Adenosine 5'-phosphosulfate
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Identification
- Generic Name
- Adenosine 5'-phosphosulfate
- DrugBank Accession Number
- DB03708
- Background
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.
- Type
- Small Molecule
- Groups
- Experimental, Investigational
- Structure
- Weight
- Average: 427.284
Monoisotopic: 427.019898895 - Chemical Formula
- C10H14N5O10PS
- Synonyms
- 5'-adenylyl sulfate
- adenosine phosphosulfate
- Adenosine-5'-phosphosulfate
- Adenylylsulfate
- APS
Pharmacology
- Indication
Not Available
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- Pharmacodynamics
Not Available
- Mechanism of action
Target Actions Organism UBifunctional 3'-phosphoadenosine 5'-phosphosulfate synthase 1 Not Available Humans UATP sulfurylase (Sulfate adenylyltransferase) Not Available Thermus thermophilus (strain HB8 / ATCC 27634 / DSM 579) - 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
- Adverse Effects
- Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.
- Toxicity
Not Available
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.Not Available
- Food Interactions
- Not Available
Categories
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- 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
- 1,2-diol / 6-aminopurine / Alcohol / Alkyl phosphate / Amine / Aminopyrimidine / Aromatic heteropolycyclic compound / Azacycle / Azole / Glycosyl compound show 30 more
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- adenosine 5'-phosphate, acyl sulfate, acyl monophosphate (CHEBI:17709)
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- U98POO8KQU
- CAS number
- 485-84-7
- 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
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
- ZINC
- ZINC000004228246
- PDBe Ligand
- ADX
- PDB Entries
- 1g8g / 1g8h / 1i2d / 1jee / 1m7g / 1m7h / 1v47 / 1xnj / 2fja / 2goy … show 16 more
Clinical Trials
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
Property Value Source Water Solubility 3.29 mg/mL ALOGPS logP -1.6 ALOGPS logP -5.6 Chemaxon logS -2.1 ALOGPS pKa (Strongest Acidic) -2.1 Chemaxon pKa (Strongest Basic) 4.92 Chemaxon Physiological Charge -2 Chemaxon Hydrogen Acceptor Count 12 Chemaxon Hydrogen Donor Count 5 Chemaxon Polar Surface Area 229.44 Å2 Chemaxon Rotatable Bond Count 6 Chemaxon Refractivity 84.06 m3·mol-1 Chemaxon Polarizability 35.07 Å3 Chemaxon Number of Rings 3 Chemaxon Bioavailability 0 Chemaxon Rule of Five No Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule Yes Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption - 0.5151 Blood Brain Barrier + 0.7759 Caco-2 permeable - 0.65 P-glycoprotein substrate Non-substrate 0.7762 P-glycoprotein inhibitor I Non-inhibitor 0.8189 P-glycoprotein inhibitor II Non-inhibitor 0.9728 Renal organic cation transporter Non-inhibitor 0.9539 CYP450 2C9 substrate Non-substrate 0.8772 CYP450 2D6 substrate Non-substrate 0.8126 CYP450 3A4 substrate Non-substrate 0.5706 CYP450 1A2 substrate Non-inhibitor 0.8047 CYP450 2C9 inhibitor Non-inhibitor 0.8452 CYP450 2D6 inhibitor Non-inhibitor 0.868 CYP450 2C19 inhibitor Non-inhibitor 0.8372 CYP450 3A4 inhibitor Non-inhibitor 0.9088 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9651 Ames test Non AMES toxic 0.7104 Carcinogenicity Non-carcinogens 0.6484 Biodegradation Not ready biodegradable 0.8982 Rat acute toxicity 2.4954 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9447 hERG inhibition (predictor II) Non-inhibitor 0.6978
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS Not Available Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-000i-0912300000-29cd6f42fa9d4c6c4455 Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-000i-0901000000-018ae7ee1fc1b662ec07 Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-000i-1900000000-861a01467a0191dcd31a Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-0059-0901600000-785b903b29133cefd0bc Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-003r-3900000000-d2245ba9a6f6bf6d0217 Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-056r-9700000000-3f4588ade18801775bec 1H NMR Spectrum 1D NMR Not Applicable [1H,13C] 2D NMR Spectrum 2D NMR Not Applicable
Targets

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- 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
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
- 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. [Article]
- 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. [Article]
- 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
Drug created at June 13, 2005 13:24 / Updated at June 12, 2020 16:52