Hmdb loader
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
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
Not AvailableNot Available
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
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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
AllCCS[M+H]+195.94732859911
AllCCS[M-H]-184.34532859911
DeepCCS[M+H]+189.08530932474
DeepCCS[M-H]-186.72730932474
DeepCCS[M-2H]-219.61230932474
DeepCCS[M+Na]+195.17830932474
AllCCS[M+H]+195.932859911
AllCCS[M+H-H2O]+193.932859911
AllCCS[M+NH4]+197.932859911
AllCCS[M+Na]+198.432859911
AllCCS[M-H]-184.332859911
AllCCS[M+Na-2H]-185.432859911
AllCCS[M+HCOO]-186.732859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
3,5-DiiodothyronineNC(CC1=CC(I)=C(OC2=CC=C(O)C=C2)C(I)=C1)C(O)=O4479.3Standard polar33892256
3,5-DiiodothyronineNC(CC1=CC(I)=C(OC2=CC=C(O)C=C2)C(I)=C1)C(O)=O3212.9Standard non polar33892256
3,5-DiiodothyronineNC(CC1=CC(I)=C(OC2=CC=C(O)C=C2)C(I)=C1)C(O)=O3486.0Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
3,5-Diiodothyronine,1TMS,isomer #1C[Si](C)(C)OC1=CC=C(OC2=C(I)C=C(CC(N)C(=O)O)C=C2I)C=C13202.0Semi standard non polar33892256
3,5-Diiodothyronine,1TMS,isomer #2C[Si](C)(C)OC(=O)C(N)CC1=CC(I)=C(OC2=CC=C(O)C=C2)C(I)=C13216.0Semi standard non polar33892256
3,5-Diiodothyronine,1TMS,isomer #3C[Si](C)(C)NC(CC1=CC(I)=C(OC2=CC=C(O)C=C2)C(I)=C1)C(=O)O3265.9Semi standard non polar33892256
3,5-Diiodothyronine,2TMS,isomer #1C[Si](C)(C)OC(=O)C(N)CC1=CC(I)=C(OC2=CC=C(O[Si](C)(C)C)C=C2)C(I)=C13221.8Semi standard non polar33892256
3,5-Diiodothyronine,2TMS,isomer #2C[Si](C)(C)NC(CC1=CC(I)=C(OC2=CC=C(O[Si](C)(C)C)C=C2)C(I)=C1)C(=O)O3210.0Semi standard non polar33892256
3,5-Diiodothyronine,2TMS,isomer #3C[Si](C)(C)NC(CC1=CC(I)=C(OC2=CC=C(O)C=C2)C(I)=C1)C(=O)O[Si](C)(C)C3184.6Semi standard non polar33892256
3,5-Diiodothyronine,2TMS,isomer #4C[Si](C)(C)N(C(CC1=CC(I)=C(OC2=CC=C(O)C=C2)C(I)=C1)C(=O)O)[Si](C)(C)C3357.2Semi standard non polar33892256
3,5-Diiodothyronine,3TMS,isomer #1C[Si](C)(C)NC(CC1=CC(I)=C(OC2=CC=C(O[Si](C)(C)C)C=C2)C(I)=C1)C(=O)O[Si](C)(C)C3191.5Semi standard non polar33892256
3,5-Diiodothyronine,3TMS,isomer #1C[Si](C)(C)NC(CC1=CC(I)=C(OC2=CC=C(O[Si](C)(C)C)C=C2)C(I)=C1)C(=O)O[Si](C)(C)C2850.1Standard non polar33892256
3,5-Diiodothyronine,3TMS,isomer #1C[Si](C)(C)NC(CC1=CC(I)=C(OC2=CC=C(O[Si](C)(C)C)C=C2)C(I)=C1)C(=O)O[Si](C)(C)C3105.1Standard polar33892256
3,5-Diiodothyronine,3TMS,isomer #2C[Si](C)(C)OC1=CC=C(OC2=C(I)C=C(CC(C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)C=C2I)C=C13352.8Semi standard non polar33892256
3,5-Diiodothyronine,3TMS,isomer #2C[Si](C)(C)OC1=CC=C(OC2=C(I)C=C(CC(C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)C=C2I)C=C13037.3Standard non polar33892256
3,5-Diiodothyronine,3TMS,isomer #2C[Si](C)(C)OC1=CC=C(OC2=C(I)C=C(CC(C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)C=C2I)C=C13284.8Standard polar33892256
3,5-Diiodothyronine,3TMS,isomer #3C[Si](C)(C)OC(=O)C(CC1=CC(I)=C(OC2=CC=C(O)C=C2)C(I)=C1)N([Si](C)(C)C)[Si](C)(C)C3311.9Semi standard non polar33892256
3,5-Diiodothyronine,3TMS,isomer #3C[Si](C)(C)OC(=O)C(CC1=CC(I)=C(OC2=CC=C(O)C=C2)C(I)=C1)N([Si](C)(C)C)[Si](C)(C)C3011.1Standard non polar33892256
3,5-Diiodothyronine,3TMS,isomer #3C[Si](C)(C)OC(=O)C(CC1=CC(I)=C(OC2=CC=C(O)C=C2)C(I)=C1)N([Si](C)(C)C)[Si](C)(C)C3246.9Standard polar33892256
