VOLINANSERIN

/static/temp/default.svg Search structure
Synonyms
Status
Molecule Category UNKNOWN
UNII EW71EE171J
EPA CompTox DTXSID6047363

Structure

InChI Key HXTGXYRHXAGCFP-OAQYLSRUSA-N
Smiles COc1cccc([C@H](O)C2CCN(CCc3ccc(F)cc3)CC2)c1OC
InChI
InChI=1S/C22H28FNO3/c1-26-20-5-3-4-19(22(20)27-2)21(25)17-11-14-24(15-12-17)13-10-16-6-8-18(23)9-7-16/h3-9,17,21,25H,10-15H2,1-2H3/t21-/m1/s1

Physicochemical Descriptors

Property Name Value
Molecular Formula C22H28FNO3
Molecular Weight 373.47
AlogP 3.83
Hydrogen Bond Acceptor 4.0
Hydrogen Bond Donor 1.0
Number of Rotational Bond 7.0
Polar Surface Area 41.93
Molecular species BASE
Aromatic Rings 2.0
Heavy Atoms 27.0

Bioactivity

Mechanism of Action Action Reference
Serotonin 2a (5-HT2a) receptor antagonist ANTAGONIST PubMed Wikipedia
Protein: Serotonin 2a (5-HT2a) receptor
Description: 5-hydroxytryptamine receptor 2A
Organism : Homo sapiens
P28223 ENSG00000102468
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Ion channel Voltage-gated ion channel Potassium channels Voltage-gated potassium channel
- - - 1100-1100 -
Membrane receptor Family A G protein-coupled receptor Small molecule receptor (family A GPCR) Monoamine receptor Adrenergic receptor
- - - 420 -
Membrane receptor Family A G protein-coupled receptor Small molecule receptor (family A GPCR) Monoamine receptor Dopamine receptor
- - - 1300-2250 -
Membrane receptor Family A G protein-coupled receptor Small molecule receptor (family A GPCR) Monoamine receptor Histamine receptor
- - - 1000 -
Membrane receptor Family A G protein-coupled receptor Small molecule receptor (family A GPCR) Monoamine receptor Serotonin receptor
- 5-5 - 0-2 -
Assay Description Organism Bioactivity Reference
Ability to displace [3H]ketanserin from CHO cells expressing human 5-hydroxytryptamine 2A receptor was determined None 0.3 nM
Binding affinity against 5-hydroxytryptamine 2A receptor in humans None 0.36 nM
Binding affinity for displacement of [3H]ketanserin to human 5-hydroxytryptamine 2A receptor stably expressed in CHO cells None 0.31 nM
Binding affinity for human 5-hydroxytryptamine 2A receptor Homo sapiens 1.5 nM
Binding affinity for displacement of [3H]ketanserin to rat 5-hydroxytryptamine 2A receptor stably expressed in CHO cells None 0.1 nM
Binding affinity towards rat 5-hydroxytryptamine 2A receptor None 1.4 nM
Binding affinity for displacement of [3H]mesulergine to human 5-hydroxytryptamine 2C receptor stably expressed in CHO cells None 13.0 nM
Binding affinity for displacement of [3H]prazosin to rat Alpha-1 adrenergic receptor stably expressed in rat cortical membranes None 420.0 nM
Binding affinity against rat 5-hydroxytryptamine 2A receptor Rattus norvegicus 0.1 nM
Binding affinity against human 5-hydroxytryptamine 2A receptor Homo sapiens 0.31 nM
Binding affinity against human 5-hydroxytryptamine 2c receptor Homo sapiens 13.0 nM
Binding affinity to 5HT2A receptor None 0.57 nM
Displacement of [3H]MDL from rat 5HT2A receptor expressed in GF62 cells Rattus norvegicus 2.1 nM
Displacement of [3H]MDL from rat 5HT2A receptor expressed in GF62 cells by liquid scintillation analyser Rattus norvegicus 0.38 nM Displacement of [3H]MDL from rat 5HT2A receptor expressed in GF62 cells by liquid scintillation analyser Rattus norvegicus 2.1 nM
Binding affinity to 5HT2C receptor by competitive binding experiment None 107.0 nM
Displacement of [3H]MDL100907 from rat cortical membrane 5HT2A receptor Rattus norvegicus 0.36 nM
Binding affinity to alpha1 adrenergic receptor by competitive binding experiment None 128.0 nM
Displacement of [3H]- ketanserin from human 5HT2A receptor expressed CHO cells Homo sapiens 0.31 nM
Displacement of [3H]mesulergine from human 5HT2C receptor expressed CHO cells Homo sapiens 13.0 nM
Antagonist activity at human 5HT2A receptor expressed in HEK cells assessed as inhibition of intracellular calcium accumulation by aequorin assay Homo sapiens 0.1 nM
Antagonist activity at human 5HT2C receptor expressed in human SH-SY5Y cells by FLIPR assay Homo sapiens 316.23 nM
Antagonist activity at human recombinant 5-HT2A receptor expressed in CHOK1 cells assessed as inhibition of serotonin-induced calcium release preincubated for 15 mins followed by 5-HT addition measured every 1.7 secs for 60 secs by calcium 4 dye-based FLIPR assay Homo sapiens 4.786 nM Antagonist activity at human recombinant 5-HT2A receptor expressed in CHOK1 cells assessed as inhibition of serotonin-induced calcium release preincubated for 15 mins followed by 5-HT addition measured every 1.7 secs for 60 secs by calcium 4 dye-based FLIPR assay Homo sapiens 4.8 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 -6.94 %
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 12.43 %
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 -0.01 % 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 -0.01 %

Cross References

Resources Reference
ChEMBL CHEMBL74355
DrugBank DB16351
FDA SRS EW71EE171J
Guide to Pharmacology 185
PubChem 5311271
SureChEMBL SCHEMBL675164
ZINC ZINC000000598040
CONTENTS