MRS 5698 - Moligand™, ≥96%(HPLC) , Agonist of A 3 receptor, CAS No.1377273-00-1, Agonist of A 3 receptor

CAS: 1377273-00-1 Cat. No.: M288624 Formula: C₂₈H₂₃ClF₂N₆O₃ Molecular Weight: 564.97 PubChem CID: 57523213

GRADE & PURITY Moligand™, ≥96%(HPLC)

Synonyms

(1S,2R,3S,4R,5S)-4-[6-[[(3-Chlorophenyl)methyl]amino]-2-[2-(3,4-difluorophenyl)ethynyl]-9H-purin-9-yl]-2,3-dihydroxy-N-methylbicyclo[3.1.0]hexane-1-carboxamide

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Specifications

Synonyms

(1S,2R,3S,4R,5S)-4-[6-[[(3-Chlorophenyl)methyl]amino]-2-[2-(3,4-difluorophenyl)ethynyl]-9H-purin-9-yl]-2,3-dihydroxy-N-methylbicyclo[3.1.0]hexane-1-carboxamide

Specifications & Purity

Moligand™, ≥96%(HPLC)

Biochemical and Physiological Mechanisms

High affinity and selective A3adenosine receptor agonist (Ki~ 3 nM); displays >1000-fold selectivity over A1and A2Aadenosine receptors. Reverses mechanoallodynia in several neuropathic pain modelsin vivo. Orally bioavailable.

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

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

Grade

Moligand™

Action Type

AGONIST

Mechanism of action

Agonist of A 3 receptor

Purity

≥96%(HPLC)

Names and Identifiers

Canonical Smiles

CNC(=O)C12CC1C(C(C2O)O)N3C=NC4=C(N=C(N=C43)C#CC5=CC(=C(C=C5)F)F)NCC6=CC(=CC=C6)Cl

IUPAC Name

(1S,2R,3S,4R,5S)-4-[6-[(3-chlorophenyl)methylamino]-2-[2-(3,4-difluorophenyl)ethynyl]purin-9-yl]-2,3-dihydroxy-N-methylbicyclo[3.1.0]hexane-1-carboxamide

InChIKey

LYLLLJJYBWLGHW-CIZVZKTGSA-N

INCHI

1S/C28H23ClF2N6O3/c1-32-27(40)28-11-17(28)22(23(38)24(28)39)37-13-34-21-25(33-12-15-3-2-4-16(29)9-15)35-20(36-26(21)37)8-6-14-5-7-18(30)19(31)10-14/h2-5,7,9-10,13,17,22-24,38-39H,11-12H2,1H3,(H,32,40)(H,33,35,36)/t17-,22-,23+,24+,28+/m1/s1

Isomeric SMILES

CNC(=O)[C@@]12C[C@@H]1[C@H]([C@@H]([C@@H]2O)O)N3C=NC4=C(N=C(N=C43)C#CC5=CC(=C(C=C5)F)F)NCC6=CC(=CC=C6)Cl

PubChem CID

57523213

MeSH Entry Terms

4-(6-((3-chlorobenzyl)amino)-2-((3,4-difluorophenyl)ethynyl)-9H-purin-9-yl)-2,3-dihydroxy-N-methylbicyclo(3.1.0)hexane-1-carboxamide;MRS5698

Molecular Weight

564.97

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Nucleosides, nucleotides, and analogues
    • Class Nucleoside and nucleotide analogues
      • Subclass Cyclopentyl nucleosides
        • Level5 1,3-substituted cyclopentyl nucleosides
          • Level6 1,3-substituted cyclopentyl purine nucleosides

