2.0 2012-05-31 13:56:01 -0600 2015-09-17 15:41:15 -0600 ECMDB02206 M2MDB000446 Molybdopterin Molybdopterins are a class of biochemical cofactor that are used in many different enzymes. The simplest structure of molybdopterin contains a pyranopterin coordinated to molybdenum. The pyranopterin structure is a fused ring system containing a pyran fused to pterin. In addition, the pyran ring is substituted with two thiols and an alkyl phosphate. In molybdopterin, the thiols coordinate to molybdenum. In some cases, the alkyl phosphate group is replaced by an alkyl diphosphate nucleotide. -- Wikipedia Ene-dithiol pyranopterin H2Dtpp-mP H₂Dtpp-mP MoCo Molybdenum cofactor Molybdenum enzyme molybdenum cofactor Molybdoenzyme molybdenum-containing cofactor MPT Nitrate reductase molybdenum cofactor Nitric acid reductase molybdenum cofactor Pterin molybdenum cofactor Pyranopterin-dithiolate Pyranopterin-dithiolic acid [(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 dihydrogen phosphate [(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 dihydrogen phosphoric acid [(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 dihydrogen phosphate [(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 dihydrogen phosphoric acid C10H12MoN5O8PS2 521.27 522.891898123 molybdenum(2+) ion 8-[(hydrogen phosphonooxy)methyl]-2-imino-6,7-disulfanyl-1H,2H,5H,5aH,8H,9aH,10H-pyrano[3,2-g]pteridin-4-olate dihydrate molybdenum(2+) ion 8-[(hydrogen phosphonooxy)methyl]-2-imino-6,7-disulfanyl-1H,5H,5aH,8H,9aH,10H-pyrano[3,2-g]pteridin-4-olate dihydrate 73508-07-3 NC1=NC2=C(NC3C(N2)OC(COP(O)(O)=O)C2=C3S[Mo](=O)(=O)S2)C(=O)N1 InChI=1S/C10H14N5O6PS2.Mo.2O/c11-10-14-7-4(8(16)15-10)12-3-6(24)5(23)2(21-9(3)13-7)1-20-22(17,18)19;;;/h2-3,9,12,23-24H,1H2,(H2,17,18,19)(H4,11,13,14,15,16);;;/q;+2;;/p-2 HDAJUGGARUFROU-UHFFFAOYSA-L Cytosol Cytosol logp 0.86 ALOGPS logs -2.74 ALOGPS solubility 9.79e-01 g/l ALOGPS logp -1.9 ChemAxon pka_strongest_acidic 1.19 ChemAxon pka_strongest_basic 2.91 ChemAxon iupac molybdenum(2+) ion 8-[(hydrogen phosphonooxy)methyl]-2-imino-6,7-disulfanyl-1H,2H,5H,5aH,8H,9aH,10H-pyrano[3,2-g]pteridin-4-olate dihydrate ChemAxon average_mass 521.27 ChemAxon mono_mass 522.891898123 ChemAxon smiles NC1=NC2=C(NC3C(N2)OC(COP(O)(O)=O)C2=C3S[Mo](=O)(=O)S2)C(=O)N1 ChemAxon formula C10H12MoN5O8PS2 ChemAxon inchi InChI=1S/C10H14N5O6PS2.Mo.2O/c11-10-14-7-4(8(16)15-10)12-3-6(24)5(23)2(21-9(3)13-7)1-20-22(17,18)19;;;/h2-3,9,12,23-24H,1H2,(H2,17,18,19)(H4,11,13,14,15,16);;;/q;+2;;/p-2 ChemAxon inchikey HDAJUGGARUFROU-UHFFFAOYSA-L ChemAxon polar_surface_area 174.18 ChemAxon refractivity 119.21 ChemAxon polarizability 34.18 ChemAxon rotatable_bond_count 3 ChemAxon acceptor_count 10 ChemAxon donor_count 7 ChemAxon physiological_charge -2 ChemAxon formal_charge 0 ChemAxon Folate biosynthesis The biosynthesis of folic acid begins with a product of purine nucleotides de novo biosynthesis pathway, GTP. This compound is involved in a reaction with water through a GTP cyclohydrolase 1 protein complex, resulting in a hydrogen ion, formic acid and 7,8-dihydroneopterin 3-triphosphate. The latter compound is dephosphatased through a dihydroneopterin triphosphate