3,3'-Diiodothyronine (CHEM036006)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 07:09:12 UTC
Update Date2016-11-09 01:21:25 UTC
Accession NumberCHEM036006
Identification
Common Name3,3'-Diiodothyronine
ClassSmall Molecule
Description
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
3,3'-diiodo-L-ThyronineHMDB
3,3'-T2HMDB
3-[4-(4-Hydroxy-3-iodophenoxy)-3-iodophenyl]-L-alanineHMDB
L-3-[4-(4-Hydroxy-3-iodophenoxy)-3-iodophenyl]-alanineHMDB
L-beta-[4-(4-Hydroxy-3-iodophenoxy)-3-iodophenyl]-alanineHMDB
O-(4-Hydroxy-3-iodophenyl)-3-iodo-L-tyrosineHMDB
O-(4-Hydroxy-3-iodophenyl)-3-iodo-tyrosineHMDB
O-(4-Hydroxy-3-iodophenyl)-3-iodotyrosineHMDB
3,3'-Diiodothyronine, (L)-isomerMeSH, HMDB
3,3'-Diiodothyronine, (L)-isomer, 125I-labeledMeSH, HMDB
3,3'-Diiodothyronine, (DL)-isomerMeSH, HMDB
(2R)-2-Amino-3-[4-(4-hydroxy-3-iodophenoxy)-3-iodophenyl]propanoateGenerator, HMDB
3,3'-DiiodothyronineMeSH
Chemical FormulaC15H13I2NO4
Average Molecular Mass525.077 g/mol
Monoisotopic Mass524.893 g/mol
CAS Registry Number70-40-6
IUPAC Name(2R)-2-amino-3-[4-(4-hydroxy-3-iodophenoxy)-3-iodophenyl]propanoic acid
Traditional Name3,3'-diiodo-L-thyronine
SMILESN[C@H](CC1=CC(I)=C(OC2=CC(I)=C(O)C=C2)C=C1)C(O)=O
InChI IdentifierInChI=1S/C15H13I2NO4/c16-10-7-9(2-3-13(10)19)22-14-4-1-8(5-11(14)17)6-12(18)15(20)21/h1-5,7,12,19H,6,18H2,(H,20,21)/t12-/m1/s1
InChI KeyCPCJBZABTUOGNM-GFCCVEGCSA-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
  • D-alpha-amino acid
  • Phenoxy compound
  • 2-iodophenol
  • 2-halophenol
  • Phenol ether
  • Iodobenzene
  • 1-hydroxy-2-unsubstituted benzenoid
  • Halobenzene
  • Phenol
  • Aralkylamine
  • Aryl iodide
  • Aryl halide
  • Monocyclic benzene moiety
  • Benzenoid
  • 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
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.058 g/LALOGPS
logP0.46ALOGPS
logP1.87ChemAxon
logS-4ALOGPS
pKa (Strongest Acidic)0.75ChemAxon
pKa (Strongest Basic)9.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area92.78 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity100.06 m³·mol⁻¹ChemAxon
Polarizability38.43 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-004i-6031920000-71c3f9fd5d3525d32324Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0udr-9220062000-622a98eee44fd2a653d5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0000980000-858065ad3e75dc6659f2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-0000910000-a2dcc5e08cee0881ad4eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fr6-0090400000-a070e8cbcc117f994f6cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0000090000-65d3cc7d62473f25536eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-05gi-0041490000-5c480959f3bd3dc4837aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0pir-8394100000-89e4e80d17cbdfd7d9e4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0000970000-81a694fc24040341b724Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-0001900000-ad927620975a1b760382Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0005-0092100000-8085fd591d50843db9faSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0000290000-d0a979f9285e9d348d71Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0229-2101950000-c313cc0aa358b2f36374Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-0912000000-9f2ef8ddde02d9a68c1aSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0005869
FooDB IDFDB023783
Phenol Explorer IDNot Available
KNApSAcK IDC00037453
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia Link3,3'-Diiodothyronine
Chemspider IDNot Available
ChEBI ID35430
PubChem Compound ID53477796
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Gavin LA, Bui F, McMahon F, Cavalieri RR: Sequential deiodination of thyroxine to 3,3'-diiodothyronine via 3,5,3'-triiodothyronine and 3,3',5'-triiodothyronine in rat liver homogenate. The effects of fasting versus glucose feeding. J Biol Chem. 1980 Jan 10;255(1):49-54.
