Showing metabocard for Adenosine phosphosulfate (BMDB0001003)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (2) Show 2 proteinsXML
Record Information
Version1.0
Creation Date2016-09-30 22:39:44 UTC
Update Date2020-05-21 16:28:36 UTC
BMDB IDBMDB0001003
Secondary Accession Numbers
  • BMDB01003
Metabolite Identification
Common NameAdenosine phosphosulfate
DescriptionAdenosine phosphosulfate, also known as adenylylsulfate or adenosine sulfatophosphate, 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. Adenosine phosphosulfate is a strong basic compound (based on its pKa). Adenosine phosphosulfate exists in all living species, ranging from bacteria to humans. Within cattle, adenosine phosphosulfate participates in a number of enzymatic reactions. In particular, adenosine phosphosulfate can be biosynthesized from sulfate through its interaction with the enzyme bifunctional 3'-phosphoadenosine 5'-phosphosulfate synthase 2. In addition, adenosine phosphosulfate can be converted into phosphoadenosine phosphosulfate; which is catalyzed by the enzyme bifunctional 3'-phosphoadenosine 5'-phosphosulfate synthase 2. In cattle, adenosine phosphosulfate is involved in the metabolic pathway called the sulfate/sulfite metabolism pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
Adenosine 5'-phosphosulfateChEBI
ADENOSINE-5'-phosphosulfATEChEBI
AdenylylsulfateChEBI
APSChEBI
5'-Adenylyl sulfateKegg
Adenosine 5'-phosphosulfuric acidGenerator
Adenosine 5'-phosphosulphateGenerator
Adenosine 5'-phosphosulphuric acidGenerator
ADENOSINE-5'-phosphosulfuric acidGenerator
ADENOSINE-5'-phosphosulphateGenerator
ADENOSINE-5'-phosphosulphuric acidGenerator
Adenylylsulfuric acidGenerator
AdenylylsulphateGenerator
Adenylylsulphuric acidGenerator
5'-Adenylyl sulfuric acidGenerator
5'-Adenylyl sulphateGenerator
5'-Adenylyl sulphuric acidGenerator
Adenosine phosphosulfuric acidGenerator
Adenosine phosphosulphateGenerator
Adenosine phosphosulphuric acidGenerator
Adenosine 5'-sulphatophosphateHMDB
Adenosine sulfatophosphateHMDB
Adenylic acid monoanhydride with sulfurateHMDB
Adenylic acid monoanhydride with sulfuric acidHMDB
Adenylyl sulfateHMDB
Adenylyl sulphateHMDB
Adenylyl-sulfateHMDB
Adenylyl-sulphateHMDB
AMPSHMDB
PhosphosulfateHMDB
PhosphosulphateHMDB
SulfatophosphateHMDB
5'-Phosphosulfate, adenosineHMDB
Adenosine 5' phosphosulfateHMDB
Phospho adenylsulfateHMDB
Phospho-adenylsulfateHMDB
Phosphosulfate, adenosineHMDB
Sulfate, adenylylHMDB
5’-Adenylyl sulfateHMDB
5’-Adenylyl sulphateHMDB
Adenosine 5'-monophosphosulfateHMDB
Adenosine 5'-monophosphosulphateHMDB
Adenosine 5'-sulfatophosphateHMDB
Adenosine 5’-monophosphosulfateHMDB
Adenosine 5’-monophosphosulphateHMDB
Adenosine 5’-phosphosulfateHMDB
Adenosine 5’-phosphosulphateHMDB
Adenosine 5’-sulfatophosphateHMDB
Chemical FormulaC10H14N5O10PS
Average Molecular Weight427.284
Monoisotopic Molecular Weight427.019898895
IUPAC Name[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]sulfonic acid
Traditional Nameadenosine phosphosulfate
CAS Registry Number485-84-7
SMILES
NC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](COP(O)(=O)OS(O)(=O)=O)[C@@H](O)[C@H]1O
InChI Identifier
InChI=1S/C10H14N5O10PS/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 KeyIRLPACMLTUPBCL-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 phosphoric acid derivative
  • Tetrahydrofuran
  • Heteroaromatic compound
  • Azole
  • Imidazole
  • Organic sulfuric acid or derivatives
  • 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
StatusExpected but not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-1.6ALOGPS
logP-5.6ChemAxon
logS-2.1ALOGPS
pKa (Strongest Acidic)-2.3ChemAxon
pKa (Strongest Basic)3.94ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count12ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area229.44 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity84.06 m³·mol⁻¹ChemAxon
Polarizability35.07 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
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, Positivesplash10-004i-2911100000-c7b3ba6ec47b4fb3e832View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-055b-7693530000-45cc4add4821e6fea5efView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0912300000-29cd6f42fa9d4c6c4455View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0901000000-018ae7ee1fc1b662ec07View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-1900000000-861a01467a0191dcd31aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0059-0901600000-785b903b29133cefd0bcView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-003r-3900000000-d2245ba9a6f6bf6d0217View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-056r-9700000000-3f4588ade18801775becView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0200900000-b10f97ec4ef8bff7823cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0911000000-4563fb5a2cb7fd85ab98View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-0900000000-5a937b62fdf69d198700View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0100900000-a398ce6fc250a971f068View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-056r-6900300000-d9d41d4bc70263df8221View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004j-9200000000-979bc3001281c5d76962View in MoNA
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Not AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Fibroblasts
  • Pancreas
  • Platelet
  • Prostate Tissue
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FibroblastsExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
PancreasExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
PlateletExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
Prostate TissueExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0001003
DrugBank IDDB03708
Phenol Explorer Compound IDNot Available
FooDB IDFDB022362
KNApSAcK IDC00007445
Chemspider ID9821
KEGG Compound IDC00224
BioCyc IDAPS
BiGG ID34307
Wikipedia LinkNot Available
METLIN ID5933
PubChem Compound10238
PDB IDNot Available
ChEBI ID17709
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

Enzyme Details
1. 3'(2'),5'-bisphosphate nucleotidase 1
General function:
Carbohydrate transport and metabolism
Specific function:
Converts adenosine 3'-phosphate 5'-phosphosulfate (PAPS) to adenosine 5'-phosphosulfate (APS) and 3'(2')-phosphoadenosine 5'- phosphate (PAP) to AMP. Has 1000-fold lower activity towards inositol 1,4-bisphosphate (Ins(1,4)P2) and inositol 1,3,4-trisphosphate (Ins(1,3,4)P3), but does not hydrolyze Ins(1)P, Ins(3,4)P2, Ins(1,3,4,5)P4 or InsP6 (By similarity).
Gene Name:
BPNT1
Uniprot ID:
Q3ZCK3
Molecular weight:
33328.0
Reactions
Phosphoadenosine phosphosulfate + Water → Adenosine phosphosulfate + Hydrogen phosphatedetails
Enzyme Details
2. 3'-phosphoadenosine 5'-phosphosulfate synthase 2
General function:
Not Available
Specific function:
Not Available
Gene Name:
PAPSS2
Uniprot ID:
Q0VC88
Molecular weight:
69672.0
Reactions
Adenosine triphosphate + Sulfate → Adenosine phosphosulfate + Pyrophosphatedetails
Adenosine triphosphate + Adenosine phosphosulfate → ADP + Phosphoadenosine phosphosulfatedetails