Methylthioinosine
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Identification
- Generic Name
- Methylthioinosine
- DrugBank Accession Number
- DB02896
- Background
An analog of inosine with a methylthio group replacing the hydroxyl group in the 6-position.
- Type
- Small Molecule
- Groups
- Experimental
- Structure
- Weight
- Average: 298.318
Monoisotopic: 298.073575646 - Chemical Formula
- C11H14N4O4S
- 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
Pharmacology
- Indication
Not Available
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- Pharmacodynamics
Not Available
- Mechanism of action
Target Actions Organism UPurine nucleoside phosphorylase DeoD-type Not Available Escherichia 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
- 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
IPR-RAT LD50: 65 mg/kg
- 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 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
- 6-thiopurine / Alcohol / Alkylarylthioether / Aromatic heteropolycyclic compound / Aryl thioether / Azacycle / Azole / Glycosyl compound / Heteroaromatic compound / Hydrocarbon derivative show 22 more
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- thiopurine, purine ribonucleoside (CHEBI:44081)
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- Y5G39SHR0V
- CAS number
- 342-69-8
- 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
References
- General References
- Not Available
- External Links
- PubChem Compound
- 9570
- PubChem Substance
- 46505005
- ChemSpider
- 9195
- BindingDB
- 50412071
- ChEBI
- 44081
- ChEMBL
- CHEMBL388931
- ZINC
- ZINC000000519128
- PDBe Ligand
- MTP
- PDB Entries
- 1pr4 / 2aa0 / 2ab8 / 6c9p
- MSDS
- Download (51.5 KB)
Clinical Trials
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
- Not Available
- Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 164 °C PhysProp logP 0.09 SANGSTER (1994) - Predicted Properties
Property Value Source Water Solubility 8.21 mg/mL ALOGPS logP -0.4 ALOGPS logP -0.63 Chemaxon logS -1.6 ALOGPS pKa (Strongest Acidic) 12.45 Chemaxon pKa (Strongest Basic) 3.31 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 7 Chemaxon Hydrogen Donor Count 3 Chemaxon Polar Surface Area 113.52 Å2 Chemaxon Rotatable Bond Count 3 Chemaxon Refractivity 71.25 m3·mol-1 Chemaxon Polarizability 28.85 Å3 Chemaxon Number of Rings 3 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption - 0.5 Blood Brain Barrier - 0.6699 Caco-2 permeable - 0.7396 P-glycoprotein substrate Non-substrate 0.7196 P-glycoprotein inhibitor I Non-inhibitor 0.9212 P-glycoprotein inhibitor II Non-inhibitor 0.9449 Renal organic cation transporter Non-inhibitor 0.9198 CYP450 2C9 substrate Non-substrate 0.7261 CYP450 2D6 substrate Non-substrate 0.8166 CYP450 3A4 substrate Non-substrate 0.5213 CYP450 1A2 substrate Non-inhibitor 0.9183 CYP450 2C9 inhibitor Non-inhibitor 0.9273 CYP450 2D6 inhibitor Non-inhibitor 0.9508 CYP450 2C19 inhibitor Non-inhibitor 0.9252 CYP450 3A4 inhibitor Non-inhibitor 0.9866 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9057 Ames test AMES toxic 0.8296 Carcinogenicity Non-carcinogens 0.8857 Biodegradation Not ready biodegradable 0.8971 Rat acute toxicity 2.4718 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9949 hERG inhibition (predictor II) Non-inhibitor 0.8175
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 178.7807611 predictedDarkChem Lite v0.1.0 [M-H]- 157.76994 predictedDeepCCS 1.0 (2019) [M-H]- 178.7807611 predictedDarkChem Lite v0.1.0 [M-H]- 157.76994 predictedDeepCCS 1.0 (2019) [M+H]+ 179.4393611 predictedDarkChem Lite v0.1.0 [M+H]+ 160.16551 predictedDeepCCS 1.0 (2019) [M+H]+ 179.4393611 predictedDarkChem Lite v0.1.0 [M+H]+ 160.16551 predictedDeepCCS 1.0 (2019) [M+Na]+ 178.6791611 predictedDarkChem Lite v0.1.0 [M+Na]+ 167.40265 predictedDeepCCS 1.0 (2019) [M+Na]+ 178.6791611 predictedDarkChem Lite v0.1.0 [M+Na]+ 167.40265 predictedDeepCCS 1.0 (2019)
Targets
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- 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
- 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. [Article]
Drug created at June 13, 2005 13:24 / Updated at January 07, 2021 03:10