Methylthioinosine

Identification

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Name
Methylthioinosine
Accession Number
DB02896  (EXPT02248)
Type
Small Molecule
Groups
Experimental
Description

An analog of inosine with a methylthio group replacing the hydroxyl group in the 6-position.

Structure
Thumb
Synonyms
  • 6-(Methylthio)purine ribonucleoside
  • 6-methyl MP riboside
  • 6-methyl MP-riboside
  • 6-methyl-9-ribofuranosylpurine-6-thiol
  • 6-methylmercaptopurine ribonucleoside
  • 6-methylmercaptopurine riboside
  • 6-Methylmercaptopurine-riboside
  • 6-methylthioinosine
  • 6-methylthiopurine riboside
  • 6-MMPR
  • 6-S-methyl-6-thioinosine
  • Me6MPR
  • methylmercaptopurine riboside
  • MMPR
External IDs
NCI-C04784 / NSC-40774 / NSC-49555 / SQ-21977
Categories
UNII
Y5G39SHR0V
CAS number
342-69-8
Weight
Average: 298.318
Monoisotopic: 298.073575646
Chemical Formula
C11H14N4O4S
InChI Key
ZDRFDHHANOYUTE-IOSLPCCCSA-N
InChI
InChI=1S/C11H14N4O4S/c1-20-10-6-9(12-3-13-10)15(4-14-6)11-8(18)7(17)5(2-16)19-11/h3-5,7-8,11,16-18H,2H2,1H3/t5-,7-,8-,11-/m1/s1
IUPAC Name
(2R,3S,4R,5R)-2-(hydroxymethyl)-5-[6-(methylsulfanyl)-9H-purin-9-yl]oxolane-3,4-diol
SMILES
CSC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UPurine nucleoside phosphorylase DeoD-typeNot AvailableEscherichia coli (strain K12)
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

IPR-RAT LD50: 65 mg/kg

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
PubChem Compound
9570
PubChem Substance
46505005
ChemSpider
9195
BindingDB
50412071
ChEBI
44081
ChEMBL
CHEMBL388931
HET
MTP
PDB Entries
1pr4 / 2aa0 / 2ab8 / 6c9p
MSDS
Download (51.5 KB)

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

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

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)164 °CPhysProp
logP0.09SANGSTER (1994)
Predicted Properties
PropertyValueSource
Water Solubility8.21 mg/mLALOGPS
logP-0.4ALOGPS
logP-0.63ChemAxon
logS-1.6ALOGPS
pKa (Strongest Acidic)12.45ChemAxon
pKa (Strongest Basic)4.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area113.52 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity71.25 m3·mol-1ChemAxon
Polarizability28.81 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption-0.5
Blood Brain Barrier-0.6699
Caco-2 permeable-0.7396
P-glycoprotein substrateNon-substrate0.7196
P-glycoprotein inhibitor INon-inhibitor0.9212
P-glycoprotein inhibitor IINon-inhibitor0.9449
Renal organic cation transporterNon-inhibitor0.9198
CYP450 2C9 substrateNon-substrate0.7261
CYP450 2D6 substrateNon-substrate0.8166
CYP450 3A4 substrateNon-substrate0.5213
CYP450 1A2 substrateNon-inhibitor0.9183
CYP450 2C9 inhibitorNon-inhibitor0.9273
CYP450 2D6 inhibitorNon-inhibitor0.9508
CYP450 2C19 inhibitorNon-inhibitor0.9252
CYP450 3A4 inhibitorNon-inhibitor0.9866
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9057
Ames testAMES toxic0.8296
CarcinogenicityNon-carcinogens0.8857
BiodegradationNot ready biodegradable0.8971
Rat acute toxicity2.4718 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9949
hERG inhibition (predictor II)Non-inhibitor0.8175
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/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

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
Glycosylamines / 6-thiopurines / Pentoses / Alkylarylthioethers / Pyrimidines and pyrimidine derivatives / N-substituted imidazoles / Tetrahydrofurans / Heteroaromatic compounds / Secondary alcohols / Sulfenyl compounds
show 6 more
Substituents
Purine nucleoside / Glycosyl compound / N-glycosyl compound / Pentose monosaccharide / 6-thiopurine / Imidazopyrimidine / Purine / Aryl thioether / Alkylarylthioether / Monosaccharide
show 22 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
thiopurine, purine ribonucleoside (CHEBI:44081)

Targets

Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
Unknown
General Function
Purine-nucleoside phosphorylase activity
Specific Function
Cleavage of guanosine or inosine to respective bases and sugar-1-phosphate molecules.
Gene Name
deoD
Uniprot ID
P0ABP8
Uniprot Name
Purine nucleoside phosphorylase DeoD-type
Molecular Weight
25949.68 Da
References
  1. Bennett EM, Li C, Allan PW, Parker WB, Ealick SE: Structural basis for substrate specificity of Escherichia coli purine nucleoside phosphorylase. J Biol Chem. 2003 Nov 21;278(47):47110-8. Epub 2003 Aug 21. [PubMed:12937174]

Drug created on June 13, 2005 07:24 / Updated on June 04, 2019 05:41