(+)-(S)-2-(BENZO[D][1,3]DIOXOL-5-YL)-2-(6-(HYDROXYMETHYL)-1-METHYL-1H-INDOL-3-YL)-N-(2-METHOXY-4-METHYLPHENYLSULFONYL)ACETAMIDE

/static/temp/default.svg Search structure
Molecule Category Free-form
Source Gaulton A, Kale N, van Westen GJ, Bellis LJ, Bento AP, Davies M, Hersey A, Papadatos G, Forster M, Wege P, Overington JP. A large-scale crop protection bioassay data set. Sci Data. 2015 Jul 7;2:150032. Read more ...

Structure

InChI Key PGAMLYVKCIXYNX-SANMLTNESA-N
Smiles COc1cc(C)ccc1S(=O)(=O)NC(=O)[C@@H](c2ccc3OCOc3c2)c4cn(C)c5cc(CO)ccc45
InChI
InChI=1S/C27H26N2O7S/c1-16-4-9-25(24(10-16)34-3)37(32,33)28-27(31)26(18-6-8-22-23(12-18)36-15-35-22)20-13-29(2)21-11-17(14-30)5-7-19(20)21/h4-13,26,30H,14-15H2,1-3H3,(H,28,31)/t26-/m0/s1

Physicochemical Descriptors

Property Name Value
Molecular Formula C27H26N2O7S
Molecular Weight 522.57
AlogP 3.85
Hydrogen Bond Acceptor 7.0
Hydrogen Bond Donor 2.0
Number of Rotational Bond 7.0
Polar Surface Area 124.47
Molecular species ACID
Aromatic Rings 4.0
Heavy Atoms 37.0
Assay Description Organism Bioactivity Reference
Cardiotoxicity in Canis lupus familiaris (dog) assessed as change in left ventricular contractility at 1.5 to 15 mg/kg, po Canis lupus familiaris None
Cardiotoxicity in Canis lupus familiaris (dog) assessed as change in ECG at 1.5 to 15 mg/kg, po Canis lupus familiaris None
Cardiotoxicity in Canis lupus familiaris (dog) assessed as change in heart rate at 1.5 to 15 mg/kg, po Canis lupus familiaris None
Toxicity in Rattus norvegicus (rat) at 30 mg/kg, po QD for 5 days Rattus norvegicus None
Reduction in mean arterial blood pressure in po dosed normotensive Canis lupus familiaris (dog) Canis lupus familiaris None
Antagonist activity at ETA receptor in Rattus norvegicus (rat) assessed as inhibition of ET1-induced pressor response at 10 mg/kg, po administered 3 hr post ET1-induction measured up to 12 hr Rattus norvegicus None
Antagonist activity at ETA receptor in Rattus norvegicus (rat) assessed as inhibition of ET1-induced pressor response at 0.6 mg/kg, po administered 3 hr post ET1-induction Rattus norvegicus None
Antagonist activity at ETA receptor in Rattus norvegicus (rat) assessed as inhibition of ET1-induced pressor response at 0.1 mg/kg, po administered 3 hr post ET1-induction Rattus norvegicus None
Selectivity index, ratio of Ki for Homo sapiens (human) ETB receptor to KI for Homo sapiens (human) ETA receptor Homo sapiens 600.0
Antagonist activity at ETB receptor in Oryctolagus cuniculus (rabbit) pulmonary artery Oryctolagus cuniculus 1600.0 nM
Antagonist activity at ETA receptor in Rattus norvegicus (rat) aorta assessed as inhibition of Kcl-induced contraction Rattus norvegicus 11.3 nM
Antagonist activity at ETA receptor in Homo sapiens (human) umbilical artery Homo sapiens 2.5 nM
Prodrug conversion in Sus scrofa (pig) liver cytosol assessed as (S)-3-(1-(benzo[d][1,3]dioxol-5-yl)-2-(2-methoxy-4-methylphenylsulfonamido)-2-oxoethyl)-1-methyl-1H-indole-6-carboxylic acid formation Sus scrofa None
Prodrug conversion in Homo sapiens (human) liver cytosol assessed as (S)-3-(1-(benzo[d][1,3]dioxol-5-yl)-2-(2-methoxy-4-methylphenylsulfonamido)-2-oxoethyl)-1-methyl-1H-indole-6-carboxylic acid formation Homo sapiens None
