[3,5-Dibromo-4-(4-Hydroxy-3-Phenethylcarbamoyl-Phenoxy)-Phenyl]-Acetic Acid

Identification

Name
[3,5-Dibromo-4-(4-Hydroxy-3-Phenethylcarbamoyl-Phenoxy)-Phenyl]-Acetic Acid
Accession Number
DB02106  (EXPT00196)
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: 553.24
Monoisotopic: 550.994298145
Chemical Formula
C23H23Br2NO5
InChI Key
KIRQJXNQGZAKGR-UHFFFAOYSA-N
InChI
InChI=1S/C23H23Br2NO5/c24-18-10-15(12-21(28)29)11-19(25)22(18)31-16-6-7-20(27)17(13-16)23(30)26-9-8-14-4-2-1-3-5-14/h1-7,10-11,13,21,23,26-30H,8-9,12H2
IUPAC Name
2-[3,5-dibromo-4-(4-hydroxy-3-{hydroxy[(2-phenylethyl)amino]methyl}phenoxy)phenyl]ethane-1,1-diol
SMILES
OC(O)CC1=CC(Br)=C(OC2=CC(C(O)NCCC3=CC=CC=C3)=C(O)C=C2)C(Br)=C1

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UThyroid hormone receptor betaNot 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
5287509
PubChem Substance
46505732
ChemSpider
4449873
HET
442
PDB Entries
1r6g

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 Solubility0.00816 mg/mLALOGPS
logP3.82ALOGPS
logP4.3ChemAxon
logS-4.8ALOGPS
pKa (Strongest Acidic)8.69ChemAxon
pKa (Strongest Basic)9.73ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area102.18 Å2ChemAxon
Rotatable Bond Count9ChemAxon
Refractivity125.88 m3·mol-1ChemAxon
Polarizability49.22 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.5648
Blood Brain Barrier+0.8353
Caco-2 permeable-0.556
P-glycoprotein substrateNon-substrate0.5526
P-glycoprotein inhibitor INon-inhibitor0.7336
P-glycoprotein inhibitor IINon-inhibitor0.8535
Renal organic cation transporterNon-inhibitor0.7082
CYP450 2C9 substrateNon-substrate0.7371
CYP450 2D6 substrateNon-substrate0.7552
CYP450 3A4 substrateNon-substrate0.5
CYP450 1A2 substrateInhibitor0.5553
CYP450 2C9 inhibitorNon-inhibitor0.6737
CYP450 2D6 inhibitorNon-inhibitor0.6375
CYP450 2C19 inhibitorNon-inhibitor0.6423
CYP450 3A4 inhibitorNon-inhibitor0.8501
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.7162
Ames testNon AMES toxic0.7695
CarcinogenicityNon-carcinogens0.9322
BiodegradationNot ready biodegradable0.761
Rat acute toxicity2.4108 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9539
hERG inhibition (predictor II)Non-inhibitor0.5975
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/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 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
Diarylethers / Phenoxy compounds / Phenol ethers / Bromobenzenes / 1-hydroxy-2-unsubstituted benzenoids / Aryl bromides / Carbonyl hydrates / Alkanolamines / Organobromides / Hydrocarbon derivatives
show 1 more
Substituents
Bromodiphenyl ether / Diaryl ether / Phenoxy compound / Phenol ether / 1-hydroxy-2-unsubstituted benzenoid / Bromobenzene / Phenol / Halobenzene / Aryl bromide / Aryl halide
show 12 more
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
Not Available

Targets

Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Zinc ion binding
Specific Function
Nuclear hormone receptor that can act as a repressor or activator of transcription. High affinity receptor for thyroid hormones, including triiodothyronine and thyroxine.
Gene Name
THRB
Uniprot ID
P10828
Uniprot Name
Thyroid hormone receptor beta
Molecular Weight
52787.16 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. [PubMed:17139284]
  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. [PubMed:17016423]

Drug created on June 13, 2005 07:24 / Updated on December 01, 2017 14:53