Compounds > 3,5-dibromo-4-(4-hydroxy-3-isopropylphenoxy)phenylacetic acid
Page last updated: 2024-11-12

3,5-dibromo-4-(4-hydroxy-3-isopropylphenoxy)phenylacetic acid

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Description

3,5-dibromo-4-(4-hydroxy-3-isopropylphenoxy)phenylacetic acid: a thyroid receptor beta1 agonist; structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID9933119
CHEMBL ID39174
SCHEMBL ID4352011
MeSH IDM0449721

Synonyms (12)

Synonym
bdbm18867
kb-131092
2-{3,5-dibromo-4-[4-hydroxy-3-(propan-2-yl)phenoxy]phenyl}acetic acid
dibromo phenylacetic acid, 11a
CHEMBL39174
SCHEMBL4352011
FDLOBNTWQDSHPF-UHFFFAOYSA-N
3,5-dibromo-4-(4-hydroxy-3-isopropylphenoxy)phenylacetic acid
2-[3,5-dibromo-4-(4-hydroxy-3-propan-2-ylphenoxy)phenyl]acetic acid
2-(3,5-dibromo-4-(4-hydroxy-3-isopropylphenoxy)phenyl)acetic acid
219691-88-0
PD129108
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (2)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Thyroid hormone receptor alphaHomo sapiens (human)IC50 (µMol)0.00120.00000.35494.5000AID1797783; AID1797786; AID1797797; AID213163; AID299560; AID311016
Thyroid hormone receptor betaHomo sapiens (human)IC50 (µMol)0.00030.00000.50185.1286AID1797785; AID1797787; AID1797797; AID213175; AID299561; AID299948; AID311017
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Activation Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Thyroid hormone receptor alphaHomo sapiens (human)EC50 (µMol)0.00040.00040.25843.7400AID213162
Thyroid hormone receptor betaHomo sapiens (human)EC50 (µMol)0.00020.00020.03480.2400AID213174
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (33)

Processvia Protein(s)Taxonomy
cartilage condensationThyroid hormone receptor alphaHomo sapiens (human)
ossificationThyroid hormone receptor alphaHomo sapiens (human)
regulation of thyroid hormone mediated signaling pathwayThyroid hormone receptor alphaHomo sapiens (human)
regulation of transcription by RNA polymerase IIThyroid hormone receptor alphaHomo sapiens (human)
transcription by RNA polymerase IIThyroid hormone receptor alphaHomo sapiens (human)
learning or memoryThyroid hormone receptor alphaHomo sapiens (human)
regulation of heart contractionThyroid hormone receptor alphaHomo sapiens (human)
female courtship behaviorThyroid hormone receptor alphaHomo sapiens (human)
response to coldThyroid hormone receptor alphaHomo sapiens (human)
hormone-mediated signaling pathwayThyroid hormone receptor alphaHomo sapiens (human)
negative regulation of RNA polymerase II transcription preinitiation complex assemblyThyroid hormone receptor alphaHomo sapiens (human)
erythrocyte differentiationThyroid hormone receptor alphaHomo sapiens (human)
thyroid gland developmentThyroid hormone receptor alphaHomo sapiens (human)
regulation of myeloid cell apoptotic processThyroid hormone receptor alphaHomo sapiens (human)
negative regulation of DNA-templated transcriptionThyroid hormone receptor alphaHomo sapiens (human)
positive regulation of female receptivityThyroid hormone receptor alphaHomo sapiens (human)
regulation of lipid catabolic processThyroid hormone receptor alphaHomo sapiens (human)
type I pneumocyte differentiationThyroid hormone receptor alphaHomo sapiens (human)
positive regulation of cold-induced thermogenesisThyroid hormone receptor alphaHomo sapiens (human)
negative regulation of DNA-templated transcription initiationThyroid hormone receptor alphaHomo sapiens (human)
thyroid hormone mediated signaling pathwayThyroid hormone receptor alphaHomo sapiens (human)
negative regulation of transcription by RNA polymerase IIThyroid hormone receptor alphaHomo sapiens (human)
cell differentiationThyroid hormone receptor alphaHomo sapiens (human)
positive regulation of transcription by RNA polymerase IIThyroid hormone receptor alphaHomo sapiens (human)
retinoic acid receptor signaling pathwayThyroid hormone receptor alphaHomo sapiens (human)
positive regulation of thyroid hormone mediated signaling pathwayThyroid hormone receptor betaHomo sapiens (human)
DNA-templated transcriptionThyroid hormone receptor betaHomo sapiens (human)
sensory perception of soundThyroid hormone receptor betaHomo sapiens (human)
negative regulation of female receptivityThyroid hormone receptor betaHomo sapiens (human)
regulation of heart contractionThyroid hormone receptor betaHomo sapiens (human)
female courtship behaviorThyroid hormone receptor betaHomo sapiens (human)
mRNA transcription by RNA polymerase IIThyroid hormone receptor betaHomo sapiens (human)
positive regulation of transcription by RNA polymerase IIThyroid hormone receptor betaHomo sapiens (human)
retinal cone cell developmentThyroid hormone receptor betaHomo sapiens (human)
type I pneumocyte differentiationThyroid hormone receptor betaHomo sapiens (human)
cellular response to thyroid hormone stimulusThyroid hormone receptor betaHomo sapiens (human)
retinal cone cell apoptotic processThyroid hormone receptor betaHomo sapiens (human)
retinoic acid receptor signaling pathwayThyroid hormone receptor betaHomo sapiens (human)
cell differentiationThyroid hormone receptor betaHomo sapiens (human)
thyroid hormone mediated signaling pathwayThyroid hormone receptor betaHomo sapiens (human)
negative regulation of transcription by RNA polymerase IIThyroid hormone receptor betaHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (16)

