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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (1) Show 1 protein XML

Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2021-09-14 15:20:01 UTC

HMDB ID

HMDB0000021

Secondary Accession Numbers

HMDB00021

Metabolite Identification

Common Name

Iodotyrosine

Description

Iodotyrosine is an iodated derivative of L-tyrosine. This is an early precursor to L-thyroxine, one of the primary thyroid hormones. In the thyroid gland, iodide is trapped, transported, and concentrated in the follicular lumen for thyroid hormone synthesis. Before trapped iodide can react with tyrosine residues, it must be oxidized by thyroid peroxidase. Iodotyrosine is made from tyrosine via thyroid peroxidase and then further iodinated by this enzyme to make the di-iodo and tri-iodo variants. Two molecules of di-iodotyrosine combine to form T4, and one molecule of mono-iodotyrosine combines with one molecule of di-iodotyrosine to form T3.

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>
HMDB0000021

> <DATABASE_NAME>
hmdb

> <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

View in JSmol View NMR Assignments View Stereo Labels

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

Chemical Formula

C₉H₁₀INO₃

Average Molecular Weight

307.0851

Monoisotopic Molecular Weight

306.970536611

IUPAC Name

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

Traditional Name

iodotyrosine

CAS Registry Number

70-78-0

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 )

Ontology

Physiological effect

Health effect

Endocrine system disorder

Thyroidal or parathyroidal disorder

Athyreosis (HMDB: HMDB0000021)

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 2225717)

Organ

Gland

Thyroid gland (HMDB: HMDB0000021)
Thyroid gland (HMDB: HMDB0000021)

Cellular substructure

Cytoplasm (HMDB: HMDB0000021)

Source

Exogenous

Exogenous (HMDB: HMDB0000021)

Food

Animal origin

Poultry

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)

Endogenous

Endogenous (HMDB: HMDB0000021)

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Thyroid hormone synthesis (PathBank: SMP0087269)
Thyroid hormone synthesis (HMDB: HMDB0000021)
Thyroid hormone synthesis (PathBank: SMP0063679)
Tyrosine Metabolism (HMDB: HMDB0000021)

Role

Industrial application

Pharmaceutical industry

Pharmaceutical (HMDB: HMDB0000021)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	205 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	3 mg/mL	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	Not Available	159.066	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000002

