MiMeDB: Showing metabocard for Iodotyrosine (MMDBc0031974)

Pharmaceutical

Xenobiotic

Record Information

Version

2.0

Status

Detected and Quantified

Creation Date

2021-11-18 01:57:10 UTC

Update Date

2025-11-05 17:12:59 UTC

Metabolite ID

MMDBc0031974

Metabolite Identification

Common Name

Iodotyrosine

Description

Iodotyrosine is a halogenated amino acid classified as a phenolic compound. Its chemical structure features a tyrosine backbone with one or two iodine atoms substituted at the ortho or para positions of the aromatic ring, which significantly influences its reactivity and biological functions. Iodotyrosine is involved in several biochemical pathways, particularly in the synthesis of thyroid hormones. The coupling of iodotyrosine derivatives is a critical step in the formation of thyroxine, where the iodotyrosine deprotonation is facilitated by nearby carboxylic groups, such as glutamate (PMID:39608720 ). Additionally, iodotyrosine deiodinases (IYDs) play a role in the metabolism of iodotyrosine, although they are subject to substrate inhibition, particularly in homologues like Thermotoga neapolitana (PMID:40498979 ). The presence of iodotyrosine is also noted in metabolic profiles following the application of iodoquinolines (PMID:39824073 ). Furthermore, alterations in iodotyrosine levels can affect the structural integrity of thyroglobulin, influencing the presence of thyroiditogenic epitopes (PMID:39633222 ). Overall, iodotyrosine serves as a key intermediate in thyroid hormone biosynthesis and metabolism.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI


  Mrv1652303182019222D          

 14 14  0  0  1  0            999 V2000
    2.8579    0.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 I   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  2  0  0  0  0
  4 11  1  0  0  0  0
  2 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  2  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0031974

> <DATABASE_NAME>
MIME

> <SMILES>
N[C@@H](CC1=CC=C(O)C(I)=C1)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C9H10INO3/c10-6-3-5(1-2-8(6)12)4-7(11)9(13)14/h1-3,7,12H,4,11H2,(H,13,14)/t7-/m0/s1

> <INCHI_KEY>
UQTZMGFTRHFAAM-ZETCQYMHSA-N

> <FORMULA>
C9H10INO3

> <MOLECULAR_WEIGHT>
307.0851

> <EXACT_MASS>
306.970536611

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
24

> <JCHEM_AVERAGE_POLARIZABILITY>
23.544080579143227

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-2-amino-3-(4-hydroxy-3-iodophenyl)propanoic acid

> <ALOGPS_LOGP>
-1.51

> <JCHEM_LOGP>
-0.559798647037047

> <ALOGPS_LOGS>
-2.52

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.335155330087229

> <JCHEM_PKA_STRONGEST_ACIDIC>
0.9928460641360015

> <JCHEM_PKA_STRONGEST_BASIC>
9.49549159056975

> <JCHEM_POLAR_SURFACE_AREA>
83.55000000000001

> <JCHEM_REFRACTIVITY>
60.4597

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.37e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
iodotyrosine

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 18-MAR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   18-MAR-20         0                                  
HETATM    1  N   UNK     0       5.335   1.540   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   10  I   UNK     0       1.334   3.850   0.000  0.00  0.00           I+0
HETATM   11  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       8.002   0.000   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       6.668  -2.310   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   12                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   11                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9    4                                                       
CONECT   12    2   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12                                                            
MASTER        0    0    0    0    0    0    0    0   14    0   28    0
END

Synonyms

Value	Source
(2S)-2-Amino-3-(4-hydroxy-3-iodophenyl)propanoic acid	ChEBI
3-IODO-tyrosine	ChEBI
MIT	ChEBI
(2S)-2-Amino-3-(4-hydroxy-3-iodophenyl)propanoate	Generator
3-Iodo-4-hydroxyphenylalanine	HMDB
3-Iodo-L-tyrosine	HMDB
3-Iodotyrosine	HMDB
3-Monoiodo-L-tyrosine	HMDB
4-Hydroxy-3-iodophenylalanine	HMDB
IYR	HMDB
L-Tyrosine-3-iodo	HMDB
Monoiodotyrosine	HMDB

Molecular Formula

C₉H₁₀INO₃

Average Mass

307.0851

Monoisotopic Mass

306.970536611

IUPAC Name

(2S)-2-amino-3-(4-hydroxy-3-iodophenyl)propanoic acid

Traditional Name

iodotyrosine

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C9H10INO3/c10-6-3-5(1-2-8(6)12)4-7(11)9(13)14/h1-3,7,12H,4,11H2,(H,13,14)/t7-/m0/s1

