PENTOBARBITAL

/static/temp/default.svg Search structure
Trade Names
Synonyms
Status
Molecule Category Free-form
ATC N05CA01
UNII I4744080IR
EPA CompTox DTXSID7023435

Structure

InChI Key WEXRUCMBJFQVBZ-UHFFFAOYSA-N
Smiles CCCC(C)C1(CC)C(=O)NC(=O)NC1=O
InChI
InChI=1S/C11H18N2O3/c1-4-6-7(3)11(5-2)8(14)12-10(16)13-9(11)15/h7H,4-6H2,1-3H3,(H2,12,13,14,15,16)

Physicochemical Descriptors

Property Name Value
Molecular Formula C11H18N2O3
Molecular Weight 226.28
AlogP 1.18
Hydrogen Bond Acceptor 3.0
Hydrogen Bond Donor 2.0
Number of Rotational Bond 4.0
Polar Surface Area 75.27
Molecular species NEUTRAL
Aromatic Rings 0.0
Heavy Atoms 16.0

Bioactivity

Mechanism of Action Action Reference
GABA-A receptor; anion channel positive allosteric modulator POSITIVE ALLOSTERIC MODULATOR PubMed PubMed PubMed
Protein: GABA-A receptor; anion channel
Description: Gamma-aminobutyric acid receptor subunit pi
Organism : Homo sapiens
O00591 ENSG00000094755
Protein: GABA-A receptor; anion channel
Description: Gamma-aminobutyric acid receptor subunit delta
Organism : Homo sapiens
O14764 ENSG00000187730
Protein: GABA-A receptor; anion channel
Description: Gamma-aminobutyric acid receptor subunit alpha-1
Organism : Homo sapiens
P14867 ENSG00000022355
Protein: GABA-A receptor; anion channel
Description: Gamma-aminobutyric acid receptor subunit beta-1
Organism : Homo sapiens
P18505 ENSG00000163288
Protein: GABA-A receptor; anion channel
Description: Gamma-aminobutyric acid receptor subunit gamma-2
Organism : Homo sapiens
P18507 ENSG00000113327
Protein: GABA-A receptor; anion channel
Description: Gamma-aminobutyric acid receptor subunit beta-3
Organism : Homo sapiens
P28472 ENSG00000166206
Protein: GABA-A receptor; anion channel
Description: Gamma-aminobutyric acid receptor subunit alpha-5
Organism : Homo sapiens
P31644 ENSG00000186297
Protein: GABA-A receptor; anion channel
Description: Gamma-aminobutyric acid receptor subunit alpha-3
Organism : Homo sapiens
P34903 ENSG00000011677
Protein: GABA-A receptor; anion channel
Description: Gamma-aminobutyric acid receptor subunit alpha-2
Organism : Homo sapiens
P47869 ENSG00000151834
Protein: GABA-A receptor; anion channel
Description: Gamma-aminobutyric acid receptor subunit beta-2
Organism : Homo sapiens
P47870 ENSG00000145864
Protein: GABA-A receptor; anion channel
Description: Gamma-aminobutyric acid receptor subunit alpha-4
Organism : Homo sapiens
P48169 ENSG00000109158
Protein: GABA-A receptor; anion channel
Description: Gamma-aminobutyric acid receptor subunit epsilon
Organism : Homo sapiens
P78334 ENSG00000102287
Protein: GABA-A receptor; anion channel
Description: Gamma-aminobutyric acid receptor subunit alpha-6
Organism : Homo sapiens
Q16445 ENSG00000145863
Protein: GABA-A receptor; anion channel
Description: Gamma-aminobutyric acid receptor subunit gamma-1
Organism : Homo sapiens
Q8N1C3 ENSG00000163285
Protein: GABA-A receptor; anion channel
Description: Gamma-aminobutyric acid receptor subunit gamma-3
Organism : Homo sapiens
Q99928 ENSG00000182256
Protein: GABA-A receptor; anion channel
Description: Gamma-aminobutyric acid receptor subunit theta
Organism : Homo sapiens
Q9UN88 ENSG00000268089
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Ion channel Ligand-gated ion channel GABA-A receptor
50000 1700-40000 - - -
Ion channel Voltage-gated ion channel Potassium channels Two-pore domain potassium channel
- - - - 4
Ion channel Voltage-gated ion channel Voltage-gated sodium channel
- - - - 1-8
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC21/SLCO family of organic anion transporting polypeptides
- - - - 94
Assay Description Organism Bioactivity Reference
Inhibition of binding of Batrachotoxinin [3H]BTX-B to high affinity sites on voltage dependent sodium channels in a vesicular preparation from guinea pig cerebral cortex at 10 uM Cavia porcellus 1.2 %
Inhibition of binding of Batrachotoxinin [3H]BTX-B to high-affinity sites on voltage-dependent sodium channels in a vesicular preparation from guinea pig cerebral cortex at 100 uM Cavia porcellus 7.6 %
Inhibition of human aquaporin 4 M23 isoform expressed in Xenopus laevis oocytes at 20 uM Homo sapiens 9.0 %
Inhibition of [3H]R-(-)-14-induced receptor photolabeling at human FLAG-tagged alpha1 GABA A receptor expressed in HEK293S cells relative to untreated control Homo sapiens 90.0 %
Inhibition of [3H]R-(-)-14-induced receptor photolabeling at human FLAG-tagged beta3 GABA A receptor expressed in HEK293S cells relative to untreated control Homo sapiens 90.0 %
Inhibition of sodium fluorescein uptake in OATP1B1-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM Cricetulus griseus 94.35 %
Inhibition of sodium fluorescein uptake in OATP1B3-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM Cricetulus griseus 94.07 %
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 8.12 %
Inhibition of human TASK3 expressed in Xenopus oocytes at 100 uM by whole cell patch clamp assay relative to control Homo sapiens 4.3 %
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 8.131 %
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 -0.09 % 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 -0.09 %

Related Entries

Cross References

Resources Reference
ChEBI 7983
ChEMBL CHEMBL448
DrugBank DB00312
DrugCentral 2095
FDA SRS I4744080IR
Human Metabolome Database HMDB0014457
Guide to Pharmacology 5480
KEGG C07422
PharmGKB PA450859
PubChem 4737
SureChEMBL SCHEMBL24966
ZINC ZINC00004840
CONTENTS