Prodrug conversion in male Rattus norvegicus (rat) liver cytosol assessed as (S)-3-(1-(benzo[d][1,3]dioxol-5-yl)-2-(2-methoxy-4-methylphenylsulfonamido)-2-oxoethyl)-1-methyl-1H-indole-6-carboxylic acid formation Rattus norvegicus None
Half life in Rattus norvegicus (rat) liver microsome at 1 uM Rattus norvegicus 2.0 hr
Half life in Canis lupus familiaris (dog) liver microsome at 1 uM Canis lupus familiaris 2.0 hr
Half life in Homo sapiens (human) liver microsome at 1 uM Homo sapiens 2.0 hr
Apparent elimination half life in Rattus norvegicus (rat) assessed as (S)-3-(1-(benzo[d][1,3]dioxol-5-yl)-2-(2-methoxy-4-methylphenylsulfonamido)-2-oxoethyl)-1-methyl-1H-indole-6-carboxylic acid level at 2 mg/kg, po Rattus norvegicus 9.0 hr
Drug absorption in Rattus norvegicus (rat) assessed as (S)-3-(1-(benzo[d][1,3]dioxol-5-yl)-2-(2-methoxy-4-methylphenylsulfonamido)-2-oxoethyl)-1-methyl-1H-indole-6-carboxylic acid level at 2 mg/kg Rattus norvegicus 36.0 %
Tmax in Rattus norvegicus (rat) assessed as (S)-3-(1-(benzo[d][1,3]dioxol-5-yl)-2-(2-methoxy-4-methylphenylsulfonamido)-2-oxoethyl)-1-methyl-1H-indole-6-carboxylic acid level at 2 mg/kg, po Rattus norvegicus 4.0 hr
Cmax in Rattus norvegicus (rat) assessed as (S)-3-(1-(benzo[d][1,3]dioxol-5-yl)-2-(2-methoxy-4-methylphenylsulfonamido)-2-oxoethyl)-1-methyl-1H-indole-6-carboxylic acid level at 2 mg/kg, po Rattus norvegicus 0.083 ug.mL-1
Cmax in Rattus norvegicus (rat) at 2 mg/kg, po Rattus norvegicus 0.048 ug.mL-1
Tmax in Rattus norvegicus (rat) at 2 mg/kg, po Rattus norvegicus 0.25 hr
Prodrug conversion in Rattus norvegicus (rat) assessed as (S)-3-(1-(benzo[d][1,3]dioxol-5-yl)-2-(2-methoxy-4-methylphenylsulfonamido)-2-oxoethyl)-1-methyl-1H-indole-6-carboxylic acid level at 2 mg/kg, po Rattus norvegicus None
Prodrug conversion in Rattus norvegicus (rat) assessed as (S)-3-(1-(benzo[d][1,3]dioxol-5-yl)-2-(2-methoxy-4-methylphenylsulfonamido)-2-oxoethyl)-1-methyl-1H-indole-6-carboxylic acid level at 2 mg/kg, iv Rattus norvegicus None
Elimination half life in Rattus norvegicus (rat) at 2 mg/kg, iv Rattus norvegicus 1.1 hr
Volume of distribution in Rattus norvegicus (rat) at 2 mg/kg, iv Rattus norvegicus 0.16 L.kg-1
Displacement of [I125]ET1 from Homo sapiens (human) ETB receptor expressed in CHO cells Homo sapiens 1503.0 nM Displacement of [I125]ET1 from Homo sapiens (human) ETB receptor expressed in CHO cells Homo sapiens 683.0 nM
Plasma clearance in Rattus norvegicus (rat) at 2 mg/kg, iv Rattus norvegicus 1.7 mL.min-1.kg-1
Displacement of [I125]ET1 from Homo sapiens (human) ETA receptor expressed in CHO cells Homo sapiens 2.2 nM Displacement of [I125]ET1 from Homo sapiens (human) ETA receptor expressed in CHO cells Homo sapiens 2.2 nM
Selectivity index, ratio of Kb for rabbit ETB receptor to Kb for Homo sapiens (human) ETA receptor Homo sapiens 600.0
Inhibition of endothelin converting enzyme (unknown origin) Homo sapiens 765000.0 nM

Cross References

Resources Reference
ChEMBL CHEMBL2261361
PubChem 76312118
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