Processvia Protein(s)Taxonomy
transcription cis-regulatory region bindingThyroid hormone receptor alphaHomo sapiens (human)
DNA-binding transcription factor activity, RNA polymerase II-specificThyroid hormone receptor alphaHomo sapiens (human)
DNA-binding transcription factor activityThyroid hormone receptor alphaHomo sapiens (human)
nuclear receptor activityThyroid hormone receptor alphaHomo sapiens (human)
protein bindingThyroid hormone receptor alphaHomo sapiens (human)
zinc ion bindingThyroid hormone receptor alphaHomo sapiens (human)
TBP-class protein bindingThyroid hormone receptor alphaHomo sapiens (human)
protein domain specific bindingThyroid hormone receptor alphaHomo sapiens (human)
chromatin DNA bindingThyroid hormone receptor alphaHomo sapiens (human)
thyroid hormone bindingThyroid hormone receptor alphaHomo sapiens (human)
general transcription initiation factor bindingThyroid hormone receptor alphaHomo sapiens (human)
RNA polymerase II cis-regulatory region sequence-specific DNA bindingThyroid hormone receptor alphaHomo sapiens (human)
DNA-binding transcription factor activity, RNA polymerase II-specificThyroid hormone receptor betaHomo sapiens (human)
transcription coactivator bindingThyroid hormone receptor betaHomo sapiens (human)
DNA bindingThyroid hormone receptor betaHomo sapiens (human)
DNA-binding transcription factor activityThyroid hormone receptor betaHomo sapiens (human)
nuclear receptor activityThyroid hormone receptor betaHomo sapiens (human)
protein bindingThyroid hormone receptor betaHomo sapiens (human)
zinc ion bindingThyroid hormone receptor betaHomo sapiens (human)
enzyme bindingThyroid hormone receptor betaHomo sapiens (human)
chromatin DNA bindingThyroid hormone receptor betaHomo sapiens (human)
thyroid hormone bindingThyroid hormone receptor betaHomo sapiens (human)
sequence-specific double-stranded DNA bindingThyroid hormone receptor betaHomo sapiens (human)
RNA polymerase II cis-regulatory region sequence-specific DNA bindingThyroid hormone receptor betaHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (6)

Processvia Protein(s)Taxonomy
nucleusThyroid hormone receptor alphaHomo sapiens (human)
nucleoplasmThyroid hormone receptor alphaHomo sapiens (human)
cytosolThyroid hormone receptor alphaHomo sapiens (human)
chromatinThyroid hormone receptor alphaHomo sapiens (human)
nucleusThyroid hormone receptor alphaHomo sapiens (human)
RNA polymerase II transcription regulator complexThyroid hormone receptor alphaHomo sapiens (human)
nucleoplasmThyroid hormone receptor betaHomo sapiens (human)
nuclear bodyThyroid hormone receptor betaHomo sapiens (human)
RNA polymerase II transcription regulator complexThyroid hormone receptor betaHomo sapiens (human)
chromatinThyroid hormone receptor betaHomo sapiens (human)
nucleusThyroid hormone receptor betaHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (24)

