Tiratricol (CED0015459)

Record Information

Version

1.0

Creation Date

2014-10-14 21:19:35 UTC

Update Date

2026-08-19 08:35:09 UTC

Accession Number

CHEM003937

Identification

Common Name

Tiratricol

Class

Small Molecule

Description

Tiratricol (C14H9I3O4) is an exogenous compound. Tiratricol belongs to the diphenylethers, a subclass of benzene and substituted derivatives within the organic compounds. With an average molecular weight of 621.93 g/mol, Tiratricol is a heavy molecule. Its recorded protein targets include the thyroid hormone receptor alpha (THRA), the thyroid hormone receptor beta (THRB), for which it acts as an agonist or inhibitor, and the mitochondrial dihydroorotate dehydrogenase (quinone) (DHODH). The compound is found in or released from 35 recorded sources. These include healthcare, pharmaceuticals, and veterinary products such as thyroid preparations and dermatological preparations. It is also associated with food and food processing, specifically food preservation and fermentation processes for beer. Other recorded sources include household items like watch chains, as well as building and construction materials such as sunshades awnings or outside screens and stairs and ramps. Additionally, it is found in electrical and electronic equipment, including antennas, amplifiers, coils, auxiliary devices, and adjustable resistors. The recorded exposure route for this compound is oral.

Contaminant Type

Industrial/Workplace Toxin
Synthetic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Tiracana	Kegg
3,3',5-Triiodothyroacetic acid, sodium salt	MeSH
3,5-diiodo-3'-Isopropylthyroacetic acid	MeSH
3,3',5-Triiodothyroacetic acid	MeSH
Téatrois	MeSH
3,5,3'-Triiodothyroacetic acid	MeSH
Triacana	MeSH
Triac	MeSH

Chemical Formula

C₁₄H₉I₃O₄

Average Molecular Mass

621.932 g/mol

Monoisotopic Mass

621.763 g/mol

CAS Registry Number

51-24-1

IUPAC Name

2-[4-(4-hydroxy-3-iodophenoxy)-3,5-diiodophenyl]acetic acid

Traditional Name

triac

SMILES

OC(=O)CC1=CC(I)=C(OC2=CC=C(O)C(I)=C2)C(I)=C1

InChI Identifier

InChI=1S/C14H9I3O4/c15-9-6-8(1-2-12(9)18)21-14-10(16)3-7(4-11(14)17)5-13(19)20/h1-4,6,18H,5H2,(H,19,20)

InChI Key

UOWZUVNAGUAEQC-UHFFFAOYSA-N

Chemical Taxonomy

Description

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

Substituents

Diphenylether
Diaryl ether
Phenoxy compound
2-halophenol
2-iodophenol
Phenol ether
Phenol
1-hydroxy-2-unsubstituted benzenoid
Halobenzene
Iodobenzene
Aryl halide
Aryl iodide
Carboxylic acid derivative
Carboxylic acid
Ether
Monocarboxylic acid or derivatives
Carbonyl group
Organic oxide
Organic oxygen compound
Organooxygen compound
Organoiodide
Organohalogen compound
Hydrocarbon derivative
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Organoleptic Effects

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.0054 g/L	ALOGPS
logP	5.27	ALOGPS
logP	5.59	ChemAxon
logS	-5.1	ALOGPS
pKa (Strongest Acidic)	2.31	ChemAxon
pKa (Strongest Basic)	-6.4	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	66.76 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	105.67 m³·mol⁻¹	ChemAxon
Polarizability	40.54 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0fk9-0000009000-faf2d387cb07037e1ea8	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0uk9-0000019000-73143b34cfb6772db79c	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-00dl-1359220000-af32445877396145eaf4	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-00fr-0000049000-9eb0f1e0124f4cae1f4f	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-00fr-0000279000-8449c1025cf98e1bca75	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-106v-1135912000-88d84a79f0681e18cb48	Not Available	View Spectrum

