Compound Detail

CHEMBL41632

TIRATRICOL

🧪 Phase III

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🧪 Phase III

O=C(O)Cc1cc(I)c(Oc2ccc(O)c(I)c2)c(I)c1

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL41632
Name	TIRATRICOL
Phase	Phase III
Structure Type	MOL
InChI Key	UOWZUVNAGUAEQC-UHFFFAOYSA-N
Therapeutic	✓ Yes

Known Names

3,5,3'-triiodothyroacetate Levothyroxine sodium impurity, triiodothyroacetic acid, or t3-acetic acid- NSC-759294 T3-acetic acid Tiracana Tiratricol Triac Triiodothyroacetic acid

Targets

Activities

Assay Types

PK Parameters

Publications

Known Names

Mechanisms

Molecular Properties

621.9

MW (Da)

4.63

ALogP

HBA

HBD

66.8

PSA (Å²)

0.49

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Small molecule
Chirality	Achiral

Flags

Natural Product

Extended Properties

Molecular Formula	C14H9I3O4
MW	621.93
Aromatic Rings	2
Heavy Atoms	21
NP-Likeness	0.27

Mechanism of Action

Mechanism	Action Type	Target	Direct	Efficacy
Thyroid hormone receptor agonist	AGONIST	Thyroid hormone receptor	✓	✓

ATC Classification

D11AX08

tiratricol

Level 1: DERMATOLOGICALS

Level 2: OTHER DERMATOLOGICAL PREPARATIONS

H03AA04

tiratricol

Level 1: SYSTEMIC HORMONAL PREPARATIONS, EXCL. SEX HORMONES AND INSULINS

Level 2: THYROID THERAPY

Activity Summary

IC50 16 meas. best 10.39

EC50 6 meas. best 8.7

Kd 2 meas. best 6.7

Ki 2 meas. best 9.1

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Thyroid hormone receptor beta CHEMBL1947	IC50	10.39	10.3433	0.0	3
Thyroid hormone receptor alpha CHEMBL1860	IC50	9.85	9.85	0.1	2
Thyroid hormone receptor beta CHEMBL3917	IC50	9.82	9.82	0.1	1
Rattus norvegicus CHEMBL376	Ki	9.1	9.1	0.8	1
Thyroid hormone receptor alpha CHEMBL1860	EC50	8.7	8.7	2.0	1
Thyroid hormone receptor beta CHEMBL1947	EC50	8.4	8.4	4.0	1
Peroxisome proliferator-activated receptor gamma CHEMBL235	Kd	6.7	6.7	200.0	1
Peroxisome proliferator-activated receptor gamma CHEMBL235	EC50	6.43	6.43	370.0	1
Retinoic acid receptor RXR-alpha CHEMBL2061	Kd	5.88	5.88	1320.0	1
Solute carrier organic anion transporter family member 1C1 CHEMBL2073688	Ki	5.67	5.67	2150.0	1
Unchecked CHEMBL612545	IC50	5.33	4.8383	4700.0	6
Hepatic sodium/bile acid cotransporter CHEMBL5287	IC50	5.16	5.16	6900.0	2
Retinoic acid receptor RXR-alpha CHEMBL2061	EC50	4.92	4.92	12000.0	1
Unchecked CHEMBL612545	EC50	4.87	4.795	13500.0	2
Proliferating cell nuclear antigen CHEMBL2346488	IC50	4.6	4.6	25000.0	1
Androgen receptor CHEMBL1871	IC50	4.46	4.46	34800.0	1

Pharmacokinetic Data

Parameter	Value	Units	Species
AUC	88.9	ng/g.hr	Mus musculus
AUC	5108.0	ng/g.hr	Mus musculus