pyrophosphohydrolase resulting in the release of a pyrophosphate, hydrogen ion and 7,8-dihydroneopterin 3-phosphate. The latter compound reacts with water spontaneously resulting in the release of a phosphate and a 7,8 -dihydroneopterin. This compound reacts with a dihydroneopterin aldolase, releasing a glycoaldehyde and 6-hydroxymethyl-7,9-dihydropterin. The latter compound is phosphorylated with a ATP-driven 6-hydroxymethyl-7,8-dihydropterin pyrophosphokinase resulting in a (2-amino-4-hydroxy-7,8-dihydropteridin-6-yl)methyl diphosphate. Chorismate is metabolized by reacting with L-glutamine through a 4-amino-4-deoxychorismate synthase resulting in L-glutamic acid and 4-amino-4-deoxychorismate. The latter compound then reacts through an aminodeoxychorismate lyase resulting in pyruvic acid,hydrogen ion and p-aminobenzoic acid. (2-amino-4-hydroxy-7,8-dihydropteridin-6-yl)methyl diphosphate and p-aminobenzoic acid react through a dihydropteroate synthase resulting in pyrophosphate and 7,8-dihydropteroic acid. This compound reacts with L-glutamic acid through an ATP driven bifunctional folylpolyglutamate synthetase / dihydrofolate synthetase resulting in a 7,8-dihydrofolate monoglutamate. This compound is reduced through an NADPH mediated dihydrofolate reductase resulting in a tetrahydrofate. This product goes on to a one carbon pool by folate pathway. PW000908 ec00790 Metabolic Sulfur relay system ec04122 GTP degradation GTP, produced in the nucleotide de novo biosyntheis pathway, interacts with a water molecule through a GTP cyclohydrolase resulting in a formate, hydrogen ion and a 7,8-dihydroneopterin 3'-triphosphate. The latter compound interacts with a water molecule through a dihydroneopterin triphosphate pyrophosphohydrolase resulting in the release of a pyrophosphate, a hydrogen ion and a 7,8-dihydroneopterin 3'-phosphate. The latter compound interacts with water spontaneously resulting in the release of a phosphate and a 7,8 dihydroneopterin. The latter compound interacts with a dihydroneopterin aldolase resulting in the release of a glycolaldehyde and a 6-hydroxymethyl-7,8-dihydropterin. This compound then is then diphosphorylated by reacting with a ATP driven 6-hydroxymethyl-7,8-dihydropterin pyrophosphokinase resulting in the release of a hydrogen ion, an AMP and 6-hydroxymethyl-7,8-dihydropterin diphosphate. GTP interacts with a cyclic pyranopterin monophosphate synthase resulting in the release of a diphosphate and a cyclic pyranopterin phosphate. The latter compound interacts with a thiocarboxylated small subunit of molybdopterin synthase (a protein) and a water molecule through a molybdopterin synthase resulting in the release of 4 hydrogen ions, 2 small subunits of molybdopterin synthase and a molybdopterin. The molybdopterin interacts with an ATP and a hydrogen ion through a molybdopterin adenylyltransferase resulting in the release of a diphosphate and a molybdopterin adenine dinucleotide. PW001888 Metabolic molybdenum cofactor biosynthesis PWY-6823 Specdb::NmrOneD 279218 Specdb::NmrOneD 279219 Specdb::NmrOneD 279220 Specdb::NmrOneD 279221 Specdb::NmrOneD 279222 Specdb::NmrOneD 279223 Specdb::NmrOneD 279224 