Toxicity Profile

Mechanism of Toxicity

Tiratricol is a naturally occurring metabolite of T4 (thyroxine) and a structural analog of T3 (triiodothyronine). Low concentrations of tiratricol are found in plasma, but tiratricol has no known role in thyroid physiology. Tiratricol has a high affinity for T3 receptors and suppresses thyroid stimulating hormone (TSH) secretion at therapeutic doses without causing significant peripheral effects, such as increased basal metabolism rate and heart rate. Tiratricol might lower total and LDL cholesterol, and stimulate bone formation. About 67% of an oral dose of tiratricol is absorbed; the half-life is 6 hours. (3) Serum sex hormone-binding globulin levels increased 55 +/- 13% with tiratricol, indicating an augmented hepatic response to tiratricol. Tiratricol had effected the cardiovascular function. Tiratricol has distinct augmented hepatic and skeletal thyromimetic actions of potential therapeutic value. (1)

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Minimum Risk Level

Not Available

Symptoms

Not Available

Treatment

Not Available

Toxicity Values

Toxicity Value	Unit	Value Range	Organism	Dose Descriptor	Route of Exposure	Predicted or Experimental	Reference
120.0	Log mg/kg	[70:210]	Rat	LD50	oral	predicted	Not Available

Health Effects

Health Effect	Relationship	Direction	Reference

Exposure Sources

Source ID	Source	Sector	Reference
10	Insecticides	Agriculture & land management	Not Available
315	Dermatological preparations	Healthcare, pharmaceuticals & veterinary products	Not Available
332	Thyroid preparations	Healthcare, pharmaceuticals & veterinary products	Not Available
500	Stairs And Ramps	Building & Construction	Not Available
501	Sunshades Awnings Or Outside Screens	Building & Construction	Not Available
502	Sunshades Awnings Or Outside Screens	Building & Construction	Not Available
504	Adjustable Resistors	Electrical & Electronic Equipment	Not Available
505	Amplifiers	Electrical & Electronic Equipment	Not Available
506	Antennas	Electrical & Electronic Equipment	Not Available
507	Auxiliary Devices	Electrical & Electronic Equipment	Not Available
508	Coils	Electrical & Electronic Equipment	Not Available
511	Conductors Or Conductive Bodies Characterised By The Conductive Materials	Electrical & Electronic Equipment	Not Available
512	Contacts	Electrical & Electronic Equipment	Not Available
513	Cores Yokes Or Armatures	Electrical & Electronic Equipment	Not Available
514	Discharge Lamps	Electrical & Electronic Equipment	Not Available
516	Electric Hearing Aids	Electrical & Electronic Equipment	Not Available
517	Electric Switches	Electrical & Electronic Equipment	Not Available
518	Electrically Stimulated Smoking Devices	Electrical & Electronic Equipment	Not Available
519	Electrodes	Electrical & Electronic Equipment	Not Available
520	Emergency Protective Devices	Electrical & Electronic Equipment	Not Available
521	Fixed Capacitors And Their Manufacture	Electrical & Electronic Equipment	Not Available
524	Hybrid Capacitors	Electrical & Electronic Equipment	Not Available
525	Line Transmission Systems	Electrical & Electronic Equipment	Not Available
527	Magnets	Electrical & Electronic Equipment	Not Available
529	Power Cables	Electrical & Electronic Equipment	Not Available
530	Radio Transmission Systems	Electrical & Electronic Equipment	Not Available
531	Relays	Electrical & Electronic Equipment	Not Available
533	Sparking Plugs	Electrical & Electronic Equipment	Not Available
535	Superconducting Magnets And Superconducting Coils	Electrical & Electronic Equipment	Not Available
537	Television Systems	Electrical & Electronic Equipment	Not Available
538	Thin Magnetic Films	Electrical & Electronic Equipment	Not Available
539	Video Games	Electrical & Electronic Equipment	Not Available
540	X Ray Tubes	Electrical & Electronic Equipment	Not Available
544	Fermentation Processes For Beer	Food, food processing & cookware	Not Available
545	Food Preservation	Food, food processing & cookware	Not Available
577	Watch Chains	Household items	Not Available
579	Manufacture Of Iron Or Steel	Industrial manufacturing & chemical processing	Not Available
592	Marine Propulsion Or Steering	Marine, shipping & aquaculture	Not Available
600	Herbicides And Algicides	Agriculture & land management	Not Available
603	Nematocides	Agriculture & land management	Not Available
604	Pest Attractants	Agriculture & land management	Not Available
605	Pest Repellants	Agriculture & land management	Not Available
610	Aftersun Products	Personal care & cosmetics	Not Available
612	Body Washing Or Cleaning Implements	Personal care & cosmetics	Not Available
614	Essential Oils Or Perfumes	Personal care & cosmetics	Not Available
618	Lip Makeup Products	Personal care & cosmetics	Not Available
620	Card Games	Recreation & sports surfaces	Not Available
621	Chutes And Slides	Recreation & sports surfaces	Not Available
622	Game Accessories	Recreation & sports surfaces	Not Available
630	Toys	Recreation & sports surfaces	Not Available
632	Apparel	Textiles, leather & furnishings	Not Available
640	Embroidering And Tufting	Textiles, leather & furnishings	Not Available
642	Footwear	Textiles, leather & furnishings	Not Available
643	Headwear	Textiles, leather & furnishings	Not Available
647	Multicolour Dyeing	Textiles, leather & furnishings	Not Available
653	Sewing	Textiles, leather & furnishings	Not Available
662	Yarns Or Threads	Textiles, leather & furnishings	Not Available

