.xmlAlpha-ribazole phosphataseP52086COBC_ECOLIcobChttp://ecmdb.ca/proteins/P52086.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 + Adenosylcobalamin > Adenosylcobalamin + ADP + Hydrogen ion + PhosphateAdenosine triphosphate + Water + Adenosylcobalamin > Adenosylcobalamin + ADP + Hydrogen ion + PhosphateAdenosine triphosphate + Cob(I)alamin + Hydrogen ion <> Adenosylcobalamin + TriphosphateR01492COBALADENOSYLTRANS-RXNAdenosylcobinamide-GDP + N1-(alpha-D-ribosyl)-5,6-dimethyl-benzimidazole > Adenosylcobalamin + Guanosine monophosphate + Hydrogen ionR05223COBALAMINSYN-RXNAdenosine triphosphate + Cob(I)alamin <> Triphosphate + AdenosylcobalaminR01492Adenosylcobalamin + Guanosine monophosphate <> Adenosylcobinamide-GDP + N1-(alpha-D-ribosyl)-5,6-dimethyl-benzimidazoleR05223Adenosine triphosphate + Cob(I)alamin > Adenosylcobalamin + TriphosphateCOBALADENOSYLTRANS-RXNAdenosylcobinamide-GDP + N1-(alpha-D-ribosyl)-5,6-dimethyl-benzimidazole Hydrogen ion + Adenosylcobalamin + Guanosine monophosphateCOBALAMINSYN-RXNadenosylcobalamin 5'-phosphate + Water > Adenosylcobalamin + PhosphateRXN-8770Adenosylcobalamin + Water > Adenosylcobalamin + Inorganic phosphateAdenosylcobalamin + Water > Adenosylcobalamin + Inorganic phosphateAdenosylcobinamide-GDP + N1-(alpha-D-ribosyl)-5,6-dimethyl-benzimidazole + N1-(5-Phospho-a-D-ribosyl)-5,6-dimethylbenzimidazole <> Guanosine monophosphate + Adenosylcobalamin + Adenosylcobalamin 5'-phosphateR05223