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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (2) Show 2 proteins XML

Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2006-08-12 21:39:17 UTC

Update Date

2021-09-14 15:20:03 UTC

HMDB ID

HMDB0003474

Secondary Accession Numbers

HMDB03474

Metabolite Identification

Common Name

3,5-Diiodo-L-tyrosine

Description

3,5-Diiodo-L-tyrosine, also known as diiy or DIT, 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. 3,5-Diiodo-L-tyrosine exists in all living organisms, ranging from bacteria to humans. In humans, 3,5-diiodo-L-tyrosine is involved in thyroid hormone synthesis. 3,5-Diiodo-L-tyrosine is a product from the iodination of monoiodotyrosine.

Structure

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

TYI
  Mrv1652305261923582D          

 16 16  0  0  0  0            999 V2000
   -0.0572    1.2630    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6573    0.8505    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6573    0.0255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0572   -0.3870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0572   -1.2120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7716   -1.6245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7716    0.0255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4861   -0.3870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4861   -1.2120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2006   -1.6245    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3718    1.2630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3718    2.0880    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0863    0.8505    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7716   -2.4495    0.0000 I   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2006    0.0255    0.0000 I   0  0  0  0  0  0  0  0  0  0  0  0
    0.1516    0.5585    0.0000 H   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
  2 11  1  0  0  0  0
  2 16  1  1  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  7  1  0  0  0  0
  5  6  1  0  0  0  0
  6  9  2  0  0  0  0
  6 14  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  8 15  1  0  0  0  0
  9 10  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0003474

> <DATABASE_NAME>
hmdb

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

> <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

> <FORMULA>
C9H9I2NO3

> <MOLECULAR_WEIGHT>
432.9816

> <EXACT_MASS>
432.867179999

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
24

> <JCHEM_AVERAGE_POLARIZABILITY>
29.104949295435578

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S)-2-amino-3-(4-hydroxy-3,5-diiodophenyl)propanoic acid

> <ALOGPS_LOGP>
-0.70

> <JCHEM_LOGP>
0.3690120783842349

> <ALOGPS_LOGS>
-2.92

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
7.248809557381356

> <JCHEM_PKA_STRONGEST_ACIDIC>
0.4803141368137829

> <JCHEM_PKA_STRONGEST_BASIC>
9.448403835672156

> <JCHEM_POLAR_SURFACE_AREA>
83.55

> <JCHEM_REFRACTIVITY>
73.82220000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.19e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3,5-diiodotyrosine

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 26-MAY-19   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: TYI                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-MAY-19         0                                  
HETATM    1  N   UNK     0      -0.107   2.358   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0       1.227   1.588   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.227   0.048   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.107  -0.722   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.107  -2.262   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.440  -3.032   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.440   0.048   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.774  -0.722   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.774  -2.262   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -4.108  -3.032   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       2.561   2.358   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       2.561   3.898   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       3.894   1.588   0.000  0.00  0.00           O+0
HETATM   14  I   UNK     0      -1.440  -4.572   0.000  0.00  0.00           I+0
HETATM   15  I   UNK     0      -4.108   0.048   0.000  0.00  0.00           I+0
HETATM   16  H   UNK     0       0.283   1.043   0.000  0.00  0.00           H+0
CONECT    1    2                                                            
CONECT    2    1    3   11   16                                             
CONECT    3    2    4                                                       
CONECT    4    3    5    7                                                  
CONECT    5    4    6                                                       
CONECT    6    5    9   14                                                  
CONECT    7    4    8                                                       
CONECT    8    7    9   15                                                  
CONECT    9    6    8   10                                                  
CONECT   10    9                                                            
CONECT   11    2   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11                                                            
CONECT   14    6                                                            
CONECT   15    8                                                            
CONECT   16    2                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   32    0
END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
(2S)-2-Amino-3-(4-hydroxy-3,5-diiodophenyl)propanoic acid	ChEBI
3,5-Diiodotyrosine	ChEBI
Diiodotyrosine	ChEBI
DiIY	ChEBI
DIT	ChEBI
L-3,5-Diiodotyrosine	ChEBI
L-Diiodotyrosine	ChEBI
(2S)-2-Amino-3-(4-hydroxy-3,5-diiodophenyl)propanoate	Generator
3,5-Diiodotyrocine	HMDB
3,5-Iodo-L-tyrosine	HMDB
3,5-L-Diiodotyrosine	HMDB
4-Hydroxy-3,5-diiodophenylalanine	HMDB
Iodogorgoic acid	HMDB
Acid, iodogorgoic	HMDB

