Cyclic pyranopterin monophosphate (PAMDB001401)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 11:54:54 AM
Metabolite IDPAMDB001401
Identification
Name: Cyclic pyranopterin monophosphate
Description:Cyclic pyranopterin monophosphate is a member of the chemical class known as Pterins and Derivatives. These are polycyclic aromatic compounds containing a pterin moeity, which consist of a pteridine ring bearing a ketone and an amine group to form 2-aminopteridin-4(3H)-one. cPMP is a precursor to molybdenum cofactor, which is required for the enyzme activity of sulfite oxidase, xanthine dehydrogenase/oxidase and aldehyde oxidase. The transition element molybdenum (Mo) has been long known as an essential micronutrient across the kingdoms of plants, animals, fungi and bacteria. However, molybdate itself is catalytically inactive and, with the exception of bacterial nitrogenase, needs to be activated through complexation by a special cofactor. There are several molybdenum cofactors, including molybdopterin (MPT), guanylyl molybdenum cofactor (MGD), cytidylyl molybdenum cofactor, or others. In Pseudomonas aeruginosa, the MoaD protein plays a central role in the conversion of precursor Z to molybdopterin (MPT) during molybdenum cofactor biosynthesis. (PMID 17223713) In Pseudomonas aeruginosa, MPT is formed by incorporation of two sulfur atoms into precursor Z, which is catalyzed by MPT synthase. (PMID 11459846)
Structure
Thumb
🔍MOLSDFPDBSMILESInChIView Structure
Synonyms:
  • 8-Amino-2,12,12-trihydroxy-4,4a,5a,6,9,10,11,11a,12,12a-decahydro-[1,3,2]dioxaphosphinino[4',5':5,6]pyrano[3,2-g]pteridine 2-oxide
  • 8-Amino-2,12,12-trihydroxy-4a,5a,6,9,11,11a,12,12a-octahydro[1,3,2]dioxaphosphinino[4',5':5,6]pyrano[3,2-g]pteridin-10(4H)-one 2-oxide
  • CPMP
  • Cyclic pyranopterin monophosphate
  • Cyclic pyranopterin monophosphoric acid
  • Precursor z
  • Precursor-Z
Chemical Formula: C10H14N5O8P
Average Molecular Weight: 363.2206
Monoisotopic Molecular Weight: 363.057998961
InChI Key: CZAKJJUNKNPTTO-AJFJRRQVSA-N
InChI:InChI=1S/C10H14N5O8P/c11-9-14-6-3(7(16)15-9)12-4-8(13-6)22-2-1-21-24(19,20)23-5(2)10(4,17)18/h2,4-5,8,12,17-18H,1H2,(H,19,20)(H4,11,13,14,15,16)/t2-,4-,5+,8-/m1/s1
CAS number: Not Available
IUPAC Name:(4aR,5aR,11aR,12aS)-2,10,12,12-tetrahydroxy-8-imino-4,4a,5a,6,7,8,11,11a,12,12a-decahydro-2H-1,3,5-trioxa-6,7,9,11-tetraaza-2???phosphatetracen-2-one
Traditional IUPAC Name: (4aR,5aR,11aR,12aS)-2,10,12,12-tetrahydroxy-8-imino-4,4a,5a,6,7,11,11a,12a-octahydro-1,3,5-trioxa-6,7,9,11-tetraaza-2???phosphatetracen-2-one
SMILES:[H][C@@]12COP(O)(=O)O[C@]1([H])C(O)(O)[C@]1([H])NC3=C(NC(=N)N=C3O)N[C@]1([H])O2
Chemical Taxonomy
Taxonomy DescriptionThis compound 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.
Kingdom Organic compounds
Super ClassOrganoheterocyclic compounds
Class Pteridines and derivatives
Sub ClassPterins and derivatives
Direct Parent Pyranopterins and derivatives
Alternative Parents
Substituents
  • Pyranopterin
  • Hydroxypyrimidine
  • Secondary aliphatic/aromatic amine
  • Pyrimidine
  • Oxane
  • Organic phosphoric acid derivative
  • Organic phosphate
  • Monosaccharide
  • Heteroaromatic compound
  • Polyol
  • Oxacycle
  • Azacycle
  • 1,1-diol
  • Secondary amine
  • Carbonyl hydrate
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Amine
  • Aromatic heteropolycyclic compound
Molecular Framework Aromatic heteropolycyclic compounds
External Descriptors
Physical Properties
State: Not Available
Charge:0
Melting point: Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility9.05 mg/mLALOGPS
logP-2ALOGPS
logP-5.3ChemAxon
logS-1.6ALOGPS
pKa (Strongest Acidic)-13ChemAxon
pKa (Strongest Basic)15ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count11ChemAxon
Hydrogen Donor Count8ChemAxon
Polar Surface Area197.98 Å2ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity93.04 m3·mol-1ChemAxon
Polarizability29.91 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Cytoplasm
Reactions:
Guanosine triphosphate + Water <> Cyclic pyranopterin monophosphate + Pyrophosphate
Cyclic pyranopterin monophosphate + Copper + 2 MoaD Protein with thiocarboxylate >5 Hydrogen ion +2 MoaD Protein with carboxylate + Molybdopterin
Cyclic pyranopterin monophosphate + 2 Sulfur donor <> Molybdopterin
Guanosine triphosphate > Cyclic pyranopterin monophosphate + Pyrophosphate
Cyclic pyranopterin monophosphate + Water + Thiocarboxylated-MPT-synthases > Molybdopterin + MPT-Synthases
Guanosine triphosphate > Cyclic pyranopterin monophosphate + Pyrophosphate
Cyclic pyranopterin monophosphate + Water + thiocarboxylated small subunit of molybdopterin synthase >4 Hydrogen ion +2 thiocarboxylated small subunit of molybdopterin synthase + Molybdopterin + Molybdopterin
Pathways:
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0009000000-409073732cecfccd1306View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01qa-1069000000-41d8aad4b65debf6b22fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0560-5970000000-c418a7d872c8d58d4e1fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-1749000000-d08212ceb7e994db0f40View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-0900000000-3b25595e096bedd044e0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0059-9200000000-90cd7a3b87256a3d7e40View in MoNA
References
References:
  • Gutzke, G., Fischer, B., Mendel, R. R., Schwarz, G. (2001). "Thiocarboxylation of molybdopterin synthase provides evidence for the mechanism of dithiolene formation in metal-binding pterins." J Biol Chem 276:36268-36274. Pubmed: 11459846
  • 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
  • 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 ID60210
HMDB IDHMDB59639
Pubchem Compound ID25202908
Kegg IDC18239
ChemSpider ID17221217
Wikipedia IDNot Available
BioCyc IDPRECURSOR-Z
EcoCyc IDPRECURSOR-Z

Enzymes

Protein Details
• Molybdopterin synthase sulfur carrier subunit
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
Locus Tag:
PA3917
Molecular weight:
9.2 kDa
Protein Details
• Molybdopterin synthase catalytic subunit
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
Locus Tag:
PA3916
Molecular weight:
16.7 kDa
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].
Protein Details
• Molybdenum cofactor biosynthesis protein C
General function:
Involved in Mo-molybdopterin cofactor biosynthetic process
Specific function:
Together with moaA, is involved in the conversion of a guanosine derivative (5'-GTP) into molybdopterin precursor Z
Gene Name:
moaC
Locus Tag:
PA3918
Molecular weight:
17.3 kDa