Specdb::NmrOneD 279225 Specdb::NmrOneD 279226 Specdb::NmrOneD 279227 Specdb::NmrOneD 279228 Specdb::NmrOneD 279229 Specdb::NmrOneD 279230 Specdb::NmrOneD 279231 Specdb::NmrOneD 279232 Specdb::NmrOneD 279233 Specdb::NmrOneD 279234 Specdb::NmrOneD 279235 Specdb::NmrOneD 279236 Specdb::NmrOneD 279237 Specdb::MsMs 28046 Specdb::MsMs 28047 Specdb::MsMs 28048 Specdb::MsMs 34604 Specdb::MsMs 34605 Specdb::MsMs 34606 HMDB02206 446 C05924 21437 CPD-4 Molybdopterin 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 van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. 17765195 Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. 18331064 Molybdopterin synthase sulfur carrier subunit P30748 MOAD_ECOLI moaD http://ecmdb.ca/proteins/P30748.xml Molybdopterin synthase catalytic subunit P30749 MOAE_ECOLI moaE http://ecmdb.ca/proteins/P30749.xml Molybdopterin-guanine dinucleotide biosynthesis protein A P32173 MOBA_ECOLI mobA http://ecmdb.ca/proteins/P32173.xml Molybdopterin molybdenumtransferase P12281 MOEA_ECOLI moeA http://ecmdb.ca/proteins/P12281.xml Molybdopterin-guanine dinucleotide biosynthesis protein B P32125 MOBB_ECOLI mobB http://ecmdb.ca/proteins/P32125.xml Molybdopterin adenylyltransferase P0AF03 MOG_ECOLI mog http://ecmdb.ca/proteins/P0AF03.xml Uncharacterized protein ygfJ Q46810 YGFJ_ECOLI ygfJ http://ecmdb.ca/proteins/Q46810.xml Cyclic pyranopterin monophosphate + Copper + 2 MoaD Protein with thiocarboxylate >5 Hydrogen ion +2 MoaD Protein with carboxylate + Molybdopterin Guanosine triphosphate + Hydrogen ion + Molybdopterin > Molybdopterin guanine dinucleotide + Pyrophosphate Adenosine triphosphate + Hydrogen ion + Molybdopterin <> Adenylated molybdopterin + Pyrophosphate R09726 RXN-8344 Molybdopterin + Adenylated molybdopterin > Adenosine monophosphate + bis-molybdenum cofactor + Copper 2 Hydrogen ion + Molybdate + Adenylated molybdopterin > Adenosine monophosphate + Copper + Water + Molybdopterin Cytidine triphosphate + Hydrogen ion + Molybdopterin > Molybdopterin cytosine dinucleotide + Pyrophosphate Cyclic pyranopterin monophosphate + 2 Sulfur donor <> Molybdopterin R09395 Adenosine triphosphate + Molybdopterin <> Pyrophosphate + Adenylated molybdopterin R09726 Cyclic pyranopterin monophosphate + Water + Thiocarboxylated-MPT-synthases > Molybdopterin + MPT-Synthases RXN-8342 Hydrogen ion + Molybdopterin + Adenosine triphosphate > Adenylated molybdopterin + Pyrophosphate RXN-8344 Guanosine triphosphate + Molybdopterin > Pyrophosphate + Guanylyl molybdenum cofactor Cytidine triphosphate + Molybdopterin > Pyrophosphate + Cytidylyl molybdenum cofactor Adenylyl-molybdopterin + Molybdate > Molybdopterin + Adenosine monophosphate Cyclic pyranopterin monophosphate + Water + thiocarboxylated small subunit of molybdopterin synthase >4 Hydrogen ion +2 thiocarboxylated small subunit of molybdopterin synthase + Molybdopterin + Molybdopterin PW_R005153 Molybdopterin + Adenosine triphosphate + Hydrogen ion + Molybdopterin > Pyrophosphate + Adenylyl-molybdopterin + Adenylyl-molybdopterin PW_R005154 Cyclic pyranopterin monophosphate + 2 Sulfur donor <> Molybdopterin Cyclic pyranopterin monophosphate + 2 Sulfur donor <> Molybdopterin