Chemical Formula

C₉H₉I₂NO₃

Average Molecular Weight

432.9816

Monoisotopic Molecular Weight

432.867179999

IUPAC Name

(2S)-2-amino-3-(4-hydroxy-3,5-diiodophenyl)propanoic acid

Traditional Name

3,5-diiodotyrosine

CAS Registry Number

300-39-0

SMILES

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

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

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
Amphetamine or derivatives
Alpha-amino acid
L-alpha-amino acid
2-iodophenol
2-halophenol
Aralkylamine
Halobenzene
Phenol
Iodobenzene
Aryl iodide
Monocyclic benzene moiety
Benzenoid
Aryl halide
Amino acid
Carboxylic acid
Monocarboxylic acid or derivatives
Amine
Primary aliphatic amine
Organonitrogen compound
Organooxygen compound
Primary amine
Organic nitrogen compound
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organoiodide
Organohalogen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

non-proteinogenic L-alpha-amino acid (CHEBI:15768 )
L-tyrosine derivative (CHEBI:15768 )
diiodotyrosine (CHEBI:15768 )
Other amino acids (C01060 )

Ontology

Physiological effect

Health effect

Endocrine system disorder

Thyroidal or parathyroidal disorder

Thyroid dysfunction (HMDB: HMDB0003474)

Renal system and urinary system

Renal disorder

Chronic kidney disease (HMDB: HMDB0003474)

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 11344555)

Excreta

Biofluid or Excreta

Urine (PMID: 3098453)

Cellular substructure

Cytoplasm (HMDB: HMDB0003474)

Source

Exogenous

Exogenous (HMDB: HMDB0003474)

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: HMDB0003474)

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Thyroid hormone synthesis (PathBank: SMP0087269)
Thyroid hormone synthesis (HMDB: HMDB0003474)
Thyroid hormone synthesis (PathBank: SMP0063679)
Tyrosine Metabolism (HMDB: HMDB0003474)

Role

Industrial application

Pharmaceutical industry

Pharmaceutical (HMDB: HMDB0003474)

Biomarker

Chronic kidney disease (MarkerDB: MDB00000425)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.62 mg/mL at 25 °C	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	171.8	http://allccs.zhulab.cn/database/detail?ID=AllCCS00002156

