5′-Deoxy-5′-(methylthio)adenosine - Moligand™,≥95% , CAS No.2457-80-9

CAS: 2457-80-9 Cat. No.: D168979 Molecular Weight: 297.33 EC Number: 626-314-3

GRADE & PURITY Moligand™, ≥95%

Synonyms

Vitamin L2 | MFCD00010533 | 5'-(Methylthio)adenosine | 9-(5-S-methyl-5-thio-beta-D-ribofuranosyl)-9H-purin-6-amine | (2R,3R,4S,5S)-2-(6-aminopurin-9-yl)-5-(methylsulfanylmethyl)oxolane-3,4-diol | 5'-DEOXY-5'-METHYLTHIOADENOSINE | 5'-Deoxy-5'-methylthio-ad

Storage

Store at -20°C,Argon charged

Shipped In

Ice chest + Ice pads

Overview

A cell-permeable, reversible, and ATP-competitive naturally-occurring co-product of polyamine biosynthesis that acts as an endogenous substrate of methylthioadenosine phosphorylase (MTAP). Potently inhibits the protein carboxymethyltransferase and induces apoptosis in leukemia U937 cells. Also inhibits FGF-2 receptor tyrosine kinase activity as well as the proliferation of human astrocytes and glioma cells.
A naturally occurring co-product of polyamine biosynthesis that acts as an endogenous substrate of methylthioadenosine phosphorylase (MTAP). A cell-permeable, reversible, and ATP-competitive inhibitor of protein carboxymethyltransferase and induces apoptosis in leukemia U937 cells. Also acts as an inhibitor of NGF-induced tyrosine phosphorylation in PC12 cells and blocks FGF-2 receptor tyrosine kinase in astrocytes and glioma cells.

Specifications

Synonyms

Vitamin L2 | MFCD00010533 | 5'-(Methylthio)adenosine | 9-(5-S-methyl-5-thio-beta-D-ribofuranosyl)-9H-purin-6-amine | (2R, 3R, 4S, 5S)-2-(6-aminopurin-9-yl)-5-(methylsulfanylmethyl)oxolane-3, 4-diol | 5'-DEOXY-5'-METHYLTHIOADENOSINE | 5'-Deoxy-5'-methylthio-ad

Specifications & Purity

Moligand™, ≥95%

Biochemical and Physiological Mechanisms

Potent A 1 receptor agonist (K i = 10 μM). Also an A 2 receptor antagonist and potent cAMP phosphodiesterase inhibitor (K i = 62 μM). Regulates gene expression, proliferation, differentiation and apoptosis. Anti-inflammatory agent. Orally active. Active i

Storage

Store at -20°C, Argon charged

Shipped In

Ice chest + Ice pads

This product requires cold chain shipping. Ground and other economy services are not available.

Grade

Moligand™

Note

Wherever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20°C. Generally, these will be useable for up to one month. Before use, and prior to opening the vial we recommend that you allow your product to equilibrate to room temperature for at least 1 hour. Need more advice on solubility, usage and handling? Please visit our frequently asked questions (FAQ) page for more details.

Purity

≥95%

Names and Identifiers

• Pubchem Sid: 504758686
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/504758686
• Canonical Smiles: CSCC1C(C(C(O1)N2C=NC3=C(N=CN=C32)N)O)O
• IUPAC Name: (2R,3R,4S,5S)-2-(6-aminopurin-9-yl)-5-(methylsulfanylmethyl)oxolane-3,4-diol
• InChIKey: WUUGFSXJNOTRMR-IOSLPCCCSA-N
• 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
• Isomeric SMILES: CSC[C@@H]1[C@H]([C@H]([C@@H](O1)N2C=NC3=C(N=CN=C32)N)O)O
• Molecular Weight: 297.33
• Reaxy-Rn: 24733578
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=24733578&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Nucleosides, nucleotides, and analogues
    • Class 5'-deoxyribonucleosides
      • Subclass 5'-deoxy-5'-thionucleosides

