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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2017-12-07 01:18:52 UTC
HMDB IDHMDB0000582
Secondary Accession Numbers
  • HMDB00582
  • HMDB00627
Metabolite Identification
Common Name3,5-Diiodothyronine
Description3,5-diiodothyronine, also known as D-O-(4-hydroxyphenyl)-3,5-diiodo-tyrosine or 3,5-diiodothyronine, (dl)-isomer, belongs to phenylalanine and derivatives class of compounds. Those are compounds containing phenylalanine or a derivative thereof resulting from reaction of phenylalanine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. 3,5-diiodothyronine is practically insoluble (in water) and an extremely strong acidic compound (based on its pKa). 3,5-diiodothyronine can be found primarily in blood and urine, as well as in human brain tissue. Within the cell, 3,5-diiodothyronine is primarily located in the cytoplasm. Moreover, 3,5-diiodothyronine is found to be associated with hyperthyroidism, brain tumors, sepsis, and cirrhosis. 3,5-Diiodothyronine is a metabolite of thyroid hormones (thyroxine and triiodo-L-thyronine). It has specific actions and those actions do not involve thyroid hormone receptors (PMID 15807655 )..
Structure
Thumb
Synonyms
ValueSource
35-DiiodothyronineChEMBL
(3,5-diiodo-4-(-P-Hydroxyphenoxy)phenyl)-alanineHMDB
3',5'-DiiodothyronineHMDB
3,5-diiodo-D-ThyronineHMDB
3,5-diiodo-DL-ThryronineHMDB
3,5-diiodo-DL-ThyronineHMDB
3,5-diiodo-L-ThyronineHMDB
3,5-T2HMDB
4-(4-Hydroxyphenoxy)-3,5-diiodophenylalanineHMDB
D-O-(4-Hydroxyphenyl)-3,5-diiodo-tyrosineHMDB
diiodo-L-ThyronineHMDB
DiiodothyronineHMDB
DL-3,5-DiiodothyronineHMDB
DL-DiiodothyronineHMDB
L-3,5-DiiodothyronineHMDB
L-O-(4-Hydroxyphenyl)-3,5-diiodo-tyrosineHMDB
O-(4-Hydroxyphenyl)-3,5-diiodo-tyrosineHMDB
3,5-Diiodothyronine, (L)-isomerMeSH
3,5-Diiodothyronine, (DL)-isomerMeSH
Chemical FormulaC15H13I2NO4
Average Molecular Weight525.077
Monoisotopic Molecular Weight524.893394749
IUPAC Name2-amino-3-[4-(4-hydroxyphenoxy)-3,5-diiodophenyl]propanoic acid
Traditional Name3,5-diiodo-DL-thyronine
CAS Registry Number534-51-0
SMILES
NC(CC1=CC(I)=C(OC2=CC=C(O)C=C2)C(I)=C1)C(O)=O
InChI Identifier
InChI=1S/C15H13I2NO4/c16-11-5-8(7-13(18)15(20)21)6-12(17)14(11)22-10-3-1-9(19)2-4-10/h1-6,13,19H,7,18H2,(H,20,21)
InChI KeyZHSOTLOTTDYIIK-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as phenylalanine and derivatives. These are compounds containing phenylalanine or a derivative thereof resulting from reaction of phenylalanine 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 ParentPhenylalanine and derivatives
Alternative Parents
Substituents
  • Phenylalanine or derivatives
  • Diphenylether
  • Diaryl ether
  • 3-phenylpropanoic-acid
  • Alpha-amino acid
  • Amphetamine or derivatives
  • Phenoxy compound
  • Phenol ether
  • Iodobenzene
  • Halobenzene
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Aralkylamine
  • Aryl iodide
  • Aryl halide
  • Benzenoid
  • Monocyclic benzene moiety
  • Amino acid
  • Ether
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organic nitrogen compound
  • Primary aliphatic amine
  • Organohalogen compound
  • 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 DescriptorsNot Available
Ontology
Physiological effect

Health effect:

