2.0 2012-10-10 12:18:06 -0600 2015-10-02 02:25:54 -0600 ECMDB23132 M2MDB003522 Adenosylcob(III)yrinic acid a,c-diamide Most prokaryotic organisms as well as animals (including human) and protists have enzyme that require adenosylcobalamin as cofactor, whereas plants and fungi are thought not to use it. It is one of the most structurally complex protein cofactors ans its biosynthesis remains one of the most enigmatic and exigent metabolic pathways in nature, requiring around 30 enzymes. Two distinct yet similar routes exist, known as the oxygene-dependent (aerobic route) and oxygen-independent (anaerobic route) pathways. These pathways diverge at precorrin-2 and merge again at adenosylcobyrate. The major difference between these two routes include the timing of cobalt insertion, the requirement for oxygen and the nature of the extruded carbon fragment which is lost during the ring construction process. Adenosylcob(iii)yrinate a,c-diamide C55H75CoN11O15 1189.1819 1188.477610979 cobalt(3+) ion (2R,3R,4S,5R)-2-(6-amino-9H-purin-9-yl)-5-methyloxolane-3,4-diol 3-[(2R,3S,4S,8S,9S,14S,18R,19R)-4,14,18-tris(2-carboxyethyl)-19-(carboxymethyl)-3,8-bis(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-9-yl]propanoic acid cobalt(3+) ion 3-[(2R,3S,4S,8S,9S,14S,18R,19R)-4,14,18-tris(2-carboxyethyl)-19-(carboxymethyl)-3,8-bis(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-9-yl]propanoic acid 5'-deoxyadenosine [Co+3].[H][C@]1(C)O[C@@]([H])(N2C=NC3=C(N)N=CN=C23)[C@]([H])(O)[C@]1([H])O.[H][C@@]1(CCC(O)=O)C2=CC3=NC(=C(C)C4=NC([H])([C@]([H])(CC(O)=O)[C@@]4(C)CCC(O)=O)[C@]4(C)NC(=C(C)C(=N2)[C@@]1(C)CC(O)=N)[C@@]([H])(CCC(O)=O)[C@]4(C)CC(O)=N)[C@@]([H])(CCC(O)=O)C3(C)C InChI=1S/C45H62N6O12.C10H13N5O3.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;1-4-6(16)7(17)10(18-4)15-3-14-5-8(11)12-2-13-9(5)15;/h18,23-26,40,51H,9-17,19-20H2,1-8H3,(H2,46,52)(H2,47,53)(H,54,55)(H,56,57)(H,58,59)(H,60,61)(H,62,63);2-4,6-7,10,16-17H,1H3,(H2,11,12,13);/q;;+3/t23-,24-,25-,26+,40?,42-,43+,44+,45+;4-,6-,7-,10-;/m11./s1 MEXRZHASDDAAJB-QOCQOLRHSA-N logp 0.88 ChemAxon pka_strongest_acidic 3.19 ChemAxon pka_strongest_basic 8.95 ChemAxon iupac cobalt(3+) ion (2R,3R,4S,5R)-2-(6-amino-9H-purin-9-yl)-5-methyloxolane-3,4-diol 3-[(2R,3S,4S,8S,9S,14S,18R,19R)-4,14,18-tris(2-carboxyethyl)-19-(carboxymethyl)-3,8-bis(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-9-yl]propanoic acid ChemAxon average_mass 1189.1819 ChemAxon mono_mass 1188.477610979 ChemAxon smiles [Co+3].[H][C@]1(C)O[C@@]([H])(N2C=NC3=C(N)N=CN=C23)[C@]([H])(O)[C@]1([H])O.[H][C@@]1(CCC(O)=O)C2=CC3=NC(=C(C)C4=NC([H])([C@]([H])(CC(O)=O)[C@@]4(C)CCC(O)=O)[C@]4(C)NC(=C(C)C(=N2)[C@@]1(C)CC(O)=N)[C@@]([H])(CCC(O)=O)[C@]4(C)CC(O)=N)[C@@]([H])(CCC(O)=O)C3(C)C ChemAxon formula C55H75CoN11O15 ChemAxon inchi InChI=1S/C45H62N6O12.C10H13N5O3.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;1-4-6(16)7(17)10(18-4)15-3-14-5-8(11)12-2-13-9(5)15;/h18,23-26,40,51H,9-17,19-20H2,1-8H3,(H2,46,52)(H2,47,53)(H,54,55)(H,56,57)(H,58,59)(H,60,61)(H,62,63);2-4,6-7,10,16-17H,1H3,(H2,11,12,13);/q;;+3/t23-,24-,25-,26+,40?,42-,43+,44+,45+;4-,6-,7-,10-;/m11./s1 ChemAxon inchikey MEXRZHASDDAAJB-QOCQOLRHSA-N ChemAxon polar_surface_area 323.77 ChemAxon refractivity 251.16 ChemAxon polarizability 91.96 ChemAxon rotatable_bond_count 19 ChemAxon acceptor_count 18 ChemAxon donor_count 10 ChemAxon physiological_charge -1 ChemAxon formal_charge 3 ChemAxon Specdb::CMs 1085755 Specdb::NmrOneD 295695 Specdb::NmrOneD 295696 Specdb::NmrOneD 295697 Specdb::NmrOneD 295698 Specdb::NmrOneD 295699 Specdb::NmrOneD 295700 Specdb::NmrOneD 295701 Specdb::NmrOneD 295702 Specdb::NmrOneD 295703 Specdb::NmrOneD 295704 Specdb::NmrOneD 295705 Specdb::NmrOneD 295706 Specdb::NmrOneD 295707 Specdb::NmrOneD 295708 Specdb::NmrOneD 295709 Specdb::NmrOneD 295710 Specdb::NmrOneD 295711 Specdb::NmrOneD 295712 Specdb::NmrOneD 295713 Specdb::NmrOneD 295714 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 Adenosine triphosphate + Cob(I)yrinate a,c diamide > Triphosphate + Adenosylcob(III)yrinic acid a,c-diamide