Pathways

0 pathways

No pathways found

No metabolic pathways have been associated with this synthetic chemical

Targets

Structure	Protein	UniProt ID	Organism	Relationship	Details
Click to view 3D structure	Thyroid hormone receptor alpha	P10827	Humans	Predicted (SEA)	0.0778492
Click to view 3D structure	Thyroid hormone receptor beta	P10828	Humans	Predicted (SEA)	0.0778492
Click to view 3D structure	Peroxisome proliferator-activated receptor gamma	P37231	Humans	Predicted (SEA)	0.467095
Click to view 3D structure	Solute carrier organic anion transporter family member 1C1	Q9ERB5	Mus musculus	Predicted (SEA)	0.0778492
Click to view 3D structure	Thyroid hormone receptor beta	P18113	Rattus norvegicus	Predicted (SEA)	0.0778492
Click to view 3D structure	Retinoic acid receptor RXR-alpha	P19793	Humans	Predicted (SEA)	3.81461
Click to view 3D structure	Tyrosine 3-monooxygenase	P04177	Rattus norvegicus	Predicted (SEA)	0.311397
Click to view 3D structure	Proliferating cell nuclear antigen	P12004	Humans	Predicted (SEA)	0.233548
Click to view 3D structure	Cytochrome P450	A0A0T9WNE5	Mycobacterium tuberculosis	Predicted (SEA)	1.01204
Click to view 3D structure	Hepatic sodium/bile acid cotransporter	Q14973	Humans	Predicted (SEA)	2.25763
Click to view 3D structure	Transthyretin	P02766	Humans	Predicted (SEA)	15.8034
Click to view 3D structure	Trace amine-associated receptor 5	O14804	Humans	Predicted (SEA)	1.01204
Click to view 3D structure	Carbonic anhydrase 2	Q3I4V7	Cryptococcus neoformans	Predicted (SEA)	40.0145
Click to view 3D structure	Carbonic anhydrase	Q5AJ71	Candida albicans (strain SC5314 / ATCC MYA-2876) (Yeast)	Predicted (SEA)	46.3981
Click to view 3D structure	HTH-type transcriptional regulator MgrA	P0C1S0	Staphylococcus aureus	Predicted (SEA)	4.12601
Click to view 3D structure	Prothrombin	P00734	Humans	Predicted (SEA)	386.054
Click to view 3D structure	Prostaglandin G/H synthase 1	P23219	Humans	Predicted (SEA)	123.78
Click to view 3D structure	Carbonic anhydrase 2	P00918	Humans	Predicted (SEA)	584.959
Click to view 3D structure	Adenosine receptor A1	P30542	Humans	Predicted (SEA)	277.766
Click to view 3D structure	Bile acid receptor	Q96RI1	Humans	Predicted (SEA)	141.296
Click to view 3D structure	Aldo-keto reductase family 1 member C3	P42330	Humans	Predicted (SEA)	145.189
Click to view 3D structure	Aldo-keto reductase family 1 member B1	P15121	Humans	Predicted (SEA)	143.009
Click to view 3D structure	Tyrosine-protein kinase Lck	P06239	Humans	Predicted (SEA)	2793.39
Click to view 3D structure	p-hydroxybenzoate hydroxylase	P00438	Pseudomonas fluorescens	Predicted (SEA)	83.6101
Click to view 3D structure	Prostaglandin G/H synthase 2	Q05769	Mus musculus	Predicted (SEA)	87.269
Click to view 3D structure	Thyroid hormone receptor beta	P10828	Humans	Known	Not Available