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.52 g/L	ALOGPS
logP	-0.7	ALOGPS
logP	0.37	ChemAxon
logS	-2.9	ALOGPS
pKa (Strongest Acidic)	0.48	ChemAxon
pKa (Strongest Basic)	9.45	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	73.82 m³·mol⁻¹	ChemAxon
Polarizability	29.1 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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
DeepCCS	[M+H]+	169.525	30932474
DeepCCS	[M-H]-	167.167	30932474
DeepCCS	[M-2H]-	200.054	30932474
DeepCCS	[M+Na]+	175.619	30932474
AllCCS	[M+H]+	178.7	32859911
AllCCS	[M+H-H2O]+	176.0	32859911
AllCCS	[M+NH4]+	181.2	32859911
AllCCS	[M+Na]+	182.0	32859911
AllCCS	[M-H]-	168.0	32859911
AllCCS	[M+Na-2H]-	169.6	32859911
AllCCS	[M+HCOO]-	171.5	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.	4.06 minutes	32390414
Predicted by Siyang on May 30, 2022	10.3449 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	5.58 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	375.3 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	537.2 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	328.6 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	66.9 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	188.3 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	52.3 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	332.1 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	310.2 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	737.7 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	648.1 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	234.1 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	815.9 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	189.9 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	232.2 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	645.9 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	474.2 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	434.0 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
3,5-Diiodo-L-tyrosine	[H][C@](N)(CC1=CC(I)=C(O)C(I)=C1)C(O)=O	3609.8	Standard polar	33892256
3,5-Diiodo-L-tyrosine	[H][C@](N)(CC1=CC(I)=C(O)C(I)=C1)C(O)=O	2625.2	Standard non polar	33892256
3,5-Diiodo-L-tyrosine	[H][C@](N)(CC1=CC(I)=C(O)C(I)=C1)C(O)=O	2669.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
3,5-Diiodo-L-tyrosine,1TMS,isomer #1	C[Si](C)(C)OC1=C(I)C=C(C[C@H](N)C(=O)O)C=C1I	2515.5	Semi standard non polar	33892256
3,5-Diiodo-L-tyrosine,1TMS,isomer #2	C[Si](C)(C)OC(=O)[C@@H](N)CC1=CC(I)=C(O)C(I)=C1	2487.2	Semi standard non polar	33892256
3,5-Diiodo-L-tyrosine,1TMS,isomer #3	C[Si](C)(C)N[C@@H](CC1=CC(I)=C(O)C(I)=C1)C(=O)O	2535.7	Semi standard non polar	33892256
3,5-Diiodo-L-tyrosine,2TMS,isomer #1	C[Si](C)(C)OC(=O)[C@@H](N)CC1=CC(I)=C(O[Si](C)(C)C)C(I)=C1	2547.0	Semi standard non polar	33892256
3,5-Diiodo-L-tyrosine,2TMS,isomer #2	C[Si](C)(C)N[C@@H](CC1=CC(I)=C(O[Si](C)(C)C)C(I)=C1)C(=O)O	2536.0	Semi standard non polar	33892256
3,5-Diiodo-L-tyrosine,2TMS,isomer #3	C[Si](C)(C)N[C@@H](CC1=CC(I)=C(O)C(I)=C1)C(=O)O[Si](C)(C)C	2488.4	Semi standard non polar	33892256
3,5-Diiodo-L-tyrosine,2TMS,isomer #4	C[Si](C)(C)N([C@@H](CC1=CC(I)=C(O)C(I)=C1)C(=O)O)[Si](C)(C)C	2618.1	Semi standard non polar	33892256
3,5-Diiodo-L-tyrosine,3TMS,isomer #1	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	2575.7	Semi standard non polar	33892256
3,5-Diiodo-L-tyrosine,3TMS,isomer #1	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	2347.9	Standard non polar	33892256
3,5-Diiodo-L-tyrosine,3TMS,isomer #1	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	2201.3	Standard polar	33892256
3,5-Diiodo-L-tyrosine,3TMS,isomer #2	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	2670.3	Semi standard non polar	33892256
3,5-Diiodo-L-tyrosine,3TMS,isomer #2	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	2465.5	Standard non polar	33892256
3,5-Diiodo-L-tyrosine,3TMS,isomer #2	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	2370.6	Standard polar	33892256
3,5-Diiodo-L-tyrosine,3TMS,isomer #3	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	2615.3	Semi standard non polar	33892256
3,5-Diiodo-L-tyrosine,3TMS,isomer #3	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	2427.1	Standard non polar	33892256
3,5-Diiodo-L-tyrosine,3TMS,isomer #3	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	2397.9	Standard polar	33892256
3,5-Diiodo-L-tyrosine,4TMS,isomer #1	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	2732.9	Semi standard non polar	33892256
3,5-Diiodo-L-tyrosine,4TMS,isomer #1	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	2508.6	Standard non polar	33892256
3,5-Diiodo-L-tyrosine,4TMS,isomer #1	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	2157.2	Standard polar	33892256
3,5-Diiodo-L-tyrosine,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=C(I)C=C(C[C@H](N)C(=O)O)C=C1I	2786.2	Semi standard non polar	33892256
3,5-Diiodo-L-tyrosine,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)[C@@H](N)CC1=CC(I)=C(O)C(I)=C1	2765.9	Semi standard non polar	33892256
3,5-Diiodo-L-tyrosine,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N[C@@H](CC1=CC(I)=C(O)C(I)=C1)C(=O)O	2799.4	Semi standard non polar	33892256
3,5-Diiodo-L-tyrosine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)[C@@H](N)CC1=CC(I)=C(O[Si](C)(C)C(C)(C)C)C(I)=C1	3041.7	Semi standard non polar	33892256
3,5-Diiodo-L-tyrosine,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N[C@@H](CC1=CC(I)=C(O[Si](C)(C)C(C)(C)C)C(I)=C1)C(=O)O	3055.2	Semi standard non polar	33892256
3,5-Diiodo-L-tyrosine,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N[C@@H](CC1=CC(I)=C(O)C(I)=C1)C(=O)O[Si](C)(C)C(C)(C)C	2959.6	Semi standard non polar	33892256
3,5-Diiodo-L-tyrosine,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)N([C@@H](CC1=CC(I)=C(O)C(I)=C1)C(=O)O)[Si](C)(C)C(C)(C)C	3069.2	Semi standard non polar	33892256
3,5-Diiodo-L-tyrosine,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N[C@@H](CC1=CC(I)=C(O[Si](C)(C)C(C)(C)C)C(I)=C1)C(=O)O[Si](C)(C)C(C)(C)C	3295.6	Semi standard non polar	33892256
3,5-Diiodo-L-tyrosine,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N[C@@H](CC1=CC(I)=C(O[Si](C)(C)C(C)(C)C)C(I)=C1)C(=O)O[Si](C)(C)C(C)(C)C	3008.3	Standard non polar	33892256
3,5-Diiodo-L-tyrosine,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N[C@@H](CC1=CC(I)=C(O[Si](C)(C)C(C)(C)C)C(I)=C1)C(=O)O[Si](C)(C)C(C)(C)C	2604.6	Standard polar	33892256