  Health condition:

    Infections and infestations:

    Endocrine disorders:

Disposition

Biological location:

  Subcellular:

  Biofluid and excreta:

  Organ and components:

Source:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.052 g/LALOGPS
logP0.45ALOGPS
logP1.87ChemAxon
logS-4ALOGPS
pKa (Strongest Acidic)0.33ChemAxon
pKa (Strongest Basic)9.23ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area92.78 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity100.06 m³·mol⁻¹ChemAxon
Polarizability38.7 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-004i-5200920000-b93c897ae4b72c23519bView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00di-9600058000-453c4267903543f11c76View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-004i-0000090000-0c32e1647fb8ad73f0b7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-003r-0003970000-f35e706ebe5a01fd53a0View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0fb9-0129700000-6535af9505fe3bcdc464View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0100890000-a4c3898b3f5e77f46dbeView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-0000910000-e0bf5e5b19dbc8da3983View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-016u-2009200000-ed00e535f6a635c85b0fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0100090000-71fa162482707b5eb3d7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0ab9-1600390000-2a1c97e2e04e68ad8521View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05iu-9102200000-a695396d7ea8bb382a70View in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Cytoplasm
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Brain
PathwaysNot Available
NameSMPDB/PathwhizKEGG
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.000016 +/- 0.000006 uMAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.000018 umol/mmol creatinineAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.000046 +/- 0.000048 uMAdult (>18 years old)BothSepsis details
BloodDetected and Quantified0.000024 +/- 0.000014 uMAdult (>18 years old)BothCirrhosis details
BloodDetected and Quantified0.000021 +/- 0.000005 uMAdult (>18 years old)BothBrain tumors details
UrineDetected and Quantified0.000086 umol/mmol creatinineAdult (>18 years old)BothHyperthyroidism details
UrineDetected and Quantified0.00001 umol/mmol creatinineAdult (>18 years old)BothHypothyroidism details
Associated Disorders and Diseases
Disease References
Brain tumors
  1. Pinna G, Meinhold H, Hiedra L, Thoma R, Hoell T, Graf KJ, Stoltenburg-Didinger G, Eravci M, Prengel H, Brodel O, Finke R, Baumgartner A: Elevated 3,5-diiodothyronine concentrations in the sera of patients with nonthyroidal illnesses and brain tumors. J Clin Endocrinol Metab. 1997 May;82(5):1535-42. [PubMed:9141546 ]
Cirrhosis
  1. Pinna G, Meinhold H, Hiedra L, Thoma R, Hoell T, Graf KJ, Stoltenburg-Didinger G, Eravci M, Prengel H, Brodel O, Finke R, Baumgartner A: Elevated 3,5-diiodothyronine concentrations in the sera of patients with nonthyroidal illnesses and brain tumors. J Clin Endocrinol Metab. 1997 May;82(5):1535-42. [PubMed:9141546 ]
Hyperthyroidism
  1. Hommel E, Faber J, Kirkegaard C, Siersbaek-Nielsen K, Friis T: Urinary excretion of unconjugated and conjugated 3,5-diiodothyronine. Horm Metab Res. 1985 Feb;17(2):90-2. [PubMed:3988241 ]
Hypothyroidism
  1. Hommel E, Faber J, Kirkegaard C, Siersbaek-Nielsen K, Friis T: Urinary excretion of unconjugated and conjugated 3,5-diiodothyronine. Horm Metab Res. 1985 Feb;17(2):90-2. [PubMed:3988241 ]