• Kingdom: Organic compounds
• Superclass: Nucleosides, nucleotides, and analogues
• Class: 5'-deoxyribonucleosides
• Subclass: 5'-deoxy-5'-thionucleosides
• Intermediate Tree Nodes: Not available
• 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 Dialkylthioethers Azacyclic compounds Sulfenyl compounds Oxacyclic compounds Organopnictogen compounds Hydrocarbon derivatives Primary amines
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: 5'-deoxy-5'-thionucleoside - Glycosyl compound - N-glycosyl compound - 6-aminopurine - Pentose monosaccharide - Imidazopyrimidine - Purine - Aminopyrimidine - Monosaccharide - N-substituted imidazole - Pyrimidine - Imidolactam - Azole - Tetrahydrofuran - Imidazole - Heteroaromatic compound - Secondary alcohol - 1,2-diol - Organoheterocyclic compound - Dialkylthioether - Sulfenyl compound - Thioether - Azacycle - Oxacycle - Organic oxygen compound - Alcohol - Hydrocarbon derivative - Organopnictogen compound - Amine - Primary amine - Organic nitrogen compound - Organonitrogen compound - Organooxygen compound - Organosulfur compound - Aromatic heteropolycyclic compound
• 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.
• External Descriptors: thioadenosine

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Associated Targets(Human)

COMT Tclin Catechol O-methyltransferase (404 Activities)

Discover Target: COMT

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

ADORA1 Tclin Adenosine A1 receptor (17603 Activities)

Discover Target: ADORA1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

ADORA2A Tclin Adenosine A2a receptor (16305 Activities)

Discover Target: ADORA2A

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

ADORA2B Tclin Adenosine A2b receptor (7672 Activities)

Discover Target: ADORA2B

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

ADORA3 Tchem Adenosine A3 receptor (15931 Activities)

Discover Target: ADORA3

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

MTAP Tchem S-methyl-5-thioadenosine phosphorylase (233 Activities)

Discover Target: MTAP

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

INMT Tchem Indolethylamine N-methyltransferase (111 Activities)

Discover Target: INMT

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

FASN Tchem Fatty acid synthase (3390 Activities)

Discover Target: FASN

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

CCRF-CEM (65223 Activities)

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MOLT-4 (49676 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

ADORA1 Tclin Adenosine receptor (26 Activities)

Discover Target: ADORA1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Associated Targets(non-human)

Srm Spermidine synthase (60 Activities)

Discover Target: Srm

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Ahcy Adenosylhomocysteinase (45 Activities)

Discover Target: Ahcy

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Trypanosoma brucei brucei (13300 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

L1210 (27553 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

L5178Y (1809 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

mtaD 5-methylthioadenosine/S-adenosylhomocysteine deaminase (15 Activities)

Discover Target: mtaD

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Adora2b Adenosine A2 receptor (1828 Activities)

Discover Target: Adora2b

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Mechanisms of Action

Chemical and Physical Properties

• Sensitivity: air sensitive; heat sensitive
• Molecular Weight: 297.340 g/mol
• XLogP3: -0.300
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 3
• Exact Mass: 297.09 Da
• Monoisotopic Mass: 297.09 Da
• Topological Polar Surface Area: 145.000 Ų
• Heavy Atom Count: 20
• Formal Charge: 0
• Complexity: 352.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 4
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

References

1. Baoyan Ding, Wei Meng, Xiaoling Zang, Zhihua Lv.  (2024)  Metabolic characteristics of prostate cancer cells with high metastatic potential revealed by (S)-ethyl 1-(3-(4-chlorophenoxy)-2-hydroxypropyl)-3-(4-methoxyphenyl)-1H-pyrazole-5-carboxylate inhibition.  JOURNAL OF PHARMACEUTICAL AND BIOMEDICAL ANALYSIS,      [PMID:39662125] [10.1016/j.jpba.2024.116611]