NAV

(2s)-2-[(2,4-Dichloro-Benzoyl)-(3-Trifluoromethyl-Benzyl)-Amino]-3-Phenyl-Propionic Acid

Identification

Generic Name
(2s)-2-[(2,4-Dichloro-Benzoyl)-(3-Trifluoromethyl-Benzyl)-Amino]-3-Phenyl-Propionic Acid
DrugBank Accession Number
DB03605
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 496.306
Monoisotopic: 495.061583476
Chemical Formula
C24H18Cl2F3NO3
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 phenylalanine and derivatives. These are compounds containing phenylalanine or a derivative thereof resulting from reaction of phenylalanine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Carboxylic acids and derivatives
Sub Class
Amino acids, peptides, and analogues
Direct Parent
Phenylalanine and derivatives
Alternative Parents
N-acyl-alpha amino acids / Hippuric acids / Phenylpropanoic acids / Trifluoromethylbenzenes / 2-halobenzoic acids and derivatives / 4-halobenzoic acids and derivatives / Amphetamines and derivatives / Benzoyl derivatives / Dichlorobenzenes / Aryl chlorides
show 12 more
Substituents
1,3-dichlorobenzene / 2-halobenzoic acid or derivatives / 3-phenylpropanoic-acid / 4-halobenzoic acid or derivatives / Alkyl fluoride / Alkyl halide / Amphetamine or derivatives / Aromatic homomonocyclic compound / Aryl chloride / Aryl halide
show 30 more
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
Not Available
InChI Key
LAJJKGIZTCCOHY-NRFANRHFSA-N
InChI
InChI=1S/C24H18Cl2F3NO3/c25-18-9-10-19(20(26)13-18)22(31)30(14-16-7-4-8-17(11-16)24(27,28)29)21(23(32)33)12-15-5-2-1-3-6-15/h1-11,13,21H,12,14H2,(H,32,33)/t21-/m0/s1
IUPAC Name
(2S)-2-[1-(2,4-dichlorophenyl)-N-{[3-(trifluoromethyl)phenyl]methyl}formamido]-3-phenylpropanoic acid
SMILES
[H][C@@](CC1=CC=CC=C1)(N(CC1=CC(=CC=C1)C(F)(F)F)C(=O)C1=C(Cl)C=C(Cl)C=C1)C(O)=O

References

General References
Not Available
PubChem Compound
447368
PubChem Substance
46506684
ChemSpider
394492
BindingDB
50126661
ChEMBL
CHEMBL24547
ZINC
ZINC000001554205
PDBe Ligand
153
PDB Entries
1nhu

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 Solubility0.000379 mg/mLALOGPS
logP5.52ALOGPS
logP6.78Chemaxon
logS-6.1ALOGPS
pKa (Strongest Acidic)3.59Chemaxon
pKa (Strongest Basic)-2Chemaxon
Physiological Charge-1Chemaxon
Hydrogen Acceptor Count3Chemaxon
Hydrogen Donor Count1Chemaxon
Polar Surface Area57.61 Å2Chemaxon
Rotatable Bond Count8Chemaxon
Refractivity120.32 m3·mol-1Chemaxon
Polarizability44.21 Å3Chemaxon
Number of Rings3Chemaxon
Bioavailability1Chemaxon
Rule of FiveNoChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleYesChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9836
Blood Brain Barrier+0.9715
Caco-2 permeable+0.5308
P-glycoprotein substrateNon-substrate0.6903
P-glycoprotein inhibitor INon-inhibitor0.8395
P-glycoprotein inhibitor IINon-inhibitor0.9301
Renal organic cation transporterNon-inhibitor0.7815
CYP450 2C9 substrateNon-substrate0.7429
CYP450 2D6 substrateNon-substrate0.8129
CYP450 3A4 substrateNon-substrate0.5136
CYP450 1A2 substrateNon-inhibitor0.672
CYP450 2C9 inhibitorNon-inhibitor0.697
CYP450 2D6 inhibitorNon-inhibitor0.8779
CYP450 2C19 inhibitorInhibitor0.717
CYP450 3A4 inhibitorNon-inhibitor0.6447
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.5224
Ames testNon AMES toxic0.8139
CarcinogenicityNon-carcinogens0.805
BiodegradationNot ready biodegradable1.0
Rat acute toxicity2.4603 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9871
hERG inhibition (predictor II)Non-inhibitor0.7154
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/MSsplash10-00dj-0911600000-f57e331090e260bc3a13
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0006-0202900000-db1dd90de10d7a0cb8fc
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-004j-0309700000-dc7edcda729341794d37
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-001i-9256700000-f9d64fd5a17b20f8fcbf
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-00di-2901000000-e94c0cbb7a0307a2d086
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-001i-9000000000-b98222a55870af7ee94a
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]-194.9735
predicted
DeepCCS 1.0 (2019)
[M+H]+197.36903
predicted
DeepCCS 1.0 (2019)
[M+Na]+203.28157
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