2.0 2012-07-30 14:55:23 -0600 2015-06-03 17:21:12 -0600 ECMDB21346 M2MDB001744 Molybdopterin cytosine dinucleotide Molybdopterin cytosine dinucleotide is a member of the chemical class known as Pyrimidine Ribonucleoside Diphosphates. These are pyrimidine ribobucleotides with diphosphate group linked to the ribose moiety. MocA is a specific cytidylyltransferase involved in molybdopterin cytosine dinucleotide biosynthesis in Escherichia coli. (PMID 19542235) Qox is the first MCD-containing enzyme to be synthesized in a catalytically fully competent form by a heterologous host, P. (PMID 12730200) 5'-O-[(S)-{[(S)-{[(8R)-2-Amino-4-hydroxy-6,7-disulfanyl-8H-pyrano[3,2-g]pteridin-8-yl]methoxy}(hydroxy)phosphoryl]oxy}(hydroxy)phosphoryl]cytidine 5'-O-[(S)-{[(S)-{[(8R)-2-Amino-4-hydroxy-6,7-disulphanyl-8H-pyrano[3,2-g]pteridin-8-yl]methoxy}(hydroxy)phosphoryl]oxy}(hydroxy)phosphoryl]cytidine 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]methyl}oxy)(hydroxy)phosphoryl]oxy}(hydroxy)phosphoryl]cytidine 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]methyl}oxy)(hydroxy)phosphoryl]oxy}(hydroxy)phosphoryl]cytidine Dtpp-mCDP H2Dtpp-mCDP MCD Molybdopterin cytosine dinucleotide MoO2(OH)Dtpp-mCDP MoO₂(OH)Dtpp-mCDP PTERIN CYTOSINE DINUCLEOTIDE C19H23N8O13P2S2 697.509 697.030122266 [(5aR,8R,9aR)-2-amino-8-({[({[(2R,3S,4R,5R)-5-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methyl phosphonato}oxy)phosphinato]oxy}methyl)-4-oxo-7-sulfanyl-1H,4H,5H,5aH,8H,9aH,10H-pyrano[3,2-g]pteridin-6-yl]sulfanide [(5aR,8R,9aR)-2-amino-8-{[({[(2R,3S,4R,5R)-5-(4-amino-2-oxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methyl phosphonato}oxyphosphinato)oxy]methyl}-4-oxo-7-sulfanyl-1H,5H,5aH,8H,9aH,10H-pyrano[3,2-g]pteridin-6-yl]sulfanide [H]O[C@@]1([H])[C@@]([H])(O[C@]([H])(C([H])([H])OP([O-])(=O)OP([O-])(=O)OC([H])([H])[C@@]2([H])O[C@@]3([H])N([H])C4=C(N([H])[C@@]3([H])C([S-])=C2S[H])C(=O)N=C(N([H])[H])N4[H])[C@@]1([H])O[H])N1C([H])=C([H])C(=NC1=O)N([H])[H] InChI=1S/C19H26N8O13P2S2/c20-7-1-2-27(19(31)22-7)17-11(29)10(28)5(39-17)3-36-41(32,33)40-42(34,35)37-4-6-12(43)13(44)8-16(38-6)24-14-9(23-8)15(30)26-18(21)25-14/h1-2,5-6,8,10-11,16-17,23,28-29,43-44H,3-4H2,(H,32,33)(H,34,35)(H2,20,22,31)(H4,21,24,25,26,30)/p-3/t5-,6-,8+,10-,11-,16-,17-/m1/s1 WKSPNQYEWZEMMI-FEFZDOOUSA-K Cytosol logp -0.59 ALOGPS logs -2.01 ALOGPS solubility 7.39e+00 g/l ALOGPS logp -5.7 ChemAxon pka_strongest_acidic 1.82 ChemAxon pka_strongest_basic 3.13 ChemAxon iupac [(5aR,8R,9aR)-2-amino-8-({[({[(2R,3S,4R,5R)-5-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methyl phosphonato}oxy)phosphinato]oxy}methyl)-4-oxo-7-sulfanyl-1H,4H,5H,5aH,8H,9aH,10H-pyrano[3,2-g]pteridin-6-yl]sulfanide ChemAxon average_mass 697.509 ChemAxon mono_mass 697.030122266 ChemAxon smiles [H]O[C@@]1([H])[C@@]([H])(O[C@]([H])(C([H])([H])OP([O-])(=O)OP([O-])(=O)OC([H])([H])[C@@]2([H])O[C@@]3([H])N([H])C4=C(N([H])[C@@]3([H])C([S-])=C2S[H])C(=O)N=C(N([H])[H])N4[H])[C@@]1([H])O[H])N1C([H])=C([H])C(=NC1=O)N([H])[H] ChemAxon formula C19H23N8O13P2S2 ChemAxon inchi InChI=1S/C19H26N8O13P2S2/c20-7-1-2-27(19(31)22-7)17-11(29)10(28)5(39-17)3-36-41(32,33)40-42(34,35)37-4-6-12(43)13(44)8-16(38-6)24-14-9(23-8)15(30)26-18(21)25-14/h1-2,5-6,8,10-11,16-17,23,28-29,43-44H,3-4H2,(H,32,33)(H,34,35)(H2,20,22,31)(H4,21,24,25,26,30)/p-3/t5-,6-,8+,10-,11-,16-,17-/m1/s1 ChemAxon inchikey WKSPNQYEWZEMMI-FEFZDOOUSA-K ChemAxon polar_surface_area 317.1 ChemAxon refractivity 158.9 ChemAxon polarizability 58.45 ChemAxon rotatable_bond_count 9 ChemAxon acceptor_count 17 ChemAxon donor_count 8 ChemAxon physiological_charge -3 ChemAxon formal_charge -3 ChemAxon cytidylyl molybdenum cofactor biosynthesis PWY-6476 Specdb::MsMs 25289 Specdb::MsMs 25290 Specdb::MsMs 25291 Specdb::MsMs 31847 Specdb::MsMs 31848 Specdb::MsMs 31849 49792073 26331972 43955 CPD0-1882 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 Neumann, M., Mittelstadt, G., Seduk, F., Iobbi-Nivol, C., Leimkuhler, S. (2009). "MocA is a specific cytidylyltransferase involved in molybdopterin cytosine dinucleotide biosynthesis in Escherichia coli." J Biol Chem 284:21891-21898. 19542235 Parschat, K., Hauer, B., Kappl, R., Kraft, R., Huttermann, J., Fetzner, S. (2003). "Gene cluster of Arthrobacter ilicis Ru61a involved in the degradation of quinaldine to anthranilate: characterization and functional expression of the quinaldine 4-oxidase qoxLMS genes." J Biol Chem 278:27483-27494. 12730200 Uncharacterized protein ygfJ Q46810 YGFJ_ECOLI ygfJ http://ecmdb.ca/proteins/Q46810.xml Cytidine triphosphate + Hydrogen ion + Molybdopterin > Molybdopterin cytosine dinucleotide + Pyrophosphate Hydrogen ion + molybdenum cofactor + Cytidine triphosphate > Molybdopterin cytosine dinucleotide + Pyrophosphate RXN0-6254 molybdenum cofactor + Cytidine triphosphate + Hydrogen ion > Molybdopterin cytosine dinucleotide + Pyrophosphate PW_R006148