3,5-Diiodothyronine,4TMS,isomer #1C[Si](C)(C)OC(=O)C(CC1=CC(I)=C(OC2=CC=C(O[Si](C)(C)C)C=C2)C(I)=C1)N([Si](C)(C)C)[Si](C)(C)C3361.2Semi standard non polar33892256
3,5-Diiodothyronine,4TMS,isomer #1C[Si](C)(C)OC(=O)C(CC1=CC(I)=C(OC2=CC=C(O[Si](C)(C)C)C=C2)C(I)=C1)N([Si](C)(C)C)[Si](C)(C)C3007.0Standard non polar33892256
3,5-Diiodothyronine,4TMS,isomer #1C[Si](C)(C)OC(=O)C(CC1=CC(I)=C(OC2=CC=C(O[Si](C)(C)C)C=C2)C(I)=C1)N([Si](C)(C)C)[Si](C)(C)C3019.0Standard polar33892256
3,5-Diiodothyronine,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC=C(OC2=C(I)C=C(CC(N)C(=O)O)C=C2I)C=C13478.8Semi standard non polar33892256
3,5-Diiodothyronine,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(=O)C(N)CC1=CC(I)=C(OC2=CC=C(O)C=C2)C(I)=C13487.6Semi standard non polar33892256
3,5-Diiodothyronine,1TBDMS,isomer #3CC(C)(C)[Si](C)(C)NC(CC1=CC(I)=C(OC2=CC=C(O)C=C2)C(I)=C1)C(=O)O3524.0Semi standard non polar33892256
3,5-Diiodothyronine,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C(N)CC1=CC(I)=C(OC2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2)C(I)=C13725.5Semi standard non polar33892256
3,5-Diiodothyronine,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)NC(CC1=CC(I)=C(OC2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2)C(I)=C1)C(=O)O3735.7Semi standard non polar33892256
3,5-Diiodothyronine,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)NC(CC1=CC(I)=C(OC2=CC=C(O)C=C2)C(I)=C1)C(=O)O[Si](C)(C)C(C)(C)C3719.1Semi standard non polar33892256
3,5-Diiodothyronine,2TBDMS,isomer #4CC(C)(C)[Si](C)(C)N(C(CC1=CC(I)=C(OC2=CC=C(O)C=C2)C(I)=C1)C(=O)O)[Si](C)(C)C(C)(C)C3820.5Semi standard non polar33892256
3,5-Diiodothyronine,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC(CC1=CC(I)=C(OC2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2)C(I)=C1)C(=O)O[Si](C)(C)C(C)(C)C3936.0Semi standard non polar33892256
3,5-Diiodothyronine,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC(CC1=CC(I)=C(OC2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2)C(I)=C1)C(=O)O[Si](C)(C)C(C)(C)C3523.4Standard non polar33892256
3,5-Diiodothyronine,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC(CC1=CC(I)=C(OC2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2)C(I)=C1)C(=O)O[Si](C)(C)C(C)(C)C3393.5Standard polar33892256
3,5-Diiodothyronine,3TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=CC=C(OC2=C(I)C=C(CC(C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C2I)C=C14073.5Semi standard non polar33892256
3,5-Diiodothyronine,3TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=CC=C(OC2=C(I)C=C(CC(C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C2I)C=C13616.3Standard non polar33892256
3,5-Diiodothyronine,3TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=CC=C(OC2=C(I)C=C(CC(C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C2I)C=C13476.7Standard polar33892256
3,5-Diiodothyronine,3TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC(=O)C(CC1=CC(I)=C(OC2=CC=C(O)C=C2)C(I)=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C4043.1Semi standard non polar33892256
3,5-Diiodothyronine,3TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC(=O)C(CC1=CC(I)=C(OC2=CC=C(O)C=C2)C(I)=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3617.7Standard non polar33892256
