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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2006-08-13 11:13:16 UTC
Update Date2020-07-20 21:11:24 UTC
HMDB IDHMDB0004112
Secondary Accession Numbers
  • HMDB0011109
  • HMDB04112
  • HMDB11109
Metabolite Identification
Common NameAdenylylselenate
DescriptionAdenylylselenate belongs to the class of organic compounds known as purine ribonucleoside monophosphates. These are nucleotides consisting of a purine base linked to a ribose to which one monophosphate group is attached. Adenylylselenate is a strong basic compound (based on its pKa). Adenylylselenate exists in all living organisms, ranging from bacteria to humans. Within humans, adenylylselenate participates in a number of enzymatic reactions. In particular, adenylylselenate can be biosynthesized from selenic acid; which is mediated by the enzyme bifunctional 3'-phosphoadenosine 5'-phosphosulfate synthase 1. In addition, adenylylselenate can be converted into 3-phosphoadenylylselenate; which is catalyzed by the enzyme bifunctional 3'-phosphoadenosine 5'-phosphosulfate synthase 1. In humans, adenylylselenate is involved in selenoamino acid metabolism. Outside of the human body, Adenylylselenate has been detected, but not quantified in, several different foods, such as biscuits, garden cress, common buckwheats, peanuts, and onion-family vegetables. This could make adenylylselenate a potential biomarker for the consumption of these foods. The 5'-selenonooxyphosphate ester of adenosine.
Structure
Data?1595279484
Synonyms
ValueSource
Adenosine-5'-phosphoselenateChEBI
Adenosine-5'-phosphoselenic acidGenerator
Adenylylselenic acidGenerator
APSeHMDB
Adenosine 5'-phosphoselenateHMDB
Adenosine 5’-phosphoselenateHMDB
Adenosine phosphoselenateHMDB
Adenosine-5’-phosphoselenateHMDB
Adenylyl selenateHMDB
Adenylyl-selenateHMDB
AdenylylselenateHMDB
Chemical FormulaC10H14N5O10PSe
Average Molecular Weight474.18
Monoisotopic Molecular Weight474.964350033
IUPAC Name[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]selenonic acid
Traditional Nameadenylylselenate
CAS Registry Number90120-86-8
SMILES
NC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](COP(O)(=O)O[Se](O)(=O)=O)[C@@H](O)[C@H]1O
InChI Identifier
InChI=1S/C10H14N5O10PSe/c11-8-5-9(13-2-12-8)15(3-14-5)10-7(17)6(16)4(24-10)1-23-26(18,19)25-27(20,21)22/h2-4,6-7,10,16-17H,1H2,(H,18,19)(H2,11,12,13)(H,20,21,22)/t4-,6-,7-,10-/m1/s1
InChI KeyXCADVMZZFPIERR-KQYNXXCUSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as purine ribonucleoside monophosphates. These are nucleotides consisting of a purine base linked to a ribose to which one monophosphate group is attached.
KingdomOrganic compounds
Super ClassNucleosides, nucleotides, and analogues
ClassPurine nucleotides
Sub ClassPurine ribonucleotides
Direct ParentPurine ribonucleoside monophosphates
Alternative Parents
Substituents
  • Purine ribonucleoside monophosphate
  • Pentose phosphate
  • Pentose-5-phosphate
  • Glycosyl compound
  • N-glycosyl compound
  • 6-aminopurine
  • Monosaccharide phosphate
  • Pentose monosaccharide
  • Imidazopyrimidine
  • Purine
  • Monoalkyl phosphate
  • Aminopyrimidine
  • Alkyl phosphate
  • Pyrimidine
  • Monosaccharide
  • Imidolactam
  • Phosphoric acid ester
  • N-substituted imidazole
  • Organic selenate
  • Organic phosphoric acid derivative
  • Tetrahydrofuran
  • Heteroaromatic compound
  • Azole
  • Imidazole
  • Secondary alcohol
  • 1,2-diol
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Organic nitrogen compound
  • Organic oxide
  • Organonitrogen compound
  • Organopnictogen compound
  • Organic oxygen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Amine
  • Alcohol
  • Primary amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Process

Naturally occurring process:

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 Solubility2.4 g/LALOGPS
logP-2.7ALOGPS
logP-6.3ChemAxon
logS-2.3ALOGPS
pKa (Strongest Acidic)-3.5ChemAxon
pKa (Strongest Basic)3.94ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count13ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area229.44 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity91.42 m³·mol⁻¹ChemAxon
Polarizability35.23 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-004i-2940000000-8da9fb1061152d8d9cc6Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-004i-4923102000-45ab0e680c1e9cca633aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-002b-0239400000-9274ba8c2eddcf7cda72Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0903000000-b3aca12b8ccca273290bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-0920000000-f693f982884b4dd43214Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-05ir-0941600000-aff3b2656094a681374eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-003r-3921100000-8a098bd0a058f4100b04Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-056r-9470000000-e126e179315a7f4a03c5Spectrum
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 IDFDB023314
KNApSAcK IDNot Available
Chemspider ID389628
KEGG Compound IDC05686
BioCyc IDCPD-13713
BiGG ID46285
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound440758
PDB IDNot Available
ChEBI ID2485
Food Biomarker OntologyNot Available
VMH IDADSEL
MarkerDB ID
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Involved in ATP binding
Specific function:
Bifunctional enzyme with both ATP sulfurylase and APS kinase activity, which mediates two steps in the sulfate activation pathway. The first step is the transfer of a sulfate group to ATP to yield adenosine 5'-phosphosulfate (APS), and the second step is the transfer of a phosphate group from ATP to APS yielding 3'-phosphoadenylylsulfate (PAPS: activated sulfate donor used by sulfotransferase). In mammals, PAPS is the sole source of sulfate; APS appears to be only an intermediate in the sulfate-activation pathway. Also involved in the biosynthesis of sulfated L-selectin ligands in endothelial cells.
Gene Name:
PAPSS1
Uniprot ID:
O43252
Molecular weight:
70832.725
Reactions
Adenosine triphosphate + Adenylylselenate → ADP + 3-Phosphoadenylylselenatedetails
Adenosine triphosphate + Selenocystathionine → Pyrophosphate + Adenylylselenatedetails
General function:
Involved in ATP binding
Specific function:
Bifunctional enzyme with both ATP sulfurylase and APS kinase activity, which mediates two steps in the sulfate activation pathway. The first step is the transfer of a sulfate group to ATP to yield adenosine 5'-phosphosulfate (APS), and the second step is the transfer of a phosphate group from ATP to APS yielding 3'-phosphoadenylylsulfate (PAPS: activated sulfate donor used by sulfotransferase). In mammals, PAPS is the sole source of sulfate; APS appears to be only an intermediate in the sulfate-activation pathway. May have a important role in skeletogenesis during postnatal growth (By similarity).
Gene Name:
PAPSS2
Uniprot ID:
O95340
Molecular weight:
69969.8
Reactions
Adenosine triphosphate + Adenylylselenate → ADP + 3-Phosphoadenylylselenatedetails
Adenosine triphosphate + Selenocystathionine → Pyrophosphate + Adenylylselenatedetails