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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2021-09-14 15:20:01 UTC
HMDB IDHMDB0000021
Secondary Accession Numbers
  • HMDB00021
Metabolite Identification
Common NameIodotyrosine
DescriptionIodotyrosine 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
Data?1582752108
Synonyms
ValueSource
(2S)-2-Amino-3-(4-hydroxy-3-iodophenyl)propanoic acidChEBI
3-IODO-tyrosineChEBI
MITChEBI
(2S)-2-Amino-3-(4-hydroxy-3-iodophenyl)propanoateGenerator
3-Iodo-4-hydroxyphenylalanineHMDB
3-Iodo-L-tyrosineHMDB
3-IodotyrosineHMDB
3-Monoiodo-L-tyrosineHMDB
4-Hydroxy-3-iodophenylalanineHMDB
IYRHMDB
L-Tyrosine-3-iodoHMDB
MonoiodotyrosineHMDB
Chemical FormulaC9H10INO3
Average Molecular Weight307.0851
Monoisotopic Molecular Weight306.970536611
IUPAC Name(2S)-2-amino-3-(4-hydroxy-3-iodophenyl)propanoic acid
Traditional Nameiodotyrosine
CAS Registry Number70-78-0
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 KeyUQTZMGFTRHFAAM-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.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentTyrosine 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 FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Disposition
Process
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point205 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility3 mg/mLNot Available
LogPNot AvailableNot Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M+H]+Not Available159.066http://allccs.zhulab.cn/database/detail?ID=AllCCS00000002
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.94 g/LALOGPS
logP-1.5ALOGPS
logP-0.56ChemAxon
logS-2.5ALOGPS
pKa (Strongest Acidic)0.99ChemAxon
pKa (Strongest Basic)9.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area83.55 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity60.46 m³·mol⁻¹ChemAxon
Polarizability23.54 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
AllCCS[M+H]+162.42732859911
AllCCS[M-H]-152.38232859911
DeepCCS[M+H]+153.07830932474
DeepCCS[M-H]-150.7230932474
DeepCCS[M-2H]-184.84230932474
DeepCCS[M+Na]+159.64830932474
AllCCS[M+H]+162.432859911
AllCCS[M+H-H2O]+159.032859911
AllCCS[M+NH4]+165.632859911
AllCCS[M+Na]+166.632859911
AllCCS[M-H]-152.432859911
AllCCS[M+Na-2H]-153.632859911
AllCCS[M+HCOO]-154.932859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
IodotyrosineN[C@@H](CC1=CC=C(O)C(I)=C1)C(O)=O3274.6Standard polar33892256
IodotyrosineN[C@@H](CC1=CC=C(O)C(I)=C1)C(O)=O2241.8Standard non polar33892256
IodotyrosineN[C@@H](CC1=CC=C(O)C(I)=C1)C(O)=O2279.3Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Iodotyrosine,1TMS,isomer #1C[Si](C)(C)OC1=CC=C(C[C@H](N)C(=O)O)C=C1I2230.6Semi standard non polar33892256
Iodotyrosine,1TMS,isomer #2C[Si](C)(C)OC(=O)[C@@H](N)CC1=CC=C(O)C(I)=C12146.8Semi standard non polar33892256
Iodotyrosine,1TMS,isomer #3C[Si](C)(C)N[C@@H](CC1=CC=C(O)C(I)=C1)C(=O)O2218.0Semi standard non polar33892256
Iodotyrosine,2TMS,isomer #1C[Si](C)(C)OC(=O)[C@@H](N)CC1=CC=C(O[Si](C)(C)C)C(I)=C12195.4Semi standard non polar33892256
Iodotyrosine,2TMS,isomer #2C[Si](C)(C)N[C@@H](CC1=CC=C(O[Si](C)(C)C)C(I)=C1)C(=O)O2252.1Semi standard non polar33892256
Iodotyrosine,2TMS,isomer #3C[Si](C)(C)N[C@@H](CC1=CC=C(O)C(I)=C1)C(=O)O[Si](C)(C)C2168.6Semi standard non polar33892256
Iodotyrosine,2TMS,isomer #4C[Si](C)(C)N([C@@H](CC1=CC=C(O)C(I)=C1)C(=O)O)[Si](C)(C)C2319.4Semi standard non polar33892256
Iodotyrosine,3TMS,isomer #1C[Si](C)(C)N[C@@H](CC1=CC=C(O[Si](C)(C)C)C(I)=C1)C(=O)O[Si](C)(C)C2217.0Semi standard non polar33892256
Iodotyrosine,3TMS,isomer #1C[Si](C)(C)N[C@@H](CC1=CC=C(O[Si](C)(C)C)C(I)=C1)C(=O)O[Si](C)(C)C2188.2Standard non polar33892256
Iodotyrosine,3TMS,isomer #1C[Si](C)(C)N[C@@H](CC1=CC=C(O[Si](C)(C)C)C(I)=C1)C(=O)O[Si](C)(C)C2140.3Standard polar33892256
Iodotyrosine,3TMS,isomer #2C[Si](C)(C)OC1=CC=C(C[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)C=C1I2373.8Semi standard non polar33892256
Iodotyrosine,3TMS,isomer #2C[Si](C)(C)OC1=CC=C(C[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)C=C1I2287.7Standard non polar33892256
Iodotyrosine,3TMS,isomer #2C[Si](C)(C)OC1=CC=C(C[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)C=C1I2284.7Standard polar33892256
Iodotyrosine,3TMS,isomer #3C[Si](C)(C)OC(=O)[C@H](CC1=CC=C(O)C(I)=C1)N([Si](C)(C)C)[Si](C)(C)C2323.4Semi standard non polar33892256
Iodotyrosine,3TMS,isomer #3C[Si](C)(C)OC(=O)[C@H](CC1=CC=C(O)C(I)=C1)N([Si](C)(C)C)[Si](C)(C)C2247.8Standard non polar33892256
Iodotyrosine,3TMS,isomer #3C[Si](C)(C)OC(=O)[C@H](CC1=CC=C(O)C(I)=C1)N([Si](C)(C)C)[Si](C)(C)C2304.4Standard polar33892256
Iodotyrosine,4TMS,isomer #1C[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)C2432.9Semi standard non polar33892256
Iodotyrosine,4TMS,isomer #1C[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)C2339.7Standard non polar33892256
Iodotyrosine,4TMS,isomer #1C[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)C2095.6Standard polar33892256
Iodotyrosine,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC=C(C[C@H](N)C(=O)O)C=C1I2482.5Semi standard non polar33892256