InChI Key

UQTZMGFTRHFAAM-ZETCQYMHSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as tyrosine and derivatives. Tyrosine and derivatives are compounds containing tyrosine or a derivative thereof resulting from reaction of tyrosine 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

Tyrosine and derivatives

Alternative Parents

Substituents

Tyrosine or derivatives
Phenylalanine or derivatives
3-phenylpropanoic-acid
Alpha-amino acid
Amphetamine or derivatives
L-alpha-amino acid
2-iodophenol
2-halophenol
1-hydroxy-2-unsubstituted benzenoid
Iodobenzene
Halobenzene
Phenol
Aralkylamine
Aryl iodide
Aryl halide
Benzenoid
Monocyclic benzene moiety
Amino acid
Carboxylic acid
Monocarboxylic acid or derivatives
Organic nitrogen compound
Organohalogen compound
Primary aliphatic amine
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

non-proteinogenic L-alpha-amino acid (CHEBI:27847 )
L-tyrosine derivative (CHEBI:27847 )
monoiodotyrosine (CHEBI:27847 )
Other amino acids (C02515 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.94 g/L	ALOGPS
logP	-1.5	ALOGPS
logP	-0.56	ChemAxon
logS	-2.5	ALOGPS
pKa (Strongest Acidic)	0.99	ChemAxon
pKa (Strongest Basic)	9.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	83.55 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	60.46 m³·mol⁻¹	ChemAxon
Polarizability	23.54 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
GC-MS	GC-MS Spectrum - GC-MS (2 TMS)	splash10-0a4j-3913000000-be57e889200c60dc46d4	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (3 TMS)	splash10-014i-1790000000-785b6d6a13d0a8822946	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-0a4j-3913000000-be57e889200c60dc46d4	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-014i-1790000000-785b6d6a13d0a8822946	2017-09-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-03e9-3090000000-2e5cb717605e800d4359	2017-08-28	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-00sr-9335100000-f5b1c103a54222cc59a3	2017-10-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_4) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_2) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_3) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_4) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-08fu-0094000000-1cca0021f92a06ea8b50	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-01q9-1890000000-ff62addb3c23234d3cef	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-001i-2910000000-1938a4966cb53b4f5ed1	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-0a4i-0009000000-29fdc92cbeae7ec37e5d	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-056r-0923000000-1f98738c0cc639f98dc7	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-004i-1900000000-92c150757accb8a27fd9	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative	splash10-004i-2900000000-82ef54ff210098156f8c	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative	splash10-004i-2900000000-fffc0c2d97089650aada	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive	splash10-0a4i-0329000000-39b160c87443d51e7611	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive	splash10-03dl-0591000000-c54470130afba37dca28	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive	splash10-03dr-1980000000-31e2dd7b1defc7cfb8c3	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive	splash10-000i-1920000000-8e40ba504d905aa7a528	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive	splash10-05n3-3900000000-368aad6dbdcc312ac3df	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positive	splash10-01ox-0090000000-6e7318a85f3480d07477	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positive	splash10-03ka-0790000000-ed59bbe7e20256d8ad06	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positive	splash10-000i-0900000000-6de0b405d60b85059abc	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positive	splash10-0006-0090000000-9e84651efead6b6bfa2c	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positive	splash10-00di-0900000000-972b9ebadf10c99787c4	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positive	splash10-014i-0900000000-6150f13b1005b3ec9eff	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positive	splash10-000b-0900000000-7b5ecd0f27a3ed9d67e2	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positive	splash10-0a5i-0900000000-ec4129da39ac628164dc	2012-08-31	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-08fr-0093000000-003526fc59bf6620307f	2017-07-26	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03di-0090000000-33a24ab6c37733eed168	2017-07-26	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0f89-1190000000-9bcf2d08fe940cf418a1	2017-07-26	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-0029000000-b815bb002ee417365e6f	2017-07-26	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)		2012-12-04	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-29	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)		2012-12-04	View Spectrum

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	484.6
Liquid Chromatography	HILIC	Accucore 150 Amide HILIC (eluted)	2025-10-23	354.7
Liquid Chromatography	Reversed-phase	Hypersil Gold 1.9 µm C18 (eluted)	2025-10-23	181.4
Liquid Chromatography	Reversed-phase	Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) (eluted)	2025-10-23	274.4
Liquid Chromatography	Reversed-phase	XBridge C18 3.5u 2.1x50 mm (eluted)	2025-10-23	299.6
Liquid Chromatography	Reversed-phase	Ascentis Express C18 (void)	2025-10-23	302.7
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-23	517.4
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (eluted)	2025-10-23	764.1
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC (eluted)	2025-10-23	627.4
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-23	159.9
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (eluted)	2025-10-23	503.7
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-23	173.7
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-23	71.0
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (eluted)	2025-10-23	369.8
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (eluted)	2025-10-23	616.6
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-23	50.8
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-23	210.4
Liquid Chromatography	Reversed-phase	Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex (eluted)	2025-10-23	745.9
Liquid Chromatography	Reversed-phase	Waters Atlantis T3 (2.1 x 150 mm, 5 um) (eluted)	2025-10-23	641.6

