5'-O-(L-Cysteinylsulfamoyl)adenosine

Identification

Generic Name
5'-O-(L-Cysteinylsulfamoyl)adenosine
DrugBank Accession Number
DB02684
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
Weight
Average: 449.463
Monoisotopic: 449.078737377
Chemical Formula
C13H19N7O7S2
Synonyms
  • 5'-O-(N-(L-Cysteinyl)-sulfamoyl)adenosine

Pharmacology

Indication

Not Available

Reduce drug development failure rates
Build, train, & validate machine-learning models
with evidence-based and structured datasets.
See how
Build, train, & validate predictive machine-learning models with structured datasets.
See how
Contraindications & Blackbox Warnings
Prevent Adverse Drug Events Today
Tap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.
Learn more
Avoid life-threatening adverse drug events with our Clinical API
Learn more
Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UBifunctional glutamate/proline--tRNA ligaseNot 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

Adverse Effects
Improve decision support & research outcomes
With structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!
See the data
Improve decision support & research outcomes with our structured adverse effects data.
See a data sample
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
Not Available
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as purine nucleosides. These are compounds comprising a purine base attached to a ribosyl or deoxyribosyl moiety.
Kingdom
Organic compounds
Super Class
Nucleosides, nucleotides, and analogues
Class
Purine nucleosides
Sub Class
Not Available
Direct Parent
Purine nucleosides
Alternative Parents
Cysteine and derivatives / Glycosylamines / Pentoses / 6-aminopurines / Aminopyrimidines and derivatives / N-substituted imidazoles / Imidolactams / Tetrahydrofurans / Organic sulfuric acids and derivatives / Heteroaromatic compounds
show 10 more
Substituents
1,2-diol / 6-aminopurine / Alcohol / Alkylthiol / Alpha-amino acid or derivatives / Amine / Amino acid or derivatives / Aminopyrimidine / Aromatic heteropolycyclic compound / Azacycle
show 31 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
Not Available
InChI Key
FTSDEWPMACCNGN-YTMOPEAISA-N
InChI
InChI=1S/C13H19N7O7S2/c14-5(2-28)12(23)19-29(24,25)26-1-6-8(21)9(22)13(27-6)20-4-18-7-10(15)16-3-17-11(7)20/h3-6,8-9,13,21-22,28H,1-2,14H2,(H,19,23)(H2,15,16,17)/t5-,6+,8+,9+,13+/m0/s1
IUPAC Name
(2R)-2-amino-1-[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}sulfonyl)amino]-3-sulfanylpropan-1-one
SMILES
[H]N([H])[C@@H](CS)C(=O)N([H])S(=O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=NC2=C(N=CN=C12)N([H])[H]

References

General References
Not Available
PubChem Compound
447377
PubChem Substance
46504849
ChemSpider
394497
BindingDB
50339905
ChEMBL
CHEMBL1163074
ZINC
ZINC000024951193
PDBe Ligand
5CA
PDB Entries
1nj1 / 2i4n / 2z0x / 3c8z

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

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 Solubility2.52 mg/mLALOGPS
logP-1.3ALOGPS
logP-3.8Chemaxon
logS-2.2ALOGPS
pKa (Strongest Acidic)2.7Chemaxon
pKa (Strongest Basic)6.47Chemaxon
Physiological Charge-1Chemaxon
Hydrogen Acceptor Count12Chemaxon
Hydrogen Donor Count6Chemaxon
Polar Surface Area217.8 Å2Chemaxon
Rotatable Bond Count6Chemaxon
Refractivity99.87 m3·mol-1Chemaxon
Polarizability42.76 Å3Chemaxon
Number of Rings3Chemaxon
Bioavailability0Chemaxon
Rule of FiveNoChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleYesChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9576
Blood Brain Barrier+0.5369
Caco-2 permeable-0.6554
P-glycoprotein substrateNon-substrate0.6293
P-glycoprotein inhibitor INon-inhibitor0.816
P-glycoprotein inhibitor IINon-inhibitor0.9598
Renal organic cation transporterNon-inhibitor0.9483
CYP450 2C9 substrateNon-substrate0.8792
CYP450 2D6 substrateNon-substrate0.8026
CYP450 3A4 substrateNon-substrate0.5448
CYP450 1A2 substrateNon-inhibitor0.8027
CYP450 2C9 inhibitorNon-inhibitor0.8143
CYP450 2D6 inhibitorNon-inhibitor0.8709
CYP450 2C19 inhibitorNon-inhibitor0.8158
CYP450 3A4 inhibitorNon-inhibitor0.767
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9395
Ames testNon AMES toxic0.6434
CarcinogenicityNon-carcinogens0.5536
BiodegradationNot ready biodegradable0.9273
Rat acute toxicity2.5079 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9446
hERG inhibition (predictor II)Non-inhibitor0.6879
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 MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0udi-0006900000-43aa5e98fa28c82f0c10
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-01po-0407900000-e67dfe5103237c5b8925
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-000x-6549200000-ecd7c029467b069a91ce
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-000i-0920200000-b5d4b99865aa388fa1c9
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-052r-2910100000-83df88eaf5983d236623
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-001i-0911300000-6301801bbc57cecef11a
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-178.70007
predicted
DeepCCS 1.0 (2019)
[M+H]+180.52496
predicted
DeepCCS 1.0 (2019)
[M+Na]+186.20143
predicted
DeepCCS 1.0 (2019)

Targets

Build, predict & validate machine-learning models
Use our structured and evidence-based datasets to unlock new
insights and accelerate drug research.
Learn more
Use our structured and evidence-based datasets to unlock new insights and accelerate drug research.
Learn more
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Rna stem-loop binding
Specific Function
Catalyzes the attachment of the cognate amino acid to the corresponding tRNA in a two-step reaction: the amino acid is first activated by ATP to form a covalent intermediate with AMP and is then tr...
Gene Name
EPRS
Uniprot ID
P07814
Uniprot Name
Bifunctional glutamate/proline--tRNA ligase
Molecular Weight
170589.705 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]

Drug created at June 13, 2005 13:24 / Updated at August 01, 2020 13:45