NAV

3-(1,1-dioxido-4H-1,2,4-benzothiadiazin-3-yl)-4-hydroxy-1-(3-methylbutyl)quinolin-2(1H)-one

Identification

Generic Name
3-(1,1-dioxido-4H-1,2,4-benzothiadiazin-3-yl)-4-hydroxy-1-(3-methylbutyl)quinolin-2(1H)-one
DrugBank Accession Number
DB07275
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
Similar Structures
Weight
Average: 411.474
Monoisotopic: 411.125276865
Chemical Formula
C21H21N3O4S
Synonyms
Not Available
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Pharmacology

Indication

Not Available

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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UGenome polyproteinNot AvailableHepatitis C virus subtype 1b
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
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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 1,2,4-benzothiadiazine-1,1-dioxides. These are aromatic heterocyclic compounds containing a 1,2,4-benzothiadiazine ring system with two S=O bonds at the 1-position.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Thiadiazines
Sub Class
Benzothiadiazines
Direct Parent
1,2,4-benzothiadiazine-1,1-dioxides
Alternative Parents
Hydroquinolones / Hydroquinolines / Pyridinones / Hydroxypyridines / Benzenoids / Imidolactams / Vinylogous acids / Organosulfonic acids and derivatives / Heteroaromatic compounds / Lactams
show 6 more
Substituents
1,2,4-benzothiadiazine-1,1-dioxide / Amidine / Aromatic heteropolycyclic compound / Azacycle / Benzenoid / Dihydroquinoline / Dihydroquinolone / Heteroaromatic compound / Hydrocarbon derivative / Hydroxypyridine
show 14 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
MQFPIRFODWNQIO-UHFFFAOYSA-N
InChI
InChI=1S/C21H21N3O4S/c1-13(2)11-12-24-16-9-5-3-7-14(16)19(25)18(21(24)26)20-22-15-8-4-6-10-17(15)29(27,28)23-20/h3-10,13,25H,11-12H2,1-2H3,(H,22,23)
IUPAC Name
3-[4-hydroxy-1-(3-methylbutyl)-2-oxo-1,2-dihydroquinolin-3-yl]-4H-1lambda6,2,4-benzothiadiazine-1,1-dione
SMILES
CC(C)CCN1C(=O)C(C2=NS(=O)(=O)C3=CC=CC=C3N2)=C(O)C2=CC=CC=C12

References

General References
Not Available
PubChem Compound
16001653
PubChem Substance
99443746
ChemSpider
20130494
BindingDB
30406
ChEMBL
CHEMBL176058
ZINC
ZINC000100035344
PDBe Ligand
888
PDB Entries
2fvc

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

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 Solubility0.0392 mg/mLALOGPS
logP2.64ALOGPS
logP2.53Chemaxon
logS-4ALOGPS
pKa (Strongest Acidic)6.46Chemaxon
pKa (Strongest Basic)-2.2Chemaxon
Physiological Charge-1Chemaxon
Hydrogen Acceptor Count6Chemaxon
Hydrogen Donor Count2Chemaxon
Polar Surface Area99.07 Å2Chemaxon
Rotatable Bond Count4Chemaxon
Refractivity112.18 m3·mol-1Chemaxon
Polarizability43.27 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-0.7191
Caco-2 permeable+0.7023
P-glycoprotein substrateSubstrate0.6697
P-glycoprotein inhibitor INon-inhibitor0.7001
P-glycoprotein inhibitor IIInhibitor0.9239
Renal organic cation transporterNon-inhibitor0.7614
CYP450 2C9 substrateSubstrate0.5355
CYP450 2D6 substrateNon-substrate0.7972
CYP450 3A4 substrateNon-substrate0.5084
CYP450 1A2 substrateNon-inhibitor0.7368
CYP450 2C9 inhibitorNon-inhibitor0.5514
CYP450 2D6 inhibitorNon-inhibitor0.8346
CYP450 2C19 inhibitorNon-inhibitor0.7039
CYP450 3A4 inhibitorNon-inhibitor0.7679
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.6479
Ames testNon AMES toxic0.6398
CarcinogenicityNon-carcinogens0.6346
BiodegradationNot ready biodegradable0.9831
Rat acute toxicity2.4920 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9881
hERG inhibition (predictor II)Non-inhibitor0.6638
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/MSsplash10-03di-0000900000-67ca021e1fb2e86bd3ef
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-03di-0002900000-845641549b7d9bc78a91
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-03di-3004900000-f8487dbc412145f5daff
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0002-0019100000-cdef1470581234f5fddd
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a4i-7319100000-dc9a4a9de549c6a81ac1
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0f6w-1229000000-e30f6b7f6e6aefd289ca
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-193.14807
predicted
DeepCCS 1.0 (2019)
[M+H]+195.50609
predicted
DeepCCS 1.0 (2019)
[M+Na]+202.08604
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Genome polyprotein
Kind
Protein
Organism
Hepatitis C virus subtype 1b
Pharmacological action
Unknown
General Function
Zinc ion binding
Specific Function
Not Available
Gene Name
Not Available
Uniprot ID
Q99AU2
Uniprot Name
Genome polyprotein
Molecular Weight
327008.345 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. [Article]

Drug created at September 15, 2010 21:20 / Updated at June 12, 2020 16:52