Dextrothyroxine (CED0016595)

Record Information

Version

1.0

Creation Date

2016-05-25 18:20:52 UTC

Update Date

2026-05-14 16:40:48 UTC

SynCED ID

CED0016595

Secondary Accession Numbers

CHEM022123

Identification

Common Name

Dextrothyroxine

Class

Small Molecule

Description

Dextrothyroxine is an organic compound with the chemical formula C15H11I4NO4. Dextrothyroxine belongs to the amino acids, peptides, and analogues, a subclass of carboxylic acids and derivatives within the organic compounds. With an average molecular weight of 776.87 g/mol, Dextrothyroxine is a heavy molecule. The compound is identified as an agonist of three specific protein targets: Thyroid peroxidase (TPO), Thyroid hormone receptor alpha (THRA), and Thyroid hormone receptor beta (THRB). Regarding its occurrence, Dextrothyroxine is found in or released from three recorded sources. These include antennas within electrical and electronic equipment, ceilings in building and construction, and lipid modifying agents within healthcare, pharmaceuticals, and veterinary products. The recorded exposure route for this compound is oral.

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
D-T4	ChEBI
DT4	ChEBI
O-(4-Hydroxy-3,5-diiodophenyl)-3,5-diiodo-D-tyrosine	ChEBI
D-Thyroxine	HMDB
Choloxin	HMDB
Sodium dextrothyroxine	HMDB
D Thyroxine	HMDB
D-T4 Thyroid hormone	HMDB
Dextrothyroxine sodium	HMDB
Dextrothyroxine	ChEBI

Chemical Formula

C₁₅H₁₁I₄NO₄

Average Molecular Mass

776.870 g/mol

Monoisotopic Mass

776.687 g/mol

CAS Registry Number

51-49-0

IUPAC Name

(2R)-2-amino-3-[4-(4-hydroxy-3,5-diiodophenoxy)-3,5-diiodophenyl]propanoic acid

Traditional Name

dextrothyroxine

SMILES

N[C@H](CC1=CC(I)=C(OC2=CC(I)=C(O)C(I)=C2)C(I)=C1)C(O)=O

InChI Identifier

InChI=1S/C15H11I4NO4/c16-8-4-7(5-9(17)13(8)21)24-14-10(18)1-6(2-11(14)19)3-12(20)15(22)23/h1-2,4-5,12,21H,3,20H2,(H,22,23)/t12-/m1/s1

InChI Key

XUIIKFGFIJCVMT-GFCCVEGCSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenylalanine and derivatives. Phenylalanine and derivatives are compounds containing phenylalanine or a derivative thereof resulting from reaction of phenylalanine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Phenylalanine and derivatives

Alternative Parents

Substituents

Phenylalanine or derivatives
Diphenylether
Diaryl ether
3-phenylpropanoic-acid
Alpha-amino acid
Amphetamine or derivatives
D-alpha-amino acid
Phenoxy compound
Phenol ether
2-halophenol
2-iodophenol
Aralkylamine
Phenol
Halobenzene
Iodobenzene
Aryl halide
Aryl iodide
Benzenoid
Monocyclic benzene moiety
Amino acid
Carboxylic acid
Ether
Monocarboxylic acid or derivatives
Organoiodide
Organonitrogen compound
Organooxygen compound
Organopnictogen compound
Organic nitrogen compound
Organic oxide
Carbonyl group
Primary amine
Amine
Hydrocarbon derivative
Primary aliphatic amine
Organic oxygen compound
Organohalogen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

thyroxine (CHEBI:30659 )
D-tyrosine derivative (CHEBI:30659 )

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

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	0.009 g/L	ALOGPS
logP	1.15	ALOGPS
logP	3.73	ChemAxon
logS	-4.9	ALOGPS
pKa (Strongest Acidic)	0.27	ChemAxon
pKa (Strongest Basic)	9.43	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	92.78 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	126.79 m³·mol⁻¹	ChemAxon
Polarizability	49.31 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	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 GC-MS	Predicted GC-MS Spectrum	splash10-0f89-4002002900-0d489fed1cb888a2d9d0	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-01si-0000000900-524d052a32c1fe4b904d	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-001i-0000001900-553f6a4045ef2241fd85	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-014i-0009000000-d2431d885a79bb80b7a5	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-004i-0000000900-137b5f8f48031bc9aa4f	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-03fr-0004001900-db1d8cdb93785d786382	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0h9u-7029014300-3bd9620b0c6a8dd20c93	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-004i-0000000900-d76aec17d3d890cb64c1	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-001i-0000001900-daf0bb8e065f55b0cda3	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-001i-0001013900-6d1177cb9a243bb761eb	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-004i-0000000900-95266ab7e52b7d3cb322	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-004i-1700000900-195c16ab7434b857e712	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-004i-0900000000-0dba40d354fa6a5575e0	Not Available	View Spectrum

Toxicity Profile

Toxicity Values

Toxicity Value	Organism	Dose Descriptor	Route of Exposure	Predicted or Experimental	Toxicity Rating	Reference
520.0 Log mg/kg [290:920]	Rat	LD50	oral	predicted	Not Available	Not Available