Iodotyrosine,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(=O)[C@@H](N)CC1=CC=C(O)C(I)=C12406.3Semi standard non polar33892256
Iodotyrosine,1TBDMS,isomer #3CC(C)(C)[Si](C)(C)N[C@@H](CC1=CC=C(O)C(I)=C1)C(=O)O2474.8Semi standard non polar33892256
Iodotyrosine,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)[C@@H](N)CC1=CC=C(O[Si](C)(C)C(C)(C)C)C(I)=C12743.2Semi standard non polar33892256
Iodotyrosine,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)N[C@@H](CC1=CC=C(O[Si](C)(C)C(C)(C)C)C(I)=C1)C(=O)O2785.8Semi standard non polar33892256
Iodotyrosine,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)N[C@@H](CC1=CC=C(O)C(I)=C1)C(=O)O[Si](C)(C)C(C)(C)C2648.8Semi standard non polar33892256
Iodotyrosine,2TBDMS,isomer #4CC(C)(C)[Si](C)(C)N([C@@H](CC1=CC=C(O)C(I)=C1)C(=O)O)[Si](C)(C)C(C)(C)C2775.6Semi standard non polar33892256
Iodotyrosine,3TBDMS,isomer #1CC(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)C2983.5Semi standard non polar33892256
Iodotyrosine,3TBDMS,isomer #1CC(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)C2857.2Standard non polar33892256
Iodotyrosine,3TBDMS,isomer #1CC(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)C2530.2Standard polar33892256
Iodotyrosine,3TBDMS,isomer #2CC(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=C1I3115.7Semi standard non polar33892256
Iodotyrosine,3TBDMS,isomer #2CC(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=C1I2907.1Standard non polar33892256
Iodotyrosine,3TBDMS,isomer #2CC(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=C1I2588.3Standard polar33892256
Iodotyrosine,3TBDMS,isomer #3CC(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)C3001.2Semi standard non polar33892256
Iodotyrosine,3TBDMS,isomer #3CC(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)C2889.5Standard non polar33892256
Iodotyrosine,3TBDMS,isomer #3CC(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)C2596.5Standard polar33892256
Iodotyrosine,4TBDMS,isomer #1CC(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)C3356.4Semi standard non polar33892256
Iodotyrosine,4TBDMS,isomer #1CC(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)C3099.5Standard non polar33892256
Iodotyrosine,4TBDMS,isomer #1CC(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)C2545.6Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Iodotyrosine GC-MS (2 TMS)splash10-0a4j-3913000000-be57e889200c60dc46d42014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Iodotyrosine GC-MS (3 TMS)splash10-014i-1790000000-785b6d6a13d0a88229462014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Iodotyrosine GC-MS (Non-derivatized)splash10-0a4j-3913000000-be57e889200c60dc46d42017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Iodotyrosine GC-MS (Non-derivatized)splash10-014i-1790000000-785b6d6a13d0a88229462017-09-12HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Iodotyrosine GC-MS (Non-derivatized) - 70eV, Positivesplash10-03e9-3090000000-2e5cb717605e800d43592017-08-28Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Iodotyrosine GC-MS (2 TMS) - 70eV, Positivesplash10-00sr-9335100000-f5b1c103a54222cc59a32017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Iodotyrosine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Iodotyrosine GC-MS (TMS_1_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Iodotyrosine GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Iodotyrosine GC-MS (TMS_1_3) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Iodotyrosine GC-MS (TMS_2_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Iodotyrosine GC-MS (TMS_2_3) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Iodotyrosine GC-MS (TMS_2_4) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Iodotyrosine GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Iodotyrosine GC-MS (TBDMS_1_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Iodotyrosine GC-MS (TBDMS_1_3) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Iodotyrosine GC-MS (TBDMS_2_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Iodotyrosine GC-MS (TBDMS_2_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Iodotyrosine GC-MS (TBDMS_2_3) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Iodotyrosine GC-MS (TBDMS_2_4) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Iodotyrosine LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative-QTOFsplash10-0a4i-0009000000-29fdc92cbeae7ec37e5d2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Iodotyrosine LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative-QTOFsplash10-056r-0923000000-1f98738c0cc639f98dc72012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Iodotyrosine LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative-QTOFsplash10-004i-1900000000-92c150757accb8a27fd92012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Iodotyrosine LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative-QTOFsplash10-004i-2900000000-82ef54ff210098156f8c2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Iodotyrosine LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative-QTOFsplash10-004i-2900000000-fffc0c2d97089650aada2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Iodotyrosine