Predicted Molecular 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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
AllCCS	[M+H]+	162.427	32859911
AllCCS	[M-H]-	152.382	32859911
DeepCCS	[M+H]+	153.078	30932474
DeepCCS	[M-H]-	150.72	30932474
DeepCCS	[M-2H]-	184.842	30932474
DeepCCS	[M+Na]+	159.648	30932474
AllCCS	[M+H]+	162.4	32859911
AllCCS	[M+H-H2O]+	159.0	32859911
AllCCS	[M+NH4]+	165.6	32859911
AllCCS	[M+Na]+	166.6	32859911
AllCCS	[M-H]-	152.4	32859911
AllCCS	[M+Na-2H]-	153.6	32859911
AllCCS	[M+HCOO]-	154.9	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	3.57 minutes	32390414
Predicted by Siyang on May 30, 2022	9.9054 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	6.71 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	354.7 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	517.4 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	302.7 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	71.0 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	173.7 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	50.8 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	299.6 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	274.4 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	764.1 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	641.6 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	175.7 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	745.9 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	172.3 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	210.4 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	616.6 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	503.7 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	369.8 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Iodotyrosine	N[C@@H](CC1=CC=C(O)C(I)=C1)C(O)=O	3274.6	Standard polar	33892256
Iodotyrosine	N[C@@H](CC1=CC=C(O)C(I)=C1)C(O)=O	2241.8	Standard non polar	33892256
Iodotyrosine	N[C@@H](CC1=CC=C(O)C(I)=C1)C(O)=O	2279.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Iodotyrosine,1TMS,isomer #1	C[Si](C)(C)OC1=CC=C(C[C@H](N)C(=O)O)C=C1I	2230.6	Semi standard non polar	33892256
Iodotyrosine,1TMS,isomer #2	C[Si](C)(C)OC(=O)[C@@H](N)CC1=CC=C(O)C(I)=C1	2146.8	Semi standard non polar	33892256
Iodotyrosine,1TMS,isomer #3	C[Si](C)(C)N[C@@H](CC1=CC=C(O)C(I)=C1)C(=O)O	2218.0	Semi standard non polar	33892256
Iodotyrosine,2TMS,isomer #1	C[Si](C)(C)OC(=O)[C@@H](N)CC1=CC=C(O[Si](C)(C)C)C(I)=C1	2195.4	Semi standard non polar	33892256
Iodotyrosine,2TMS,isomer #2	C[Si](C)(C)N[C@@H](CC1=CC=C(O[Si](C)(C)C)C(I)=C1)C(=O)O	2252.1	Semi standard non polar	33892256
Iodotyrosine,2TMS,isomer #3	C[Si](C)(C)N[C@@H](CC1=CC=C(O)C(I)=C1)C(=O)O[Si](C)(C)C	2168.6	Semi standard non polar	33892256
Iodotyrosine,2TMS,isomer #4	C[Si](C)(C)N([C@@H](CC1=CC=C(O)C(I)=C1)C(=O)O)[Si](C)(C)C	2319.4	Semi standard non polar	33892256
Iodotyrosine,3TMS,isomer #1	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	2217.0	Semi standard non polar	33892256
Iodotyrosine,3TMS,isomer #1	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	2188.2	Standard non polar	33892256
Iodotyrosine,3TMS,isomer #1	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	2140.3	Standard polar	33892256
Iodotyrosine,3TMS,isomer #2	C[Si](C)(C)OC1=CC=C(C[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)C=C1I	2373.8	Semi standard non polar	33892256
Iodotyrosine,3TMS,isomer #2	C[Si](C)(C)OC1=CC=C(C[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)C=C1I	2287.7	Standard non polar	33892256
Iodotyrosine,3TMS,isomer #2	C[Si](C)(C)OC1=CC=C(C[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)C=C1I	2284.7	Standard polar	33892256
Iodotyrosine,3TMS,isomer #3	C[Si](C)(C)OC(=O)[C@H](CC1=CC=C(O)C(I)=C1)N([Si](C)(C)C)[Si](C)(C)C	2323.4	Semi standard non polar	33892256
Iodotyrosine,3TMS,isomer #3	C[Si](C)(C)OC(=O)[C@H](CC1=CC=C(O)C(I)=C1)N([Si](C)(C)C)[Si](C)(C)C	2247.8	Standard non polar	33892256
Iodotyrosine,3TMS,isomer #3	C[Si](C)(C)OC(=O)[C@H](CC1=CC=C(O)C(I)=C1)N([Si](C)(C)C)[Si](C)(C)C	2304.4	Standard polar	33892256
Iodotyrosine,4TMS,isomer #1	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	2432.9	Semi standard non polar	33892256
Iodotyrosine,4TMS,isomer #1	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	2339.7	Standard non polar	33892256
Iodotyrosine,4TMS,isomer #1	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	2095.6	Standard polar	33892256
Iodotyrosine,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C(C[C@H](N)C(=O)O)C=C1I	2482.5	Semi standard non polar	33892256
Iodotyrosine,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)[C@@H](N)CC1=CC=C(O)C(I)=C1	2406.3	Semi standard non polar	33892256
Iodotyrosine,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N[C@@H](CC1=CC=C(O)C(I)=C1)C(=O)O	2474.8	Semi standard non polar	33892256
Iodotyrosine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)[C@@H](N)CC1=CC=C(O[Si](C)(C)C(C)(C)C)C(I)=C1	2743.2	Semi standard non polar	33892256
Iodotyrosine,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N[C@@H](CC1=CC=C(O[Si](C)(C)C(C)(C)C)C(I)=C1)C(=O)O	2785.8	Semi standard non polar	33892256
Iodotyrosine,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N[C@@H](CC1=CC=C(O)C(I)=C1)C(=O)O[Si](C)(C)C(C)(C)C	2648.8	Semi standard non polar	33892256
Iodotyrosine,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)N([C@@H](CC1=CC=C(O)C(I)=C1)C(=O)O)[Si](C)(C)C(C)(C)C	2775.6	Semi standard non polar	33892256
Iodotyrosine,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N[C@@H](CC1=CC=C(O[Si](C)(C)C(C)(C)C)C(I)=C1)C(=O)O[Si](C)(C)C(C)(C)C	2983.5	Semi standard non polar	33892256
Iodotyrosine,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N[C@@H](CC1=CC=C(O[Si](C)(C)C(C)(C)C)C(I)=C1)C(=O)O[Si](C)(C)C(C)(C)C	2857.2	Standard non polar	33892256
Iodotyrosine,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N[C@@H](CC1=CC=C(O[Si](C)(C)C(C)(C)C)C(I)=C1)C(=O)O[Si](C)(C)C(C)(C)C	2530.2	Standard polar	33892256
Iodotyrosine,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC=C(C[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1I	3115.7	Semi standard non polar	33892256
Iodotyrosine,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC=C(C[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1I	2907.1	Standard non polar	33892256
Iodotyrosine,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC=C(C[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1I	2588.3	Standard polar	33892256
Iodotyrosine,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CC1=CC=C(O)C(I)=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3001.2	Semi standard non polar	33892256
Iodotyrosine,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CC1=CC=C(O)C(I)=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2889.5	Standard non polar	33892256
Iodotyrosine,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CC1=CC=C(O)C(I)=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2596.5	Standard polar	33892256
