Adenylated molybdopterin (ECMDB21307) (M2MDB001711)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes (2)XML
Proteins (646)
Record Information
Version2.0
Creation Date2012-07-30 14:55:16 -0600
Update Date2015-06-03 17:21:08 -0600
Secondary Accession Numbers
  • ECMDB21307
Identification
Name:Adenylated molybdopterin
DescriptionAdenylated molybdopterin is a member of the chemical class known as Purine Ribonucleoside Diphosphates. These are purine ribobucleotides with diphosphate group linked to the ribose moiety. MPT-AMP is the reaction product of Cnx1G. Catalytically inactive Cnx1G mutant variants showed impaired MPT adenylation confirming that MPT-AMP is the reaction product of Cnx1G. (PMID 15504727)
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms:
  • 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]methoxy}(hydroxy)phosphoryl]oxy}(hydroxy)phosphoryl]adenosine
  • 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]methoxy}(hydroxy)phosphoryl]oxy}(hydroxy)phosphoryl]adenosine
  • Adenylated molybdopterin
  • Adenylyl-molybdopterin
  • H2Dtpp-mADP
  • Molybdopterin-AMP
  • MPT-AMP
Chemical Formula:C20H26N10O12P2S2
Weight:Average: 724.558
Monoisotopic: 724.06483075
InChI Key:XJXFAXLUOKQPAQ-UHFFFAOYSA-N
InChI:InChI=1S/C20H26N10O12P2S2/c21-14-8-16(24-3-23-14)30(4-25-8)19-11(32)10(31)5(41-19)1-38-43(34,35)42-44(36,37)39-2-6-12(45)13(46)7-18(40-6)27-15-9(26-7)17(33)29-20(22)28-15/h3-7,10-11,18-19,26,31-32,45-46H,1-2H2,(H,34,35)(H,36,37)(H2,21,23,24)(H4,22,27,28,29,33)
CAS number:Not Available
IUPAC Name:({2-amino-4-oxo-6,7-disulfanyl-3H,4H,5H,5aH,8H,9aH,10H-pyrano[3,2-g]pteridin-8-yl}methoxy)[({[5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]phosphinic acid
Traditional IUPAC Name:{2-amino-4-oxo-6,7-disulfanyl-3H,5H,5aH,8H,9aH,10H-pyrano[3,2-g]pteridin-8-yl}methoxy({[5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy)phosphinic acid
SMILES:NC1=NC2=C(NC3C(N2)OC(COP(O)(=O)OP(O)(=O)OCC2OC(C(O)C2O)N2C=NC4=C2N=CN=C4N)C(S)=C3S)C(=O)N1
Chemical Taxonomy
Description belongs to the class of organic compounds known as molybdopterin dinucleotides. These are a dinucleotide that is made up of a molybdopterin and a purine or pyrimidine base linked to each other through a phosphate chain.
