Adenosine 5'-phosphosulfate

Identification

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Name
Adenosine 5'-phosphosulfate
Accession Number
DB03708  (EXPT00441)
Type
Small Molecule
Groups
Experimental, Investigational
Description

5'-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.

Structure
Thumb
Synonyms
  • 5'-adenylyl sulfate
  • adenosine phosphosulfate
  • Adenosine-5'-phosphosulfate
  • Adenylylsulfate
  • APS
Categories
UNII
Not Available
CAS number
485-84-7
Weight
Average: 427.284
Monoisotopic: 427.019898895
Chemical Formula
C10H14N5O10PS
InChI Key
IRLPACMLTUPBCL-KQYNXXCUSA-N
InChI
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
IUPAC Name
[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]sulfonic acid
SMILES
NC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](COP(O)(=O)OS(O)(=O)=O)[C@@H](O)[C@H]1O

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UATP sulfurylase (Sulfate adenylyltransferase)Not AvailableThermus thermophilus (strain HB8 / ATCC 27634 / DSM 579)
UBifunctional 3'-phosphoadenosine 5'-phosphosulfate synthase 1Not AvailableHumans
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

General References
Not Available
External Links
Human Metabolome Database
HMDB0001003
KEGG Compound
C00224
PubChem Compound
10238
PubChem Substance
46507829
ChemSpider
9821
BindingDB
25461
ChEBI
17709
ChEMBL
CHEMBL572546
HET
ADX
PDB Entries
1g8g / 1g8h / 1i2d / 1jee / 1m7g / 1m7h / 1v47 / 1xnj / 2fja / 2goy
show 10 more

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1CompletedTreatmentKnee Osteoarthritis (Knee OA)1
Not AvailableActive Not RecruitingNot AvailableKnee Osteoarthritis (Knee OA)1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility3.29 mg/mLALOGPS
logP-1.6ALOGPS
logP-5.8ChemAxon
logS-2.1ALOGPS
pKa (Strongest Acidic)-2.1ChemAxon
pKa (Strongest Basic)4.99ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count12ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area229.44 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity84.06 m3·mol-1ChemAxon
Polarizability35.24 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption-0.5151
Blood Brain Barrier+0.7759
Caco-2 permeable-0.65
P-glycoprotein substrateNon-substrate0.7762
P-glycoprotein inhibitor INon-inhibitor0.8189
P-glycoprotein inhibitor IINon-inhibitor0.9728
Renal organic cation transporterNon-inhibitor0.9539
CYP450 2C9 substrateNon-substrate0.8772
CYP450 2D6 substrateNon-substrate0.8126
CYP450 3A4 substrateNon-substrate0.5706
CYP450 1A2 substrateNon-inhibitor0.8047
CYP450 2C9 inhibitorNon-inhibitor0.8452
CYP450 2D6 inhibitorNon-inhibitor0.868
CYP450 2C19 inhibitorNon-inhibitor0.8372
CYP450 3A4 inhibitorNon-inhibitor0.9088
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9651
Ames testNon AMES toxic0.7104
CarcinogenicityNon-carcinogens0.6484
BiodegradationNot ready biodegradable0.8982
Rat acute toxicity2.4954 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9447
hERG inhibition (predictor II)Non-inhibitor0.6978
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-000i-0912300000-29cd6f42fa9d4c6c4455
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-000i-0901000000-018ae7ee1fc1b662ec07
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-000i-1900000000-861a01467a0191dcd31a
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0059-0901600000-785b903b29133cefd0bc
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-003r-3900000000-d2245ba9a6f6bf6d0217
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-056r-9700000000-3f4588ade18801775bec
1H NMR Spectrum1D NMRNot Applicable
[1H,13C] 2D NMR Spectrum2D NMRNot Applicable

Taxonomy

Description
This 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.
Kingdom
Organic compounds
Super Class
Nucleosides, nucleotides, and analogues
Class
Purine nucleotides
Sub Class
Purine ribonucleotides
Direct Parent
Purine ribonucleoside monophosphates
Alternative Parents
Pentose phosphates / Glycosylamines / 6-aminopurines / Monosaccharide phosphates / Monoalkyl phosphates / Aminopyrimidines and derivatives / N-substituted imidazoles / Imidolactams / Organic sulfuric acids and derivatives / Heteroaromatic compounds
show 9 more
Substituents
Purine ribonucleoside monophosphate / Pentose phosphate / Pentose-5-phosphate / Glycosyl compound / N-glycosyl compound / 6-aminopurine / Monosaccharide phosphate / Pentose monosaccharide / Imidazopyrimidine / Purine
show 30 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
adenosine 5'-phosphate, acyl sulfate, acyl monophosphate (CHEBI:17709)

Targets

Kind
Protein
Organism
Thermus thermophilus (strain HB8 / ATCC 27634 / DSM 579)
Pharmacological action
Unknown
General Function
Sulfate adenylyltransferase (atp) activity
Specific Function
Not Available
Gene Name
Not Available
Uniprot ID
Q5SKH7
Uniprot Name
ATP sulfurylase (Sulfate adenylyltransferase)
Molecular Weight
38837.68 Da
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Sulfate adenylyltransferase (atp) activity
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 ...
Gene Name
PAPSS1
Uniprot ID
O43252
Uniprot Name
Bifunctional 3'-phosphoadenosine 5'-phosphosulfate synthase 1
Molecular Weight
70832.725 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
  3. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235]

Drug created on June 13, 2005 07:24 / Updated on June 04, 2019 05:55