Molybdopterin guanine dinucleotide (PAMDB001121)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 12:54:54 PM
Metabolite IDPAMDB001121
Identification
Name: Molybdopterin guanine dinucleotide
Description:Molybdopterin guanine dinucleotide is a member of the chemical class known as Purine Ribonucleoside Diphosphates. These are purine ribobucleotides with diphosphate group linked to the ribose moiety. It appears that the molybdopterin present in the nitrate reductase of a chlB mutant is converted to molybdopterin guanine dinucleotide during activation. (PMID 1459941) We propose therefore that MobB is an adapter protein that acts in concert with MobA to achieve the efficient biosynthesis and utilization of molybdopterin guanine dinucleotide. (PMID 12682065)
Structure
Thumb
🔍MOLSDFPDBSMILESInChIView Structure
Synonyms:
  • bis-molybdopterin guanine dinucleotide
  • Bis-molybdopterin guanine dinucleotide
  • MGD
  • Molybdopterin guanine dinucleotide
  • Molybdopteringuaninedinucleotide
  • MoO2(OH)Dtpp-mGDP
  • MoO2(OH)Dtpp-mGDP
  • MPT-GMP
Chemical Formula: C20H24N10O13P2S2
Average Molecular Weight: 738.541
Monoisotopic Molecular Weight: 738.044095308
InChI Key: MNEQOJMCKOBWNR-UHFFFAOYSA-N
InChI:InChI=1S/C20H24N10O13P2S2/c21-19-26-14-8(16(34)28-19)25-5(1-23-14)12(46)13(47)6(31)2-40-44(36,37)43-45(38,39)41-3-7-10(32)11(33)18(42-7)30-4-24-9-15(30)27-20(22)29-17(9)35/h1,4,6-7,10-11,18,25,31-33H,2-3H2,(H,36,37)(H,38,39)(H3,22,27,29,35)(H4,21,23,26,28,34)
CAS number: 128007-95-4
IUPAC Name:[({[3,4-dihydroxy-5-(6-hydroxy-2-imino-3,9-dihydro-2H-purin-9-yl)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy][2-hydroxy-4-(4-hydroxy-2-imino-1,2,5,8-tetrahydropteridin-6-yl)-3,4-disulfanylidenebutoxy]phosphinic acid
Traditional IUPAC Name: {[3,4-dihydroxy-5-(6-hydroxy-2-imino-3H-purin-9-yl)oxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(2-hydroxy-4-(4-hydroxy-2-imino-5,8-dihydro-1H-pteridin-6-yl)-3,4-disulfanylidenebutoxy)phosphinic acid
SMILES:OC(COP(O)(=O)OP(O)(=O)OCC1OC(C(O)C1O)N1C=NC2=C1NC(=N)N=C2O)C(=S)C(=S)C1=CNC2=C(N1)C(O)=NC(=N)N2
Chemical Taxonomy
Taxonomy DescriptionThis compound belongs to the class of organic compounds known as purine ribonucleoside diphosphates. These are purine ribobucleotides with diphosphate group linked to the ribose moiety.
Kingdom Organic compounds
Super ClassNucleosides, nucleotides, and analogues
Class Purine nucleotides
Sub ClassPurine ribonucleotides
Direct Parent Purine ribonucleoside diphosphates
Alternative Parents
Substituents
  • Purine ribonucleoside diphosphate
  • Pterin
  • N-glycosyl compound
  • Glycosyl compound
  • Pteridine
  • Organic pyrophosphate
  • Monosaccharide phosphate
  • Purine
  • Imidazopyrimidine
  • Hydroxypyrimidine
  • Monoalkyl phosphate
  • Alkyl phosphate
  • Pyrimidine
  • Phosphoric acid ester
  • Organic phosphoric acid derivative
  • Organic phosphate
  • N-substituted imidazole
  • Monosaccharide
  • Saccharide
  • Heteroaromatic compound
  • Oxolane
  • Imidazole
  • Azole
  • Thioketone
  • Secondary alcohol
  • 1,2-diol
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Hydrocarbon derivative
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Amine
  • Alcohol
  • Aromatic heteropolycyclic compound
Molecular Framework Aromatic heteropolycyclic compounds
External Descriptors Not Available
Physical Properties
State: Not Available
Charge:-1
Melting point: Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility0.246 mg/mLALOGPS
logP-0.46ALOGPS
logP-3ChemAxon
logS-3.5ALOGPS
pKa (Strongest Acidic)-4.5ChemAxon
pKa (Strongest Basic)15ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count19ChemAxon
Hydrogen Donor Count13ChemAxon
Polar Surface Area351.03 Å2ChemAxon
Rotatable Bond Count12ChemAxon
Refractivity195.57 m3·mol-1ChemAxon
Polarizability64.66 Å3ChemAxon
Number of Rings5ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Cytoplasm
Reactions:
Guanosine triphosphate + Hydrogen ion + Molybdopterin > Molybdopterin guanine dinucleotide + Pyrophosphate
Hydrogen ion + molybdenum cofactor + Guanosine triphosphate <> Molybdopterin guanine dinucleotide + Pyrophosphate
Pathways: Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0930100400-d7d4d0a58c184123438bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0911000000-1fdeb76e4ff24e3c3b47View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-2920000000-95390e018955c5db8898View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udr-0610311900-9228ca763e6b55205fb0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-1920200000-6a75b94d4c73e6089e93View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0pdi-3900000000-6295a32e18f9af17c4c4View in MoNA
References
References:
  • 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
  • McLuskey, K., Harrison, J. A., Schuttelkopf, A. W., Boxer, D. H., Hunter, W. N. (2003). "Insight into the role of Escherichia coli MobB in molybdenum cofactor biosynthesis based on the high resolution crystal structure." J Biol Chem 278:23706-23713. Pubmed: 12682065
  • Santini, C. L., Iobbi-Nivol, C., Romane, C., Boxer, D. H., Giordano, G. (1992). "Molybdoenzyme biosynthesis in Escherichia coli: in vitro activation of purified nitrate reductase from a chlB mutant." J Bacteriol 174:7934-7940. Pubmed: 1459941
  • 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
Synthesis Reference: Not Available
Material Safety Data Sheet (MSDS) Not Available
External Links:
ResourceLink
CHEBI ID30404
HMDB IDNot Available
Pubchem Compound ID5486686
Kegg IDNot Available
ChemSpider ID4589022
Wikipedia IDNot Available
BioCyc IDCPD-582
EcoCyc IDCPD-582

Enzymes

Protein Details
• Molybdopterin-guanine dinucleotide biosynthesis protein A
General function:
Involved in catalytic activity
Specific function:
Links a guanosine 5'-phosphate to molydopterin (MPT) forming molybdopterin guanine dinucleotide (MGD)
Gene Name:
mobA
Locus Tag:
PA3030
Molecular weight:
21.9 kDa
Reactions
GTP + molybdenum cofactor = diphosphate + guanylyl molybdenum cofactor.