Adenosine phosphosulfate (CHEM035026)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 05:25:42 UTC
Update Date2016-11-09 01:21:14 UTC
Accession NumberCHEM035026
Identification
Common NameAdenosine phosphosulfate
ClassSmall Molecule
Description5'-Adenylic acid, monoanhydride with sulfuric acid. The initial compound formed by the action of ATP sulfurylase on sulfate ions after sulfate uptake. Synonyms: adenosine sulfatophosphate; APS.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical 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 Mass427.284 g/mol
Monoisotopic Mass427.020 g/mol
CAS Registry Number485-84-7
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
SMILESNC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](COP(O)(=O)OS(O)(=O)=O)[C@@H](O)[C@H]1O
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
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
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
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
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-004i-2911100000-c7b3ba6ec47b4fb3e832Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-055b-7693530000-45cc4add4821e6fea5efSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0912300000-29cd6f42fa9d4c6c4455Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0901000000-018ae7ee1fc1b662ec07Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-1900000000-861a01467a0191dcd31aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0059-0901600000-785b903b29133cefd0bcSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-003r-3900000000-d2245ba9a6f6bf6d0217Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-056r-9700000000-3f4588ade18801775becSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0200900000-b10f97ec4ef8bff7823cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0911000000-4563fb5a2cb7fd85ab98Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-0900000000-5a937b62fdf69d198700Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0100900000-a398ce6fc250a971f068Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-056r-6900300000-d9d41d4bc70263df8221Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004j-9200000000-979bc3001281c5d76962Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDB03708
HMDB IDHMDB0001003
FooDB IDFDB022362
Phenol Explorer IDNot Available
KNApSAcK IDC00007445
BiGG ID34307
BioCyc IDAPS
METLIN ID5933
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID9821
ChEBI ID17709
PubChem Compound ID10238
Kegg Compound IDC00224
YMDB IDYMDB00256
ECMDB IDECMDB01003
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Mateos-Trigos G, Evans RJ, Heath MF: Effects of P2Y(1) and P2Y(12) receptor antagonists on ADP-induced shape change of equine platelets: comparison with human platelets. Platelets. 2002 Aug-Sep;13(5-6):285-92.
2. Chou HC, Lang NP, Kadlubar FF: Metabolic activation of N-hydroxy arylamines and N-hydroxy heterocyclic amines by human sulfotransferase(s). Cancer Res. 1995 Feb 1;55(3):525-9.
3. Al-Buheissi SZ, Patel HR, Meinl W, Hewer A, Bryan RL, Glatt H, Miller RA, Phillips DH: N-Acetyltransferase and sulfotransferase activity in human prostate: potential for carcinogen activation. Pharmacogenet Genomics. 2006 Jun;16(6):391-9.
4. Keogh JR, Wolf MF, Overend ME, Tang L, Eaton JW: Biocompatibility of sulphonated polyurethane surfaces. Biomaterials. 1996 Oct;17(20):1987-94.
5. Eto Y, Tokoro T, Handa T, Herschkowitz NN, Rennert OM: Acid mucopolysaccharide (AMPS) abnormality in multiple sulfatase deficiency: chemical compositions of AMPS in urine and liver. Pediatr Res. 1982 May;16(5):395-9.
6. Slomiany BL, Liau YH, Sarosiek J, Tsukada H, Mizuta K, Rosenthal W, Slomiany A: Sulfation of glycolipids by human gastric mucosa in disease. Digestion. 1987;36(4):246-52.
7. Raju U, Kadner S, Levitz M, Kaganowicz A, Blaustein A: Glucosiduronidation and esterification of androsterone by human breast tumors in vitro. Steroids. 1981 Apr;37(4):399-407.
8. Eklund E, Roden L, Malmstrom M, Malmstrom A: Dermatan is a better substrate for 4-O-sulfation than chondroitin: implications in the generation of 4-O-sulfated, L-iduronate-rich galactosaminoglycans. Arch Biochem Biophys. 2000 Nov 15;383(2):171-7.