Retention Indices

Chromatography Type	Peak Label	SMILES	Stationary Phase	Deposition Date	Retention Index
Gas Chromatography	Iodotyrosine_TMS_1	C[Si](C)(C)OC1=CC=C(C[C@H](N)C(=O)O)C=C1I	standard non polar	2025-10-24	2363.37
Gas Chromatography	Iodotyrosine_TMS_2	C[Si](C)(C)OC(=O)[C@@H](N)CC1=CC=C(O)C(I)=C1	standard non polar	2025-10-24	2028.27
Gas Chromatography	Iodotyrosine_TMS_3	C[Si](C)(C)N[C@@H](CC1=CC=C(O)C(I)=C1)C(=O)O	standard non polar	2025-10-24	2146.76
Gas Chromatography	Iodotyrosine_TMS_4	C[Si](C)(C)OC(=O)[C@@H](N)CC1=CC=C(O[Si](C)(C)C)C(I)=C1	standard non polar	2025-10-24	1535.91
Gas Chromatography	Iodotyrosine_TMS_5	C[Si](C)(C)N[C@@H](CC1=CC=C(O[Si](C)(C)C)C(I)=C1)C(=O)O	standard non polar	2025-10-24	1895.52
Gas Chromatography	Iodotyrosine_TMS_6	C[Si](C)(C)N[C@@H](CC1=CC=C(O)C(I)=C1)C(=O)O[Si](C)(C)C	standard non polar	2025-10-24	1760.26
Gas Chromatography	Iodotyrosine_TMS_7	C[Si](C)(C)N([C@@H](CC1=CC=C(O)C(I)=C1)C(=O)O)[Si](C)(C)C	standard non polar	2025-10-24	1623.88
Gas Chromatography	Iodotyrosine_TMS_8	C[Si](C)(C)N[C@@H](CC1=CC=C(O[Si](C)(C)C)C(I)=C1)C(=O)O[Si](C)(C)C	standard non polar	2025-10-24	2101.38
Gas Chromatography	Iodotyrosine_TMS_9	C[Si](C)(C)OC1=CC=C(C[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)C=C1I	standard non polar	2025-10-24	1616.29
Gas Chromatography	Iodotyrosine_TMS_10	C[Si](C)(C)OC(=O)[C@H](CC1=CC=C(O)C(I)=C1)N([Si](C)(C)C)[Si](C)(C)C	standard non polar	2025-10-24	1768.68
Gas Chromatography	Iodotyrosine_TMS_11	C[Si](C)(C)OC(=O)[C@H](CC1=CC=C(O[Si](C)(C)C)C(I)=C1)N([Si](C)(C)C)[Si](C)(C)C	standard non polar	2025-10-24	2262.8
Gas Chromatography	Iodotyrosine_TMS_1	C[Si](C)(C)OC1=CC=C(C[C@H](N)C(=O)O)C=C1I	standard polar	2025-10-24	2462.62
Gas Chromatography	Iodotyrosine_TMS_2	C[Si](C)(C)OC(=O)[C@@H](N)CC1=CC=C(O)C(I)=C1	standard polar	2025-10-24	2255.84
Gas Chromatography	Iodotyrosine_TMS_3	C[Si](C)(C)N[C@@H](CC1=CC=C(O)C(I)=C1)C(=O)O	standard polar	2025-10-24	2193.24
Gas Chromatography	Iodotyrosine_TMS_4	C[Si](C)(C)OC(=O)[C@@H](N)CC1=CC=C(O[Si](C)(C)C)C(I)=C1	standard polar	2025-10-24	2484.03
Gas Chromatography	Iodotyrosine_TMS_5	C[Si](C)(C)N[C@@H](CC1=CC=C(O[Si](C)(C)C)C(I)=C1)C(=O)O	standard polar	2025-10-24	2163.55
Gas Chromatography	Iodotyrosine_TMS_6	C[Si](C)(C)N[C@@H](CC1=CC=C(O)C(I)=C1)C(=O)O[Si](C)(C)C	standard polar	2025-10-24	1644.14
Gas Chromatography	Iodotyrosine_TMS_7	C[Si](C)(C)N([C@@H](CC1=CC=C(O)C(I)=C1)C(=O)O)[Si](C)(C)C	standard polar	2025-10-24	2240.75
Gas Chromatography	Iodotyrosine_TMS_8	C[Si](C)(C)N[C@@H](CC1=CC=C(O[Si](C)(C)C)C(I)=C1)C(=O)O[Si](C)(C)C	standard polar	2025-10-24	2071.47
Gas Chromatography	Iodotyrosine_TMS_9	C[Si](C)(C)OC1=CC=C(C[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)C=C1I	standard polar	2025-10-24	1929.45
Gas Chromatography	Iodotyrosine_TMS_10	C[Si](C)(C)OC(=O)[C@H](CC1=CC=C(O)C(I)=C1)N([Si](C)(C)C)[Si](C)(C)C	standard polar	2025-10-24	2224.25
Gas Chromatography	Iodotyrosine_TMS_11	C[Si](C)(C)OC(=O)[C@H](CC1=CC=C(O[Si](C)(C)C)C(I)=C1)N([Si](C)(C)C)[Si](C)(C)C	standard polar	2025-10-24	2579.18

