5'-S-ethyl-5'-thioadenosine

Identification

Generic Name
5'-S-ethyl-5'-thioadenosine
DrugBank Accession Number
DB07052
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
Weight
Average: 311.36
Monoisotopic: 311.105210125
Chemical Formula
C12H17N5O3S
Synonyms
Not Available

Pharmacology

Indication

Not Available

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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UAdenosylhomocysteinaseNot AvailableMycobacterium tuberculosis
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
Not Available
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as 5'-deoxy-5'-thionucleosides. These are 5'-deoxyribonucleosides in which the ribose is thio-substituted at the 5'position by a S-alkyl group.
Kingdom
Organic compounds
Super Class
Nucleosides, nucleotides, and analogues
Class
5'-deoxyribonucleosides
Sub Class
5'-deoxy-5'-thionucleosides
Direct Parent
5'-deoxy-5'-thionucleosides
Alternative Parents
Glycosylamines / 6-aminopurines / Pentoses / Aminopyrimidines and derivatives / Imidolactams / N-substituted imidazoles / Tetrahydrofurans / Heteroaromatic compounds / 1,2-diols / Secondary alcohols
show 7 more
Substituents
1,2-diol / 5'-deoxy-5'-thionucleoside / 6-aminopurine / Alcohol / Amine / Aminopyrimidine / Aromatic heteropolycyclic compound / Azacycle / Azole / Dialkylthioether
show 25 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
thioadenosine (CHEBI:74046)
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
Not Available
InChI Key
HMXHURAGFHWODC-WOUKDFQISA-N
InChI
InChI=1S/C12H17N5O3S/c1-2-21-3-6-8(18)9(19)12(20-6)17-5-16-7-10(13)14-4-15-11(7)17/h4-6,8-9,12,18-19H,2-3H2,1H3,(H2,13,14,15)/t6-,8-,9-,12-/m1/s1
IUPAC Name
(2R,3R,4S,5S)-2-(6-amino-9H-purin-9-yl)-5-[(ethylsulfanyl)methyl]oxolane-3,4-diol
SMILES
[H][C@]1(CSCC)O[C@@]([H])(N2C=NC3=C2N=CN=C3N)[C@]([H])(O)[C@]1([H])O

References

General References
Not Available
PubChem Compound
10041129
PubChem Substance
99443523
ChemSpider
8216693
ChEBI
74046
ChEMBL
CHEMBL195660
ZINC
ZINC000013507220
PDBe Ligand
3DH
PDB Entries
3dhy

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 Solubility5.0 mg/mLALOGPS
logP0.42ALOGPS
logP-0.36Chemaxon
logS-1.8ALOGPS
pKa (Strongest Acidic)12.47Chemaxon
pKa (Strongest Basic)3.94Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count7Chemaxon
Hydrogen Donor Count3Chemaxon
Polar Surface Area119.31 Å2Chemaxon
Rotatable Bond Count4Chemaxon
Refractivity78.83 m3·mol-1Chemaxon
Polarizability31.6 Å3Chemaxon
Number of Rings3Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.8197
Caco-2 permeable-0.6998
P-glycoprotein substrateSubstrate0.5974
P-glycoprotein inhibitor INon-inhibitor0.9287
P-glycoprotein inhibitor IINon-inhibitor0.9946
Renal organic cation transporterNon-inhibitor0.9399
CYP450 2C9 substrateNon-substrate0.8484
CYP450 2D6 substrateNon-substrate0.809
CYP450 3A4 substrateNon-substrate0.5697
CYP450 1A2 substrateNon-inhibitor0.8942
CYP450 2C9 inhibitorNon-inhibitor0.8711
CYP450 2D6 inhibitorNon-inhibitor0.9261
CYP450 2C19 inhibitorNon-inhibitor0.8522
CYP450 3A4 inhibitorNon-inhibitor0.9317
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8918
Ames testNon AMES toxic0.5729
CarcinogenicityNon-carcinogens0.8894
BiodegradationNot ready biodegradable1.0
Rat acute toxicity2.3993 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9818
hERG inhibition (predictor II)Non-inhibitor0.8444
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-MSsplash10-004m-5960000000-fb1f8587eac099847d9a
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-03di-0009000000-3e83f4e6cb23fa164ecb
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-03di-1239000000-bc459c4728d1a1ea8dff
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-06si-8901000000-9525e42d48b8b6d8f7af
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-01p9-1947000000-fb8f54080dc3cc03f65f
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-001i-3900000000-8afe0d73dc0b5782c6fa
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-000i-3900000000-c82407e398d48f84047a
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]-183.2716723
predicted
DarkChem Lite v0.1.0
[M-H]-169.36003
predicted
DeepCCS 1.0 (2019)
[M+H]+183.5456723
predicted
DarkChem Lite v0.1.0
[M+H]+171.75558
predicted
DeepCCS 1.0 (2019)
[M+Na]+183.0636723
predicted
DarkChem Lite v0.1.0
[M+Na]+179.04417
predicted
DeepCCS 1.0 (2019)

Targets

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Kind
Protein
Organism
Mycobacterium tuberculosis
Pharmacological action
Unknown
General Function
May play a key role in the regulation of the intracellular concentration of adenosylhomocysteine.
Specific Function
Adenosylhomocysteinase activity
Gene Name
ahcY
Uniprot ID
P9WGV3
Uniprot Name
Adenosylhomocysteinase
Molecular Weight
54323.25 Da
References
  1. 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 September 15, 2010 21:18 / Updated at June 12, 2020 16:52