NAMODENOSON

/static/temp/default.svg Search structure
Synonyms
Status
Molecule Category Free-form
UNII Z07JR07J6C
EPA CompTox DTXSID80167504

Structure

InChI Key IPSYPUKKXMNCNQ-PFHKOEEOSA-N
Smiles CNC(=O)[C@H]1O[C@@H](n2cnc3c(NCc4cccc(I)c4)nc(Cl)nc32)[C@H](O)[C@@H]1O
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

Physicochemical Descriptors

Property Name Value
Molecular Formula C18H18ClIN6O4
Molecular Weight 544.74
AlogP 1.06
Hydrogen Bond Acceptor 9.0
Hydrogen Bond Donor 4.0
Number of Rotational Bond 5.0
Polar Surface Area 134.42
Molecular species NEUTRAL
Aromatic Rings 3.0
Heavy Atoms 30.0

Bioactivity

Mechanism of Action Action Reference
Adenosine A3 receptor agonist AGONIST PubMed
Protein: Adenosine A3 receptor
Description: Adenosine receptor A3
Organism : Homo sapiens
P0DMS8 ENSG00000282608
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Membrane receptor Family A G protein-coupled receptor Small molecule receptor (family A GPCR) Monoamine receptor Serotonin receptor
- - - 10000 30
Membrane receptor Family A G protein-coupled receptor Small molecule receptor (family A GPCR) Nucleotide-like receptor (family A GPCR) Adenosine receptor
1-4 1-2 - 0-60 -
Transcription factor Nuclear receptor Nuclear hormone receptor subfamily 1 Nuclear hormone receptor subfamily 1 group C Nuclear hormone receptor subfamily 1 group C member 1
- - - - 47
Transcription factor Nuclear receptor Nuclear hormone receptor subfamily 1 Nuclear hormone receptor subfamily 1 group C Nuclear hormone receptor subfamily 1 group C member 2
191-29800 - - 0 75
Transcription factor Nuclear receptor Nuclear hormone receptor subfamily 1 Nuclear hormone receptor subfamily 1 group C Nuclear hormone receptor subfamily 1 group C member 3
2940 - - 2 59
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC28 and SLC29 families of nucleoside transporters SLC29 Facilitative nucleoside transporter family
- - - 15200 -
Assay Description Organism Bioactivity Reference
Binding affinity using [125I]ABA against human Adenosine A1 receptor Homo sapiens 99.0 nM
Binding affinity for rat Adenosine A1 receptor in CHO cells using [3H]N6-(R)-phenylisopropyladenosine Rattus norvegicus 820.0 nM
Binding affinity for adenosine A1 receptor as inhibition of 3[H]-R-PIA binding in rat brain Rattus norvegicus 54.0 nM
Binding affinity for adenosine A1 receptor as displacement of [3H]R-PIA from rat brain membranes at 10e-4 M Rattus norvegicus 820.0 nM
Tested for the binding affinity of A1 receptor by displacing the [3H]-PIA in rat brain membranes None 820.0 nM
Binding affinity using [125I]ABA against human Adenosine A3 receptor Homo sapiens 14.0 nM
Binding affinity for rat adenosine A2A receptor of CHO cells using [3H]CGS-21680 Rattus norvegicus 470.0 nM
Binding affinity for adenosine A2A receptor as displacement of [3H]-CGS- 21680 from rat striatal membranes at 10e-4 M Rattus norvegicus 470.0 nM
Binding affinity of adenosine derivative for endogenous rat Adenosine A3 receptor expressed on CHO cell None 0.9 nM
Binding affinity for rat Adenosine A3 receptor in CHO cells [125I]-iodo-AB-MECA Rattus norvegicus 0.33 nM
Binding affinity for rat Adenosine A3 receptor Rattus norvegicus 0.33 nM
Tested for the binding affinity of A3 receptor by displacing N6-[[125I]-4-amino-3-iodobenzyl]-adenosine-5''-N-methyluronamide from membranes of CHO cells transfected with rat A3-cDNA None 0.33 nM
Binding affinity towards human Adenosine A3 receptor wild type None 2.3 nM
Binding affinity for adenosine A2a receptor as inhibition of 3[H]-CGS 21680 binding in rat striatum Rattus norvegicus 56.0 nM
Tested for the binding affinity of A2a receptor by displacing the [3H]-CGS- 21680 in rat striatal membranes None 470.0 nM