KingdomOrganic compounds
Super ClassNucleosides, nucleotides, and analogues
ClassMolybdopterin dinucleotides
Sub ClassNot Available
Direct ParentMolybdopterin dinucleotides
Alternative Parents
Substituents
  • Molybdopterin dinucleotide
  • Purine ribonucleoside diphosphate
  • Molybdopterin
  • Purine ribonucleoside monophosphate
  • Pentose phosphate
  • Pentose-5-phosphate
  • Pyranopterin
  • Pterin
  • Glycosyl compound
  • N-glycosyl compound
  • 6-aminopurine
  • Monosaccharide phosphate
  • Organic pyrophosphate
  • Pentose monosaccharide
  • Pteridine
  • Imidazopyrimidine
  • Purine
  • Secondary aliphatic/aromatic amine
  • Pyrimidone
  • Aminopyrimidine
  • Monoalkyl phosphate
  • Monosaccharide
  • N-substituted imidazole
  • Pyrimidine
  • Pyran
  • Organic phosphoric acid derivative
  • Alkyl phosphate
  • Imidolactam
  • Phosphoric acid ester
  • Tetrahydrofuran
  • Imidazole
  • Azole
  • Heteroaromatic compound
  • Vinylogous amide
  • 1,2-diol
  • Secondary alcohol
  • Azacycle
  • Secondary amine
  • Thioenol
  • Oxacycle
  • Alkylthiol
  • Organoheterocyclic compound
  • Amine
  • Organopnictogen compound
  • Alcohol
  • Organic oxygen compound
  • Organic nitrogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Organosulfur compound
  • Organic oxide
  • Hydrocarbon derivative
  • Primary amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Physical Properties
State:Not Available
Charge:-3
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility2.72 g/LALOGPS
logP-0.36ALOGPS
logP-5.5ChemAxon
logS-2.4ALOGPS
pKa (Strongest Acidic)1.85ChemAxon
pKa (Strongest Basic)4.01ChemAxon
Physiological Charge-3ChemAxon
Hydrogen Acceptor Count17ChemAxon
Hydrogen Donor Count11ChemAxon
Polar Surface Area322.37 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity169.25 m³·mol⁻¹ChemAxon
Polarizability62.78 ųChemAxon
Number of Rings6ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
Adenosine triphosphate + Hydrogen ion + Molybdopterin <> Adenylated molybdopterin + Pyrophosphate
Molybdopterin + Adenylated molybdopterin > Adenosine monophosphate + bis-molybdenum cofactor + Copper
Adenylated molybdopterin + tungsten binding cofactor > Adenosine monophosphate + tungsten bispterin cofactor + Copper
2 Hydrogen ion + Molybdate + Adenylated molybdopterin > Adenosine monophosphate + Copper + Water + Molybdopterin
2 Hydrogen ion + Adenylated molybdopterin + Tungstate > Adenosine monophosphate + Copper + Water + tungsten binding cofactor
Adenosine triphosphate + Molybdopterin <> Pyrophosphate + Adenylated molybdopterin
Adenylated molybdopterin + Molybdate <> Molybdoenzyme molybdenum cofactor + Adenosine monophosphate + Water + Molybdoenzyme molybdenum cofactor
Hydrogen ion + Molybdopterin + Adenosine triphosphate > Adenylated molybdopterin + Pyrophosphate
Adenylated molybdopterin + Molybdate > molybdenum cofactor + Adenosine monophosphate + Water
SMPDB Pathways:Not Available
KEGG Pathways:
EcoCyc Pathways:
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-004l-1723920100-bb1613d2f84a938b7a7eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0931101300-8d586fe7752001dd24cbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0911000000-b051063e6b7a0a63f1f6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-1910000000-34bc9592e93856ccd5c2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-08n9-1790232100-43f0c1f38049a8fdaf61View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-0910600000-682c0ffebbb9af7a0134View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a7i-3900000000-6aece1e85f04e32c2771View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0001000900-ffa1a59ff1824e74917aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-002b-0393011600-d5404022df3e8fd231bfView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-0923000000-b412c4768c1614066341View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0000002900-a1df204dd3a6582fbd67View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00gr-9502308500-32959dd120e465001372View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-4905805200-c9d6b2442ad99b0bcf05View in MoNA
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
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
  • Llamas, A., Mendel, R. R., Schwarz, G. (2004). "Synthesis of adenylated molybdopterin: an essential step for molybdenum insertion." J Biol Chem 279:55241-55246. Pubmed: 15504727
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI ID62728
HMDB IDHMDB0012262
Pubchem Compound ID25245677
Kegg IDC19848
ChemSpider ID35032425
Wikipedia IDNot Available
BioCyc IDCPD-8122
EcoCyc IDCPD-8122

Enzymes

Protein Details
1. Molybdopterin molybdenumtransferase
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.
Protein Details
2. Molybdopterin adenylyltransferase
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.