ALMOREXANT

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Synonyms
Status
Molecule Category UNKNOWN
UNII 9KCW39P2EI

Structure

InChI Key DKMACHNQISHMDN-RPLLCQBOSA-N
Smiles CNC(=O)[C@@H](c1ccccc1)N1CCc2cc(OC)c(OC)cc2[C@@H]1CCc1ccc(C(F)(F)F)cc1
InChI
InChI=1S/C29H31F3N2O3/c1-33-28(35)27(20-7-5-4-6-8-20)34-16-15-21-17-25(36-2)26(37-3)18-23(21)24(34)14-11-19-9-12-22(13-10-19)29(30,31)32/h4-10,12-13,17-18,24,27H,11,14-16H2,1-3H3,(H,33,35)/t24-,27+/m0/s1

Physicochemical Descriptors

Property Name Value
Molecular Formula C29H31F3N2O3
Molecular Weight 512.57
AlogP 5.74
Hydrogen Bond Acceptor 4.0
Hydrogen Bond Donor 1.0
Number of Rotational Bond 8.0
Polar Surface Area 50.8
Molecular species NEUTRAL
Aromatic Rings 3.0
Heavy Atoms 37.0

Bioactivity

Mechanism of Action Action Reference
Orexin receptor antagonist ANTAGONIST PubMed PubMed
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Membrane receptor Family A G protein-coupled receptor Peptide receptor (family A GPCR) Short peptide receptor (family A GPCR) Orexin receptor
- 13-119 - 5-8 -
Assay Description Organism Bioactivity Reference
Inhibition of OX1 receptor None 13.0 nM
Inhibition of OX2 receptor None 8.0 nM
Antagonist activity at human OX2R expressed in CHO cells assessed as inhibition of calcium mobilization by FLIPR assay Homo sapiens 8.0 nM
Antagonist activity at human OX1R expressed in CHO cells assessed as inhibition of calcium mobilization by FLIPR assay Homo sapiens 13.0 nM
Binding affinity to orexin receptor 1 (unknown origin) Homo sapiens 13.0 nM
Binding affinity to orexin receptor 2 (unknown origin) Homo sapiens 8.0 nM
Antagonist activity at OX1 receptor (unknown origin) Homo sapiens 119.0 nM
Displacement of [125I]-Orexin A from human OX2R expressed in CHO cells after 30 mins by topcount analysis Homo sapiens 4.7 nM
Induction of sleep in Wistar rat assessed as decrease in home cage activity at 100 mg/kg, po after 12 hrs relative to control Rattus norvegicus 43.0 %
Antagonist activity at human OX1R expressed in CHO cells assessed as inhibition of orexin-A-induced intracellular calcium release Homo sapiens 13.0 nM
Antagonist activity at human OX2R expressed in CHO cells assessed as inhibition of orexin-A-induced intracellular calcium release Homo sapiens 8.0 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 -4.8 %
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 20.79 % SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 5.268 %
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 0.14 % 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 1.0 % 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 1.0 % 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 0.14 %

Related Entries

Cross References

Resources Reference
ChEMBL CHEMBL455136
DrugBank DB06673
FDA SRS 9KCW39P2EI
Guide to Pharmacology 2886
PubChem 23727689
SureChEMBL SCHEMBL196577
ZINC ZINC000035953488
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