Biological Properties

Cellular Locations

Cytoplasm

Biospecimen Locations

Blood
Feces
Thyroid Gland

Tissue Locations

Thyroid Gland

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

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
Athyreosis	Decreased	Association	Human Blood	HMDB	2225717

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

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Units	Age	Sex	Health Condition	Data Source	Reference
Human Feces	Detected but not Quantified							HMDB
Human Blood	Detected and Quantified	0.00032	0.00008	uM	Adult (>18 years old)	Both	Athyroic patients	HMDB	2225717
Human Blood	Detected and Quantified	0.00069	0.00020	uM	Adult (>18 years old)	Both	Normal	HMDB	2225717
Human Thyroid gland	Detected but not Quantified				Not Specified	Not Specified	Normal	HMDB	34986597

External Links

HMDB ID

HMDB0000021

DrugBank ID

DB01758

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB021875

KNApSAcK ID

Not Available

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Wikipedia Link

METLIN ID

Not Available

PubChem Compound

439744

PDB ID

Not Available

ChEBI ID

27847

Food Biomarker Ontology

Not Available

CMMC Knowledgebase

Not Available

General References

Painter K, Vader CR: Interference of iodine-125 ligands in radioimmunoassay: evidence implicating thyroxine-binding globulin. Clin Chem. 1979 May;25(5):797-9. [PubMed:108034 ]
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 ]
Smythe GA, Compton PJ, Lazarus L: The stimulation of human prolactin secretion by 3-Iodo-L-tyrosine. J Clin Endocrinol Metab. 1975 Apr;40(4):714-6. doi: 10.1210/jcem-40-4-714. [PubMed:1127080 ]
Muller EE, Locatelli V, Cella S, Penalva A, Novelli A, Cocchi D: Prolactin-lowering and -releasing drugs. Mechanisms of action and therapeutic applications. Drugs. 1983 Apr;25(4):399-432. doi: 10.2165/00003495-198325040-00004. [PubMed:6133737 ]
Kucerova Z, Ticha M: Aromatic amino acids and their derivatives as ligands for the isolation of aspartic proteinases. J Chromatogr B Analyt Technol Biomed Life Sci. 2002 Apr 25;770(1-2):121-8. doi: 10.1016/s1570-0232(01)00599-2. [PubMed:12013218 ]
Sakamoto K, Hayashi A, Sakamoto A, Kiga D, Nakayama H, Soma A, Kobayashi T, Kitabatake M, Takio K, Saito K, Shirouzu M, Hirao I, Yokoyama S: Site-specific incorporation of an unnatural amino acid into proteins in mammalian cells. Nucleic Acids Res. 2002 Nov 1;30(21):4692-9. doi: 10.1093/nar/gkf589. [PubMed:12409460 ]

Showing metabocard for Iodotyrosine (MMDBc0031974)

MOL for #<Metabolite:0x00007f9aaa096108>

3D MOL for #<Metabolite:0x00007f9aaa096108>

3D SDF for #<Metabolite:0x00007f9aaa096108>

3D-SDF for #<Metabolite:0x00007f9aaa096108>

PDB for #<Metabolite:0x00007f9aaa096108>

3D PDB for #<Metabolite:0x00007f9aaa096108>

SMILES for #<Metabolite:0x00007f9aaa096108>

INCHI for #<Metabolite:0x00007f9aaa096108>

Structure for #<Metabolite:0x00007f9aaa096108>

3D Structure for #<Metabolite:0x00007f9aaa096108>