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2-Cl-IB-MECA - 10mM in DMSO, high purity , CAS No.163042-96-4, Adenosine A3 receptor agonist

COA COA
In stock
Item Number
C422001
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Availability
 Price Qty
C422001-1ml
1ml
Available within 4-8 weeks(?)
Items will be manufactured post-order and can take 4-8 weeks. Thank you for your patience!
$310.90
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Highly selective A3agonist

View related series
Class A GPCR (4138) Compound libraries (12325)

Basic Description

Synonyms 2-Cl-IB-Meca | 2Cl-IB-MECA | (2S,3S,4R,5R)-5-(2-Chloro-6-((3-iodobenzyl)amino)-9H-purin-9-yl)-3,4-dihydroxy-N-methyltetrahydrofuran-2-carboxamide | EX-A2882 | Namodenoson (CF-102) | Namodenoson [USAN] | (2S,3S,4R,5R)-5-[2-chloro-6-[(3-iodophenyl)methylami
Specifications & Purity Moligand™, 10mM in DMSO
Biochemical and Physiological Mechanisms High affinity and extremely selective A3adenosine receptor agonist (Ki= 0.33 nM). Displays 2500- and 1400-fold selectivity over A1and A2Areceptors respectively. Exhibits high selectivity over the Na+-independent adenosine transporter.
Storage Temp Store at -80°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 Adenosine A3 receptor agonist
Product Description

An adenosine analog that acts as a highly selective agonist of adenosine A3 receptor (Ki = 330 pM, 820 nM, 470 nM for A3, A1 and A2A, respectively). Shown to reduce ischemia reperfusion injury in mice and limit infarct size in isolated rat hearts. Shown to reversibly increase field excitatory postsynaptic potentials in hippocampal slices and exhibits excitatory effects on both evoked and spontaneous epileptiform discharges.

A highly selective agonist of adenosine A3 receptor (Ki = 330 pM)

Taxonomic Classification

Taxonomy Tree

Kingdom Organic compounds
Superclass Nucleosides, nucleotides, and analogues
Class Purine nucleosides
Subclass Not available
Intermediate Tree Nodes Not available
Direct Parent Purine nucleosides
Alternative Parents Glycosylamines  6-alkylaminopurines  Benzylamines  Secondary alkylarylamines  Aminopyrimidines and derivatives  Iodobenzenes  2-halopyrimidines  Aryl iodides  Aryl chlorides  Imidolactams  N-substituted imidazoles  Tetrahydrofurans  Heteroaromatic compounds  Secondary alcohols  Secondary carboxylic acid amides  Amino acids and derivatives  1,2-diols  Oxacyclic compounds  Azacyclic compounds  Carbonyl compounds  Hydrocarbon derivatives  Organic oxides  Organochlorides  Organoiodides  Organopnictogen compounds  
Molecular Framework Aromatic heteropolycyclic compounds
Substituents Purine nucleoside - Glycosyl compound - N-glycosyl compound - 6-alkylaminopurine - 6-aminopurine - Imidazopyrimidine - Purine - Benzylamine - Aminopyrimidine - Halobenzene - Halopyrimidine - 2-halopyrimidine - Iodobenzene - Secondary aliphatic/aromatic amine - Aryl chloride - Aryl halide - Aryl iodide - Monocyclic benzene moiety - Imidolactam - Benzenoid - N-substituted imidazole - Pyrimidine - Tetrahydrofuran - Azole - Heteroaromatic compound - Imidazole - Secondary carboxylic acid amide - Secondary alcohol - 1,2-diol - Carboxamide group - Amino acid or derivatives - Secondary amine - Oxacycle - Azacycle - Carboxylic acid derivative - Organoheterocyclic compound - Carbonyl group - Amine - Organohalogen compound - Alcohol - Organic nitrogen compound - Organooxygen compound - Organic oxide - Hydrocarbon derivative - Organoiodide - Organochloride - Organic oxygen compound - Organopnictogen compound - Organonitrogen compound - Aromatic heteropolycyclic compound
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.
External Descriptors Not available

Product Properties

ALogP 1.9

Associated Targets(Human)

