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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2021-11-15 21:04:30 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 phenylalanines 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. It is also a member of the class of compounds known as iodothyronines. Iodothyronines are phenolic amino acids with iodine substituents. 3,5-Diiodothyronine is a metabolite of the two main thyroid hormones T3 and T4 (thyroxine and triiodo-L-thyronine). It is a biologically active iodothyronine with mitochondria and bioenergetic mechanisms being the major targets of 3,5-T2. Nanomolar concentrations of 3,5-T2 significantly increases cytochrome oxidase (COX) activity (PMID: 30090086 ). It increases COX activity by preventing the interaction of adenosine triphosphate (ATP) as an allosteric inhibitor. At 1 pM concentration, 3,5-T2 stimulates oxygen consumption more rapidly than thyroxine (T3). A case report involving two human participants revealed that administration of 3,5-T2 to humans (1-5 ug/kg BW) rapidly (after 4-6 h) increased resting metabolic rate. Chronic 3,5-T2 administration (28 days, approximately 5 ug/kg BW) increased resting metabolic rate by approximately 15% and decreased body weight by approximately 4 kg in both participants (PMID: 22217997 ). 3,5-T2 stimulates the thyroid receptor (TR)-beta receptor for thyroid hormones and thus increases energy expenditure. It has agonistic (thyromimetic) effects on myocardial tissue and on the pituitary, which results in 3,5-T2 suppressing thyroid stimulating hormone release.
Structure
Thumb
Synonyms
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
Disposition
ProcessNot Available
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M-H]-MetCCS_train_neg186.4430932474
[M+H]+MetCCS_train_pos198.20830932474
[M-H]-Not Available186.44http://allccs.zhulab.cn/database/detail?ID=AllCCS00000021
[M+H]+Not Available198.5http://allccs.zhulab.cn/database/detail?ID=AllCCS00000021
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
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
MarkerDB IDMDB00000193
Good Scents 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)Not Available
General References