LC-ESI-QQ , negative-QTOFsplash10-0a4i-0009000000-44efbf86abf86218185b2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Iodotyrosine LC-ESI-QQ , negative-QTOFsplash10-056r-0923000000-f702b07a620f77aeef9f2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Iodotyrosine LC-ESI-QQ , negative-QTOFsplash10-004i-1900000000-151c357f1c3d1af4b1682017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Iodotyrosine LC-ESI-QQ , negative-QTOFsplash10-004i-2900000000-3a76280be1a51177051d2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Iodotyrosine LC-ESI-QQ , negative-QTOFsplash10-004i-2900000000-fffc0c2d97089650aada2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Iodotyrosine Quattro_QQQ 10V, Positive-QTOF (Annotated)splash10-08fu-0094000000-1cca0021f92a06ea8b502012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Iodotyrosine Quattro_QQQ 25V, Positive-QTOF (Annotated)splash10-01q9-1890000000-ff62addb3c23234d3cef2012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Iodotyrosine Quattro_QQQ 40V, Positive-QTOF (Annotated)splash10-001i-2910000000-1938a4966cb53b4f5ed12012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Iodotyrosine LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive-QTOFsplash10-0a4i-0329000000-39b160c87443d51e76112012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Iodotyrosine LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive-QTOFsplash10-03dl-0591000000-c54470130afba37dca282012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Iodotyrosine LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive-QTOFsplash10-03dr-1980000000-31e2dd7b1defc7cfb8c32012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Iodotyrosine LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive-QTOFsplash10-000i-1920000000-8e40ba504d905aa7a5282012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Iodotyrosine LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive-QTOFsplash10-05n3-3900000000-368aad6dbdcc312ac3df2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Iodotyrosine LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positive-QTOFsplash10-01ox-0090000000-6e7318a85f3480d074772012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Iodotyrosine LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positive-QTOFsplash10-03ka-0790000000-ed59bbe7e20256d8ad062012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Iodotyrosine LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positive-QTOFsplash10-000i-0900000000-6de0b405d60b85059abc2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Iodotyrosine LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positive-QTOFsplash10-0006-0090000000-9e84651efead6b6bfa2c2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Iodotyrosine LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positive-QTOFsplash10-00di-0900000000-972b9ebadf10c99787c42012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Iodotyrosine LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positive-QTOFsplash10-014i-0900000000-6150f13b1005b3ec9eff2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Iodotyrosine LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positive-QTOFsplash10-000b-0900000000-7b5ecd0f27a3ed9d67e22012-08-31HMDB team, MONAView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Experimental 1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)2012-12-04Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)2012-12-04Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Blood
Tissue Locations
  • Thyroid Gland
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.00069 +/- 0.00020 uMAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.00032 +/- 0.00008 uMAdult (>18 years old)BothAthyroic patients details
Associated Disorders and Diseases
Disease References
Athyreosis
  1. 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 IDsNone
DrugBank IDDB01758
Phenol Explorer Compound IDNot Available
FooDB IDFDB021875
KNApSAcK IDNot Available
Chemspider ID388804
KEGG Compound IDC02515
BioCyc IDCPD-12288
BiGG ID39998
Wikipedia Link3-Iodotyrosine
METLIN IDNot Available
PubChem Compound439744
PDB IDNot Available
ChEBI ID27847
Food Biomarker OntologyNot Available
VMH ID3ITYR_L
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceHillmann, 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
  1. 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 ]
  2. 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 ]
  3. Ismail-Beigi F, Rahimifar M: A variant of iodotyrosine-dehalogenase deficiency. J Clin Endocrinol Metab. 1977 Mar;44(3):499-506. [PubMed:838849 ]
  4. 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 ]
  5. 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 ]
  6. 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

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-Tyrosinedetails
Iodotyrosine + 3,5-Diiodo-L-tyrosine + Hydrogen peroxide → Liothyronine + 2-Aminoacrylic acid + Waterdetails
I(-) + 3,5-Diiodo-L-tyrosine → Iodotyrosine + Iodinedetails