NAV

(2S)-({(5Z)-5-[(5-Ethyl-2-furyl)methylene]-4-oxo-4,5-dihydro-1,3-thiazol-2-yl}amino)(4-fluorophenyl)acetic acid

Identification

Generic Name
(2S)-({(5Z)-5-[(5-Ethyl-2-furyl)methylene]-4-oxo-4,5-dihydro-1,3-thiazol-2-yl}amino)(4-fluorophenyl)acetic acid
DrugBank Accession Number
DB08706
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 374.386
Monoisotopic: 374.073655873
Chemical Formula
C18H15FN2O4S
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 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 l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom.
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Carboxylic acids and derivatives
Sub Class
Amino acids, peptides, and analogues
Direct Parent
L-alpha-amino acids
Alternative Parents
Fluorobenzenes / Aryl fluorides / Thiazolines / Furans / Heteroaromatic compounds / Isothioureas / N-acylimines / Propargyl-type 1,3-dipolar organic compounds / Azacyclic compounds / Carboximidamides
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Substituents
Aromatic heteromonocyclic compound / Aryl fluoride / Aryl halide / Azacycle / Benzenoid / Carbonyl group / Carboximidamide / Carboxylic acid / Fluorobenzene / Furan
show 21 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
RNEACARJKXYVND-MZLJFPOFSA-N
InChI
InChI=1S/C18H15FN2O4S/c1-2-12-7-8-13(25-12)9-14-16(22)21-18(26-14)20-15(17(23)24)10-3-5-11(19)6-4-10/h3-9,15H,2H2,1H3,(H,23,24)(H,20,21,22)/b14-9-/t15-/m0/s1
IUPAC Name
(2S)-2-{[(5Z)-5-[(5-ethylfuran-2-yl)methylidene]-4-oxo-4,5-dihydro-1,3-thiazol-2-yl]amino}-2-(4-fluorophenyl)acetic acid
SMILES
CCC1=CC=C(O1)\C=C1/SC(N[C@H](C(O)=O)C2=CC=C(F)C=C2)=NC1=O

References

General References
Not Available
PubChem Compound
16049839
PubChem Substance
99445177
ChemSpider
13178234
ChEMBL
CHEMBL221245
ZINC
ZINC000034947225
PDBe Ligand
VRX
PDB Entries
2hwi

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 Solubility0.0349 mg/mLALOGPS
logP2.76ALOGPS
logP3.08Chemaxon
logS-4ALOGPS
pKa (Strongest Acidic)3.88Chemaxon
pKa (Strongest Basic)-2.3Chemaxon
Physiological Charge-1Chemaxon
Hydrogen Acceptor Count5Chemaxon
Hydrogen Donor Count2Chemaxon
Polar Surface Area91.9 Å2Chemaxon
Rotatable Bond Count5Chemaxon
Refractivity95.7 m3·mol-1Chemaxon
Polarizability36.62 Å3Chemaxon
Number of Rings3Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption-0.5462
Blood Brain Barrier-0.7637
Caco-2 permeable-0.636
P-glycoprotein substrateNon-substrate0.5685
P-glycoprotein inhibitor INon-inhibitor0.8234
P-glycoprotein inhibitor IINon-inhibitor0.9913
Renal organic cation transporterNon-inhibitor0.9426
CYP450 2C9 substrateNon-substrate0.7456
CYP450 2D6 substrateNon-substrate0.8271
CYP450 3A4 substrateNon-substrate0.6377
CYP450 1A2 substrateNon-inhibitor0.6547
CYP450 2C9 inhibitorInhibitor0.5096
CYP450 2D6 inhibitorNon-inhibitor0.9152
CYP450 2C19 inhibitorNon-inhibitor0.5321
CYP450 3A4 inhibitorNon-inhibitor0.9144
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.6367
Ames testNon AMES toxic0.6966
CarcinogenicityNon-carcinogens0.7773
BiodegradationNot ready biodegradable0.9833
Rat acute toxicity2.5104 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9676
hERG inhibition (predictor II)Non-inhibitor0.8806
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/MSsplash10-004i-0109000000-454d38c6876fe24335c2
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0c00-0019000000-f3eb9074428311568713
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-004i-0009000000-688b92440b64918d4f1d
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a4j-9352000000-6e09122bd5895c070d49
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0pk9-0937000000-e19dae71acca12a415fd
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-001l-7903000000-24830ae82160e426f52d
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]-190.08992
predicted
DeepCCS 1.0 (2019)
[M+H]+192.47289
predicted
DeepCCS 1.0 (2019)
[M+Na]+198.54106
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 21:34 / Updated at June 12, 2020 16:52