Identification
- Generic Name
- 5'-S-methyl-5'-thioadenosine
- DrugBank Accession Number
- DB02282
- Background
Not Available
- Type
- Small Molecule
- Groups
- Experimental
- Structure
Structure for 5'-S-methyl-5'-thioadenosine (DB02282)
- Weight
- Average: 297.334
Monoisotopic: 297.089560061 - Chemical Formula
- C11H15N5O3S
- Synonyms
- 5-Methylthioadenosine
- 5'-Deoxy-5'-(methylthio)adenosine
- 5'-Methylthioadenosine
- 9-(5-S-methyl-5-thio-β-D-ribofuranosyl)-9H-purin-6-amine
- Methylthioadenosine
- MTA
- S-Methyl-5'-thioadenosine
- Thiomethyladenosine
- Vitamin L2
- External IDs
- NSC-335422
Pharmacology
- Indication
Not Available
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Contraindications & Blackbox Warnings
Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- Pharmacodynamics
Not Available
- Mechanism of action
Target Actions Organism UModification methylase RsrI Not Available Rhodobacter sphaeroides US-methyl-5'-thioadenosine phosphorylase Not Available Humans - 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
Not Available
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
- Not Available
Interactions
- Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
- 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.
Drug Interaction Integrate drug-drug
interactions in your softwareAmbroxol The risk or severity of methemoglobinemia can be increased when 5'-S-methyl-5'-thioadenosine is combined with Ambroxol. Articaine The risk or severity of methemoglobinemia can be increased when 5'-S-methyl-5'-thioadenosine is combined with Articaine. Benzocaine The risk or severity of methemoglobinemia can be increased when 5'-S-methyl-5'-thioadenosine is combined with Benzocaine. Benzyl alcohol The risk or severity of methemoglobinemia can be increased when 5'-S-methyl-5'-thioadenosine is combined with Benzyl alcohol. Bupivacaine The risk or severity of methemoglobinemia can be increased when 5'-S-methyl-5'-thioadenosine is combined with Bupivacaine. - Food Interactions
- Not Available
Categories
- Drug Categories
- Amino Acids
- Amino Acids, Acidic
- Amino Acids, Dicarboxylic
- Amino Acids, Peptides, and Proteins
- Anti-Infective Agents
- Antineoplastic Agents
- Antiparasitic Agents
- Antiprotozoals
- Deoxyribonucleosides
- Enzyme Inhibitors
- Folic Acid Antagonists
- Glutamates
- Heterocyclic Compounds, Fused-Ring
- Nucleic Acid Synthesis Inhibitors
- Nucleic Acids, Nucleotides, and Nucleosides
- Nucleosides
- Protein O-Methyltransferase, antagonists & inhibitors
- Purine Nucleosides
- Purines
- Purinones
- Sulfur Compounds
- Xanthine derivatives
- 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:17509)
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- 634Z2VK3UQ
- CAS number
- 2457-80-9
- InChI Key
- WUUGFSXJNOTRMR-IOSLPCCCSA-N
- InChI
- InChI=1S/C11H15N5O3S/c1-20-2-5-7(17)8(18)11(19-5)16-4-15-6-9(12)13-3-14-10(6)16/h3-5,7-8,11,17-18H,2H2,1H3,(H2,12,13,14)/t5-,7-,8-,11-/m1/s1
- IUPAC Name
- (2R,3R,4S,5S)-2-(6-amino-9H-purin-9-yl)-5-[(methylsulfanyl)methyl]oxolane-3,4-diol
- SMILES
- CSC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=NC2=C1N=CN=C2N
References
- General References
- Not Available
- External Links
- Human Metabolome Database
- HMDB0001173
- KEGG Compound
- C00170
- PubChem Compound
- 439176
- PubChem Substance
- 46508330
- ChemSpider
- 388321
- BindingDB
- 22111
- ChEBI
- 17509
- ChEMBL
- CHEMBL277041
- ZINC
- ZINC000004228245
- PDBe Ligand
- MTA
- PDB Entries
