3,5-Dichloro-4-[(4-Hydroxy-3-Isopropylphenoxy)Phenylacetic Acid

Identification

Name
3,5-Dichloro-4-[(4-Hydroxy-3-Isopropylphenoxy)Phenylacetic Acid
Accession Number
DB03176  (EXPT01852)
Type
Small Molecule
Groups
Experimental
Description
Not Available
Structure
Thumb
Synonyms
Not Available
Categories
Not Available
UNII
M5P363AFVC
CAS number
Not Available
Weight
Average: 355.213
Monoisotopic: 354.042564414
Chemical Formula
C17H16Cl2O4
InChI Key
OZYQIQVPUZANTM-UHFFFAOYSA-N
InChI
InChI=1S/C17H16Cl2O4/c1-9(2)12-8-11(3-4-15(12)20)23-17-13(18)5-10(6-14(17)19)7-16(21)22/h3-6,8-9,20H,7H2,1-2H3,(H,21,22)
IUPAC Name
2-{3,5-dichloro-4-[4-hydroxy-3-(propan-2-yl)phenoxy]phenyl}acetic acid
SMILES
CC(C)C1=CC(OC2=C(Cl)C=C(CC(O)=O)C=C2Cl)=CC=C1O

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UThyroid hormone receptor betaNot AvailableHuman
UThyroid hormone receptor alphaNot 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
9863447
PubChem Substance
46506815
ChemSpider
8039143
BindingDB
18869
ChEMBL
CHEMBL41036
IUPHAR
2638
Guide to Pharmacology
GtP Drug Page
HET
IH5
PDB Entries
1nav / 1nax

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 Solubility0.00319 mg/mLALOGPS
logP4.88ALOGPS
logP5.26ChemAxon
logS-5ALOGPS
pKa (Strongest Acidic)3.27ChemAxon
pKa (Strongest Basic)-5.7ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area66.76 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity89.39 m3·mol-1ChemAxon
Polarizability34.26 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9553
Blood Brain Barrier+0.7274
Caco-2 permeable+0.677
P-glycoprotein substrateSubstrate0.5234
P-glycoprotein inhibitor INon-inhibitor0.872
P-glycoprotein inhibitor IINon-inhibitor0.9431
Renal organic cation transporterNon-inhibitor0.9081
CYP450 2C9 substrateNon-substrate0.7497
CYP450 2D6 substrateNon-substrate0.8995
CYP450 3A4 substrateSubstrate0.5299
CYP450 1A2 substrateNon-inhibitor0.5406
CYP450 2C9 inhibitorInhibitor0.7516
CYP450 2D6 inhibitorNon-inhibitor0.8876
CYP450 2C19 inhibitorNon-inhibitor0.6223
CYP450 3A4 inhibitorNon-inhibitor0.8075
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.5563
Ames testNon AMES toxic0.9263
CarcinogenicityNon-carcinogens0.7812
BiodegradationNot ready biodegradable0.9837
Rat acute toxicity3.5081 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9554
hERG inhibition (predictor II)Non-inhibitor0.8738
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 diphenylethers. These are aromatic compounds containing two benzene rings linked to each other through an ether group.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Diphenylethers
Direct Parent
Diphenylethers
Alternative Parents
Diarylethers / Phenylpropanes / Cumenes / Phenoxy compounds / Phenol ethers / Dichlorobenzenes / 1-hydroxy-2-unsubstituted benzenoids / Aryl chlorides / Monocarboxylic acids and derivatives / Carboxylic acids
show 4 more
Substituents
Diphenylether / Diaryl ether / Cumene / Phenylpropane / Phenoxy compound / 1,3-dichlorobenzene / Phenol ether / Chlorobenzene / 1-hydroxy-2-unsubstituted benzenoid / Halobenzene
show 15 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]
  3. 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]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Zinc ion binding
Specific Function
Isoform Alpha-1: Nuclear hormone receptor that can act as a repressor or activator of transcription. High affinity receptor for thyroid hormones, including triiodothyronine and thyroxine.Isoform Al...
Gene Name
THRA
Uniprot ID
P10827
Uniprot Name
Thyroid hormone receptor alpha
Molecular Weight
54815.055 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 June 13, 2005 07:24 / Updated on December 01, 2017 15:09