Record Information
Version2.0
Creation Date2012-05-31 13:56:01 -0600
Update Date2015-09-17 15:41:15 -0600
Secondary Accession Numbers
  • ECMDB02206
Identification
Name:Molybdopterin
DescriptionMolybdopterins 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
Structure
Thumb
Synonyms:
  • 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
Chemical Formula:C10H12MoN5O8PS2
Weight:Average: 521.27
Monoisotopic: 522.891898123
InChI Key:HDAJUGGARUFROU-UHFFFAOYSA-L
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
CAS number:73508-07-3
IUPAC Name:molybdenum(2+) ion (5aR,8R,9aR)-8-[(hydrogen phosphonatooxy)methyl]-2-imino-6,7-disulfanyl-1H,2H,5H,5aH,8H,9aH,10H-pyrano[3,2-g]pteridin-4-olate dihydrate
Traditional IUPAC Name:molybdenum(2+) ion (5aR,8R,9aR)-8-[(hydrogen phosphonatooxy)methyl]-2-imino-6,7-disulfanyl-1H,5H,5aH,8H,9aH,10H-pyrano[3,2-g]pteridin-4-olate dihydrate
SMILES:NC1=NC2=C(NC3C(N2)OC(COP(O)(O)=O)C2=C3S[Mo](=O)(=O)S2)C(=O)N1
Chemical Taxonomy
Description belongs to the class of organic compounds known as pyranopterins and derivatives. These are pterin derivatives in which a pyran ring is fused either to the pyrimidine ring or the pyrazine ring of the pterin moiety.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassPteridines and derivatives
Sub ClassPterins and derivatives
Direct ParentPyranopterins and derivatives
Alternative Parents
Substituents
  • Pyranopterin
  • Secondary aliphatic/aromatic amine
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Pyran
  • Pyrimidine
  • Alkyl phosphate
  • Heteroaromatic compound
  • Alkylthiol
  • Oxacycle
  • Secondary amine
  • Thioenol
  • Azacycle
  • Organic transition metal salt
  • Amine
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Organosulfur compound
  • Organic nitrogen compound
  • Organonitrogen compound
  • Organic zwitterion
  • Organic salt
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Physical Properties
State:Not Available
Charge:-2
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility0.98 g/LALOGPS
logP0.86ALOGPS
logP-1.9ChemAxon
logS-2.7ALOGPS
pKa (Strongest Acidic)1.19ChemAxon
pKa (Strongest Basic)2.91ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area174.18 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity119.21 m³·mol⁻¹ChemAxon
Polarizability33.04 ųChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
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
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
Adenosine triphosphate + Molybdopterin <> Pyrophosphate + Adenylated molybdopterin
Cyclic pyranopterin monophosphate + Water + Thiocarboxylated-MPT-synthases > Molybdopterin + MPT-Synthases
Hydrogen ion + Molybdopterin + Adenosine triphosphate > Adenylated molybdopterin + Pyrophosphate
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
Molybdopterin + Adenosine triphosphate + Hydrogen ion + Molybdopterin > Pyrophosphate + Adenylyl-molybdopterin + Adenylyl-molybdopterin
Cyclic pyranopterin monophosphate + 2 Sulfur donor <> Molybdopterin
Cyclic pyranopterin monophosphate + 2 Sulfur donor <> Molybdopterin
SMPDB Pathways:
Folate biosynthesisPW000908 ThumbThumb?image type=greyscaleThumb?image type=simple
GTP degradationPW001888 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:
EcoCyc Pathways:
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0001490000-bf4dfec34731bf10ebadView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-1606490000-e83ef8869348bf49af28View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-020r-4982200000-b29a94b7f07e6ea22651View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-05e9-9606040000-926bcbb9296f4a9cd5e0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9101010000-2dd652c6c798de5919fbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-58324c83b689024dc935View in MoNA
References
References:
  • 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. Pubmed: 22080510
  • 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. Pubmed: 21097882
  • 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. Pubmed: 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. Pubmed: 18331064
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI ID21437
HMDB IDHMDB02206
Pubchem Compound ID131750325
Kegg IDC05924
ChemSpider ID446
WikipediaMolybdopterin
BioCyc IDCPD-4
EcoCyc IDCPD-4

Enzymes

General function:
Involved in Mo-molybdopterin cofactor biosynthetic process
Specific function:
Involved in sulfur transfer in the conversion of molybdopterin precursor Z to molybdopterin
Gene Name:
moaD
Uniprot ID:
P30748
Molecular weight:
8758
General function:
Involved in Mo-molybdopterin cofactor biosynthetic process
Specific function:
Converts molybdopterin precursor Z to molybdopterin. This requires the incorporation of two sulfur atoms into precursor Z to generate a dithiolene group. The sulfur is provided by moaD
Gene Name:
moaE
Uniprot ID:
P30749
Molecular weight:
16981
Reactions
Cyclic pyranopterin monophosphate + 2 [molybdopterin-synthase sulfur-carrier protein]-Gly-NH-CH(2)-C(O)SH + H(2)O = molybdopterin + 2 [molybdopterin-synthase sulfur-carrier protein].
General function:
Involved in catalytic activity
Specific function:
Links a guanosine 5'-phosphate to molydopterin (MPT) forming molybdopterin guanine dinucleotide (MGD)
Gene Name:
mobA
Uniprot ID:
P32173
Molecular weight:
21643
Reactions
GTP + molybdenum cofactor = diphosphate + guanylyl molybdenum cofactor.
General function:
Involved in Mo-molybdopterin cofactor biosynthetic process
Specific function:
Catalyzes the insertion of molybdate into adenylated molybdopterin with the concomitant release of AMP
Gene Name:
moeA
Uniprot ID:
P12281
Molecular weight:
44067
Reactions
Adenylyl-molybdopterin + molybdate = molybdenum cofactor + AMP.
General function:
Involved in GTP binding
Specific function:
May bind the guanine nucleotide required for the synthesis of molybdopterin guanine dinucleotide
Gene Name:
mobB
Uniprot ID:
P32125
Molecular weight:
19363
General function:
Involved in Mo-molybdopterin cofactor biosynthetic process
Specific function:
Catalyzes the adenylation of molybdopterin as part of the biosynthesis of the molybdenum-cofactor
Gene Name:
mog
Uniprot ID:
P0AF03
Molecular weight:
21222
Reactions
ATP + molybdopterin = diphosphate + adenylyl-molybdopterin.
General function:
Involved in cytidylyltransferase activity
Specific function:
Specific function unknown
Gene Name:
ygfJ
Uniprot ID:
Q46810
Molecular weight:
21514
Reactions
CTP + molybdenum cofactor = diphosphate + cytidylyl molybdenum cofactor.