MiMeDB: Showing metabocard for 3,5-Diiodo-L-tyrosine (MMDBc0032011)

Pharmaceutical

Xenobiotic

Record Information

Version

2.0

Status

Detected and Quantified

Creation Date

2021-11-18 01:58:33 UTC

Update Date

2025-11-05 17:13:02 UTC

Metabolite ID

MMDBc0032011

Metabolite Identification

Common Name

3,5-Diiodo-L-tyrosine

Description

3,5-Diiodo-L-tyrosine is a halogenated amino acid belonging to the class of iodinated tyrosine derivatives. Its chemical structure features two iodine atoms substituted at the 3 and 5 positions of the aromatic ring of L-tyrosine, influencing its biochemical properties and interactions. This compound plays a role in the biosynthesis of thyroid hormones, as it is generated through the action of thyroid peroxidase (TPO) on L-tyrosine, leading to the formation of 3,3',5-Triiodo-L-thyronine (T3) and Levothyroxine (T4) (PMID:34345847 ). Additionally, 3,5-diiodo-L-tyrosine has been utilized in various research applications, such as enhancing the radiopacity of cartilage contrast agents (PMID:35536857 ) and forming complex ions with disaccharides (PMID:34740281 ). Its role as an inhibitor of the LAT1 transporter has been investigated, shedding light on its molecular mechanisms of transport and inhibition (PMID:30197880 ). Furthermore, studies have examined the changes in iodine species, including 3,5-diiodo-L-tyrosine, in marine organisms under different treatment conditions (PMID:31357004 ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Not Available

Molecular Formula

C₉H₉I₂NO₃

Average Mass

432.9816

Monoisotopic Mass

432.867179999

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

Not Available

InChI Identifier

InChI=1S/C9H9I2NO3/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)/t7-/m0/s1

InChI Key

NYPYHUZRZVSYKL-ZETCQYMHSA-N

Chemical Taxonomy

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Not Available

Spectra

Not Available

Chromatographic Retention Times and Retention Indices

Retention Times

Chromatography Type	Technique	Column	Deposition Date	Retention Time (s)
Liquid Chromatography	HILIC	Waters Acquity UPLC-BEH Amide column (eluted)	2025-10-23	519.0
Liquid Chromatography	HILIC	Accucore 150 Amide HILIC (eluted)	2025-10-23	375.3
Liquid Chromatography	Reversed-phase	Hypersil Gold 1.9 µm C18 (eluted)	2025-10-23	242.1
Liquid Chromatography	Reversed-phase	Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) (eluted)	2025-10-23	310.2
Liquid Chromatography	Reversed-phase	XBridge C18 3.5u 2.1x50 mm (eluted)	2025-10-23	332.1
Liquid Chromatography	Reversed-phase	Ascentis Express C18 (void)	2025-10-23	328.6
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-23	537.2
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (eluted)	2025-10-23	737.7
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC (eluted)	2025-10-23	746.4
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-23	178.2
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (eluted)	2025-10-23	474.2
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-23	188.3
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-23	66.9
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (eluted)	2025-10-23	434.0
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (eluted)	2025-10-23	645.9
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-23	52.3
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-23	232.2
Liquid Chromatography	Reversed-phase	Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex (eluted)	2025-10-23	815.9
Liquid Chromatography	Reversed-phase	Waters Atlantis T3 (2.1 x 150 mm, 5 um) (eluted)	2025-10-23	648.1