Assay IDTitleYearJournalArticle
AID299560Binding affinity at human thyroid hormone receptor alpha 1 expressed in CHOK1 cells2007Bioorganic & medicinal chemistry letters, Aug-01, Volume: 17, Issue:15
Thyroid receptor ligands. Part 8: Thyromimetics derived from N-acylated-alpha-amino acid derivatives displaying modulated pharmacological selectivity compared with KB-141.
AID299948Inhibition of human thyroid hormone receptor beta 12007Bioorganic & medicinal chemistry, Aug-01, Volume: 15, Issue:15
QSAR study of selective ligands for the thyroid hormone receptor beta.
AID235409Ratio of ED50TSH to that of ED50chol was determined2003Journal of medicinal chemistry, Apr-24, Volume: 46, Issue:9
Thyroid receptor ligands. 1. Agonist ligands selective for the thyroid receptor beta1.
AID299563Activity against TRAF-alpha-1 expressed in CHOK1 cells by alkaline phosphatase reporter gene assay2007Bioorganic & medicinal chemistry letters, Aug-01, Volume: 17, Issue:15
Thyroid receptor ligands. Part 8: Thyromimetics derived from N-acylated-alpha-amino acid derivatives displaying modulated pharmacological selectivity compared with KB-141.
AID311016Inhibition of thyroid hormone receptor alpha2007Bioorganic & medicinal chemistry, Jul-01, Volume: 15, Issue:13
2D QSAR studies on thyroid hormone receptor ligands.
AID213163Concentration required to inhibit 50% of I-T3 binding to hTR1 (Thyroid hormone receptor alpha) was determined2003Journal of medicinal chemistry, Apr-24, Volume: 46, Issue:9
Thyroid receptor ligands. 1. Agonist ligands selective for the thyroid receptor beta1.
AID177495Effect upon subcutaneous administration on cholesterol in rat was determined2003Journal of medicinal chemistry, Apr-24, Volume: 46, Issue:9
Thyroid receptor ligands. 1. Agonist ligands selective for the thyroid receptor beta1.
AID299564Activity against TRAFbeta expressed in CHOK1 cells by alkaline phosphatse reporter gene assay2007Bioorganic & medicinal chemistry letters, Aug-01, Volume: 17, Issue:15
Thyroid receptor ligands. Part 8: Thyromimetics derived from N-acylated-alpha-amino acid derivatives displaying modulated pharmacological selectivity compared with KB-141.
AID177494Effect upon subcutaneous administration on TSH suppression in rat was determined2003Journal of medicinal chemistry, Apr-24, Volume: 46, Issue:9
Thyroid receptor ligands. 1. Agonist ligands selective for the thyroid receptor beta1.
AID173635Effect upon subcutaneous administration on the heart rate in rat was determined2003Journal of medicinal chemistry, Apr-24, Volume: 46, Issue:9
Thyroid receptor ligands. 1. Agonist ligands selective for the thyroid receptor beta1.
AID231783Ratio of concentration required to inhibit 50% of I-T3 binding to hTR-alpha1 to that of concentration required to inhibit 50% of I-T3 binding to hTR-beta1 was determined2003Journal of medicinal chemistry, Apr-24, Volume: 46, Issue:9
Thyroid receptor ligands. 1. Agonist ligands selective for the thyroid receptor beta1.
AID299561Binding affinity at human thyroid hormone receptor beta-1 expressed in CHOK1 cells2007Bioorganic & medicinal chemistry letters, Aug-01, Volume: 17, Issue:15
Thyroid receptor ligands. Part 8: Thyromimetics derived from N-acylated-alpha-amino acid derivatives displaying modulated pharmacological selectivity compared with KB-141.
AID213174Effect on CHO-K1 cells stably transfected with Thyroid hormone receptor beta and an alkaline phosphate reporter gene downstream thyroid response element TRAF-beta1 was determined2003Journal of medicinal chemistry, Apr-24, Volume: 46, Issue:9
Thyroid receptor ligands. 1. Agonist ligands selective for the thyroid receptor beta1.
AID213162Effect on CHO-K1 cells stably transfected with Thyroid hormone receptor alpha (TRalpha1) and an alkaline phosphate reporter gene downstream thyroid response element TRAF-alpha1 was determined2003Journal of medicinal chemistry, Apr-24, Volume: 46, Issue:9
Thyroid receptor ligands. 1. Agonist ligands selective for the thyroid receptor beta1.
AID299562Selectivity ratio of IC50 for thyroid hormone receptor alpha-1 to IC50 for thyroid hormone receptor beta-12007Bioorganic & medicinal chemistry letters, Aug-01, Volume: 17, Issue:15
Thyroid receptor ligands. Part 8: Thyromimetics derived from N-acylated-alpha-amino acid derivatives displaying modulated pharmacological selectivity compared with KB-141.
AID213175Concentration required to inhibit 50% of I-T3 binding to hTR1 (Thyroid hormone receptor beta) was determined2003Journal of medicinal chemistry, Apr-24, Volume: 46, Issue:9
Thyroid receptor ligands. 1. Agonist ligands selective for the thyroid receptor beta1.
AID311017Inhibition of thyroid hormone receptor beta2007Bioorganic & medicinal chemistry, Jul-01, Volume: 15, Issue:13
2D QSAR studies on thyroid hormone receptor ligands.
AID231769Ratio of chronic administration on TRAF alpha-1 receptor to that of chronic administration on TRAF beta-1 receptor was determined2003Journal of medicinal chemistry, Apr-24, Volume: 46, Issue:9
Thyroid receptor ligands. 1. Agonist ligands selective for the thyroid receptor beta1.
AID226476Ratio of ED15HR to that of ED50chol was determined2003Journal of medicinal chemistry, Apr-24, Volume: 46, Issue:9
Thyroid receptor ligands. 1. Agonist ligands selective for the thyroid receptor beta1.
AID1797797TRalpha-Binding Assay. from Article 10.1016/j.bmcl.2004.04.032: \\Thyroid receptor ligands. Part 2: Thyromimetics with improved selectivity for the thyroid hormone receptor beta.\\2004Bioorganic & medicinal chemistry letters, Jul-05, Volume: 14, Issue:13
Thyroid receptor ligands. Part 2: Thyromimetics with improved selectivity for the thyroid hormone receptor beta.
AID1797787TRbeta-Binding Assay and Thyroid Response Element (TRAFbeta1) Reporter Assay. from Article 10.1016/j.bmcl.2007.05.049: \\Thyroid receptor ligands. Part 8: Thyromimetics derived from N-acylated-alpha-amino acid derivatives displaying modulated pharmacologic2007Bioorganic & medicinal chemistry letters, Aug-01, Volume: 17, Issue:15
Thyroid receptor ligands. Part 8: Thyromimetics derived from N-acylated-alpha-amino acid derivatives displaying modulated pharmacological selectivity compared with KB-141.
AID1797786TRalpha-Binding Assay and Thyroid Response Element (TRAFalpha1) Reporter Assay. from Article 10.1016/j.bmcl.2007.05.049: \\Thyroid receptor ligands. Part 8: Thyromimetics derived from N-acylated-alpha-amino acid derivatives displaying modulated pharmacolog2007Bioorganic & medicinal chemistry letters, Aug-01, Volume: 17, Issue:15
Thyroid receptor ligands. Part 8: Thyromimetics derived from N-acylated-alpha-amino acid derivatives displaying modulated pharmacological selectivity compared with KB-141.
AID1797785TRbeta-Binding Assay and Thyroid Response Element (TRAFbeta1) Reporter Assay. from Article 10.1021/jm021080f: \\Thyroid receptor ligands. 1. Agonist ligands selective for the thyroid receptor beta1.\\2003Journal of medicinal chemistry, Apr-24, Volume: 46, Issue:9
Thyroid receptor ligands. 1. Agonist ligands selective for the thyroid receptor beta1.
AID1797783TRalpha-Binding Assay and Thyroid Response Element (TRAFalpha1) Reporter Assay. from Article 10.1021/jm021080f: \\Thyroid receptor ligands. 1. Agonist ligands selective for the thyroid receptor beta1.\\2003Journal of medicinal chemistry, Apr-24, Volume: 46, Issue:9
Thyroid receptor ligands. 1. Agonist ligands selective for the thyroid receptor beta1.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (5)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's5 (100.00)29.6817
2010's0 (0.00)24.3611
2020's0 (0.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 12.56