Effect on forskolin-stimulated cyclic AMP production in intact chinese hamster ovary (CHO) cell expressing the human Adenosine A3 receptor None 2.8 nM
Affinity for human Adenosine A3 receptor expressed in CHO cell None 1.4 nM
Binding affinity at Mutant (H272E) human adenosine A3 receptor expressed in COS-7 cells None 20.1 nM
Binding affinity at wild-type Adenosine A3 receptor expressed in COS-7 cells None 4.3 nM
Binding affinity for human Adenosine A3 receptor in CHO cells using [125I]-iodo-AB-MECA Homo sapiens 1.0 nM
Binding affinity for adenosine A3 receptor as inhibition of [125I]AB-MECA binding to human receptor expressed in HEK 293 cells Homo sapiens 1.1 nM
Binding affinity towards Adenosine A3 receptor (H95A mutant receptor) None 60.0 nM
Binding affinity towards Adenosine A3 receptor (W243 mutant) receptor Homo sapiens 2.9 nM
Displacement of [125I]AB-MECA from adenosine A3 receptor from HEK293 cell membranes Homo sapiens 0.33 nM
Binding affinity for CHO cell membrane expressing human A3AR with GTPgammaS using [3H]8-ethyl-4-methyl-2-phenyl-(8R)-4,5,7,8-tetrahydro-1H-imidazo[2,1-i]-purin-5-one Homo sapiens 6.3 nM
Binding affinity for CHO cell membrane expressing human Adenosine A3 receptor using [3H]8-ethyl-4-methyl-2-phenyl-(8R)-4,5,7,8-tetrahydro-1H-imidazo[2,1-i]-purin-5-one Homo sapiens 1.5 nM
Displacement of [125I]-AB MECA from recombinant human adenosine A3 receptor expressed in HEK cells Homo sapiens 1.4 nM
Inhibition of [3H]R-PIA binding to human Adenosine A1 receptor expressed in CHO cells Homo sapiens 220.0 nM
Inhibition of [125I]AB-MECA binding to rat Adenosine A3 receptor expressed in CHO cells Rattus norvegicus 0.33 nM
Inhibition of [125I]-AB-MECA binding to human Adenosine A3 receptor expressed in CHO cells Homo sapiens 1.4 nM
Displacement of [3H]CHA binding to Adenosine A1 receptor expressed in CHO cells Homo sapiens 823.0 nM
Displacement of [3H]CGS-21680 binding to Adenosine A2 receptor expressed in CHO cells Homo sapiens 448.0 nM
Displacement of [125I]AB-MECA binding to Adenosine A3 receptor expressed in CHO cells Homo sapiens 0.33 nM
Binding affinity towards recombinant human Adenosine A1 receptor was determined using [3H]R-PIA (2.0 nM) as radioligand Homo sapiens 222.0 nM
Displacement of [3H]DPCPX binding to adenosine A1 receptors of bovine cortical membranes Bos taurus 890.0 nM
Displacement of [3H]CGS-21680 binding to adenosine A2A receptors of bovine striatal membranes Bos taurus 401.0 nM
Displacement of [125I]AB-MECA from adenosine A3 receptors in bovine cortical membranes Bos taurus 0.22 nM
Binding affinity towards human Adenosine A3 receptor stably transfected in CHO cells was determined using [125I]I-AB-MECA (1.0 nM) as radioligand Homo sapiens 1.4 nM
Inhibition of (10 uM) forskolin-mediated cAMP production in CHO cells expressing human Adenosine A3 receptor Homo sapiens 2.2 nM
Displacement of [125I]ABA from human adenosine A1 receptor expressed in HEK cells Homo sapiens 5.26 nM
Displacement of [125I]ZM-241385 from human adenosine A2A receptor in HEK cells at 100 uM Homo sapiens 50.0 %
Displacement of [125I]ABOPX from human adenosine A2B receptor in HEK cells at 100 uM Homo sapiens 50.0 %
Displacement of [125I]ABA from human adenosine A3 receptor expressed in HEK cells Homo sapiens 0.637 nM
Displacement of [3H]CCPA from human adenosine A1 receptor in CHO cells Homo sapiens 222.0 nM
Displacement of [125I]AB-MECA from human adenosine A3 receptor expressed in CHO cells Homo sapiens 1.4 nM
Displacement of [3H]DPCPX from human adenosine A1 receptor expressed in CHO cells Homo sapiens 890.0 nM
Displacement of [3H]NECA from human adenosine A2A receptor expressed in CHO cells Homo sapiens 401.0 nM