Retention Indices

Chromatography Type	Peak Label	SMILES	Stationary Phase	Deposition Date	Retention Index
Gas Chromatography	3,5-Diiodo-L-tyrosine_TMS_1	C[Si](C)(C)OC1=C(I)C=C(C[C@H](N)C(=O)O)C=C1I	standard non polar	2025-10-24	2081.71
Gas Chromatography	3,5-Diiodo-L-tyrosine_TMS_2	C[Si](C)(C)OC(=O)[C@@H](N)CC1=CC(I)=C(O)C(I)=C1	standard non polar	2025-10-24	1792.71
Gas Chromatography	3,5-Diiodo-L-tyrosine_TMS_3	C[Si](C)(C)N[C@@H](CC1=CC(I)=C(O)C(I)=C1)C(=O)O	standard non polar	2025-10-24	1339.08
Gas Chromatography	3,5-Diiodo-L-tyrosine_TMS_4	C[Si](C)(C)OC(=O)[C@@H](N)CC1=CC(I)=C(O[Si](C)(C)C)C(I)=C1	standard non polar	2025-10-24	2116.43
Gas Chromatography	3,5-Diiodo-L-tyrosine_TMS_5	C[Si](C)(C)N[C@@H](CC1=CC(I)=C(O[Si](C)(C)C)C(I)=C1)C(=O)O	standard non polar	2025-10-24	1845.28
Gas Chromatography	3,5-Diiodo-L-tyrosine_TMS_6	C[Si](C)(C)N[C@@H](CC1=CC(I)=C(O)C(I)=C1)C(=O)O[Si](C)(C)C	standard non polar	2025-10-24	2025.84
Gas Chromatography	3,5-Diiodo-L-tyrosine_TMS_7	C[Si](C)(C)N([C@@H](CC1=CC(I)=C(O)C(I)=C1)C(=O)O)[Si](C)(C)C	standard non polar	2025-10-24	2230.78
Gas Chromatography	3,5-Diiodo-L-tyrosine_TMS_8	C[Si](C)(C)N[C@@H](CC1=CC(I)=C(O[Si](C)(C)C)C(I)=C1)C(=O)O[Si](C)(C)C	standard non polar	2025-10-24	1548.89
Gas Chromatography	3,5-Diiodo-L-tyrosine_TMS_9	C[Si](C)(C)OC1=C(I)C=C(C[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)C=C1I	standard non polar	2025-10-24	2395.31
Gas Chromatography	3,5-Diiodo-L-tyrosine_TMS_10	C[Si](C)(C)OC(=O)[C@H](CC1=CC(I)=C(O)C(I)=C1)N([Si](C)(C)C)[Si](C)(C)C	standard non polar	2025-10-24	2620.79
Gas Chromatography	3,5-Diiodo-L-tyrosine_TMS_11	C[Si](C)(C)OC(=O)[C@H](CC1=CC(I)=C(O[Si](C)(C)C)C(I)=C1)N([Si](C)(C)C)[Si](C)(C)C	standard non polar	2025-10-24	1241.87
Gas Chromatography	3,5-Diiodo-L-tyrosine_TMS_1	C[Si](C)(C)OC1=C(I)C=C(C[C@H](N)C(=O)O)C=C1I	standard polar	2025-10-24	2497.76
Gas Chromatography	3,5-Diiodo-L-tyrosine_TMS_2	C[Si](C)(C)OC(=O)[C@@H](N)CC1=CC(I)=C(O)C(I)=C1	standard polar	2025-10-24	1562.74
Gas Chromatography	3,5-Diiodo-L-tyrosine_TMS_3	C[Si](C)(C)N[C@@H](CC1=CC(I)=C(O)C(I)=C1)C(=O)O	standard polar	2025-10-24	2363.0
Gas Chromatography	3,5-Diiodo-L-tyrosine_TMS_4	C[Si](C)(C)OC(=O)[C@@H](N)CC1=CC(I)=C(O[Si](C)(C)C)C(I)=C1	standard polar	2025-10-24	1928.46
Gas Chromatography	3,5-Diiodo-L-tyrosine_TMS_5	C[Si](C)(C)N[C@@H](CC1=CC(I)=C(O[Si](C)(C)C)C(I)=C1)C(=O)O	standard polar	2025-10-24	2075.14
Gas Chromatography	3,5-Diiodo-L-tyrosine_TMS_6	C[Si](C)(C)N[C@@H](CC1=CC(I)=C(O)C(I)=C1)C(=O)O[Si](C)(C)C	standard polar	2025-10-24	1912.55
Gas Chromatography	3,5-Diiodo-L-tyrosine_TMS_7	C[Si](C)(C)N([C@@H](CC1=CC(I)=C(O)C(I)=C1)C(=O)O)[Si](C)(C)C	standard polar	2025-10-24	2339.76
Gas Chromatography	3,5-Diiodo-L-tyrosine_TMS_8	C[Si](C)(C)N[C@@H](CC1=CC(I)=C(O[Si](C)(C)C)C(I)=C1)C(=O)O[Si](C)(C)C	standard polar	2025-10-24	1411.7
Gas Chromatography	3,5-Diiodo-L-tyrosine_TMS_9	C[Si](C)(C)OC1=C(I)C=C(C[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)C=C1I	standard polar	2025-10-24	1846.23
Gas Chromatography	3,5-Diiodo-L-tyrosine_TMS_10	C[Si](C)(C)OC(=O)[C@H](CC1=CC(I)=C(O)C(I)=C1)N([Si](C)(C)C)[Si](C)(C)C	standard polar	2025-10-24	925.669
Gas Chromatography	3,5-Diiodo-L-tyrosine_TMS_11	C[Si](C)(C)OC(=O)[C@H](CC1=CC(I)=C(O[Si](C)(C)C)C(I)=C1)N([Si](C)(C)C)[Si](C)(C)C	standard polar	2025-10-24	2293.64

