ChemFOnt: Showing chemical card for 3,5-Diiodothyronine (CFc000000454)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:44:50 UTC

Chemfont ID

CFc000000454

Molecule Identification

Common Name

3,5-Diiodothyronine

Definition

3,5-Diiodothyronine, also known as 3,5-T2, belongs to the class of organic compounds known as phenylalanines 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. It is also a member of the class of compounds known as iodothyronines. Iodothyronines are phenolic amino acids with iodine substituents. 3,5-Diiodothyronine is a metabolite of the two main thyroid hormones T3 and T4 (thyroxine and triiodo-L-thyronine). It is a biologically active iodothyronine with mitochondria and bioenergetic mechanisms being the major targets of 3,5-T2. Nanomolar concentrations of 3,5-T2 significantly increases cytochrome oxidase (COX) activity (PMID: 30090086 ). It increases COX activity by preventing the interaction of adenosine triphosphate (ATP) as an allosteric inhibitor. At 1 pM concentration, 3,5-T2 stimulates oxygen consumption more rapidly than thyroxine (T3). A case report involving two human participants revealed that administration of 3,5-T2 to humans (1-5 ug/kg BW) rapidly (after 4-6 h) increased resting metabolic rate. Chronic 3,5-T2 administration (28 days, approximately 5 ug/kg BW) increased resting metabolic rate by approximately 15% and decreased body weight by approximately 4 kg in both participants (PMID: 22217997 ). 3,5-T2 stimulates the thyroid receptor (TR)-beta receptor for thyroid hormones and thus increases energy expenditure. It has agonistic (thyromimetic) effects on myocardial tissue and on the pituitary, which results in 3,5-T2 suppressing thyroid stimulating hormone release.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
35-Diiodothyronine	HMDB
(3,5-Diiodo-4-(-p-hydroxyphenoxy)phenyl)-alanine	HMDB
3',5'-Diiodothyronine	HMDB
3,5-Diiodo-D-thyronine	HMDB
3,5-Diiodo-DL-thryronine	HMDB
3,5-Diiodo-DL-thyronine	HMDB
3,5-Diiodo-L-thyronine	HMDB
3,5-T2	HMDB
4-(4-Hydroxyphenoxy)-3,5-diiodophenylalanine	HMDB
D-O-(4-Hydroxyphenyl)-3,5-diiodo-tyrosine	HMDB
Diiodo-L-thyronine	HMDB
Diiodothyronine	HMDB
DL-3,5-Diiodothyronine	HMDB
DL-Diiodothyronine	HMDB
L-3,5-Diiodothyronine	HMDB
L-O-(4-Hydroxyphenyl)-3,5-diiodo-tyrosine	HMDB
O-(4-Hydroxyphenyl)-3,5-diiodo-tyrosine	HMDB
3,5-Diiodothyronine, (L)-isomer	HMDB
3,5-Diiodothyronine, (DL)-isomer	HMDB
2-Amino-3-[4-(4-hydroxyphenoxy)-3,5-diiodophenyl]propanoate	HMDB
3,5-Diiodothyronine	MeSH

Chemical Formula

C₁₅H₁₃I₂NO₄

Average Molecular Weight

525.077

Monoisotopic Molecular Weight

524.893394749

IUPAC Name

2-amino-3-[4-(4-hydroxyphenoxy)-3,5-diiodophenyl]propanoic acid

Traditional Name

3,5-diiodo-dl-thryronine

CAS Registry Number

534-51-0

SMILES

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

InChI Identifier

InChI=1S/C15H13I2NO4/c16-11-5-8(7-13(18)15(20)21)6-12(17)14(11)22-10-3-1-9(19)2-4-10/h1-6,13,19H,7,18H2,(H,20,21)

InChI Key

ZHSOTLOTTDYIIK-UHFFFAOYSA-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
Phenoxy compound
Phenol ether
Iodobenzene
Halobenzene
1-hydroxy-2-unsubstituted benzenoid
Phenol
Aralkylamine
Aryl iodide
Aryl halide
Benzenoid
Monocyclic benzene moiety
Amino acid
Ether
Carboxylic acid
Monocarboxylic acid or derivatives
Organic nitrogen compound
Primary aliphatic amine
Organohalogen compound
Organoiodide
Organonitrogen compound
Organooxygen compound
Primary amine
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Amine
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Functional Ontology

Physiological effect

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 9141546)

Organ

Brain (HMDB: HMDB0000582)

Excreta

Biofluid or Excreta

Urine (PMID: 3988241)

Cellular substructure

Cytoplasm (HMDB: HMDB0000582)

Source

Endogenous

Endogenous (HMDB: HMDB0000582)

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Process

Not Available

Role

Industrial application

Pharmaceutical industry

Biomarker

Hyperthyroidism (MarkerDB: MDB00000193)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.052 g/L	ALOGPS
logP	0.45	ALOGPS
logP	1.87	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Acidic)	0.33	ChemAxon
pKa (Strongest Basic)	9.23	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	100.06 m³·mol⁻¹	ChemAxon
Polarizability	38.7 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

External Links

HMDB ID

HMDB0000582

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022128

KNApSAcK ID

Not Available

Chemspider ID

110252

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

3,5-Diiodothyronine

METLIN ID

5564

PubChem Compound

123675

PDB ID

Not Available

ChEBI ID

350682

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Valashek, I. E.; Kochergin, P. M.; Vinogradova, E. M.; Budanova, L. I. Synthesis of 3,5-diiodo-DL-thyronine. Khimiko-Farmatsevticheskii Zhurnal (1995), 29(6), 44.

Showing chemical card for 3,5-Diiodothyronine (CFc000000454)

MOL for CFc000000454 (3,5-Diiodothyronine)

3D MOL for CFc000000454 (3,5-Diiodothyronine)

3D SDF for CFc000000454 (3,5-Diiodothyronine)

3D-SDF for CFc000000454 (3,5-Diiodothyronine)

PDB for CFc000000454 (3,5-Diiodothyronine)

3D PDB for CFc000000454 (3,5-Diiodothyronine)

SMILES for CFc000000454 (3,5-Diiodothyronine)

INCHI for CFc000000454 (3,5-Diiodothyronine)

Structure for CFc000000454 (3,5-Diiodothyronine)

3D Structure for CFc000000454 (3,5-Diiodothyronine)