2.0 2012-05-31 13:44:51 -0600 2015-09-17 16:24:05 -0600 ECMDB01083 M2MDB000247 Cob(I)yrinate a,c diamide Cob(I)yrinate a,c diamide is an intermediate in porphyrin and chlorophyll metabolism. It is the sixth to last step in the synthesis of vitamin B12 coenzyme and is converted from Cob(II)yrinate a,c diamide via the enzyme cob(II)yrinic acid a,c-diamide reductase [EC:1.16.8.1]. It is then converted to adenosyl cobyrinate a,c diamide via the enzyme cob(I)alamin adenosyltransferase [EC:2.5.1.17]. Ubiquinone (also known as coenzyme Q) is an isoprenoid quinone that functions as an electron carrier in membranes. Ubiquinone synthesis involves the conversion of chorismate to 4-hydroxybenzoate by choris Cbi Cob(I)yrinate a,c-diamide Cob(I)yrinate diamide Cob(I)yrinic acid a,c diamide Cob(I)yrinic acid a,c-diamide Cob(I)yrinic acid diamide Cobyrinate a,c-diamide Cobyrinic acid a,c-diamide C45H61CoN6O12 936.932 936.36794664 λ¹-cobalt(1+) ion 2-[(1R,2R,3S,4S,8S,9S,14S,18R,19R)-4,9,14,18-tetrakis(2-carboxyethyl)-19-(carboxymethyl)-3-[(C-hydroxycarbonimidoyl)methyl]-2,3,6,8,13,13,16,18-octamethyl-20,21,22,23-tetraazapentacyclo[15.2.1.1²,⁵.1⁷,¹⁰.1¹²,¹⁵]tricosa-5,7(22),10,12(21),15,17(20)-hexaen-8-yl]ethan-1-aminide λ¹-cobalt(1+) ion 2-[(1R,2R,3S,4S,8S,9S,14S,18R,19R)-4,9,14,18-tetrakis(2-carboxyethyl)-19-(carboxymethyl)-3-(C-hydroxycarbonimidoylmethyl)-2,3,6,8,13,13,16,18-octamethyl-20,21,22,23-tetraazapentacyclo[15.2.1.1²,⁵.1⁷,¹⁰.1¹²,¹⁵]tricosa-5,7(22),10,12(21),15,17(20)-hexaen-8-yl]ethanaminide [Co]N1\C2=C(C)/C3=N/C(=C\C4=N\C(=C(C)/C5=N[C@@](C)([C@@]1([H])[C@H](CC(=O)O)[C@@]2(C)CCC(=O)O)[C@@](C)(CC(=O)N)[C@@H]5CCC(=O)O)\[C@@](C)(CC(=O)N)[C@@H]4CCC(=O)O)/C(C)(C)[C@@H]3CCC(=O)O InChI=1S/C45H62N6O12.Co/c1-21-36-24(10-13-32(56)57)41(3,4)28(49-36)18-27-23(9-12-31(54)55)43(6,19-29(46)52)39(48-27)22(2)37-25(11-14-33(58)59)44(7,20-30(47)53)45(8,51-37)40-26(17-35(62)63)42(5,38(21)50-40)16-15-34(60)61;/h18,23-26,40H,9-17,19-20H2,1-8H3,(H10,46,47,48,49,50,51,52,53,54,55,56,57,58,59,60,61,62,63);/q;+1/p-1/t23-,24-,25-,26+,40-,42-,43+,44+,45+;/m1./s1 NKLHEMWEQJCPPF-OKJGWHJPSA-M Solid Cytoplasm Periplasm logp 0.83 ALOGPS logs -4.22 ALOGPS solubility 5.71e-02 g/l ALOGPS logp -2.8 ChemAxon pka_strongest_acidic 3.52 ChemAxon pka_strongest_basic 8.94 ChemAxon iupac λ¹-cobalt(1+) ion 2-[(1R,2R,3S,4S,8S,9S,14S,18R,19R)-4,9,14,18-tetrakis(2-carboxyethyl)-19-(carboxymethyl)-3-[(C-hydroxycarbonimidoyl)methyl]-2,3,6,8,13,13,16,18-octamethyl-20,21,22,23-tetraazapentacyclo[15.2.1.1²,⁵.1⁷,¹⁰.1¹²,¹⁵]tricosa-5,7(22),10,12(21),15,17(20)-hexaen-8-yl]ethan-1-aminide ChemAxon average_mass 936.932 ChemAxon mono_mass 936.36794664 ChemAxon smiles [Co]N1\C2=C(C)/C3=N/C(=C\C4=N\C(=C(C)/C5=N[C@@](C)([C@@]1([H])[C@H](CC(=O)O)[C@@]2(C)CCC(=O)O)[C@@](C)(CC(=O)N)[C@@H]5CCC(=O)O)\[C@@](C)(CC(=O)N)[C@@H]4CCC(=O)O)/C(C)(C)[C@@H]3CCC(=O)O ChemAxon formula C45H61CoN6O12 ChemAxon inchi InChI=1S/C45H62N6O12.Co/c1-21-36-24(10-13-32(56)57)41(3,4)28(49-36)18-27-23(9-12-31(54)55)43(6,19-29(46)52)39(48-27)22(2)37-25(11-14-33(58)59)44(7,20-30(47)53)45(8,51-37)40-26(17-35(62)63)42(5,38(21)50-40)16-15-34(60)61;/h18,23-26,40H,9-17,19-20H2,1-8H3,(H10,46,47,48,49,50,51,52,53,54,55,56,57,58,59,60,61,62,63);/q;+1/p-1/t23-,24-,25-,26+,40-,42-,43+,44+,45+;/m1./s1 ChemAxon inchikey NKLHEMWEQJCPPF-OKJGWHJPSA-M ChemAxon polar_surface_area 316.99 ChemAxon refractivity 239.43 ChemAxon polarizability 91.71 ChemAxon rotatable_bond_count 18 ChemAxon acceptor_count 18 ChemAxon donor_count 9 ChemAxon physiological_charge -2 ChemAxon formal_charge 0 ChemAxon Porphyrin and chlorophyll metabolism ec00860 Metabolic pathways eco01100 adenosylcobalamin salvage from cobinamide I COBALSYN-PWY-1 Specdb::MsMs 1286572 Specdb::MsMs 1286573 Specdb::MsMs 1286574 Specdb::MsMs 1401370 Specdb::MsMs 1401371 Specdb::MsMs 1401372 HMDB06904 C06505 28531 COBINAMIDE 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 Cob(I)yrinic acid a,c-diamide adenosyltransferase P0A9H5 BTUR_ECOLI btuR http://ecmdb.ca/proteins/P0A9H5.xml Ethanolamine utilization cobalamin adenosyltransferase P65643 EUTT_ECOLI eutT http://ecmdb.ca/proteins/P65643.xml Cob(I)yrinate a,c diamide + Adenosine triphosphate <> Adenosyl cobyrinate a,c diamide + Triphosphate R05220 Cob(I)yrinate a,c diamide + Adenosine triphosphate > Adenosyl cobinamide + Triphosphate BTUR2-RXN Adenosine triphosphate + Cob(I)yrinate a,c diamide > Triphosphate + Adenosylcob(III)yrinic acid a,c-diamide Adenosine triphosphate + Cob(I)yrinate a,c diamide + Cobinamide <> Triphosphate + Adenosyl cobyrinate a,c diamide + Adenosyl cobinamide R05220