Biological Properties

Cellular Locations

Cytoplasm

Biospecimen Locations

Blood
Feces
Urine

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species
MMDBp0191946	Thyroid peroxidase	Unknown	P07202	Homo sapiens
MMDBp0195066	Iodotyrosine dehalogenase 1	Unknown	Q6PHW0	Homo sapiens

Human Pathways

Pathways

Name	SMPDB/PathBank

Microbial Pathways

Pathways

Not Available

Metabolic Reactions

Reactions

This table shows at most 20 reactions. For the full list of associated reactions:

See All Associated Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference
Chronic kidney disease	Slight Increase	Association	Human Urine	HMDB	3098453
Hyperthyroidism		Association	Human Blood	HMDB	11344555

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria/Eubacteria	Proteobacteria	1	Human ; Human feces; Human feces; pleural fluid plaque; bal	Unknown

Exposure Sources

Other Exposures

Source Type	Data Source	Reference
Drugs - Antimicrobial	U.S. Environmental Protection Agency	CompTox
Cosmetics	U.S. Environmental Protection Agency	CompTox
Domestics	U.S. Environmental Protection Agency	CompTox
Domestics	U.S. Environmental Protection Agency	CompTox

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Feces	Detected but not Quantified									HMDB
Human Urine	Detected and Quantified	0.00013	0.000098			umol/mmol creatinine	Adult (>18 years old)	Both	Chronic renal disease	HMDB	3098453
Human Blood	Detected and Quantified	0.0036		0.0010	0.0134	uM	Adult (>18 years old)	Both	Hyperthyroidism	HMDB	11344555
Human Urine	Detected and Quantified	0.000049	0.000027			umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	3098453
Human Blood	Detected and Quantified	0.0036		0.0014	0.0099	uM	Adult (>18 years old)	Both	Normal	HMDB	11344555

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

CMMC Knowledgebase

Not Available

General References

Bismuth J, Castay M, Lissitzky S: Binding of 3,5-diiodotyrosine to serum proteins. Clin Chim Acta. 1976 Jun 15;69(3):417-22. doi: 10.1016/0009-8981(76)90113-3. [PubMed:59643 ]
Ismail-Beigi F, Rahimifar M: A variant of iodotyrosine-dehalogenase deficiency. J Clin Endocrinol Metab. 1977 Mar;44(3):499-506. doi: 10.1210/jcem-44-3-499. [PubMed:838849 ]
Tompkins RK, Croke JC: Bile acids inhibit pepsin activity against a refined substrate. Am J Surg. 1980 Feb;139(2):237-9. doi: 10.1016/0002-9610(80)90262-7. [PubMed:6766680 ]

Showing metabocard for 3,5-Diiodo-L-tyrosine (MMDBc0032011)

MOL for #<Metabolite:0x00007f9ab9cd98c0>

3D MOL for #<Metabolite:0x00007f9ab9cd98c0>

3D SDF for #<Metabolite:0x00007f9ab9cd98c0>

3D-SDF for #<Metabolite:0x00007f9ab9cd98c0>

PDB for #<Metabolite:0x00007f9ab9cd98c0>

3D PDB for #<Metabolite:0x00007f9ab9cd98c0>

SMILES for #<Metabolite:0x00007f9ab9cd98c0>

INCHI for #<Metabolite:0x00007f9ab9cd98c0>

Structure for #<Metabolite:0x00007f9ab9cd98c0>

3D Structure for #<Metabolite:0x00007f9ab9cd98c0>