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
Thyroid hormone receptor beta	IC50	=	0.04074	nM	10.39	Inhibition of thyroid hormone receptor beta	17467994
Thyroid hormone receptor beta	IC50	=	0.048	nM	10.32	Concentration required to inhibit 50% of I-T3 binding to hTR1 (Thyroid hormone r...	12699376
Thyroid hormone receptor beta	IC50	=	0.04786	nM	10.32	Inhibition of human thyroid hormone receptor beta 1	17524652
Thyroid hormone receptor alpha	IC50	=	0.14	nM	9.85	Concentration required to inhibit 50% of I-T3 binding to hTR1 (Thyroid hormone r...	12699376
Thyroid hormone receptor alpha	IC50	=	0.1413	nM	9.85	Inhibition of thyroid hormone receptor alpha	17467994
Thyroid hormone receptor beta	IC50	=	0.15	nM	9.82	In vitro inhibition of the bound [125I]L-T3 rat liver nuclear L-triiodothyronine...	7861417
Rattus norvegicus	Ki	=	0.79	nM	9.1	In vitro concentration required to displace [125I]L-T3 from rat hepatic nuclei.	1738147
Thyroid hormone receptor alpha	EC50	=	2.0	nM	8.7	Affinity On-target Cellular interaction: (Reporter gene assay (HEK293T cells)) E...	-
Thyroid hormone receptor beta	EC50	=	4.0	nM	8.4	Affinity On-target Cellular interaction: (Reporter gene assay (HEK293T cells)) E...	-
Peroxisome proliferator-activated receptor gamma	Kd	=	200.0	nM	6.7	Binding affinity to recombinant PPARgamma LBD (unknown origin) by isothermal tit...	32356658
Peroxisome proliferator-activated receptor gamma	EC50	=	370.0	nM	6.43	Agonist activity at recombinant human pFA-CMV fused PPARgamma expressed in HEK29...	32356658
Retinoic acid receptor RXR-alpha	Kd	=	1320.0	nM	5.88	Binding affinity to RXRalpha LBD (unknown origin) by isothermal titration calori...	32356658
Solute carrier organic anion transporter family member 1C1	Ki	=	2150.0	nM	5.67	TP_TRANSPORTER: inhibition of L-T4 uptake in Oatp14-expressing HEK293 cells	15166123
Unchecked	IC50	=	4700.0	nM	5.33	Biochemical Characterization of Cif Inhibitors: The first step in characterizing...	-
Unchecked	IC50	=	4700.0	nM	5.33	Inhibition of Pseudomonas aeruginosa recombinant His-tagged CFTR inhibitory fact...	27120257
Hepatic sodium/bile acid cotransporter	IC50	=	6900.0	nM	5.16	Inhibition of HA-tagged human NTCP expressed in human U2OS cells assessed as red...	31439379
Hepatic sodium/bile acid cotransporter	IC50	=	6900.0	nM	5.16	Inhibition of human NTCP mediated TCA uptake in U2OS expresseing HA-tagged NTCP ...	36111355
Retinoic acid receptor RXR-alpha	EC50	=	12000.0	nM	4.92	Agonist activity at recombinant human pFA-CMV fused RXRalpha LBD expressed in HE...	32356658
Unchecked	EC50	=	13500.0	nM	4.87	PUBCHEM_BIOASSAY: Fluorescent HTS Cytotoxicity/Cell viability assay (HPDE-C7 cel...	-
Unchecked	IC50	=	15550.0	nM	4.81	PUBCHEM_BIOASSAY: A Cell Based HTS Approach for the Discovery of New Inhibitors ...	-

Literature References

PubMed	DOI	Target Context	# Activities
32356658	10.1021/acs.jmedchem.9b02150	Peroxisome proliferator-activated receptor gamma	9
-	10.6019/CHEMBL5303304	Fibroblast	7
-	10.6019/CHEMBL5303304	HEK-293T	7
-	10.6019/CHEMBL5303304	U2OS	5
32356658	10.1021/acs.jmedchem.9b02150	Retinoic acid receptor RXR-alpha	4
-	10.6019/CHEMBL5724696	TERT-RPE1	4
32787092	10.1021/acs.jmedchem.0c00868	ADMET	3
1738147	10.1021/jm00081a017	Glycerol-3-phosphate dehydrogenase [NAD(+)], cytoplasmic	3
1738147	10.1021/jm00081a017	NADP-dependent malic enzyme	3
20014752	10.1021/tx900326k	Hepatotoxicity	3
37468498	10.1038/s41467-023-40064-9	D(1A) dopamine receptor	2
-	10.6019/CHEMBL4495565	SARS-CoV-2	2
36111355	10.1021/acs.jmedchem.2c01097	Hepatic sodium/bile acid cotransporter	2
37468498	10.1038/s41467-023-40064-9	Peroxisome proliferator-activated receptor gamma	2
18975928	10.1021/jm800824d	Rattus norvegicus	2
17911242	10.1073/pnas.0708036104	Androgen receptor	2
37468498	10.1038/s41467-023-40064-9	Estrogen receptor	2
-	10.6019/CHEMBL4651402	SARS-CoV-2	2
37468498	10.1038/s41467-023-40064-9	Muscarinic acetylcholine receptor M2	2
1738147	10.1021/jm00081a017	Rattus norvegicus	2

Data from ChEMBL 36 via Core Engine