Displacement of [3H]AB-MECA from human adenosine A3 receptor expressed in CHO cells Homo sapiens 0.22 nM
Displacement of [3H]CCPA from human adenosine A1 receptor expressed in CHO cells Homo sapiens 222.0 nM
Displacement of [3H]ABMECA from human adenosine A3 receptor expressed in CHO cells Homo sapiens 1.4 nM
Agonist activity at human adenosine A3 receptor expressed in CHO cells assessed as inhibition of forskolin-stimulated cAMP Homo sapiens 1.2 nM
Displacement of [3H]DPDPX from human adenosine A1 receptor expressed in CHO cells Homo sapiens 890.0 nM
Displacement of [3H]NECA from human adenosine A2A receptor expressed in CHO cells Homo sapiens 401.0 nM
Displacement of [125I]AB-MECA from human adenosine A3 receptor expressed in CHO cells Homo sapiens 0.22 nM
Displacement of [125I]N6-(4-amino-3-iodobenzyl)adenosine-5'-N-methyl-uronamide from mouse recombinant adenosine A1 receptor expressed in HEK293 cells Mus musculus 35.0 nM
Displacement of [125I]N6-(-amino-3-iodobenzyl)adenosine-5'-N-methyl-uronamide from mouse recombinant adenosine A3 receptor expressed in HEK293 cells Mus musculus 0.18 nM
Displacement of radioligand from human adenosine A1 receptor expressed in CHO cells Homo sapiens 220.0 nM
Displacement of radioligand from human adenosine A3 receptor expressed in CHO cells Homo sapiens 1.4 nM
Displacement of radioligand from rat adenosine A1 receptor Rattus norvegicus 820.0 nM
Displacement of radioligand from rat adenosine A2A receptor Rattus norvegicus 470.0 nM
Displacement of radioligand from rat A3 adenosine receptor Rattus norvegicus 0.33 nM
Displacement of [125I]I-AB-MEAC from human adenosine A3 receptor expressed in CHO cells Homo sapiens 0.3802 nM
Displacement of [3H]CCPA form human adenosine A1 receptor expressed in CHO cells Homo sapiens 222.0 nM
Displacement of [3H]CGS21680 form human adenosine A3 receptor expressed in CHO cells Homo sapiens 1.4 nM
Displacement of [3H]CCPA from human adenosine A1 receptor expressed in CHO cells Homo sapiens 222.0 nM
Displacement of [125I]I-AB-MECA from human adenosine A3 receptor expressed in CHO cells Homo sapiens 1.4 nM
Displacement of [125I]I-AB-MECA from rat adenosine A3 receptor expressed in CHO cells Rattus norvegicus 0.33 nM
Displacement of [3H]NECA from human recombinant adenosine A1 receptor expressed in CHO cells by liquid scintillation counting Homo sapiens 220.0 nM
Displacement of [3H]I-AB-MECA from human recombinant adenosine A3 receptor expressed in CHO cells by liquid scintillation counting Homo sapiens 1.4 nM
Binding affinity to human adenosine A3 receptor Homo sapiens 1.0 nM
Displacement of [3H]R-PIA from human adenosine A1 receptor expressed in CHO cells Homo sapiens 222.0 nM
Displacement of [125I]AB-MECA from human adenosine A3 receptor expressed in CHO cells Homo sapiens 1.4 nM
Displacement of [3H]DPCPX from human A1 adenosine receptor expressed in CHO cell membrane Homo sapiens 890.0 nM
Displacement of [3H]NECA from human A2A adenosine receptor expressed in CHO cell membrane Homo sapiens 401.0 nM
Displacement of [125I]AB-MECA from human A3 adenosine receptor expressed in CHO cell membrane Homo sapiens 0.22 nM
Displacement of [125I]I-AB-MECA from human recombinant adenosine A3 receptor expressed in CHO cells after 60 mins by gamma counter Homo sapiens 2.2 nM
Displacement of [125I]I-AB-MECA from human rat adenosine A3 receptor expressed in CHO cells after 60 mins by gamma counter Rattus norvegicus 0.33 nM
Displacement of [3H]CCPA from rat adenosine A1 receptor expressed in CHO cells after 60 mins by gamma counter Rattus norvegicus 820.0 nM
Displacement of [3H]CGS21680 from rat adenosine A2A receptor expressed in CHO cells after 60 mins by gamma counter Rattus norvegicus 470.0 nM
