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Record Information
Version3.6
Creation Date2006-08-13 11:13:16 UTC
Update Date2016-02-11 01:06:34 UTC
HMDB IDHMDB04112
Secondary Accession Numbers
  • HMDB11109
Metabolite Identification
Common NameAdenylylselenate
DescriptionAdenylylselenate is an intermediate in selenoamino acid metabolism. Adenylylselenate is produced from selenate via the enzyme sulfate adenylyltransferase [EC:2.7.7.4] and then converted to selenite via the enzyme adenylylsulfate reductase [EC:1.8.99.2]. The reaction between adenylselenate and adenylylsulfate kinase [EC:2.7.1.25] also gives rise to the 3'-Phosphoadenylylselenate.
Structure
Thumb
Synonyms
ValueSource
Adenosine-5'-phosphoselenateChEBI
AdenylylselenateChEBI
Adenosine-5'-phosphoselenic acidGenerator
Adenylylselenic acidHMDB
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 NumberNot Available
SMILES
NC1=C2N=CN([C@@H]3O[C@H](COP(O)(=O)O[Se](O)(=O)=O)[C@@H](O)[C@H]3O)C2=NC=N1
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 KeyInChIKey=XCADVMZZFPIERR-KQYNXXCUSA-N
Chemical Taxonomy
DescriptionThis compound 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
  • N-glycosyl compound
  • Glycosyl compound
  • Monosaccharide phosphate
  • 6-aminopurine
  • Purine
  • Imidazopyrimidine
  • Monoalkyl phosphate
  • Aminopyrimidine
  • Imidolactam
  • Alkyl phosphate
  • Pyrimidine
  • Primary aromatic amine
  • Phosphoric acid ester
  • Organic selenate
  • Organic phosphoric acid derivative
  • Organic phosphate
  • N-substituted imidazole
  • Monosaccharide
  • Saccharide
  • Heteroaromatic compound
  • Oxolane
  • Imidazole
  • Azole
  • Secondary alcohol
  • 1,2-diol
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Hydrocarbon derivative
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Amine
  • Alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot 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 Solubility2.4 mg/mLALOGPS
logP-2.7ALOGPS
logP-5.6ChemAxon
logS-2.3ALOGPS
pKa (Strongest Acidic)1.63ChemAxon
pKa (Strongest Basic)4.99ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count12ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area229.44 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity91.42 m3·mol-1ChemAxon
Polarizability35.4 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-002b-0239400000-9274ba8c2eddcf7cda72View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0903000000-b3aca12b8ccca273290bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-0920000000-f693f982884b4dd43214View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-05ir-0941600000-aff3b2656094a681374eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-003r-3921100000-8a098bd0a058f4100b04View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-056r-9470000000-e126e179315a7f4a03c5View in MoNA
Biological Properties
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationNot Available
Pathways
NameSMPDB LinkKEGG Link
Selenoamino Acid MetabolismSMP00029map00450
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB023314
KNApSAcK IDNot Available
Chemspider ID389628
KEGG Compound IDC05686
BioCyc IDNot Available
BiGG ID46285
Wikipedia LinkNot Available
NuGOwiki LinkHMDB04112
Metagene LinkHMDB04112
METLIN IDNot Available
PubChem Compound440758
PDB IDNot Available
ChEBI ID2485
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