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be weak demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index12.56 (24.57)
Research Supply Index1.79 (2.92)
Research Growth Index4.36 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.56)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other5 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
3,3',5-triiodothyroacetic acid
tiratricol : A monocarboxylic acid that is (4-hydroxy-3,5-diiodophenyl)acetic acid in which the phenolic hydroxy group has been replaced by a 4-hydroxy-3-iodophenoxy group. It is a thyroid hormone analogue that has been used in the treatment of thyroid hormone resistance syndrome.		2.7230
3,3',5-triiodothyropropionic acid
[no description available]		2.7230aromatic ether
triiodothyronine
Triiodothyronine: A T3 thyroid hormone normally synthesized and secreted by the thyroid gland in much smaller quantities than thyroxine (T4). Most T3 is derived from peripheral monodeiodination of T4 at the 5' position of the outer ring of the iodothyronine nucleus. The hormone finally delivered and used by the tissues is mainly T3.. 3,3',5-triiodo-L-thyronine : An iodothyronine compound having iodo substituents at the 3-, 3'- and 5-positions. Although some is produced in the thyroid, most of the 3,3',5-triiodo-L-thyronine in the body is generated by mono-deiodination of L-thyroxine in the peripheral tissues. Its metabolic activity is about 3 to 5 times that of L-thyroxine. The sodium salt is used in the treatment of hypothyroidism.		2.94402-halophenol;
amino acid zwitterion;
iodophenol;
iodothyronine		human metabolite;
mouse metabolite;
thyroid hormone
kb 141
KB 141: an anticholesteremic agent; structure in first source		3.1250
kb 130015
KB 130015: structure in first source		2.0310
ConditionIndicatedRelationship StrengthStudiesTrials