Iodotyrosine,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CC1=CC=C(O[Si](C)(C)C(C)(C)C)C(I)=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3356.4	Semi standard non polar	33892256
Iodotyrosine,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CC1=CC=C(O[Si](C)(C)C(C)(C)C)C(I)=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3099.5	Standard non polar	33892256
Iodotyrosine,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CC1=CC=C(O[Si](C)(C)C(C)(C)C)C(I)=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2545.6	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Iodotyrosine GC-MS (2 TMS)	splash10-0a4j-3913000000-be57e889200c60dc46d4	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Iodotyrosine GC-MS (3 TMS)	splash10-014i-1790000000-785b6d6a13d0a8822946	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Iodotyrosine GC-MS (Non-derivatized)	splash10-0a4j-3913000000-be57e889200c60dc46d4	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Iodotyrosine GC-MS (Non-derivatized)	splash10-014i-1790000000-785b6d6a13d0a8822946	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Iodotyrosine GC-MS (Non-derivatized) - 70eV, Positive	splash10-03e9-3090000000-2e5cb717605e800d4359	2017-08-28	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Iodotyrosine GC-MS (2 TMS) - 70eV, Positive	splash10-00sr-9335100000-f5b1c103a54222cc59a3	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Iodotyrosine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Iodotyrosine GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Iodotyrosine GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Iodotyrosine GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Iodotyrosine GC-MS (TMS_2_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Iodotyrosine GC-MS (TMS_2_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Iodotyrosine GC-MS (TMS_2_4) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Iodotyrosine GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Iodotyrosine GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Iodotyrosine GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Iodotyrosine GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Iodotyrosine GC-MS (TBDMS_2_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Iodotyrosine GC-MS (TBDMS_2_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Iodotyrosine GC-MS (TBDMS_2_4) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Iodotyrosine Quattro_QQQ 10V, Positive-QTOF (Annotated)	splash10-08fu-0094000000-1cca0021f92a06ea8b50	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Iodotyrosine Quattro_QQQ 25V, Positive-QTOF (Annotated)	splash10-01q9-1890000000-ff62addb3c23234d3cef	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Iodotyrosine Quattro_QQQ 40V, Positive-QTOF (Annotated)	splash10-001i-2910000000-1938a4966cb53b4f5ed1	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Iodotyrosine LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative-QTOF	splash10-0a4i-0009000000-29fdc92cbeae7ec37e5d	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Iodotyrosine LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative-QTOF	splash10-056r-0923000000-1f98738c0cc639f98dc7	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Iodotyrosine LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative-QTOF	splash10-004i-1900000000-92c150757accb8a27fd9	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Iodotyrosine LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative-QTOF	splash10-004i-2900000000-82ef54ff210098156f8c	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Iodotyrosine LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative-QTOF	splash10-004i-2900000000-fffc0c2d97089650aada	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Iodotyrosine LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive-QTOF	splash10-0a4i-0329000000-39b160c87443d51e7611	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Iodotyrosine LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive-QTOF	splash10-03dl-0591000000-c54470130afba37dca28	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Iodotyrosine LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive-QTOF	splash10-03dr-1980000000-31e2dd7b1defc7cfb8c3	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Iodotyrosine LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive-QTOF	splash10-000i-1920000000-8e40ba504d905aa7a528	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Iodotyrosine LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive-QTOF	splash10-05n3-3900000000-368aad6dbdcc312ac3df	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Iodotyrosine LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positive-QTOF	splash10-01ox-0090000000-6e7318a85f3480d07477	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Iodotyrosine LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positive-QTOF	splash10-03ka-0790000000-ed59bbe7e20256d8ad06	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Iodotyrosine LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positive-QTOF	splash10-000i-0900000000-6de0b405d60b85059abc	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Iodotyrosine LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positive-QTOF	splash10-0006-0090000000-9e84651efead6b6bfa2c	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Iodotyrosine LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positive-QTOF	splash10-00di-0900000000-972b9ebadf10c99787c4	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Iodotyrosine LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positive-QTOF	splash10-014i-0900000000-6150f13b1005b3ec9eff	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Iodotyrosine LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positive-QTOF	splash10-000b-0900000000-7b5ecd0f27a3ed9d67e2	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Iodotyrosine LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positive-QTOF	splash10-0a5i-0900000000-ec4129da39ac628164dc	2012-08-31	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Iodotyrosine 10V, Positive-QTOF	splash10-08fr-0093000000-003526fc59bf6620307f	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Iodotyrosine 20V, Positive-QTOF	splash10-03di-0090000000-33a24ab6c37733eed168	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Iodotyrosine 40V, Positive-QTOF	splash10-0f89-1190000000-9bcf2d08fe940cf418a1	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Iodotyrosine 10V, Negative-QTOF	splash10-0a4i-0029000000-b815bb002ee417365e6f	2017-07-26	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Experimental 1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)	2012-12-04	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Experimental 2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	2012-12-04	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm

Biospecimen Locations

Blood

Tissue Locations

Thyroid Gland

Pathways

Name	SMPDB/PathBank	KEGG
Tyrosine metabolism	Not Available
Thyroid hormone synthesis		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.00069 +/- 0.00020 uM	Adult (>18 years old)	Both	Normal	2225717	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.00032 +/- 0.00008 uM	Adult (>18 years old)	Both	Athyroic patients	2225717	details

Associated Disorders and Diseases

Disease References

Athyreosis
Tan SA, Lewis JE, Berk LS, Wilcox RB: Extrathyroidal physiology of monoiodotyrosine in humans. Clin Physiol Biochem. 1990;8(3):109-15. [PubMed:2225717 ]

Associated OMIM IDs

None

External Links

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

VMH ID

3ITYR_L

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Hillmann, Gunther; Hillmann-Elies, Anneliese. Synthesis of 3-iodo-L-tyrosine. Hoppe-Seyler's Zeitschrift fuer Physiologische Chemie (1956), 305 177-81.

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

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. [PubMed:12409460 ]
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. [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. [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. [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. [PubMed:12013218 ]

Enzymes

Enzyme Details

1. Thyroid peroxidase

General function:: Involved in calcium ion binding
Specific function:: Iodination and coupling of the hormonogenic tyrosines in thyroglobulin to yield the thyroid hormones T(3) and T(4).
Gene Name:: TPO
Uniprot ID:: P07202
Molecular weight:: 102961.63

Reactions

I(-) + Iodotyrosine → Iodine + L-Tyrosine	details
Iodotyrosine + 3,5-Diiodo-L-tyrosine + Hydrogen peroxide → Liothyronine + 2-Aminoacrylic acid + Water	details
I(-) + 3,5-Diiodo-L-tyrosine → Iodotyrosine + Iodine	details

Showing metabocard for Iodotyrosine (HMDB0000021)

MOL for HMDB0000021 (Iodotyrosine)

3D MOL for HMDB0000021 (Iodotyrosine)

3D SDF for HMDB0000021 (Iodotyrosine)

3D-SDF for HMDB0000021 (Iodotyrosine)

PDB for HMDB0000021 (Iodotyrosine)

3D PDB for HMDB0000021 (Iodotyrosine)

SMILES for HMDB0000021 (Iodotyrosine)

INCHI for HMDB0000021 (Iodotyrosine)

Structure for HMDB0000021 (Iodotyrosine)

3D Structure for HMDB0000021 (Iodotyrosine)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes

Reactions