(2Z)-2-(Benzoylamino)-3-[4-(2-bromophenoxy)phenyl]acrylic acid

Identification

Generic Name
(2Z)-2-(Benzoylamino)-3-[4-(2-bromophenoxy)phenyl]acrylic acid
DrugBank Accession Number
DB01720
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
Weight
Average: 438.271
Monoisotopic: 437.026270652
Chemical Formula
C22H16BrNO4
Synonyms
  • (2Z)-2-(benzoylamino)-3-[4-(2-bromophenoxy)phenyl]-2-propenoic acid

Pharmacology

Indication

Not Available

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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UGenome polyproteinNot AvailableHCV
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 bromodiphenyl ethers. These are compounds that contain two benzene groups linked to each other via an ether bond, and where at least one ring is substituted with a bromo group.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Diphenylethers
Direct Parent
Bromodiphenyl ethers
Alternative Parents
N-acyl-alpha amino acids / Hippuric acids / Cinnamic acids / Diarylethers / Phenoxy compounds / Phenol ethers / Benzoyl derivatives / Bromobenzenes / Aryl bromides / Secondary carboxylic acid amides
show 8 more
Substituents
Alpha-amino acid or derivatives / Aromatic homomonocyclic compound / Aryl bromide / Aryl halide / Benzamide / Benzoic acid or derivatives / Benzoyl / Bromobenzene / Bromodiphenyl ether / Carbonyl group
show 25 more
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
639517-90-1
InChI Key
WLPJLQNKCJWAFL-RGEXLXHISA-N
InChI
InChI=1S/C22H16BrNO4/c23-18-8-4-5-9-20(18)28-17-12-10-15(11-13-17)14-19(22(26)27)24-21(25)16-6-2-1-3-7-16/h1-14H,(H,24,25)(H,26,27)/b19-14-
IUPAC Name
(2Z)-3-[4-(2-bromophenoxy)phenyl]-2-(phenylformamido)prop-2-enoic acid
SMILES
[H]N(\C(=C/C1=CC=C(OC2=CC=CC=C2Br)C=C1)C(O)=O)C(=O)C1=CC=CC=C1

References

General References
Not Available
PubChem Compound
657131
PubChem Substance
46508533
ChemSpider
571325
BindingDB
50166405
ChEMBL
CHEMBL188442
PDBe Ligand
PH7
PDB Entries
1yvf

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 Solubility0.000356 mg/mLALOGPS
logP4.72ALOGPS
logP4.92Chemaxon
logS-6.1ALOGPS
pKa (Strongest Acidic)3.05Chemaxon
pKa (Strongest Basic)-3.7Chemaxon
Physiological Charge-1Chemaxon
Hydrogen Acceptor Count3Chemaxon
Hydrogen Donor Count2Chemaxon
Polar Surface Area75.63 Å2Chemaxon
Rotatable Bond Count6Chemaxon
Refractivity110.66 m3·mol-1Chemaxon
Polarizability40.22 Å3Chemaxon
Number of Rings3Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleYesChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.828
Blood Brain Barrier+0.574
Caco-2 permeable-0.5554
P-glycoprotein substrateNon-substrate0.5884
P-glycoprotein inhibitor INon-inhibitor0.8469
P-glycoprotein inhibitor IINon-inhibitor0.9743
Renal organic cation transporterNon-inhibitor0.9295
CYP450 2C9 substrateNon-substrate0.7695
CYP450 2D6 substrateNon-substrate0.8462
CYP450 3A4 substrateNon-substrate0.5549
CYP450 1A2 substrateInhibitor0.5922
CYP450 2C9 inhibitorNon-inhibitor0.5539
CYP450 2D6 inhibitorNon-inhibitor0.93
CYP450 2C19 inhibitorNon-inhibitor0.8059
CYP450 3A4 inhibitorNon-inhibitor0.579
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.6399
Ames testNon AMES toxic0.808
CarcinogenicityNon-carcinogens0.8982
BiodegradationNot ready biodegradable0.894
Rat acute toxicity2.2503 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9806
hERG inhibition (predictor II)Non-inhibitor0.8674
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/MSsplash10-000i-0304900000-46a53b0d59718c074754
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-002o-3009400000-90fa09b4b2b1cc0d925c
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-000i-1169400000-8488fb3f9e88570e7a1c
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-000i-2094000000-ac415551334b2cb5ce0e
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-004i-9153000000-8a4e7725572f44cc2daa
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0w4r-9882100000-d5dcf21cca4dad35d5e2
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]-187.74998
predicted
DeepCCS 1.0 (2019)
[M+H]+190.108
predicted
DeepCCS 1.0 (2019)
[M+Na]+196.85631
predicted
DeepCCS 1.0 (2019)

Targets

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Kind
Protein
Organism
HCV
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
P26662
Uniprot Name
Genome polyprotein
Molecular Weight
327018.235 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 16:51