ROLOFYLLINE

/static/temp/default.svg Search structure
Synonyms
Status
Molecule Category UNKNOWN
UNII 7805S5HIHX

Structure

InChI Key PJBFVWGQFLYWCB-UHFFFAOYSA-N
Smiles CCCn1c(=O)c2nc(C34CC5CC(CC3C5)C4)[nH]c2n(CCC)c1=O
InChI
InChI=1S/C20H28N4O2/c1-3-5-23-16-15(17(25)24(6-4-2)19(23)26)21-18(22-16)20-10-12-7-13(11-20)9-14(20)8-12/h12-14H,3-11H2,1-2H3,(H,21,22)

Physicochemical Descriptors

Property Name Value
Molecular Formula C20H28N4O2
Molecular Weight 356.47
AlogP 2.78
Hydrogen Bond Acceptor 5.0
Hydrogen Bond Donor 1.0
Number of Rotational Bond 5.0
Polar Surface Area 72.68
Molecular species NEUTRAL
Aromatic Rings 2.0
Heavy Atoms 26.0

Bioactivity

Mechanism of Action Action Reference
Adenosine A1 receptor antagonist ANTAGONIST PubMed PubMed
Protein: Adenosine A1 receptor
Description: Adenosine receptor A1
Organism : Homo sapiens
P30542 ENSG00000163485
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
- - - 0-13 -
Assay Description Organism Bioactivity Reference
Binding affinity for adenosine A2 receptor using N-[3H]-ethyladenosin-5''-uronamide in guinea pig forebrain membranes Cavia porcellus 430.0 nM
Binding affinity for Adenosine A2 receptor from Guinea pig membranes Cavia porcellus 230.0 nM
Inhibition of binding to membranes from HEK293 cells expressing human Adenosine A1 receptor Homo sapiens 0.72 nM
Inhibition of binding to membranes from HEK293 cells expressing human Adenosine A2 receptor Homo sapiens 108.0 nM
Binding affinity at bovine Adenosine A1 receptor. None 0.19 nM
Binding affinity for Adenosine A1 receptor of rat forebrain Rattus norvegicus 12.6 nM
Binding affinity against adenosine A1 receptor using N6-[3H]cyclohexyladenosine as radioligand in guinea pig forebrain membranes Cavia porcellus 1.3 nM
Binding affinity for Adenosine A1 receptor from Guinea pig membranes Cavia porcellus 1.1 nM
Binding affinity against adenosine A1 receptor using [3H]-CHA or [3H]PIA as radioligand None 1.3 nM
Binding affinity towards adenosine A1 receptor in rat forebrain membranes using N6-[3H]cyclohexyladenosine Rattus norvegicus 0.19 nM
Binding affinity towards adenosine A1 receptor using N6-[3H]cyclohexyladenosine in guinea pig forebrain membranes Cavia porcellus 1.3 nM
Binding affinity against adenosine A1 receptor in guinea pig forebrain membranes using N6-[3H]cyclohexyladenosine as radioligand Cavia porcellus 1.3 nM
Binding affinity against adenosine A2 receptor using N-[3H]-ethyladenosin-5''-uronamide as radioligand in rat striatal membranes. None 380.0 nM
Binding affinity for Adenosine A2 receptor from rat striatal membranes Rattus norvegicus 510.0 nM
Binding affinity against adenosine A2 receptor in rat striatal membranes using N-[3H]-ethyladenosin-5''-uronamide as radioligand in the presence of 50 nM cyclopentyladenosine None 380.0 nM
Percent inhibition of serum creatinine by the compound given as ratio of Cr value in treated to vehicle treated ones after intraperitoneal administration of 1 mg/kg of compound to rats(vehicle 2.75+/-0.43) Rattus norvegicus 47.0 %
Percent inhibition of Urea nitrogen by the compound given as ratio of UN value in treated to vehicle treated ones after intraperitoneal administration of 1 mg/kg of compound to rats(vehicle 123.2+/-14.2) Rattus norvegicus 46.0 %
Binding affinity to human adenosine A1 receptor Homo sapiens 0.295 nM
Binding affinity to rat adenosine A1 receptor Rattus norvegicus 0.19 nM
Binding affinity to rat adenosine A2A receptor Rattus norvegicus 170.0 nM
Binding affinity to mouse adenosine A1 receptor Mus musculus 0.145 nM
Binding affinity to guinea pig adenosine A2A receptor Cavia porcellus 230.0 nM
Binding affinity to guinea pig adenosine A1 receptor Cavia porcellus 1.1 nM
The A2A-StaR2 receptor has been purified from membranes in n-decyl-beta-D-maltoside as detergent. Ligands were prepared over a five-fold concentration series and injected in either a multi- or a single-cycle format depending on the kinetic parameters of the ligand. The actual concentrations as well as contact and dissociation times varied between the ligands depended on the kinetics and affinity of the interaction. The data were fitted to a 1:1 interaction model using the kinetics evaluation software from Biacore. A minimum of three measurements were recorded for each interaction. Homo sapiens 34.81 nM
The A2A-StaR2 receptor has been purified from membranes in n-decyl-beta-D-maltoside as detergent. Then it has been reconstituted into rHDLs membrane discs.Ligands were prepared over a five-fold concentration series and injected in either a multi- or a single-cycle format depending on the kinetic parameters of the ligand. The actual concentrations as well as contact and dissociation times varied between the ligands depended on the kinetics and affinity of the interaction. The data were fitted to a 1:1 interaction model using the kinetics evaluation software from Biacore. A minimum of three measurements were recorded for each interaction. Homo sapiens 131.15 nM
The A1-StaR receptor has been purified from membranes in n-decyl-beta-D-maltoside as detergent. Ligands were prepared over a five-fold concentration series and injected in either a multi- or a single-cycle format depending on the kinetic parameters of the ligand. The actual concentrations as well as contact and dissociation times varied between the ligands depended on the kinetics and affinity of the interaction. The data were fitted to a 1:1 interaction model using the kinetics evaluation software from Biacore. Homo sapiens 11.38 nM
Binding affinity to human adenosine A1 receptor by radioligand displacement assay Homo sapiens 0.72 nM
Binding affinity to human adenosine A2A receptor by radioligand displacement assay Homo sapiens 108.0 nM
Binding affinity to human adenosine A2B receptor by radioligand displacement assay Homo sapiens 269.0 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 12.66 %
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 15.41 %
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 0.31 % 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 0.31 %
Displacement of [3H]CCPA from human adenosine receptor A1 expressed in CHO cell membranes incubated for 90 mins by radioligand competition assay Homo sapiens 0.7 nM
Displacement of [3H]CCPA from adenosine receptor A1 in rat brain cortex membranes incubated for 90 mins by radioligand competition assay Rattus norvegicus 0.19 nM
Displacement of [3H]MSX2 from human adenosine receptor A2A expressed in HEK293 cell membranes incubated for 30 mins by radioligand competition assay Homo sapiens 108.0 nM
Displacement of [3H]MSX2 from adenosine receptor A2A in rat brain striatum membranes incubated for 30 mins by radioligand competition assay Rattus norvegicus 380.0 nM
Displacement of [3H]PSB-603 from human adenosine receptor A2B expressed in CHO cell membranes incubated for 75 mins by radioligand competition assay Homo sapiens 296.0 nM

Related Entries

Cross References

Resources Reference
ChEMBL CHEMBL52333
FDA SRS 7805S5HIHX
Guide to Pharmacology 5604
PubChem 11948288
SureChEMBL SCHEMBL18029490
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