- 1cg6 / 1eg2 / 1jdt / 1z5o / 2a8y / 2e5w / 2hte / 2ipx / 2o05 / 2o06 … show 87 more
Clinical Trials
- Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Phase Status Purpose Conditions Count 1, 2 Recruiting Treatment Advanced MTAP-null Solid Tumors 1
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
Property Value Source Water Solubility 6.5 mg/mL ALOGPS logP -0.14 ALOGPS logP -0.61 Chemaxon logS -1.7 ALOGPS pKa (Strongest Acidic) 12.47 Chemaxon pKa (Strongest Basic) 3.94 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 7 Chemaxon Hydrogen Donor Count 3 Chemaxon Polar Surface Area 119.31 Å2 Chemaxon Rotatable Bond Count 3 Chemaxon Refractivity 74.03 m3·mol-1 Chemaxon Polarizability 29.26 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 + 1.0 Blood Brain Barrier + 0.7984 Caco-2 permeable - 0.7152 P-glycoprotein substrate Non-substrate 0.5431 P-glycoprotein inhibitor I Non-inhibitor 0.9292 P-glycoprotein inhibitor II Non-inhibitor 0.9741 Renal organic cation transporter Non-inhibitor 0.9405 CYP450 2C9 substrate Non-substrate 0.8436 CYP450 2D6 substrate Non-substrate 0.8225 CYP450 3A4 substrate Substrate 0.5148 CYP450 1A2 substrate Non-inhibitor 0.895 CYP450 2C9 inhibitor Non-inhibitor 0.8866 CYP450 2D6 inhibitor Non-inhibitor 0.9371 CYP450 2C19 inhibitor Non-inhibitor 0.8575 CYP450 3A4 inhibitor Non-inhibitor 0.9365 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9444 Ames test Non AMES toxic 0.5859 Carcinogenicity Non-carcinogens 0.9304 Biodegradation Not ready biodegradable 1.0 Rat acute toxicity 2.3307 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9821 hERG inhibition (predictor II) Non-inhibitor 0.874
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 178.7569907 predictedDarkChem Lite v0.1.0 [M-H]- 178.3901907 predictedDarkChem Lite v0.1.0 [M-H]- 173.8497907 predictedDarkChem Lite v0.1.0 [M-H]- 174.7414907 predictedDarkChem Lite v0.1.0 [M-H]- 156.09691 predictedDeepCCS 1.0 (2019) [M+H]+ 178.8585907 predictedDarkChem Lite v0.1.0 [M+H]+ 179.0341907 predictedDarkChem Lite v0.1.0 [M+H]+ 174.6947907 predictedDarkChem Lite v0.1.0 [M+H]+ 174.9887907 predictedDarkChem Lite v0.1.0 [M+H]+ 158.49248 predictedDeepCCS 1.0 (2019) [M+Na]+ 178.7988907 predictedDarkChem Lite v0.1.0 [M+Na]+ 178.7613907 predictedDarkChem Lite v0.1.0 [M+Na]+ 174.0237907 predictedDarkChem Lite v0.1.0 [M+Na]+ 173.7980907 predictedDarkChem Lite v0.1.0 [M+Na]+ 165.06392 predictedDeepCCS 1.0 (2019)
Targets
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- Kind
- Protein
- Organism
- Rhodobacter sphaeroides
- Pharmacological action
- Unknown
- General Function
- Site-specific dna-methyltransferase (adenine-specific) activity
- Specific Function
- This methylase recognizes the double-stranded sequence GAATTC, causes specific methylation on A-? on both strands, and protects the DNA from cleavage by the RsrI endonuclease.
- Gene Name
- rsrIM
- Uniprot ID
- P14751
- Uniprot Name
- Modification methylase RsrI
- Molecular Weight
- 35654.88 Da
References
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- S-methyl-5-thioadenosine phosphorylase activity
- Specific Function
- Catalyzes the reversible phosphorylation of S-methyl-5'-thioadenosine (MTA) to adenine and 5-methylthioribose-1-phosphate. Involved in the breakdown of MTA, a major by-product of polyamine biosynth...
- Gene Name
- MTAP
- Uniprot ID
- Q13126
- Uniprot Name
- S-methyl-5'-thioadenosine phosphorylase
- Molecular Weight
- 31235.76 Da
References
Drug created at June 13, 2005 13:24 / Updated at July 02, 2020 13:14