(2-{[(4-BROMO-2-FLUOROBENZYL)AMINO]CARBONYL}-5-CHLOROPHENOXY)ACETIC ACID

Identification

Name
(2-{[(4-BROMO-2-FLUOROBENZYL)AMINO]CARBONYL}-5-CHLOROPHENOXY)ACETIC ACID
Accession Number
DB07028
Type
Small Molecule
Groups
Experimental
Description
Not Available
Structure
Thumb
Synonyms
Not Available
Categories
Not Available
UNII
Not Available
CAS number
Not Available
Weight
Average: 416.626
Monoisotopic: 414.962226436
Chemical Formula
C16H12BrClFNO4
InChI Key
ZLIGBZRXAQNUFO-UHFFFAOYSA-N
InChI
InChI=1S/C16H12BrClFNO4/c17-10-2-1-9(13(19)5-10)7-20-16(23)12-4-3-11(18)6-14(12)24-8-15(21)22/h1-6H,7-8H2,(H,20,23)(H,21,22)
IUPAC Name
2-(2-{[(4-bromo-2-fluorophenyl)methyl]carbamoyl}-5-chlorophenoxy)acetic acid
SMILES
OC(=O)COC1=CC(Cl)=CC=C1C(=O)NCC1=C(F)C=C(Br)C=C1

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UAldose reductaseNot AvailableHuman
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
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

General References
Not Available
External Links
PubChem Compound
16058629
PubChem Substance
99443499
ChemSpider
17218348
BindingDB
16238
HET
388
PDB Entries
2iki / 3lep / 3lqg / 3lz3 / 3m4h / 5liu

Clinical Trials

Clinical Trials
Not Available

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 Solubility0.00355 mg/mLALOGPS
logP3.77ALOGPS
logP3.61ChemAxon
logS-5.1ALOGPS
pKa (Strongest Acidic)2.97ChemAxon
pKa (Strongest Basic)-1.4ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area75.63 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity89.84 m3·mol-1ChemAxon
Polarizability35.58 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9237
Blood Brain Barrier+0.8925
Caco-2 permeable-0.5832
P-glycoprotein substrateNon-substrate0.6518
P-glycoprotein inhibitor INon-inhibitor0.576
P-glycoprotein inhibitor IINon-inhibitor0.6637
Renal organic cation transporterNon-inhibitor0.8561
CYP450 2C9 substrateNon-substrate0.8203
CYP450 2D6 substrateNon-substrate0.8152
CYP450 3A4 substrateNon-substrate0.6072
CYP450 1A2 substrateInhibitor0.5529
CYP450 2C9 inhibitorNon-inhibitor0.5613
CYP450 2D6 inhibitorNon-inhibitor0.8773
CYP450 2C19 inhibitorNon-inhibitor0.6397
CYP450 3A4 inhibitorNon-inhibitor0.6138
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.5934
Ames testNon AMES toxic0.8112
CarcinogenicityNon-carcinogens0.7952
BiodegradationNot ready biodegradable0.9834
Rat acute toxicity2.3248 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9834
hERG inhibition (predictor II)Non-inhibitor0.6111
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 GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This compound belongs to the class of organic compounds known as n-benzylbenzamides. These are compounds containing a benzamide moiety that is N-linked to a benzyl group.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Benzoic acids and derivatives
Direct Parent
N-benzylbenzamides
Alternative Parents
Chlorophenoxyacetates / 4-halobenzoic acids and derivatives / Phenoxy compounds / Phenol ethers / Benzoyl derivatives / Alkyl aryl ethers / Bromobenzenes / Chlorobenzenes / Fluorobenzenes / Aryl chlorides
show 13 more
Substituents
N-benzylbenzamide / Chlorophenoxyacetate / Phenoxyacetate / 4-halobenzoic acid or derivatives / Halobenzoic acid or derivatives / Phenoxy compound / Benzoyl / Phenol ether / Fluorobenzene / Halobenzene
show 26 more
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
Not Available

Targets

Details
1. Aldose reductase
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Glyceraldehyde oxidoreductase activity
Specific Function
Catalyzes the NADPH-dependent reduction of a wide variety of carbonyl-containing compounds to their corresponding alcohols with a broad range of catalytic efficiencies.
Gene Name
AKR1B1
Uniprot ID
P15121
Uniprot Name
Aldose reductase
Molecular Weight
35853.125 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. [PubMed:10592235]

Drug created on September 15, 2010 15:18 / Updated on December 01, 2017 15:45