Toxicity / Toxin Class

Not Available

Mechanism of Toxicity

Not Available

Carcinogenicity (IARC Classification)

Not Available

Minimum Risk Level

Not Available

Symptoms

Not Available

Treatment

Not Available

Health Effects

Health Effect	Relationship	Direction	Reference

Exposure Sources

Source ID	Source	Sector	Reference
CEDs000298	Lipid modifying agents?Lipid modifying agents are synthetic chemicals used to alter the lipid profiles of living organisms, often employed in the treatment of hyperlipidemia and related cardiovascular conditions.	Healthcare, pharmaceuticals & veterinary products	Not Available
CEDs000495	Ceilings?Ceilings in built environments can be a source of synthetic chemical contamination due to the materials used in their construction and finishes.	Building & Construction	Not Available
CEDs000506	Antennas?Antennas, commonly used in communication technologies, can be a source of synthetic chemical contamination through the materials and coatings used in their construction.	Electrical & Electronic Equipment	Not Available
CEDs000678	Nitrogenous Fertilisers?Nitrogenous fertilizers are synthetic chemical compounds primarily used to enhance plant growth by supplying essential nitrogen, a crucial nutrient for photosynthesis and protein synthesis.	Agriculture & land management	Not Available
CEDs000679	Phosphatic Fertilisers?Phosphatic fertilizers are synthetic chemical products primarily composed of phosphorus, which is essential for plant growth.	Agriculture & land management	Not Available
CEDs000685	Ceramics?Ceramics can be a source of synthetic chemical contamination through various additives and processing agents used in their production.	Building & Construction	Not Available
CEDs000686	Clay Wares?Clay wares are ceramic products made from natural clay, often utilized in various construction applications such as tiles, bricks, and sanitary ware.	Building & Construction	Not Available
CEDs000688	Glass Coatings?Glass coatings are synthetic chemical formulations applied to glass surfaces to enhance properties such as durability, UV resistance, and aesthetic appeal.	Building & Construction	Not Available
CEDs000696	Nanotechnology?Nanotechnology involves the manipulation of materials at the molecular or atomic level, typically within the range of 1 to 100 nanometers.	Industrial manufacturing & chemical processing	Not Available
CEDs000727	Printing Machines Or Presses?Printing machines or presses commonly utilize synthetic chemicals such as inks, solvents, and cleaning agents.	Paper, pulp & fiber products	Not Available
CEDs000734	Coating Compositions?Coating compositions, which include paints, sealants, and varnishes, are formulated with a variety of synthetic chemicals such as solvents, resins, pigments, and additives.	Building & Construction	Not Available
CEDs000739	Inks?Inks are complex mixtures composed of pigments or dyes, solvents, resins, and additives used primarily for printing and writing applications.	Paper, pulp & fiber products	Not Available
CEDs000740	Paper?Paper production involves the processing of wood fibers and the use of various chemicals, which can lead to synthetic chemical contamination.	Paper, pulp & fiber products	Not Available
CEDs000744	Water, Wastewater, & Sewage Treatment?Water, wastewater, and sewage treatment processes are critical for managing and mitigating pollutants in water systems.	Wastewater, sanitation & biosolids	Not Available