ADORA2A Tclin Adenosine receptor A2a (3 Activities)
Activity Type Activity Value -log(M) Mechanism of Action Activity Reference Publications (PubMed IDs)
ADORA2B Tclin Adenosine receptor A2b (2 Activities)
Activity Type Activity Value -log(M) Mechanism of Action Activity Reference Publications (PubMed IDs)
ADORA1 Tclin Adenosine receptor A1 (5 Activities)
Activity Type Activity Value -log(M) Mechanism of Action Activity Reference Publications (PubMed IDs)
ADORA3 Tchem Adenosine receptor A3 (48 Activities)
Activity Type Activity Value -log(M) Mechanism of Action Activity Reference Publications (PubMed IDs)
PPARD Tchem Peroxisome proliferator-activated receptor delta (1 Activities)
Activity Type Activity Value -log(M) Mechanism of Action Activity Reference Publications (PubMed IDs)
PPARG Tclin Peroxisome proliferator-activated receptor gamma (1 Activities)
Activity Type Activity Value -log(M) Mechanism of Action Activity Reference Publications (PubMed IDs)
NR3C1 Tclin Glucocorticoid receptor (14987 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
HTR1A Tclin Serotonin 1a (5-HT1a) receptor (14969 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
HTR1D Tclin Serotonin 1d (5-HT1d) receptor (2897 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
HTR1B Tclin Serotonin 1b (5-HT1b) receptor (2801 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
HTR2A Tclin Serotonin 2a (5-HT2a) receptor (14758 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
HTR2C Tclin Serotonin 2c (5-HT2c) receptor (11471 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
ADORA1 Tclin Adenosine A1 receptor (17603 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
PPARG Tclin Peroxisome proliferator-activated receptor gamma (15191 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
HTR3A Tclin Serotonin 3a (5-HT3a) receptor (3366 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
PPARA Tclin Peroxisome proliferator-activated receptor alpha (9197 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
HTR4 Tclin Serotonin 4 (5-HT4) receptor (2068 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
SLC29A1 Tclin Equilibrative nucleoside transporter 1 (1711 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
HTR2B Tclin Serotonin 2b (5-HT2b) receptor (10323 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
ADORA2A Tclin Adenosine A2a receptor (16305 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
ADORA2B Tclin Adenosine A2b receptor (7672 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
ADORA3 Tchem Adenosine A3 receptor (15931 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
HTR1E Tchem Serotonin 1e (5-HT1e) receptor (696 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
HTR5A Tchem Serotonin 5a (5-HT5a) receptor (1433 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
HTR6 Tchem Serotonin 6 (5-HT6) receptor (9749 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
NR1H3 Tchem LXR-alpha (2891 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
SMPD1 Tchem Sphingomyelin phosphodiesterase (13561 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
PIN1 Tchem Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1 (36611 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
NR1H2 Tchem LXR-beta (3841 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
ABCG2 Tchem ATP-binding cassette sub-family G member 2 (4927 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
TDP1 Tchem Tyrosyl-DNA phosphodiesterase 1 (345557 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
GMNN Tbio Geminin (128009 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
ATAD5 Tbio ATPase family AAA domain-containing protein 5 (122566 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
RGS4 Tchem Regulator of G-protein signaling 4 (13867 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
CDK5 Tchem Cyclin-dependent kinase 5/CDK5 activator 1 (3697 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
ADORA1 Tclin Adenosine receptors; A1 & A3 (1051 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
ADORA3 Tchem Adenosine receptors; A2a & A3 (373 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
TARDBP Tchem TAR DNA-binding protein 43 (40113 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID

Associated Targets(non-human)

Htr7 Serotonin 7 (5-HT7) receptor (19 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
Ppard Peroxisome proliferator-activated receptor delta (358 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
Hdac6 Histone deacetylase 6 (222 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
Plasmodium falciparum (966862 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
Mus musculus (284745 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
rep Replicase polyprotein 1ab (378 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
Nfe2l2 Nuclear factor erythroid 2-related factor 2 (214 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
FTL Ferritin light chain (43324 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
Adora1 Adenosine receptors; A1 & A2a (368 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
Adora2a Adenosine receptor A2a and A3 (172 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID

Mechanisms of Action

Mechanism of Action Action Type target ID Target Name Target Type Target Organism Binding Site Name References

Names and Identifiers

IUPAC Name (2S,3S,4R,5R)-5-[2-chloro-6-[(3-iodophenyl)methylamino]purin-9-yl]-3,4-dihydroxy-N-methyloxolane-2-carboxamide
INCHI InChI=1S/C18H18ClIN6O4/c1-21-16(29)13-11(27)12(28)17(30-13)26-7-23-10-14(24-18(19)25-15(10)26)22-6-8-3-2-4-9(20)5-8/h2-5,7,11-13,17,27-28H,6H2,1H3,(H,21,29)(H,22,24,25)/t11-,12+,13-,17+/m0/s1
InChIKey IPSYPUKKXMNCNQ-PFHKOEEOSA-N
Smiles CNC(=O)C1C(C(C(O1)N2C=NC3=C(N=C(N=C32)Cl)NCC4=CC(=CC=C4)I)O)O
Isomeric SMILES CNC(=O)[C@@H]1[C@H]([C@H]([C@@H](O1)N2C=NC3=C(N=C(N=C32)Cl)NCC4=CC(=CC=C4)I)O)O
WGK Germany 3
Molecular Weight 544.73
Reaxy-Rn 24720887
Reaxys-RN_link_address https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=24720887&ln=

Certificates（CoA,COO,BSE/TSE and Analysis Chart)

C of A & Other Certificates(BSE/TSE, COO):
Analytical Chart:

Chemical and Physical Properties

Sensitivity Heat Sensitive
Melt Point(°C) 207.0 to 211.0 °C
Molecular Weight 544.700 g/mol
XLogP3 1.900
Hydrogen Bond Donor Count 4
Hydrogen Bond Acceptor Count 8
Rotatable Bond Count 5
Exact Mass 544.012 Da
Monoisotopic Mass 544.012 Da
Topological Polar Surface Area 134.000 Ų
Heavy Atom Count 30
Formal Charge 0
Complexity 623.000
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

Solution Calculators

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