(5S)-1-benzyl-3-(1,1-dioxido-1,2-benzisothiazol-3-yl)-4-hydroxy-5-(1-methylethyl)-1,5-dihydro-2H-pyrrol-2-one

Identification

Name
(5S)-1-benzyl-3-(1,1-dioxido-1,2-benzisothiazol-3-yl)-4-hydroxy-5-(1-methylethyl)-1,5-dihydro-2H-pyrrol-2-one
Accession Number
DB07414
Type
Small Molecule
Groups
Experimental
Description
Not Available
Structure
Thumb
Synonyms
Not Available
Categories
Not Available
UNII
Not Available
CAS number
Not Available
Weight
Average: 396.459
Monoisotopic: 396.114377828
Chemical Formula
C21H20N2O4S
InChI Key
XKOAFAIRGVAHRA-IBGZPJMESA-N
InChI
InChI=1S/C21H20N2O4S/c1-13(2)19-20(24)17(21(25)23(19)12-14-8-4-3-5-9-14)18-15-10-6-7-11-16(15)28(26,27)22-18/h3-11,13,19,24H,12H2,1-2H3/t19-/m0/s1
IUPAC Name
3-[(5S)-1-benzyl-4-hydroxy-2-oxo-5-(propan-2-yl)-2,5-dihydro-1H-pyrrol-3-yl]-1λ⁶,2-benzothiazole-1,1-dione
SMILES
[H][C@@]1(C(C)C)N(CC2=CC=CC=C2)C(=O)C(=C1O)C1=NS(=O)(=O)C2=C1C=CC=C2

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UGenome polyproteinNot AvailableHepatitis C virus genotype 1b (isolate BK)
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Not Available
Food Interactions
Not Available

References

General References
Not Available
External Links
PubChem Compound
46937070
PubChem Substance
99443885
ChemSpider
23329100
ChEMBL
CHEMBL518647
ZINC
ZINC000100035503
PDBe Ligand
B34
PDB Entries
3d28

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0289 mg/mLALOGPS
logP1.85ALOGPS
logP2.68ChemAxon
logS-4.1ALOGPS
pKa (Strongest Acidic)6.08ChemAxon
pKa (Strongest Basic)0.095ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area87.04 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity107.02 m3·mol-1ChemAxon
Polarizability40.9 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier-0.5458
Caco-2 permeable-0.5473
P-glycoprotein substrateSubstrate0.5514
P-glycoprotein inhibitor INon-inhibitor0.6374
P-glycoprotein inhibitor IIInhibitor0.9531
Renal organic cation transporterNon-inhibitor0.7721
CYP450 2C9 substrateSubstrate0.5667
CYP450 2D6 substrateNon-substrate0.8134
CYP450 3A4 substrateSubstrate0.5232
CYP450 1A2 substrateNon-inhibitor0.7796
CYP450 2C9 inhibitorNon-inhibitor0.5338
CYP450 2D6 inhibitorNon-inhibitor0.7532
CYP450 2C19 inhibitorNon-inhibitor0.6434
CYP450 3A4 inhibitorInhibitor0.6627
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.6022
Ames testNon AMES toxic0.6176
CarcinogenicityNon-carcinogens0.5084
BiodegradationNot ready biodegradable0.9748
Rat acute toxicity2.5620 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9939
hERG inhibition (predictor II)Non-inhibitor0.7501
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This compound belongs to the class of organic compounds known as benzothiazoles. These are organic compounds containing a benzene fused to a thiazole ring (a five-membered ring with four carbon atoms, one nitrogen atom and one sulfur atom).
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Benzothiazoles
Sub Class
Not Available
Direct Parent
Benzothiazoles
Alternative Parents
Benzene and substituted derivatives / Vinylogous acids / Tertiary carboxylic acid amides / Pyrrolines / Organosulfonic acids and derivatives / Lactams / Enols / Azacyclic compounds / Organopnictogen compounds / Organonitrogen compounds
show 3 more
Substituents
1,2-benzothiazole / Monocyclic benzene moiety / Benzenoid / Pyrroline / Organic sulfonic acid or derivatives / Vinylogous acid / Tertiary carboxylic acid amide / Organosulfonic acid or derivatives / Carboxamide group / Lactam
show 12 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available

Targets

Kind
Protein
Organism
Hepatitis C virus genotype 1b (isolate BK)
Pharmacological action
Unknown
General Function
Zinc ion binding
Specific Function
Core protein packages viral RNA to form a viral nucleocapsid, and promotes virion budding. Modulates viral translation initiation by interacting with HCV IRES and 40S ribosomal subunit. Also regula...
Gene Name
Not Available
Uniprot ID
P26663
Uniprot Name
Genome polyprotein
Molecular Weight
327190.435 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235]

Drug created on September 15, 2010 15:21 / Updated on March 01, 2020 19:57

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