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Showing Compound Adenosine phosphosulfate (FDB022362)

Record Information
Version1.0
Creation date2011-09-21 00:12:46 UTC
Update date2025-11-19 02:41:31 UTC
Primary IDFDB022362
Secondary Accession Numbers
  • FDB030652
Chemical Information
FooDB 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 humans, adenosine phosphosulfate participates in a number of enzymatic reactions. In particular, adenosine phosphosulfate can be biosynthesized from sulfate through the action of 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 humans, adenosine phosphosulfate is involved in sulfate/sulfite metabolism. Outside of the human body, Adenosine phosphosulfate has been detected, but not quantified in, several different foods, such as chia, yardlong beans, swiss chards, sapodilla, and chicory leaves. This could make adenosine phosphosulfate a potential biomarker for the consumption of these foods. An adenosine 5'-phosphate having a sulfo group attached to one the phosphate OH groups.
CAS Number485-84-7
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
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
Adenosine 5'-OsulfateChEBI
Adenosine 5'-Osulfuric acidGenerator
Adenosine 5'-OsulphateGenerator
Adenosine 5'-Osulphuric acidGenerator
Adenosine 5'-sulphatoateHMDB
adenosine 5'-sulphatophosphatehmdb
Adenosine OsulfateChEBI
Adenosine Osulfuric acidGenerator
Adenosine OsulphateGenerator
Adenosine Osulphuric acidGenerator
Adenosine Phosphosulfatehmdb
Adenosine phosphosulfic acidhmdb
Adenosine sulfatoateHMDB
adenosine sulfatophosphatehmdb
ADENOSINE-5'-OsulfATEChEBI
ADENOSINE-5'-Osulfuric acidGenerator
ADENOSINE-5'-OsulphateGenerator
ADENOSINE-5'-Osulphuric acidGenerator
adenylic acid monoanhydride with sulfuratehmdb
adenylic acid monoanhydride with sulfuric acidhmdb
adenylyl sulfatehmdb
adenylyl-sulfatehmdb
OSulfateHMDB
OSulphateHMDB
phosphosulfatehmdb
SulfatoateHMDB
sulfatophosphatehmdb
Predicted Properties
PropertyValueSource
Water Solubility3.29 g/LALOGPS
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
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC10H14N5O10PS
IUPAC name[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]sulfonic acid
InChI IdentifierInChI=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
Isomeric SMILESNC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](COP(O)(=O)OS(O)(=O)=O)[C@@H](O)[C@H]1O
Average Molecular Weight427.284
Monoisotopic Molecular Weight427.019898895
Classification
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
Disposition

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSAdenosine phosphosulfate, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-004i-2911100000-c7b3ba6ec47b4fb3e832Spectrum
Predicted GC-MSAdenosine phosphosulfate, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-055b-7693530000-45cc4add4821e6fea5efSpectrum
Predicted GC-MSAdenosine phosphosulfate, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0912300000-29cd6f42fa9d4c6c44552015-09-15View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0901000000-018ae7ee1fc1b662ec072015-09-15View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-1900000000-861a01467a0191dcd31a2015-09-15View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0059-0901600000-785b903b29133cefd0bc2015-09-15View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-003r-3900000000-d2245ba9a6f6bf6d02172015-09-15View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-056r-9700000000-3f4588ade18801775bec2015-09-15View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0200900000-b10f97ec4ef8bff7823c2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0911000000-4563fb5a2cb7fd85ab982021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-0900000000-5a937b62fdf69d1987002021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0100900000-a398ce6fc250a971f0682021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-056r-6900300000-d9d41d4bc70263df82212021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004j-9200000000-979bc3001281c5d769622021-09-24View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Spectrum
ChemSpider ID9821
ChEMBL IDCHEMBL572546
KEGG Compound IDC00224
Pubchem Compound ID10238
Pubchem Substance IDNot Available
ChEBI ID17709
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB01003
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG ID34307
KNApSAcK IDC00007445
HET IDADX
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDamps
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
Enzymes
NameGene NameUniProt ID
Bifunctional 3'-phosphoadenosine 5'-phosphosulfate synthase 1PAPSS1O43252
Adenosine 3'-phospho 5'-phosphosulfate transporter 1SLC35B2Q8TB61
Bifunctional 3'-phosphoadenosine 5'-phosphosulfate synthase 2PAPSS2O95340
Pathways
NameSMPDB LinkKEGG Link
Sulfate/Sulfite MetabolismSMP00041 map00920
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content ReferenceNot Available