3,5-Diiodo-L-tyrosine,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=C(I)C=C(C[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1I	3361.8	Semi standard non polar	33892256
3,5-Diiodo-L-tyrosine,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=C(I)C=C(C[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1I	3073.3	Standard non polar	33892256
3,5-Diiodo-L-tyrosine,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=C(I)C=C(C[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1I	2675.1	Standard polar	33892256
3,5-Diiodo-L-tyrosine,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CC1=CC(I)=C(O)C(I)=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3276.9	Semi standard non polar	33892256
3,5-Diiodo-L-tyrosine,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CC1=CC(I)=C(O)C(I)=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3066.5	Standard non polar	33892256
3,5-Diiodo-L-tyrosine,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CC1=CC(I)=C(O)C(I)=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2681.9	Standard polar	33892256
3,5-Diiodo-L-tyrosine,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CC1=CC(I)=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	3654.1	Semi standard non polar	33892256
3,5-Diiodo-L-tyrosine,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CC1=CC(I)=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	3265.5	Standard non polar	33892256
3,5-Diiodo-L-tyrosine,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CC1=CC(I)=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	2619.5	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - 3,5-Diiodo-L-tyrosine GC-MS (3 TMS)	splash10-014i-1890000000-abcce0f0eb05b9c55156	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 3,5-Diiodo-L-tyrosine GC-MS (Non-derivatized)	splash10-014i-1890000000-abcce0f0eb05b9c55156	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3,5-Diiodo-L-tyrosine GC-MS (Non-derivatized) - 70eV, Positive	splash10-052r-3009200000-5d38989f994f24e925d9	2017-08-28	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3,5-Diiodo-L-tyrosine GC-MS (2 TMS) - 70eV, Positive	splash10-0avr-9302530000-665bd4d1e52bd2a50a9c	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3,5-Diiodo-L-tyrosine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3,5-Diiodo-L-tyrosine LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative-QTOF	splash10-001i-0000900000-ae6a8b173bc71991a4ac	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3,5-Diiodo-L-tyrosine LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative-QTOF	splash10-001i-0200900000-0ba2bdb29d10e206243b	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3,5-Diiodo-L-tyrosine LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative-QTOF	splash10-004i-0922200000-9937df05a2005a9dccdc	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3,5-Diiodo-L-tyrosine LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative-QTOF	splash10-004i-0911000000-7b8269ff37ddf87ca91e	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3,5-Diiodo-L-tyrosine LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative-QTOF	splash10-004i-0900000000-b8211c790d768a3d3ca4	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3,5-Diiodo-L-tyrosine LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive-QTOF	splash10-001i-0000900000-22bf410c5cb442851336	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3,5-Diiodo-L-tyrosine LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive-QTOF	splash10-001r-0017900000-b678ad76193892db31d6	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3,5-Diiodo-L-tyrosine LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive-QTOF	splash10-000i-0049100000-d8fdce763cb949d3c346	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3,5-Diiodo-L-tyrosine LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive-QTOF	splash10-01p9-0197000000-70418018a4eb3733c732	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3,5-Diiodo-L-tyrosine LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive-QTOF	splash10-03di-0191000000-83c286061170a2257b7c	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3,5-Diiodo-L-tyrosine LC-ESI-qTof , Positive-QTOF	splash10-03ei-2492000000-758324f5bb036f5e7439	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3,5-Diiodo-L-tyrosine LC-ESI-QQ , negative-QTOF	splash10-001i-0000900000-ae6a8b173bc71991a4ac	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3,5-Diiodo-L-tyrosine LC-ESI-QQ , negative-QTOF	splash10-001i-0200900000-10d7f46230d75a69ca8a	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3,5-Diiodo-L-tyrosine LC-ESI-QQ , negative-QTOF	splash10-004i-0922200000-9937df05a2005a9dccdc	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3,5-Diiodo-L-tyrosine LC-ESI-QQ , negative-QTOF	splash10-004i-0911000000-7b8269ff37ddf87ca91e	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3,5-Diiodo-L-tyrosine LC-ESI-QQ , negative-QTOF	splash10-004i-0900000000-afdb17f670e1a6b9d237	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3,5-Diiodo-L-tyrosine LC-ESI-QQ , positive-QTOF	splash10-001i-0000900000-22bf410c5cb442851336	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3,5-Diiodo-L-tyrosine LC-ESI-QQ , positive-QTOF	splash10-001r-0017900000-b678ad76193892db31d6	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3,5-Diiodo-L-tyrosine LC-ESI-QQ , positive-QTOF	splash10-000i-0049100000-d8fdce763cb949d3c346	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,5-Diiodo-L-tyrosine 10V, Positive-QTOF	splash10-0019-0009600000-f51bf251094f35e469e4	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,5-Diiodo-L-tyrosine 20V, Positive-QTOF	splash10-000i-0009000000-68414bff61726c960b96	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,5-Diiodo-L-tyrosine 40V, Positive-QTOF	splash10-0a6r-0009000000-7623a376300575297b5f	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,5-Diiodo-L-tyrosine 10V, Negative-QTOF	splash10-001i-0001900000-dce45ddc0efcbd787f4a	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,5-Diiodo-L-tyrosine 20V, Negative-QTOF	splash10-001i-2006900000-6fb8e76ede4b97e18a40	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,5-Diiodo-L-tyrosine 40V, Negative-QTOF	splash10-00di-9036000000-4a8ca25b7e8f09067ce0	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, 100%_DMSO, experimental)	2012-12-05	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Experimental 2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, 100%_DMSO, experimental)	2012-12-05	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

