2.0 2012-07-30 14:55:16 -0600 2015-06-03 17:21:08 -0600 ECMDB21307 M2MDB001711 Adenylated molybdopterin Adenylated molybdopterin is a member of the chemical class known as Purine Ribonucleoside Diphosphates. These are purine ribobucleotides with diphosphate group linked to the ribose moiety. MPT-AMP is the reaction product of Cnx1G. Catalytically inactive Cnx1G mutant variants showed impaired MPT adenylation confirming that MPT-AMP is the reaction product of Cnx1G. (PMID 15504727) 5'-O-[{[{[(5aR,8R,9aR)-2-amino-4-oxo-6,7-disulfanyl-3,5,5a,8,9a,10-hexahydro-4H-pyrano[3,2-g]pteridin-8-yl]methoxy}(hydroxy)phosphoryl]oxy}(hydroxy)phosphoryl]adenosine 5'-O-[{[{[(5aR,8R,9aR)-2-amino-4-oxo-6,7-disulphanyl-3,5,5a,8,9a,10-hexahydro-4H-pyrano[3,2-g]pteridin-8-yl]methoxy}(hydroxy)phosphoryl]oxy}(hydroxy)phosphoryl]adenosine Adenylated molybdopterin Adenylyl-molybdopterin H2Dtpp-mADP Molybdopterin-AMP MPT-AMP C20H26N10O12P2S2 724.558 724.06483075 ({2-amino-4-oxo-6,7-disulfanyl-3H,4H,5H,5aH,8H,9aH,10H-pyrano[3,2-g]pteridin-8-yl}methoxy)[({[5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]phosphinic acid {2-amino-4-oxo-6,7-disulfanyl-3H,5H,5aH,8H,9aH,10H-pyrano[3,2-g]pteridin-8-yl}methoxy({[5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy)phosphinic acid NC1=NC2=C(NC3C(N2)OC(COP(O)(=O)OP(O)(=O)OCC2OC(C(O)C2O)N2C=NC4=C2N=CN=C4N)C(S)=C3S)C(=O)N1 InChI=1S/C20H26N10O12P2S2/c21-14-8-16(24-3-23-14)30(4-25-8)19-11(32)10(31)5(41-19)1-38-43(34,35)42-44(36,37)39-2-6-12(45)13(46)7-18(40-6)27-15-9(26-7)17(33)29-20(22)28-15/h3-7,10-11,18-19,26,31-32,45-46H,1-2H2,(H,34,35)(H,36,37)(H2,21,23,24)(H4,22,27,28,29,33) XJXFAXLUOKQPAQ-UHFFFAOYSA-N Cytosol logp -0.36 ALOGPS logs -2.43 ALOGPS solubility 2.72e+00 g/l ALOGPS logp -5.5 ChemAxon pka_strongest_acidic 1.85 ChemAxon pka_strongest_basic 4.01 ChemAxon iupac ({2-amino-4-oxo-6,7-disulfanyl-3H,4H,5H,5aH,8H,9aH,10H-pyrano[3,2-g]pteridin-8-yl}methoxy)[({[5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]phosphinic acid ChemAxon average_mass 724.558 ChemAxon mono_mass 724.06483075 ChemAxon smiles NC1=NC2=C(NC3C(N2)OC(COP(O)(=O)OP(O)(=O)OCC2OC(C(O)C2O)N2C=NC4=C2N=CN=C4N)C(S)=C3S)C(=O)N1 ChemAxon formula C20H26N10O12P2S2 ChemAxon inchi InChI=1S/C20H26N10O12P2S2/c21-14-8-16(24-3-23-14)30(4-25-8)19-11(32)10(31)5(41-19)1-38-43(34,35)42-44(36,37)39-2-6-12(45)13(46)7-18(40-6)27-15-9(26-7)17(33)29-20(22)28-15/h3-7,10-11,18-19,26,31-32,45-46H,1-2H2,(H,34,35)(H,36,37)(H2,21,23,24)(H4,22,27,28,29,33) ChemAxon inchikey XJXFAXLUOKQPAQ-UHFFFAOYSA-N ChemAxon polar_surface_area 322.37 ChemAxon refractivity 169.25 ChemAxon polarizability 62.78 ChemAxon rotatable_bond_count 9 ChemAxon acceptor_count 17 ChemAxon donor_count 11 ChemAxon physiological_charge -3 ChemAxon formal_charge 0 ChemAxon Sulfur relay system ec04122 molybdenum cofactor biosynthesis PWY-6823 Specdb::CMs 63998 Specdb::NmrOneD 96778 Specdb::NmrOneD 96779 Specdb::NmrOneD 96780 Specdb::NmrOneD 96781 Specdb::NmrOneD 96782 Specdb::NmrOneD 96783 Specdb::NmrOneD 96784 Specdb::NmrOneD 96785 Specdb::NmrOneD 96786 Specdb::NmrOneD 96787 Specdb::NmrOneD 96788 Specdb::NmrOneD 96789 Specdb::NmrOneD 96790 Specdb::NmrOneD 96791 Specdb::NmrOneD 96792 Specdb::NmrOneD 96793 Specdb::NmrOneD 96794 Specdb::NmrOneD 96795 Specdb::NmrOneD 96796 Specdb::NmrOneD 96797 Specdb::MsMs 29204 Specdb::MsMs 29205 Specdb::MsMs 29206 Specdb::MsMs 35762 Specdb::MsMs 35763 Specdb::MsMs 35764 Specdb::MsMs 2840355 Specdb::MsMs 2840356 Specdb::MsMs 2840357 Specdb::MsMs 2864676 Specdb::MsMs 2864677 Specdb::MsMs 2864678 25245677 C19848 62728 CPD-8122 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 Llamas, A., Mendel, R. R., Schwarz, G. (2004). "Synthesis of adenylated molybdopterin: an essential step for molybdenum insertion." J Biol Chem 279:55241-55246. 15504727 Molybdopterin molybdenumtransferase P12281 MOEA_ECOLI moeA http://ecmdb.ca/proteins/P12281.xml Molybdopterin adenylyltransferase P0AF03 MOG_ECOLI mog http://ecmdb.ca/proteins/P0AF03.xml Adenosine triphosphate + Hydrogen ion + Molybdopterin <> Adenylated molybdopterin + Pyrophosphate R09726 RXN-8344 Molybdopterin + Adenylated molybdopterin > Adenosine monophosphate + bis-molybdenum cofactor + Copper Adenylated molybdopterin + tungsten binding cofactor > Adenosine monophosphate + tungsten bispterin cofactor + Copper 2 Hydrogen ion + Molybdate + Adenylated molybdopterin > Adenosine monophosphate + Copper + Water + Molybdopterin 2 Hydrogen ion + Adenylated molybdopterin + Tungstate > Adenosine monophosphate + Copper + Water + tungsten binding cofactor Adenosine triphosphate + Molybdopterin <> Pyrophosphate + Adenylated molybdopterin R09726 Adenylated molybdopterin + Molybdate <> Molybdoenzyme molybdenum cofactor + Adenosine monophosphate + Water + Molybdoenzyme molybdenum cofactor R09735 Hydrogen ion + Molybdopterin + Adenosine triphosphate > Adenylated molybdopterin + Pyrophosphate RXN-8344 Adenylated molybdopterin + Molybdate > molybdenum cofactor + Adenosine monophosphate + Water RXN-8348