PRELADENANT

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Synonyms
Status
Molecule Category Free-form
UNII 950O97NUPO
EPA CompTox DTXSID90191219

Structure

InChI Key DTYWJKSSUANMHD-UHFFFAOYSA-N
Smiles COCCOc1ccc(N2CCN(CCn3ncc4c3nc(N)n3nc(-c5ccco5)nc43)CC2)cc1
InChI
InChI=1S/C25H29N9O3/c1-35-15-16-36-19-6-4-18(5-7-19)32-11-8-31(9-12-32)10-13-33-23-20(17-27-33)24-28-22(21-3-2-14-37-21)30-34(24)25(26)29-23/h2-7,14,17H,8-13,15-16H2,1H3,(H2,26,29)

Physicochemical Descriptors

Property Name Value
Molecular Formula C25H29N9O3
Molecular Weight 503.57
AlogP 2.16
Hydrogen Bond Acceptor 12.0
Hydrogen Bond Donor 1.0
Number of Rotational Bond 9.0
Polar Surface Area 125.0
Molecular species NEUTRAL
Aromatic Rings 5.0
Heavy Atoms 37.0

Bioactivity

Mechanism of Action Action Reference
Adenosine A2a receptor antagonist ANTAGONIST PubMed PubMed Wikipedia
Protein: Adenosine A2a receptor
Description: Adenosine receptor A2a
Organism : Homo sapiens
P29274 ENSG00000128271
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Membrane receptor Family A G protein-coupled receptor Small molecule receptor (family A GPCR) Nucleotide-like receptor (family A GPCR) Adenosine receptor
- - 0 1-5 120
Assay Description Organism Bioactivity Reference
Binding affinity to human adenosine A2A receptor Homo sapiens 1.1 nM
Inhibition of haloperidol-induced catalepsy in rat at 1 mg/kg, po after 1 hr Rattus norvegicus 77.0 %
Inhibition of haloperidol-induced catalepsy in rat at 1 mg/kg, po after 4 hrs Rattus norvegicus 70.0 %
Binding affinity to rat adenosine A2A receptor Rattus norvegicus 2.5 nM
Inhibition of haloperidol-induced catalepsy in rat at 1 mg/kg, po after 1 hr Rattus norvegicus 77.0 %
Inhibition of haloperidol-induced catalepsy in rat at 1 mg/kg, po after 4 hrs Rattus norvegicus 70.0 %
Inhibition of haloperidol-induced catalepsy in rat at 0.3 mg/kg, po after 1 hr Rattus norvegicus 25.0 %
Inhibition of haloperidol-induced catalepsy in rat at 0.3 mg/kg, po after 4 hrs Rattus norvegicus 25.0 %
Inhibition of haloperidol-induced catalepsy in rat at 0.1 mg/kg, po after 1 hr Rattus norvegicus 60.0 %
Inhibition of haloperidol-induced catalepsy in rat at 0.1 mg/kg, po after 4 hrs Rattus norvegicus 60.0 %
Displacement of [3H]ZM241385 from human adenosine A2A receptor expressed in buculovirus system by liquid scintillation counting Homo sapiens 5.0 nM
Displacement of [3H]-ZM241385 from human adenosine A2A receptor expressed in high five cells after 30 mins by scintillation counting Homo sapiens 5.0 nM
Displacement of [3H]-DPCPX from human adenosine A1 receptor expressed in CHO cells at 200 nM after 30 mins by scintillation counting Homo sapiens 30.0 %
Inhibition of haloperidol -induced catalepsy in rat at 10 mg/kg, po measured after 1 hr Rattus norvegicus 75.0 %
Inhibition of haloperidol -induced catalepsy in rat at 10 mg/kg, po measured after 4 hrs Rattus norvegicus 80.0 %
Displacement of [3H]ZM241385 from stabilized human adenosine receptor A2a expressed in HEK293 cells followed by receptor capturing on Biocore chips by SPR method Homo sapiens 1.585 nM Displacement of [3H]ZM241385 from stabilized human adenosine receptor A2a expressed in HEK293 cells followed by receptor capturing on Biocore chips by SPR method Homo sapiens 0.3162 nM
Displacement of [3H]MSX2 from human recombinant adenosine A2A receptor expressed in CHO cells after 30 mins by liquid scintillation counting analysis Homo sapiens 0.884 nM
Displacement of [3H]CCPA from human recombinant adenosine A1 receptor expressed in CHO cells after 90 mins by liquid scintillation counting analysis Homo sapiens 295.0 nM
Displacement of [3H]MSX2 from adenosine A2A receptor in rat brain striatal membranes after 30 mins by liquid scintillation counting analysis Rattus norvegicus 0.66 nM
Displacement of [3H]CCPA from adenosine A1 receptor in rat brain cortical membranes after 90 mins by liquid scintillation counting analysis Rattus norvegicus 68.7 nM
Inhibition of adenosine A2A receptor (unknown origin) at 100 umol/L relative to control Homo sapiens 120.0 %
Displacement of [3H]-ZM241385 from human adenosine A2A receptor expressed in HEK293 cells Homo sapiens 1.0 nM
Inhibition of human recombinant adenosine receptor A2a Homo sapiens 0.6 nM Inhibition of human recombinant adenosine receptor A2a Homo sapiens 1.1 nM
Inhibition of human recombinant adenosine A1 receptor Homo sapiens 996.0 nM
Anticataleptic activity in rat assessed as inhibition at 1 mg/kg, po after 1 hr Rattus norvegicus 75.0 % Anticataleptic activity in rat assessed as inhibition at 1 mg/kg, po after 1 hr Rattus norvegicus 77.0 %
Anticataleptic activity in rat assessed as inhibition at 1 mg/kg, po after 4 hrs Rattus norvegicus 80.0 % Anticataleptic activity in rat assessed as inhibition at 1 mg/kg, po after 4 hrs Rattus norvegicus 70.0 %
Antiviral activity against Zika virus infected in human A549 cells preincubated for 5 hrs followed by compound wash measured after 48 hrs by viral plague-forming assay Zika virus 136.1 nM
Antagonist activity at adenosine A2A receptor (unknown origin) Homo sapiens 0.5 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 3.62 %
Antagonist activity at human adenosine A2A receptor Homo sapiens 1.1 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 9.582 %
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 -0.1 % 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 -0.1 %
Displacement of [3H]SCH58261 from human adenosine 2A receptor expressed in HEK293 cell membranes incubated for 1.5 hrs by radioligand competition binding assay Homo sapiens 1.1 nM
Displacement of [3H]CCPA from human recombinant adenosine A1 receptor expressed in CHO cells by liquid scintillation counting analysis Homo sapiens 295.0 nM
Displacement of [3H]MSX-2 from human recombinant adenosine A2A receptor expressed in CHO cells by liquid scintillation counting analysis Homo sapiens 0.88 nM

Cross References

Resources Reference
ChEMBL CHEMBL240624
DrugBank DB11864
FDA SRS 950O97NUPO
Guide to Pharmacology 5614
PubChem 10117987
SureChEMBL SCHEMBL2856554
ZINC ZINC000053006885
CONTENTS