2. Sorimachi K, Niwa A, Yasumura Y: Metabolism of 3,3'-Diiodothyronine and 3'-monoiodothyronine, and effect of potassium cyanide and dinitrophenol and glucuronidation of thyroxine in cultured rat hepatoma cells. Endocrinol Jpn. 1980 Oct;27(5):631-6.
3. Campos-Barros A, Meinhold H, Stula M, Muller F, Kohler R, Eravci M, Putzien O, Baumgartner A: The influence of desipramine on thyroid hormone metabolism in rat brain. J Pharmacol Exp Ther. 1994 Mar;268(3):1143-52.
4. Burman KD, Strum D, Dimond RC, Djuh YY, Wright FD, Earll JM, Wartofsky L: A radioimmunoassay for 3,3'-L-diiodothyronine (3,3'T2). J Clin Endocrinol Metab. 1977 Aug;45(2):339-52.
5. Corcoran JM, Eastman CJ: Measurement of 3'-monoiodothyronine in human serum. Clin Endocrinol (Oxf). 1981 Jul;15(1):11-8.
6. Dickstein Y, Schwartz H, Gross J, Gordon A: The metabolism of T4 and T3 in cultured chick-embryo heart cells. Mol Cell Endocrinol. 1980 Oct;20(1):45-57.
7. Burman KD, Dimond RC, Djuh YY, Bruton J, Washburn TB, Wright FD, Wartofsky L: Failure of 3,3'-diiodothyronine administration to alter TSH and prolactin responses to TRH stimulation. Metabolism. 1978 Jun;27(6):677-83.
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.
9. Esfandiari A, Gavaret JM, Lennon AM, Pierre M, Courtin F: Sulfation after deiodination of 3,5,3'-triiodothyronine in rat cultured astrocytes. Endocrinology. 1994 Nov;135(5):2086-92.
10. Baumgartner A, Campos-Barros A, Gaio U, Hessenius C, Flechner A, Meinhold H: Carbamazepine affects triiodothyronine production and metabolization in rat hippocampus. Life Sci. 1994;54(23):PL401-7.
11. Burman KD: Recent developments in thyroid hormone metabolism: interpretation and significance of measurements of reverse T3, 3,3'T2, and thyroglobulin. Metabolism. 1978 May;27(5):615-30.
12. Nishikawa M, Inada M, Naito K, Ishii H, Tanaka K, Mashio Y, Imura H: Age-related changes of serum 3,3'-diiodothyronine, 3',5'-diiodothyronine, and 3,5-diiodothyronine concentrations in man. J Clin Endocrinol Metab. 1981 Mar;52(3):517-22.
13. Burman KD, Read J, Dimond RC, Strum D, Wright FD, Patow W, Earll JM, Wartofsky L: Measurement of 3,3',5'-Triiodothyroinine (reverse T3), 3,3'-L-diiodothyronine, T3 and T4 in human amniotic fluid and in cord and maternal serum. J Clin Endocrinol Metab. 1976 Dec;43(6):1351-9.
14. Langer P, Foldes O, Straussova K, Gschwendtova K: Preliminary observations on the absorption of biliary iodothyronines from the intestine in vivo in rats. Endocrinol Exp. 1982 Jun;16(2):117-27.
15. Smallridge RC, Wartofsky L, Chopra IJ, Marinelli PV, Broughton RE, Dimond RC, Burman KD: Neonatal thyrotoxicosis: alterations in serum concentrations of LATS-protector, T4, T3, reverse T3, and 3,3'T2. J Pediatr. 1978 Jul;93(1):118-20.