U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C9H9I2NO3.2H2O
Molecular Weight 469.0122
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of 3,5-Diiodo-L-tyrosine dihydrate

SMILES

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

InChI

InChIKey=YWAGQOOMOOUEGY-KLXURFKVSA-N
InChI=1S/C9H9I2NO3.2H2O/c10-5-1-4(2-6(11)8(5)13)3-7(12)9(14)15;;/h1-2,7,13H,3,12H2,(H,14,15);2*1H2/t7-;;/m0../s1

HIDE SMILES / InChI

Molecular Formula C9H9I2NO3
Molecular Weight 432.9816
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

Molecular Formula H2O
Molecular Weight 18.0153
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Diiodotyrosine (DIT) is a regulatory ligand for thyroid peroxidase, enzyme, which is involved in the production of thyroxine (T4) and triiodothyronine (T3), the thyroid hormones. Diiodotyrosine was proposed to be a new marker of leukocyte phagocytic activity in sepsis and severe infections.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: P07202|||Q8TCI9
Gene ID: 7173.0
Gene Symbol: TPO
Target Organism: Homo sapiens (Human)
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Diagnostic
Unknown

Approved Use

Unknown
Diagnostic
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Elevated serum diiodotyrosine (DIT) in severe infections and sepsis: DIT, a possible new marker of leukocyte activity.
1991-04
Diiodotyrosine (DIT): a new marker of leukocyte phagocytic activity in sepsis and severe infections.
1989
Free diiodotyrosine effects on protein iodination and thyroid hormone synthesis catalyzed by thyroid peroxidase.
1975-02-21
Enzymatic deiodination of diiodotyrosine; possible mediation by reduced flavin nucleotide.
1969-04
Inhibition of deiodination of diiodotyrosine in vivo; relation to catecholamine biosynthesis.
1969-03-15
Patents

Patents

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Unknown
In Vitro Use Guide
Inhibition of thyroglobulin iodination catalyzed by thyroid peroxidase was observed when free diiodotyrosine concentration was higher than 5 muM. This inhibition was competitive, suggesting that free diiodotyrosine interacts with the substrate site(s) of thyroid peroxidase. Free diiodotyrosine also competively inhibited iodide peroxidation to I2. 2. Free diiodotyrosine, when incubated with thyroid peroxidase in the absence of iodide was recovered unmodified; in the presence of iodide an exchange reaction was observed between the iodine atoms present in the diiodotyrosine molecule and iodide present in the medium. Using 14C-labelled diiodotyrosine, 14C-labelled non-iodinated products were also observed, showing that deiodination occurred as a minor degradation pathway.
Substance Class Chemical
Created
by admin
on Wed Apr 02 19:53:18 GMT 2025
Edited
by admin
on Wed Apr 02 19:53:18 GMT 2025
Record UNII
KRK9BLM8E8
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
(S)-2-Amino-3-(4-hydroxy-3,5-diiodophenyl) propanoic acid dihydrate
Preferred Name English
3,5-Diiodo-L-tyrosine dihydrate
Common Name English
L-Tyrosine, 3,5-diiodo-, hydrate (1:2)
Systematic Name English
Code System Code Type Description
FDA UNII
KRK9BLM8E8
Created by admin on Wed Apr 02 19:53:18 GMT 2025 , Edited by admin on Wed Apr 02 19:53:18 GMT 2025
PRIMARY
PUBCHEM
2724330
Created by admin on Wed Apr 02 19:53:18 GMT 2025 , Edited by admin on Wed Apr 02 19:53:18 GMT 2025
PRIMARY
EPA CompTox
DTXSID501017673
Created by admin on Wed Apr 02 19:53:18 GMT 2025 , Edited by admin on Wed Apr 02 19:53:18 GMT 2025
PRIMARY
CAS
18835-59-1
Created by admin on Wed Apr 02 19:53:18 GMT 2025 , Edited by admin on Wed Apr 02 19:53:18 GMT 2025
PRIMARY
Related Record Type Details
ANHYDROUS->SOLVATE