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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
3D
Similar Structures
Weight
Average: 427.284
Monoisotopic: 427.019898895
Chemical Formula
C10H14N5O10PS
Synonyms
  • 5'-adenylyl sulfate
  • adenosine phosphosulfate
  • Adenosine-5'-phosphosulfate
  • Adenylylsulfate
  • APS
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Pharmacology

Indication

Not Available

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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UBifunctional 3'-phosphoadenosine 5'-phosphosulfate synthase 1Not AvailableHumans
UATP sulfurylase (Sulfate adenylyltransferase)Not AvailableThermus 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
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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
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

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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-5.6Chemaxon
logS-2.1ALOGPS
pKa (Strongest Acidic)-2.1Chemaxon
pKa (Strongest Basic)4.92Chemaxon
Physiological Charge-2Chemaxon
Hydrogen Acceptor Count12Chemaxon
Hydrogen Donor Count5Chemaxon
Polar Surface Area229.44 Å2Chemaxon
Rotatable Bond Count6Chemaxon
Refractivity84.06 m3·mol-1Chemaxon
Polarizability35.07 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-MSsplash10-004i-2911100000-c7b3ba6ec47b4fb3e832
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-004i-0010900000-feeaa3736bb2fdf86576
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-004i-0100900000-1f769c0c912581dc4b64
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0f80-0859000000-fb3c0a44106604498c59
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-004i-9600600000-91cb551ce327cd04b993
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-000i-0911000000-5a9f17f756ceabdd9ba1
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0032-9604000000-6968b027684973c3783f
1H NMR Spectrum1D NMRNot Applicable
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
[1H,13C] 2D NMR Spectrum2D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-206.9836776
predicted
DarkChem Lite v0.1.0
[M-H]-203.5455776
predicted
DarkChem Lite v0.1.0
[M-H]-168.08394
predicted
DeepCCS 1.0 (2019)
[M+H]+207.2758776
predicted
DarkChem Lite v0.1.0
[M+H]+201.9759776
predicted
DarkChem Lite v0.1.0
[M+H]+170.4795
predicted
DeepCCS 1.0 (2019)
[M+Na]+206.6394776
predicted
DarkChem Lite v0.1.0
[M+Na]+201.7922776
predicted
DarkChem Lite v0.1.0
[M+Na]+176.50516
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Bifunctional 3'-phosphoadenosine 5'-phosphosulfate synthase 1
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General 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 adenosine 5'-phosphosulfate (APS), and the second step is the transfer of a phosphate group from ATP to APS yielding 3'-phosphoadenylylsulfate (PAPS: activated sulfate donor used by sulfotransferase). In mammals, PAPS is the sole source of sulfate; APS appears to be only an intermediate in the sulfate-activation pathway (PubMed:14747722, PubMed:9576487, PubMed:9648242, PubMed:9668121). Required for normal biosynthesis of sulfated L-selectin ligands in endothelial cells (PubMed:9576487)
Specific Function
adenylylsulfate kinase activity
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. [Article]
  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. [Article]
  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. [Article]
Details2. ATP sulfurylase (Sulfate adenylyltransferase)
Kind
Protein
Organism
Thermus thermophilus (strain HB8 / ATCC 27634 / DSM 579)
Pharmacological action
Unknown
General Function
Not Available
Specific Function
ATP binding
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