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	0.0036 (0.0014-0.0099) uM	Adult (>18 years old)	Both	Normal	11344555	details
Urine	Detected and Quantified	0.000049 +/- 0.000027 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	3098453	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.0036 (0.0010-0.0134) uM	Adult (>18 years old)	Both	Hyperthyroidism	11344555	details
Urine	Detected and Quantified	0.00013 +/- 0.000098 umol/mmol creatinine	Adult (>18 years old)	Both	Chronic renal disease	3098453	details

Associated Disorders and Diseases

Disease References

Hyperthyroidism
Nelson JC, Weiss RM, Lewis JE, Wilcox RB, Palmer FJ: A multiple ligand-binding radioimmunoassay of diiodotyrosine. J Clin Invest. 1974 Feb;53(2):416-22. [PubMed:11344555 ]
Chronic kidney disease
Ramsden DB, Farmer M, Mohammed MN, McGonigle RS, Sheppard MC: 3,5-Diiodotyrosine and thyronine in the urine of patients with chronic renal disease. Clin Endocrinol (Oxf). 1986 May;24(5):491-5. [PubMed:3098453 ]

Associated OMIM IDs

None

External Links

DrugBank ID

DB03374

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB023181

KNApSAcK ID

Not Available

Chemspider ID

8946

KEGG Compound ID

C01060

BioCyc ID

Not Available

BiGG ID

36719

Wikipedia Link

Not Available

METLIN ID

6940

PubChem Compound

9305

PDB ID

Not Available

ChEBI ID

15768

Food Biomarker Ontology

Not Available

VMH ID

35DIOTYR

MarkerDB ID

MDB00000425

Good Scents ID

Not Available

References

Synthesis Reference

Savitskii, A. Ya. The preparation and properties of 3,5-diiodo-l-tyrosine. Zhurnal Obshchei Khimii (1939), 9 1342-4.

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

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

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

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

Enzyme Details

2. Iodotyrosine dehalogenase 1

General function:: Involved in oxidoreductase activity
Specific function:: Catalyzes the oxidative NADPH-dependent deiodination of monoiodotyrosine (L-MIT) or diiodotyrosine (L-DIT). Acts during the hydrolysis of thyroglobulin to liberate iodide, which can then reenter the hormone-producing pathways. Acts more efficiently on monoiodotyrosine than on diiodotyrosine.
Gene Name:: IYD
Uniprot ID:: Q6PHW0
Molecular weight:: 33781.22

Reactions

L-Tyrosine + NADP + I(-) → 3,5-Diiodo-L-tyrosine + NADPH	details

Showing metabocard for 3,5-Diiodo-L-tyrosine (HMDB0003474)

MOL for HMDB0003474 (3,5-Diiodo-L-tyrosine)

3D MOL for HMDB0003474 (3,5-Diiodo-L-tyrosine)

3D SDF for HMDB0003474 (3,5-Diiodo-L-tyrosine)

3D-SDF for HMDB0003474 (3,5-Diiodo-L-tyrosine)

PDB for HMDB0003474 (3,5-Diiodo-L-tyrosine)

3D PDB for HMDB0003474 (3,5-Diiodo-L-tyrosine)

SMILES for HMDB0003474 (3,5-Diiodo-L-tyrosine)

INCHI for HMDB0003474 (3,5-Diiodo-L-tyrosine)

Structure for HMDB0003474 (3,5-Diiodo-L-tyrosine)

3D Structure for HMDB0003474 (3,5-Diiodo-L-tyrosine)

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

Reactions