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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-10-30 10:32:48 UTC
Update Date2022-03-07 03:17:34 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 compounds consist of a dinucleotide that is made up of molybdopterin and a purine or pyrimidine base linked to each other through a phosphate chain. Adenylyl-molybdopterin is a strong basic compound (based on its pKa). Adenylyl-molybdopterin exists in all living organisms, ranging from bacteria to humans. Outside of the human body, adenylyl-molybdopterin has been detected, but not quantified in, several different foods, such as leeks, lichee, winged beans, Japanese pumpkins, and alfalfa. This could make adenylyl-molybdopterin a potential biomarker for the consumption of these foods. Adenylyl-molybdopterin is involved in cofactor biosynthesis and GABAergic synapse pathways. It is a substrate for gephyrin (GPHN).
Structure
Data?1585068420
Synonyms
ValueSource
Adenylated molybdopterinChEBI
MPT-AMPChEBI
Adenylyl-molybdopterinHMDB
H2Dtpp-mADPHMDB
Molybdopterin adenine dinucleotideHMDB
Molybdopterin-AMPHMDB
Chemical FormulaC20H26N10O12P2S2
Average Molecular Weight724.558
Monoisotopic Molecular Weight724.06483075
IUPAC Name{[(5aR,8R,9aR)-2-amino-4-oxo-6,7-disulfanyl-3H,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 Namempt-amp
CAS Registry Number220456-66-6
SMILES
[H][C@]12NC3=C(N[C@@]1([H])C(S)=C(S)[C@@H](COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=NC4=C1N=CN=C4N)O2)C(=O)NC(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
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 Descriptors
Ontology
Disposition

Source

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility2.72 g/LALOGPS
logP-0.63ALOGPS
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
Polarizability60.81 ųChemAxon
Number of Rings6ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M-2H]-224.17730932474
DeepCCS[M+Na]+198.02730932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Adenylyl-molybdopterin[H][C@]12NC3=C(N[C@@]1([H])C(S)=C(S)[C@@H](COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=NC4=C1N=CN=C4N)O2)C(=O)NC(N)=N36761.4Standard polar33892256
Adenylyl-molybdopterin[H][C@]12NC3=C(N[C@@]1([H])C(S)=C(S)[C@@H](COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=NC4=C1N=CN=C4N)O2)C(=O)NC(N)=N34611.7Standard non polar33892256
Adenylyl-molybdopterin[H][C@]12NC3=C(N[C@@]1([H])C(S)=C(S)[C@@H](COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=NC4=C1N=CN=C4N)O2)C(=O)NC(N)=N36880.1Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Adenylyl-molybdopterin GC-MS (Non-derivatized) - 70eV, Positivesplash10-004l-1823920100-5911175052ebcd2a2f0a2017-11-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Adenylyl-molybdopterin GC-MS (TMS_1_1) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Adenylyl-molybdopterin GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Adenylyl-molybdopterin GC-MS (TMS_1_3) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Adenylyl-molybdopterin GC-MS (TMS_1_4) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Adenylyl-molybdopterin GC-MS (TMS_1_5) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Adenylyl-molybdopterin GC-MS (TMS_1_6) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Adenylyl-molybdopterin GC-MS (TMS_1_7) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Adenylyl-molybdopterin GC-MS (TMS_1_8) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Adenylyl-molybdopterin GC-MS (TMS_1_9) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Adenylyl-molybdopterin GC-MS (TMS_1_10) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Adenylyl-molybdopterin GC-MS (TMS_1_11) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Adenylyl-molybdopterin GC-MS (TMS_2_1) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Adenylyl-molybdopterin GC-MS (TMS_2_2) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Adenylyl-molybdopterin GC-MS (TMS_2_3) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Adenylyl-molybdopterin GC-MS (TMS_2_4) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Adenylyl-molybdopterin GC-MS (TMS_2_5) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Adenylyl-molybdopterin GC-MS (TMS_2_6) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Adenylyl-molybdopterin GC-MS (TMS_2_7) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Adenylyl-molybdopterin GC-MS (TMS_2_8) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Adenylyl-molybdopterin GC-MS (TMS_2_9) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Adenylyl-molybdopterin GC-MS (TMS_2_10) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Adenylyl-molybdopterin GC-MS (TMS_2_11) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Adenylyl-molybdopterin GC-MS (TMS_2_12) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Adenylyl-molybdopterin GC-MS (TMS_2_13) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Adenylyl-molybdopterin 10V, Positive-QTOFsplash10-000i-0931101300-ef5fe990b4d92f72e2f22017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Adenylyl-molybdopterin 20V, Positive-QTOFsplash10-000i-0911000000-38808854666917c2a75f2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Adenylyl-molybdopterin 40V, Positive-QTOFsplash10-000i-1910000000-f1aeb75ed8666ee31e042017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Adenylyl-molybdopterin 10V, Negative-QTOFsplash10-0bt9-0690232100-d26fc5b5dd5677413e632017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Adenylyl-molybdopterin 20V, Negative-QTOFsplash10-001i-1910700000-05200ca8c231199998412017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Adenylyl-molybdopterin 40V, Negative-QTOFsplash10-0a7i-3900000000-0b21f3e0e0909cfb10772017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Adenylyl-molybdopterin 10V, Negative-QTOFsplash10-000i-0000009100-473d6e9b2f544c2e1b2d2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Adenylyl-molybdopterin 20V, Negative-QTOFsplash10-00gr-6504409400-abf3abb27e37322aa8052021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Adenylyl-molybdopterin 40V, Negative-QTOFsplash10-0a6r-4904501000-e1a8740b02b1d3b20db52021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Adenylyl-molybdopterin 10V, Positive-QTOFsplash10-004i-0000000900-2c0f1d4b889e0651cf4a2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Adenylyl-molybdopterin 20V, Positive-QTOFsplash10-004s-0545010900-5e72bc431ae7444716b02021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Adenylyl-molybdopterin 40V, Positive-QTOFsplash10-000b-0693000000-ba01ef4aff331fcee6612021-09-22Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
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
FooDB 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
Food Biomarker OntologyNot Available
VMH IDM01281
MarkerDB IDNot Available
Good Scents IDNot Available
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