Agonist activity at mouse adenosine A3 receptor expressed in HEK293 cell membranes assessed as inhibition of forskolin-stimulated cAMP production preincubated for 30 mins prior to forskolin-treatment measured after 15 mins by ELISA Mus musculus 0.15 nM
Displacement of [125I]I-AB-MECA from human adenosine A3 receptor expressed in CHO cells after 90 mins by gamma counting analysis Homo sapiens 1.4 nM
Competitive binding affinity to human adenosine A3 receptor expressed in CHO cells after 90 mins by flow cytometric analysis in presence of MRS5449 Homo sapiens 27.7 nM
Displacement of [125I]AB-MECA from human adenosine A3 receptor expressed in CHO cell membrane after 90 mins Homo sapiens 0.22 nM
Displacement of [3H]NECA from human adenosine A2A receptor expressed in CHO cell membrane after 90 mins Homo sapiens 401.0 nM
Displacement of [3H]DPCPX from human adenosine A1 receptor expressed in CHO cell membrane after 180 mins Homo sapiens 890.0 nM
Binding affinity to A3AR (unknown origin) Homo sapiens 1.0 nM
Agonist activity at human recombinant A3AR expressed in CHO cells assessed as inhibition of forskolin-induced stimulation of cAMP production Homo sapiens 1.21 nM
Binding affinity to Adenosine receptor A3 (unknown origin) Homo sapiens 1.4 nM
Agonist activity at mouse adenosine A3 receptor expressed in HEK293 cell membranes assessed as inhibition of forskolin-stimulated cAMP accumulation preincubated for 30 mins followed by forsolkin addition measured after 15 mins by immunoassay Mus musculus 0.46 nM
Displacement of [3H]WAY100635 from human 5-HT1AR expressed in CHO cell membranes at 10 uM incubated for 90 mins under dark condition by microbeta scintillation counting method relative to control Homo sapiens 50.0 %
Displacement of [3H]5-CT from human 5-HT1BR expressed in HEK cell membranes at 10 uM incubated for 90 mins under dark condition by microbeta scintillation counting method relative to control Homo sapiens 50.0 %
Displacement of [3H]5-CT from human 5-HT1D receptor expressed in HEK-T cell membranes at 10 uM incubated for 90 mins under dark condition by microbeta scintillation counting method relative to control Homo sapiens 50.0 %
Displacement of [3H]5-HT from human 5-HT1E receptor expressed in HEK cell membranes at 10 uM incubated for 90 mins under dark condition by microbeta scintillation counting method relative to control Homo sapiens 50.0 %
Displacement of [3H]GR113808 from human 5-HT4 receptor at 10 uM incubated for 90 mins under dark condition by microbeta scintillation counting method relative to control Homo sapiens 50.0 %
Displacement of [3H]LSD from human 5-HT6 receptor expressed in HEK cell membranes at 10 uM incubated for 90 mins under dark condition by microbeta scintillation counting method relative to control Homo sapiens 50.0 %
Displacement of [3H]LSD from human 5-HT7A receptor expressed in HEK cell membranes at 10 uM incubated for 90 mins under dark condition by microbeta scintillation counting method relative to control Homo sapiens 50.0 %
Displacement of [3H]GR65630 from human 5-HT3 receptor expressed in HEK-T cell membranes at 10 uM incubated for 90 mins under dark condition by microbeta scintillation counting method relative to control Homo sapiens 50.0 %
Displacement of [3H]LSD from human 5-HT5A receptor expressed in Flp-In-CHO cell membranes incubated for 90 mins under dark condition by microbeta scintillation counting method relative to control Homo sapiens 50.0 %
Displacement of [3H]ketanserin from human 5-HT2A receptor expressed in HEK-T cell membranes at 10 uM incubated for 90 mins under dark condition by microbeta scintillation counting method relative to control Homo sapiens 30.0 %
