NAV

(6S)-6-CYCLOPENTYL-6-[2-(3-FLUORO-4-ISOPROPOXYPHENYL)ETHYL]-4-HYDROXY-5,6-DIHYDRO-2H-PYRAN-2-ONE

Identification

Generic Name
(6S)-6-CYCLOPENTYL-6-[2-(3-FLUORO-4-ISOPROPOXYPHENYL)ETHYL]-4-HYDROXY-5,6-DIHYDRO-2H-PYRAN-2-ONE
DrugBank Accession Number
DB08390
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 362.4351
Monoisotopic: 362.189337557
Chemical Formula
C21H27FO4
Synonyms
Not Available
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Pharmacology

Indication

Not Available

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Contraindications & Blackbox Warnings
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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

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 phenol ethers. These are aromatic compounds containing an ether group substituted with a benzene ring.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Phenol ethers
Sub Class
Not Available
Direct Parent
Phenol ethers
Alternative Parents
Phenoxy compounds / Fluorobenzenes / Dihydropyranones / Alkyl aryl ethers / Aryl fluorides / Vinylogous acids / Enoate esters / Lactones / Oxacyclic compounds / Monocarboxylic acids and derivatives
show 5 more
Substituents
Alkyl aryl ether / Alpha,beta-unsaturated carboxylic ester / Aromatic heteromonocyclic compound / Aryl fluoride / Aryl halide / Carbonyl group / Carboxylic acid derivative / Carboxylic acid ester / Dihydropyranone / Enoate ester
show 19 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
Not Available
InChI Key
AKNIHFDXRAOPAI-NRFANRHFSA-N
InChI
InChI=1S/C21H27FO4/c1-14(2)25-19-8-7-15(11-18(19)22)9-10-21(16-5-3-4-6-16)13-17(23)12-20(24)26-21/h7-8,11-12,14,16,23H,3-6,9-10,13H2,1-2H3/t21-/m0/s1
IUPAC Name
(6S)-6-cyclopentyl-6-{2-[3-fluoro-4-(propan-2-yloxy)phenyl]ethyl}-4-hydroxy-5,6-dihydro-2H-pyran-2-one
SMILES
CC(C)OC1=CC=C(CC[C@]2(CC(O)=CC(=O)O2)C2CCCC2)C=C1F

References

General References
Not Available
PubChem Compound
54688400
PubChem Substance
99444861
ChemSpider
20153859
ZINC
ZINC000100036690
PDBe Ligand
PFI
PDB Entries
2hai

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 Solubility0.00406 mg/mLALOGPS
logP4.62ALOGPS
logP4.8Chemaxon
logS-5ALOGPS
pKa (Strongest Acidic)8.32Chemaxon
pKa (Strongest Basic)-4.9Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count3Chemaxon
Hydrogen Donor Count1Chemaxon
Polar Surface Area55.76 Å2Chemaxon
Rotatable Bond Count6Chemaxon
Refractivity98.52 m3·mol-1Chemaxon
Polarizability39.1 Å3Chemaxon
Number of Rings3Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleYesChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9644
Blood Brain Barrier+0.9645
Caco-2 permeable+0.5808
P-glycoprotein substrateSubstrate0.7282
P-glycoprotein inhibitor IInhibitor0.5223
P-glycoprotein inhibitor IINon-inhibitor0.5676
Renal organic cation transporterNon-inhibitor0.8734
CYP450 2C9 substrateNon-substrate0.7702
CYP450 2D6 substrateNon-substrate0.8427
CYP450 3A4 substrateSubstrate0.6471
CYP450 1A2 substrateNon-inhibitor0.8085
CYP450 2C9 inhibitorNon-inhibitor0.551
CYP450 2D6 inhibitorNon-inhibitor0.8945
CYP450 2C19 inhibitorInhibitor0.611
CYP450 3A4 inhibitorNon-inhibitor0.7921
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.6271
Ames testNon AMES toxic0.7243
CarcinogenicityNon-carcinogens0.8912
BiodegradationNot ready biodegradable1.0
Rat acute toxicity3.7796 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9348
hERG inhibition (predictor II)Non-inhibitor0.7863
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-0009000000-a3fe959f8d7feda5e666
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-03di-0009000000-f212d2e1c5a029eac628
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-00di-0269000000-b9b36bd1dd551748a2a3
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-03xr-1049000000-ff82f1d75485c723e8bb
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-004u-1944000000-b0db1de4e8b190708e0e
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-02ai-2922000000-2450715670dcbbb88d7c
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]-181.83446
predicted
DeepCCS 1.0 (2019)
[M+H]+184.19247
predicted
DeepCCS 1.0 (2019)
[M+Na]+191.0189
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Genome 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
  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 21:31 / Updated at June 12, 2020 16:52