Sepsis
  1. Pinna G, Meinhold H, Hiedra L, Thoma R, Hoell T, Graf KJ, Stoltenburg-Didinger G, Eravci M, Prengel H, Brodel O, Finke R, Baumgartner A: Elevated 3,5-diiodothyronine concentrations in the sera of patients with nonthyroidal illnesses and brain tumors. J Clin Endocrinol Metab. 1997 May;82(5):1535-42. [PubMed:9141546 ]
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB022128
KNApSAcK IDNot Available
Chemspider ID110252
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID5564
PubChem Compound123675
PDB IDNot Available
ChEBI ID350682
References
Synthesis ReferenceValashek, I. E.; Kochergin, P. M.; Vinogradova, E. M.; Budanova, L. I. Synthesis of 3,5-diiodo-DL-thyronine. Khimiko-Farmatsevticheskii Zhurnal (1995), 29(6), 44.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Goglia F: Biological effects of 3,5-diiodothyronine (T(2)). Biochemistry (Mosc). 2005 Feb;70(2):164-72. [PubMed:15807655 ]
  2. Nishikawa M, Inada M, Naito K, Ishii H, Tanaka K, Mashio Y, Imura H: Serum concentrations of 3, 3'-diiodothyronine, 3', 5'-diiodothyronine, and 3, 5-diiodothyronine in altered thyroid states. Endocrinol Jpn. 1983 Apr;30(2):167-72. [PubMed:6641638 ]
  3. Takeshita A: [Monoiodothyronine and diiodothyronine]. Nihon Rinsho. 1999 Dec;57 Suppl:86-9. [PubMed:10778070 ]
  4. Pinna G, Meinhold H, Hiedra L, Thoma R, Hoell T, Graf KJ, Stoltenburg-Didinger G, Eravci M, Prengel H, Brodel O, Finke R, Baumgartner A: Elevated 3,5-diiodothyronine concentrations in the sera of patients with nonthyroidal illnesses and brain tumors. J Clin Endocrinol Metab. 1997 May;82(5):1535-42. [PubMed:9141546 ]
  5. Martinez MB, Ruan M, Fitzpatrick LA: Altered response to thyroid hormones by breast and ovarian cancer cells. Anticancer Res. 2000 Nov-Dec;20(6B):4141-6. [PubMed:11205239 ]
  6. Faber J, Heaf J, Kirkegaard C, Lumholtz IB, Siersbaek-Nielsen K, Kolendorf K, Friis T: Simultaneous turnover studies of thyroxine, 3,5,3' and 3,3',5'-triiodothyronine, 3,5-, 3,3'-, and 3',5'- diiodothyronine, and 3'-monoiodothyronine in chronic renal failure. J Clin Endocrinol Metab. 1983 Feb;56(2):211-7. [PubMed:6401746 ]
  7. Kirkegaard C, Faber J, Siersbaek-Nielsen K, Friis T: A radioimmunoassay of serum 3,5-diiodothyronine. Acta Endocrinol (Copenh). 1981 Jun;97(2):196-201. [PubMed:7234287 ]
  8. Jaedig S, Faber J: The effect of starvation and refeeding with oral versus intravenous glucose on serum 3,5-,3,3'-and 3'-5'-diiodothyronine and 3'-monoiodothyronine. Acta Endocrinol (Copenh). 1982 Jul;100(3):388-92. [PubMed:7113605 ]
  9. Engler D, Merkelbach U, Steiger G, Burger AG: The monodeiodination of triiodothyronine and reverse triiodothyronine in man: a quantitative evaluation of the pathway by the use of turnover rate techniques. J Clin Endocrinol Metab. 1984 Jan;58(1):49-61. [PubMed:6689682 ]
  10. Baur A, Bauer K, Jarry H, Kohrle J: 3,5-diiodo-L-thyronine stimulates type 1 5'deiodinase activity in rat anterior pituitaries in vivo and in reaggregate cultures and GH3 cells in vitro. Endocrinology. 1997 Aug;138(8):3242-8. [PubMed:9231774 ]
  11. Engler D, Burger AG: The deiodination of the iodothyronines and of their derivatives in man. Endocr Rev. 1984 Spring;5(2):151-84. [PubMed:6376077 ]
  12. Hommel E, Faber J, Kirkegaard C, Siersbaek-Nielsen K, Friis T: Urinary excretion of unconjugated and conjugated 3,5-diiodothyronine. Horm Metab Res. 1985 Feb;17(2):90-2. [PubMed:3988241 ]