Pathways

1 pathwayPathway Source: PathBank

Dextrothyroxine Drug Metabolism Action Pathway

Targets

Structure	Protein	UniProt ID	Organism	Relationship	Details
Click to view 3D structure	Peroxisome proliferator-activated receptor gamma	P37231	Humans	Predicted (SEA)	Prediction Confidence Score 0.723 Applicability Domain 1.0 Statistical Significance 4.00e-05 Supporting Reference Compounds 192 E-value 0.311397
Click to view 3D structure	Solute carrier organic anion transporter family member 1C1	Q9ERB5	Mus musculus	Predicted (SEA)	Prediction Confidence Score 0.721 Applicability Domain 1.0 Statistical Significance 1.00e-05 Supporting Reference Compounds 3 E-value 0.0778492
Click to view 3D structure	Thyroid hormone receptor alpha	P10827	Humans	Predicted (SEA)	Prediction Confidence Score 0.674 Applicability Domain 1.0 Statistical Significance 1.00e-05 Supporting Reference Compounds 27 E-value 0.0778492
Click to view 3D structure	Thyroid hormone receptor beta	P10828	Humans	Predicted (SEA)	Prediction Confidence Score 0.674 Applicability Domain 1.0 Statistical Significance 1.00e-05 Supporting Reference Compounds 37 E-value 0.0778492
Click to view 3D structure	Transthyretin	P02766	Humans	Predicted (SEA)	Prediction Confidence Score 0.543 Applicability Domain 1.0 Statistical Significance 1.00e-05 Supporting Reference Compounds 55 E-value 0.0778492
Click to view 3D structure	Thyroid hormone receptor beta	P18113	Rattus norvegicus	Predicted (SEA)	Prediction Confidence Score 0.541 Applicability Domain 1.0 Statistical Significance 2.00e-05 Supporting Reference Compounds 5 E-value 0.155698
Click to view 3D structure	Tyrosine 3-monooxygenase	P04177	Rattus norvegicus	Predicted (SEA)	Prediction Confidence Score 0.535 Applicability Domain 0.535 Statistical Significance 1.00e-05 Supporting Reference Compounds 1 E-value 0.0778492
Click to view 3D structure	Retinoic acid receptor RXR-alpha	P19793	Humans	Predicted (SEA)	Prediction Confidence Score 0.503 Applicability Domain 1.0 Statistical Significance 5.40e-04 Supporting Reference Compounds 82 E-value 4.20386
Click to view 3D structure	Proliferating cell nuclear antigen	P12004	Humans	Predicted (SEA)	Prediction Confidence Score 0.389 Applicability Domain 0.744 Statistical Significance 1.00e-05 Supporting Reference Compounds 6 E-value 0.0778492
Click to view 3D structure	Solute carrier organic anion transporter family member 4C1	Q6ZQN7	Humans	Predicted (SEA)	Prediction Confidence Score 0.378 Applicability Domain 1.0 Statistical Significance 1.00e-05 Supporting Reference Compounds 3 E-value 0.0778492
Click to view 3D structure	Bile acid receptor	Q96RI1	Humans	Predicted (SEA)	Prediction Confidence Score 0.375 Applicability Domain 1.0 Statistical Significance 0.0032 Supporting Reference Compounds 94 E-value 24.9896
Click to view 3D structure	Glutamate receptor 2	P19491	Rattus norvegicus	Predicted (SEA)	Prediction Confidence Score 0.329 Applicability Domain 0.351 Statistical Significance 1.30e-04 Supporting Reference Compounds 34 E-value 1.01204
Click to view 3D structure	Glutamate receptor 3	P19492	Rattus norvegicus	Predicted (SEA)	Prediction Confidence Score 0.329 Applicability Domain 0.351 Statistical Significance 1.50e-04 Supporting Reference Compounds 30 E-value 1.16774
Click to view 3D structure	Glutamate receptor 2	P42262	Humans	Predicted (SEA)	Prediction Confidence Score 0.326 Applicability Domain 0.351 Statistical Significance 3.00e-04 Supporting Reference Compounds 41 E-value 2.33548
Click to view 3D structure	Glutamate receptor 1	P19490	Rattus norvegicus	Predicted (SEA)	Prediction Confidence Score 0.325 Applicability Domain 0.351 Statistical Significance 0.0016 Supporting Reference Compounds 37 E-value 12.6116
Click to view 3D structure	UDP-glucuronosyltransferase 1A1	P22309	Humans	Predicted (SEA)	Prediction Confidence Score 0.324 Applicability Domain 1.0 Statistical Significance 1.50e-04 Supporting Reference Compounds 21 E-value 1.16774
Click to view 3D structure	Glutamate racemase	Q03469	Lactobacillus fermentum	Predicted (SEA)	Prediction Confidence Score 0.321 Applicability Domain 0.321 Statistical Significance 7.40e-04 Supporting Reference Compounds 1 E-value 5.76084
Click to view 3D structure	Glutamate receptor 4	P19493	Rattus norvegicus	Predicted (SEA)	Prediction Confidence Score 0.319 Applicability Domain 0.327 Statistical Significance 1.40e-04 Supporting Reference Compounds 25 E-value 1.08989
Click to view 3D structure	Prothrombin	P00734	Humans	Predicted (SEA)	Prediction Confidence Score 0.318 Applicability Domain 0.744 Statistical Significance 0.0309 Supporting Reference Compounds 331 E-value 240.243
Click to view 3D structure	Glutamate receptor ionotropic, kainate 1	P22756	Rattus norvegicus	Predicted (SEA)	Prediction Confidence Score 0.316 Applicability Domain 0.327 Statistical Significance 5.60e-04 Supporting Reference Compounds 45 E-value 4.35956
Click to view 3D structure	Glutamate receptor 1	P42261	Humans	Predicted (SEA)	Prediction Confidence Score 0.316 Applicability Domain 0.327 Statistical Significance 5.80e-04 Supporting Reference Compounds 37 E-value 4.51525
Click to view 3D structure	Glutamate receptor 4	P48058	Humans	Predicted (SEA)	Prediction Confidence Score 0.316 Applicability Domain 0.327 Statistical Significance 2.70e-04 Supporting Reference Compounds 25 E-value 2.10193
Click to view 3D structure	Glutamate receptor ionotropic, kainate 1	P39086	Humans	Predicted (SEA)	Prediction Confidence Score 0.31 Applicability Domain 0.32 Statistical Significance 4.40e-04 Supporting Reference Compounds 31 E-value 3.42537
Click to view 3D structure	Glutamate receptor 3	P42263	Humans	Predicted (SEA)	Prediction Confidence Score 0.309 Applicability Domain 0.32 Statistical Significance 1.70e-04 Supporting Reference Compounds 16 E-value 1.32344
Click to view 3D structure	Glutamate receptor ionotropic, kainate 5	Q16478	Humans	Predicted (SEA)	Prediction Confidence Score 0.308 Applicability Domain 0.327 Statistical Significance 3.10e-04 Supporting Reference Compounds 17 E-value 2.41333