Displacement of [3H]lysergic from human 5-HT2BR expressed in HEK cell membranes at 10 uM incubated for 90 mins under dark condition by microbeta scintillation counting method relative to control Homo sapiens 50.0 %
Displacement of [3H]mesulergine from human 5-HT2CR expressed in Flp-In HEK cell membranes at 10 uM incubated for 90 mins under dark condition by microbeta scintillation counting method relative to control Homo sapiens 50.0 %
Displacement of [3H]N6-phenylisopropyladenosine from recombinant human A1AR expressed in CHO cell membranes after 60 mins by liquid scintillation counting method Homo sapiens 220.0 nM
Displacement of [125I]I-AB-MECA from human adenosine A3 receptor expressed in CHO cells after 60 mins by gamma counting analysis Homo sapiens 1.4 nM
Displacement of [125I]I-AB-MECA from human A3 adenosine receptor expressed in CHO cell membranes after 60 mins by gamma counting method Homo sapiens 1.4 nM
Displacement of [3H]CCPA from human A1 receptor expressed in CHO cell membranes after 60 mins by gamma counting method Homo sapiens 222.0 nM
Displacement of Fluormone-Pan-PPAR Green from human GST-tagged PPARgamma LBD at 4 uM by TR-FRET assay relative to control Homo sapiens 59.0 %
Displacement of Fluormone-Pan-PPAR Green from human GST-tagged PPARdelta LBD at 4 uM by TR-FRET assay relative to control Homo sapiens 75.0 %
Displacement of Fluormone-Pan-PPAR Green from human GST-tagged PPARalpha LBD at 20 uM by TR-FRET assay relative to control Homo sapiens 46.5 %
Displacement of Fluormone-Pan-PPAR Green from human GST-tagged PPARgamma LBD by TR-FRET assay Homo sapiens 2.18 nM
Displacement of Fluormone-Pan-PPAR Green from human GST-tagged PPARdelta LBD by TR-FRET assay Homo sapiens 0.43 nM
Displacement of [3H]NECA from recombinant human adenosine A3 receptor expressed in CHO cell membranes measured after 180 mins Homo sapiens 0.2 nM
Displacement of [3H]CCPA from human adenosine A1 receptor expressed in CHO cell membranes after 3 hrs by micro beta scintillation counting method Homo sapiens 220.0 nM
Displacement of [3H]HEMADO from human adenosine A3 receptor expressed in CHO cell membranes after 3 hrs by micro beta scintillation counting method Homo sapiens 1.4 nM
Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of Caco-2 cells at 10 uM after 48 hours by high content imaging Homo sapiens -5.44 %
Partial agonist activity at recombinant human A3AR expressed in HEK293 cells assessed as inhibition of forskolin-stimulated cAMP accumulation measured after 30 mins in presence of A2BAR blocker PSB-603 by Glo-sensor assay Homo sapiens 4.1 nM
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 11.8 % SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 22.49 %
Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging Chlorocebus sabaeus 0.03 % Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging Chlorocebus sabaeus -0.27 % Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging Chlorocebus sabaeus -0.27 % Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging Chlorocebus sabaeus 0.03 %
Competitive binding affinity to GST-tagged human PPARdelta LBD incubated for 1 to 6 hrs by TR-FRET assay Homo sapiens 191.0 nM
Binding affinity to human A3AR assessed as inhibitor constant Homo sapiens 1.4 nM
Agonist activity at human A3 adenosine receptor expressed in CHO cells assessed as inhibition of forskolin stimulated cAMP formation incubated for 45 mins followed by forskolin stimulation and measured after 15 mins by liquid scintillation spectrometry analysis Homo sapiens 1.21 nM

Related Entries

Cross References

Resources Reference
ChEMBL CHEMBL431733
DrugBank DB12885
FDA SRS Z07JR07J6C
Guide to Pharmacology 457
PubChem 3035850
SureChEMBL SCHEMBL1170028
ZINC ZINC000003995845
CONTENTS