2.0 2012-05-31 13:59:13 -0600 2015-06-03 15:54:24 -0600 ECMDB03458 M2MDB000503 Aquacobalamin Aquacobalamin and the thiolate forms of glutathione are the precursors of glutathionylcobalamin (GSCbl, a precursor to the formation of the two coenzyme forms of vitamin B(12), adenosylcobalamin and methylcobalamin). Under biological conditions the formation of GSCbl from aquacobalamin and glutathione is essentially irreversible; upon entering cells, any free (protein-unbound) aquacobalamin could be rapidly and irreversibly converted to GSCbl. (PMID: 15476387)Aquacobalamin is reduced to cob(II)alamin by Methionine synthase reductse (MSR) in the presence of NADPH, and this reduction leads to stimulation of the conversion of apomethionine synthase and aquacobalamin to methionine synthase holoenzyme. (PMID: 16769880 ) Aquacob(III)alamin Aquacobalamin Aquocobalamin Aquocobalamin hydroxide Aquocobalamine Coalpha-[a-(5,6-dimethylbenzimidazolyl)]-cobeta-aquacobamide vitamin-b12a Coalpha-[alpha-(5,6-dimethylbenzimidazolyl)]-Cobeta-aquacobamide Vitamin-B12a Coalpha-[α-(5,6-dimethylbenzimidazolyl)]-cobeta-aquacobamide vitamin-b12a C62H90CoN13O15P 1347.3631 1346.574895981 cobalt(3+) ion 1-[(2S,3R,4S,5R)-3-hydroxy-4-{[hydroxy({[(2R)-1-({1-hydroxy-3-[(1R,3R,8S,13S,14S,18S,19S)-8,13,18-tris(2-carboximidatoethyl)-3,14,19-tris(C-hydroxycarbonimidoylmethyl)-1,4,6,9,9,14,16,19-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-4-yl]propylidene}amino)propan-2-yl]oxy})phosphoryl]oxy}-5-(hydroxymethyl)oxolan-2-yl]-5,6-dimethyl-3H-1λ⁵,3-benzodiazol-1-ylium hydrate cobalt(3+) ion 1-[(2S,3R,4S,5R)-3-hydroxy-4-({hydroxy[(2R)-1-({1-hydroxy-3-[(1R,3R,8S,13S,14S,18S,19S)-8,13,18-tris(2-carboximidatoethyl)-3,14,19-tris(C-hydroxycarbonimidoylmethyl)-1,4,6,9,9,14,16,19-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-4-yl]propylidene}amino)propan-2-yl]oxyphosphoryl}oxy)-5-(hydroxymethyl)oxolan-2-yl]-5,6-dimethyl-3H-1λ⁵,3-benzodiazol-1-ylium hydrate 13422-52-1 O.[Co+3].[H][C@@](C)(CN=C(O)CCC1(C)C2=NC([H])([C@]1([H])CC(O)=N)[C@]1(C)NC(=C(C)C3=NC(=CC4=NC(=C2C)[C@@]([H])(CCC([O-])=N)C4(C)C)[C@@]([H])(CCC([O-])=N)[C@]3(C)CC(O)=N)[C@@]([H])(CCC([O-])=N)[C@]1(C)CC(O)=N)OP(O)(=O)O[C@]1([H])[C@@]([H])(CO)O[C@]([H])([N+]2=CNC3=C2C=C(C)C(C)=C3)[C@]1([H])O InChI=1S/C62H90N13O14P.Co.H2O/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);;1H2/q;+3;/p-2 YOZNUFWCRFCGIH-UHFFFAOYSA-L Solid Cytoplasm Periplasm logp -3.1 ChemAxon pka_strongest_acidic 1.81 ChemAxon pka_strongest_basic 9.07 ChemAxon iupac cobalt(3+) ion 1-[(2S,3R,4S,5R)-3-hydroxy-4-{[hydroxy({[(2R)-1-({1-hydroxy-3-[(1R,3R,8S,13S,14S,18S,19S)-8,13,18-tris(2-carboximidatoethyl)-3,14,19-tris(C-hydroxycarbonimidoylmethyl)-1,4,6,9,9,14,16,19-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-4-yl]propylidene}amino)propan-2-yl]oxy})phosphoryl]oxy}-5-(hydroxymethyl)oxolan-2-yl]-5,6-dimethyl-3H-1λ⁵,3-benzodiazol-1-ylium hydrate ChemAxon average_mass 1347.3631 ChemAxon mono_mass 1346.574895981 ChemAxon smiles O.[Co+3].[H][C@@](C)(CN=C(O)CCC1(C)C2=NC([H])([C@]1([H])CC(O)=N)[C@]1(C)NC(=C(C)C3=NC(=CC4=NC(=C2C)[C@@]([H])(CCC([O-])=N)C4(C)C)[C@@]([H])(CCC([O-])=N)[C@]3(C)CC(O)=N)[C@@]([H])(CCC([O-])=N)[C@]1(C)CC(O)=N)OP(O)(=O)O[C@]1([H])[C@@]([H])(CO)O[C@]([H])([N+]2=CNC3=C2C=C(C)C(C)=C3)[C@]1([H])O ChemAxon formula C62H90CoN13O15P ChemAxon inchi InChI=1S/C62H90N13O14P.Co.H2O/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);;1H2/q;+3;/p-2 ChemAxon inchikey YOZNUFWCRFCGIH-UHFFFAOYSA-L ChemAxon polar_surface_area 479.79 ChemAxon refractivity 430.84 ChemAxon polarizability 133.42 ChemAxon rotatable_bond_count 26 ChemAxon acceptor_count 23 ChemAxon donor_count 15 ChemAxon physiological_charge 3 ChemAxon formal_charge 1 ChemAxon Porphyrin and chlorophyll metabolism ec00860 Riboflavin metabolism ec00740 HMDB03458 5462232 C00992 15852 AQUACOBIIIALAMIN 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 Xia, L., Cregan, A. G., Berben, L. A., Brasch, N. E. (2004). "Studies on the formation of glutathionylcobalamin: any free intracellular aquacobalamin is likely to be rapidly and irreversibly converted to glutathionylcobalamin." Inorg Chem 43:6848-6857. 15476387 Yamada, K., Gravel, R. A., Toraya, T., Matthews, R. G. (2006). "Human methionine synthase reductase is a molecular chaperone for human methionine synthase." Proc Natl Acad Sci U S A 103:9476-9481. 16769880 NAD(P)H-flavin reductase P0AEN1 FRE_ECOLI fre http://ecmdb.ca/proteins/P0AEN1.xml NAD + 2 Cob(II)alamin + 2 Water + Hydrogen ion <> NADH +2 Aquacobalamin R00097 2 Cob(II)alamin + NAD >2 Aquacobalamin + NADH