NAV

3-(4-Amino-2-Tert-Butyl-5-Methyl-Phenylsulfanyl)-6-Cyclopentyl-4-Hydroxy-6-[2-(4-Hydroxy-Phenyl)-Ethyl]-5,6-Dihydro-Pyran-2-One

Identification

Generic Name
3-(4-Amino-2-Tert-Butyl-5-Methyl-Phenylsulfanyl)-6-Cyclopentyl-4-Hydroxy-6-[2-(4-Hydroxy-Phenyl)-Ethyl]-5,6-Dihydro-Pyran-2-One
DrugBank Accession Number
DB04298
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 495.673
Monoisotopic: 495.244329367
Chemical Formula
C29H37NO4S
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 phenylpropanes. These are organic compounds containing a phenylpropane moiety.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Phenylpropanes
Direct Parent
Phenylpropanes
Alternative Parents
Aminotoluenes / Aniline and substituted anilines / Aryl thioethers / 1-hydroxy-2-unsubstituted benzenoids / Dihydropyranones / Vinylogous acids / Enoate esters / Thioenol ethers / Amino acids and derivatives / Lactones
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Substituents
1-hydroxy-2-unsubstituted benzenoid / Alpha,beta-unsaturated carboxylic ester / Amine / Amino acid or derivatives / Aminotoluene / Aniline or substituted anilines / Aromatic heteromonocyclic compound / Aryl thioether / Carbonyl group / Carboxylic acid derivative
show 23 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
ZEBFKFGJWHOOST-LJAQVGFWSA-N
InChI
InChI=1S/C29H37NO4S/c1-18-15-25(22(16-23(18)30)28(2,3)4)35-26-24(32)17-29(34-27(26)33,20-7-5-6-8-20)14-13-19-9-11-21(31)12-10-19/h9-12,15-16,20,31-32H,5-8,13-14,17,30H2,1-4H3/t29-/m0/s1
IUPAC Name
(6S)-3-[(4-amino-2-tert-butyl-5-methylphenyl)sulfanyl]-6-cyclopentyl-4-hydroxy-6-[2-(4-hydroxyphenyl)ethyl]-5,6-dihydro-2H-pyran-2-one
SMILES
CC1=CC(SC2=C(O)C[C@](CCC3=CC=C(O)C=C3)(OC2=O)C2CCCC2)=C(C=C1N)C(C)(C)C

References

General References
Not Available
PubChem Compound
54688711
PubChem Substance
46506710
ChemSpider
16744129
ZINC
ZINC000100034141
PDBe Ligand
NH1
PDB Entries
1os5

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 Solubility0.000414 mg/mLALOGPS
logP6.4ALOGPS
logP6.72Chemaxon
logS-6.1ALOGPS
pKa (Strongest Acidic)8.42Chemaxon
pKa (Strongest Basic)3.86Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count4Chemaxon
Hydrogen Donor Count3Chemaxon
Polar Surface Area92.78 Å2Chemaxon
Rotatable Bond Count7Chemaxon
Refractivity145.74 m3·mol-1Chemaxon
Polarizability55.73 Å3Chemaxon
Number of Rings4Chemaxon
Bioavailability1Chemaxon
Rule of FiveNoChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleYesChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.828
Blood Brain Barrier+0.5446
Caco-2 permeable-0.5665
P-glycoprotein substrateSubstrate0.5815
P-glycoprotein inhibitor INon-inhibitor0.8245
P-glycoprotein inhibitor IIInhibitor0.5925
Renal organic cation transporterNon-inhibitor0.9022
CYP450 2C9 substrateNon-substrate0.7028
CYP450 2D6 substrateNon-substrate0.8098
CYP450 3A4 substrateSubstrate0.6014
CYP450 1A2 substrateNon-inhibitor0.6591
CYP450 2C9 inhibitorNon-inhibitor0.6197
CYP450 2D6 inhibitorNon-inhibitor0.8344
CYP450 2C19 inhibitorInhibitor0.5573
CYP450 3A4 inhibitorNon-inhibitor0.5906
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.731
Ames testNon AMES toxic0.6785
CarcinogenicityNon-carcinogens0.8321
BiodegradationNot ready biodegradable1.0
Rat acute toxicity2.9141 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9833
hERG inhibition (predictor II)Non-inhibitor0.8537
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/MSsplash10-0f6t-0015900000-74979b05bb28630982d6
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0006-0200900000-aa575dcfb02894f04621
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0udi-0464900000-b32a07c0d0dcbfa99821
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0fkc-0927800000-f8d50685327f78506bf7
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a4j-3910700000-4efc56ac2f1f7794f605
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0fl3-0924400000-3aaae545147e1fb17bb4
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]-215.19748
predicted
DeepCCS 1.0 (2019)
[M+H]+217.59305
predicted
DeepCCS 1.0 (2019)
[M+Na]+223.50557
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. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]

Drug created at June 13, 2005 13:24 / Updated at June 12, 2020 16:52