(5S)-1-benzyl-3-(1,1-dioxido-1,2-benzisothiazol-3-yl)-4-hydroxy-5-(1-methylethyl)-1,5-dihydro-2H-pyrrol-2-one
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Identification
- Generic 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
- DrugBank Accession Number
- DB07414
- Background
Not Available
- Type
- Small Molecule
- Groups
- Experimental
- Structure
- Weight
- Average: 396.459
Monoisotopic: 396.114377828 - Chemical Formula
- C21H20N2O4S
- Synonyms
- Not Available
Pharmacology
- Indication
Not Available
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- Pharmacodynamics
Not Available
- Mechanism of action
Target Actions Organism UGenome polyprotein Not Available Hepatitis 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
- Adverse Effects
- Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.
- Toxicity
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
Categories
- Drug Categories
- Not Available
- Chemical TaxonomyProvided by Classyfire
- 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 / Aromatic heteropolycyclic compound / Azacycle / Benzenoid / Carbonyl group / Carboxamide group / Carboxylic acid derivative / Enol / Hydrocarbon derivative / Lactam show 12 more
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- Not Available
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- Not Available
- CAS number
- Not Available
- 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]-1lambda6,2-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
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
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
Property Value Source Water Solubility 0.0289 mg/mL ALOGPS logP 1.85 ALOGPS logP 2.68 Chemaxon logS -4.1 ALOGPS pKa (Strongest Acidic) 3.29 Chemaxon pKa (Strongest Basic) -0.82 Chemaxon Physiological Charge -1 Chemaxon Hydrogen Acceptor Count 5 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 87.04 Å2 Chemaxon Rotatable Bond Count 4 Chemaxon Refractivity 107.02 m3·mol-1 Chemaxon Polarizability 40.9 Å3 Chemaxon Number of Rings 4 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 1.0 Blood Brain Barrier - 0.5458 Caco-2 permeable - 0.5473 P-glycoprotein substrate Substrate 0.5514 P-glycoprotein inhibitor I Non-inhibitor 0.6374 P-glycoprotein inhibitor II Inhibitor 0.9531 Renal organic cation transporter Non-inhibitor 0.7721 CYP450 2C9 substrate Substrate 0.5667 CYP450 2D6 substrate Non-substrate 0.8134 CYP450 3A4 substrate Substrate 0.5232 CYP450 1A2 substrate Non-inhibitor 0.7796 CYP450 2C9 inhibitor Non-inhibitor 0.5338 CYP450 2D6 inhibitor Non-inhibitor 0.7532 CYP450 2C19 inhibitor Non-inhibitor 0.6434 CYP450 3A4 inhibitor Inhibitor 0.6627 CYP450 inhibitory promiscuity High CYP Inhibitory Promiscuity 0.6022 Ames test Non AMES toxic 0.6176 Carcinogenicity Non-carcinogens 0.5084 Biodegradation Not ready biodegradable 0.9748 Rat acute toxicity 2.5620 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9939 hERG inhibition (predictor II) Non-inhibitor 0.7501
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-0002-0009000000-7a9adbba412de4efce28 Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-0002-0009000000-5061788c2e2acd6f89b5 Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-0002-1049000000-bf2c471c8f26402cf868 Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-0002-0019000000-28062e07b9c454c19abb Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-002f-9340000000-ac7be37c2de7fad74050 Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-0296-0954000000-5e048b720656ba5247f1 Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 193.06412 predictedDeepCCS 1.0 (2019) [M+H]+ 195.42212 predictedDeepCCS 1.0 (2019) [M+Na]+ 201.87183 predictedDeepCCS 1.0 (2019)
Targets
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1. DetailsGenome polyprotein
- 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
- 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. [Article]
Drug created at September 15, 2010 21:21 / Updated at June 12, 2020 16:52