• Kingdom: Organic compounds
• Superclass: Nucleosides, nucleotides, and analogues
• Class: Nucleoside and nucleotide analogues
• Subclass: Cyclopentyl nucleosides
• Intermediate Tree Nodes: 1,3-substituted cyclopentyl nucleosides
• Direct Parent: 1,3-substituted cyclopentyl purine nucleosides
• Alternative Parents: 6-alkylaminopurines Benzylamines Secondary alkylarylamines Chlorobenzenes Fluorobenzenes Aminopyrimidines and derivatives Aryl fluorides Cyclopropanecarboxylic acids and derivatives Aryl chlorides Imidolactams N-substituted imidazoles Heteroaromatic compounds 1,2-diols Secondary alcohols Cyclic alcohols and derivatives Secondary carboxylic acid amides Amino acids and derivatives Azacyclic compounds Carbonyl compounds Hydrocarbon derivatives Organic oxides Organochlorides Organofluorides Organopnictogen compounds
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: 1,3-substituted cyclopentyl purine nucleoside - 6-alkylaminopurine - 6-aminopurine - Imidazopyrimidine - Purine - Benzylamine - Aminopyrimidine - Chlorobenzene - Fluorobenzene - Halobenzene - Secondary aliphatic/aromatic amine - Aryl chloride - Aryl fluoride - Aryl halide - Monocyclic benzene moiety - Cyclopropanecarboxylic acid or derivatives - N-substituted imidazole - Pyrimidine - Imidolactam - Benzenoid - Imidazole - Heteroaromatic compound - Cyclic alcohol - Azole - Secondary carboxylic acid amide - 1,2-diol - Secondary alcohol - Amino acid or derivatives - Carboxamide group - Secondary amine - Azacycle - Organoheterocyclic compound - Carboxylic acid derivative - Organic nitrogen compound - Carbonyl group - Organopnictogen compound - Amine - Organic oxide - Alcohol - Organonitrogen compound - Organooxygen compound - Hydrocarbon derivative - Organic oxygen compound - Organohalogen compound - Organochloride - Organofluoride - Aromatic heteropolycyclic compound
• Description: This compound belongs to the class of organic compounds known as 1,3-substituted cyclopentyl purine nucleosides. These are nucleoside analogues with a structure that consists of a cyclobutane that is substituted a the 1-position with a hydroxyl group and at the 3-position with either a purine base.
• External Descriptors: Not available

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)

ADORA3 Tchem Adenosine receptor A3 (8 Activities)

Discover Target: ADORA3

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

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

KCNH2 Tclin HERG (29587 Activities)

Discover Target: KCNH2

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

Mechanisms of Action

Chemical and Physical Properties

• Solubility: Solvent:DMSO, Max Conc. mg/mL: 5.65, Max Conc. mM: 10
• Molecular Weight: 565.000 g/mol
• XLogP3: 3.300
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 7
• Exact Mass: 564.149 Da
• Monoisotopic Mass: 564.149 Da
• Topological Polar Surface Area: 125.000 Ų
• Heavy Atom Count: 40
• Formal Charge: 0
• Complexity: 1030.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 5
• 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

Frequently Asked Questions

What is the purity of this product, and how is it determined?

This product is supplied at ≥96% purity, determined by HPLC. Lot-specific values are stated on the Certificate of Analysis.

How should this product be stored?

Store at ?20 °C. Freezer storage is required to maintain the specified shelf life.

What is Moligand??

Moligand? is one of Aladdin Scientific's premium product lines, formulated for high-purity applications across multiple workflows. Compared to standard grades in the same workflow, Moligand? products typically offer tighter specifications, more rigorous QC, and stronger lot-to-lot consistency.

How is this product shipped?

This product ships in an insulated container with ice pads. Unpack on arrival and transfer it to the storage condition stated above.

What are the CAS number, molecular formula and molecular weight?

The CAS Number is 1377273-00-1, the molecular formula is C28H23ClF2N6O3, and the molecular weight is 564.97 g/mol. InChIKey LYLLLJJYBWLGHW-CIZVZKTGSA-N.

What documentation is provided?

Available product documentation, including Certificates of Analysis (COA), Safety Data Sheets (SDS), and specification sheets, is shown in the product document area. Document availability and access follow the current site policy.