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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2020-02-26 21:22:21 UTC
HMDB IDHMDB0000582
Secondary Accession Numbers
  • HMDB0000627
  • HMDB00582
  • HMDB00627
Metabolite Identification
Common Name3,5-Diiodothyronine
Description3,5-Diiodothyronine, also known as 3,5-T2, belongs to the class of organic compounds known as phenylalanine and derivatives. Phenylalanine and derivatives 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 a very strong basic compound (based on its pKa).
Structure
Data?1582752141
Synonyms
ValueSource
35-DiiodothyronineHMDB
(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)-isomerHMDB
3,5-Diiodothyronine, (DL)-isomerHMDB
2-Amino-3-[4-(4-hydroxyphenoxy)-3,5-diiodophenyl]propanoateHMDB
3,5-DiiodothyronineMeSH
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-thryronine
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
Description belongs to the class of organic compounds known as phenylalanine and derivatives. Phenylalanine and derivatives 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:

Disposition

Source:

Biological location:

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
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-004i-5200920000-b93c897ae4b72c23519bSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00di-9600058000-453c4267903543f11c76Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-004i-0000090000-0c32e1647fb8ad73f0b7Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-003r-0003970000-f35e706ebe5a01fd53a0Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0fb9-0129700000-6535af9505fe3bcdc464Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0100890000-a4c3898b3f5e77f46dbeSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-0000910000-e0bf5e5b19dbc8da3983Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-016u-2009200000-ed00e535f6a635c85b0fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0100090000-71fa162482707b5eb3d7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0ab9-1600390000-2a1c97e2e04e68ad8521Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05iu-9102200000-a695396d7ea8bb382a70Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Blood
  • Urine
Tissue Locations
  • Brain
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
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
BiospecimenStatusValueAgeSexConditionReferenceDetails
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
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 ]
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 ]
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 ]
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 ]
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022128
KNApSAcK IDNot Available
Chemspider ID110252
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia Link3,5-Diiodothyronine
METLIN ID5564
PubChem Compound123675
PDB IDNot Available
ChEBI ID350682
Food Biomarker OntologyNot Available
VMH IDNot Available
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 ]