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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-10-30 10:32:48 UTC
Update Date2017-12-07 15:43:42 UTC
HMDB IDHMDB0059628
Secondary Accession Numbers
  • HMDB59628
Metabolite Identification
Common NameAdenylyl-molybdopterin
DescriptionAdenylyl-molybdopterin, also known as mpt-amp, 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. Adenylyl-molybdopterin is slightly soluble (in water) and a moderately acidic compound (based on its pKa). Outside of the human body, adenylyl-molybdopterin can be found in a number of food items such as teff, tamarind, prairie turnip, and summer savory. This makes adenylyl-molybdopterin a potential biomarker for the consumption of these food products.
Structure
Thumb
Synonyms
ValueSource
Adenylated molybdopterinChEBI
MPT-AMPChEBI
Chemical FormulaC20H26N10O12P2S2
Average Molecular Weight724.558
Monoisotopic Molecular Weight724.06483075
IUPAC Name{[(5aR,8R,9aR)-2-amino-4-oxo-6,7-disulfanyl-1H,4H,5H,5aH,8H,9aH,10H-pyrano[3,2-g]pteridin-8-yl]methoxy}[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]phosphinic acid
Traditional Name[(5aR,8R,9aR)-2-amino-4-oxo-6,7-disulfanyl-1H,5H,5aH,8H,9aH,10H-pyrano[3,2-g]pteridin-8-yl]methoxy({[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy)phosphinic acid
CAS Registry NumberNot Available
SMILES
[H][C@]1(COP(O)(=O)OP(O)(=O)OC[C@H]2O[C@H]([C@H](O)[C@@H]2O)N2C=NC3=C2N=CN=C3N)O[C@@]2([H])NC3=C(N[C@@]2([H])C(S)=C1S)C(=O)N=C(N)N3
InChI Identifier
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)/t5-,6-,7+,10-,11-,18-,19-/m1/s1
InChI KeyXJXFAXLUOKQPAQ-YPRLVJTJSA-N
Chemical Taxonomy
DescriptionThis compound 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 Descriptors
Ontology
Not Available
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility2.72 g/LALOGPS
logP-0.6ALOGPS
logP-6.7ChemAxon
logS-2.6ALOGPS
pKa (Strongest Acidic)1.81ChemAxon
pKa (Strongest Basic)4.97ChemAxon
Physiological Charge-3ChemAxon
Hydrogen Acceptor Count18ChemAxon
Hydrogen Donor Count11ChemAxon
Polar Surface Area322.37 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity169.05 m³·mol⁻¹ChemAxon
Polarizability59.86 ųChemAxon
Number of Rings6ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-004l-1823920100-5911175052ebcd2a2f0aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0931101300-ef5fe990b4d92f72e2f2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0911000000-38808854666917c2a75fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-1910000000-f1aeb75ed8666ee31e04View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0bt9-0690232100-d26fc5b5dd5677413e63View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-1910700000-05200ca8c23119999841View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a7i-3900000000-0b21f3e0e0909cfb1077View in MoNA
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB030654
KNApSAcK IDNot Available
Chemspider ID26332851
KEGG Compound IDC19848
BioCyc IDCPD-8122
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound53356705
PDB IDNot Available
ChEBI ID62728
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Nichols JD, Rajagopalan KV: In vitro molybdenum ligation to molybdopterin using purified components. J Biol Chem. 2005 Mar 4;280(9):7817-22. Epub 2005 Jan 4. [PubMed:15632135 ]

Enzymes

General function:
Involved in Mo-molybdopterin cofactor biosynthetic process
Specific function:
Microtubule-associated protein involved in membrane protein-cytoskeleton interactions. It is thought to anchor the inhibitory glycine receptor (GLYR) to subsynaptic microtubules (By similarity). Catalyzes two steps in the biosynthesis of the molybdenum cofactor. In the first step, molybdopterin is adenylated. Subsequently, molybdate is inserted into adenylated molybdopterin and AMP is released.
Gene Name:
GPHN
Uniprot ID:
Q9NQX3
Molecular weight:
79747.635
Reactions
Adenosine triphosphate + Molybdopterin → Pyrophosphate + Adenylyl-molybdopterindetails
Adenylyl-molybdopterin + Molybdate → Molybdopterin + Adenosine monophosphatedetails