3,5-Diiodothyronine,3TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC(=O)C(CC1=CC(I)=C(OC2=CC=C(O)C=C2)C(I)=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3440.5Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 3,5-Diiodothyronine GC-MS (Non-derivatized) - 70eV, Positivesplash10-004i-5200920000-b93c897ae4b72c23519b2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3,5-Diiodothyronine GC-MS (2 TMS) - 70eV, Positivesplash10-00di-9600058000-453c4267903543f11c762017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3,5-Diiodothyronine GC-MS (TMS_1_1) - 70eV, PositiveNot Available2021-11-03Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3,5-Diiodothyronine GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-11-03Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3,5-Diiodothyronine GC-MS (TMS_1_3) - 70eV, PositiveNot Available2021-11-03Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3,5-Diiodothyronine GC-MS (TMS_2_2) - 70eV, PositiveNot Available2021-11-03Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3,5-Diiodothyronine GC-MS (TMS_2_3) - 70eV, PositiveNot Available2021-11-03Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3,5-Diiodothyronine GC-MS (TMS_2_4) - 70eV, PositiveNot Available2021-11-03Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3,5-Diiodothyronine GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-11-03Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3,5-Diiodothyronine GC-MS (TBDMS_1_2) - 70eV, PositiveNot Available2021-11-03Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3,5-Diiodothyronine GC-MS (TBDMS_1_3) - 70eV, PositiveNot Available2021-11-03Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3,5-Diiodothyronine GC-MS (TBDMS_2_1) - 70eV, PositiveNot Available2021-11-03Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3,5-Diiodothyronine GC-MS (TBDMS_2_2) - 70eV, PositiveNot Available2021-11-03Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3,5-Diiodothyronine GC-MS (TBDMS_2_3) - 70eV, PositiveNot Available2021-11-03Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3,5-Diiodothyronine GC-MS (TBDMS_2_4) - 70eV, PositiveNot Available2021-11-03Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - 3,5-Diiodothyronine Quattro_QQQ 10V, Positive-QTOF (Annotated)splash10-004i-0000090000-0c32e1647fb8ad73f0b72012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3,5-Diiodothyronine Quattro_QQQ 25V, Positive-QTOF (Annotated)splash10-003r-0003970000-f35e706ebe5a01fd53a02012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3,5-Diiodothyronine Quattro_QQQ 40V, Positive-QTOF (Annotated)splash10-0fb9-0129700000-6535af9505fe3bcdc4642012-07-24HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,5-Diiodothyronine 10V, Positive-QTOFsplash10-004i-0100890000-a4c3898b3f5e77f46dbe2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,5-Diiodothyronine 20V, Positive-QTOFsplash10-004i-0000910000-e0bf5e5b19dbc8da39832017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,5-Diiodothyronine 40V, Positive-QTOFsplash10-016u-2009200000-ed00e535f6a635c85b0f2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,5-Diiodothyronine 10V, Negative-QTOFsplash10-00di-0100090000-71fa162482707b5eb3d72017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,5-Diiodothyronine 20V, Negative-QTOFsplash10-0ab9-1600390000-2a1c97e2e04e68ad85212017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,5-Diiodothyronine 40V, Negative-QTOFsplash10-05iu-9102200000-a695396d7ea8bb382a702017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,5-Diiodothyronine 10V, Positive-QTOFsplash10-004i-0000290000-18b94b7e0180ef2e9c952021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,5-Diiodothyronine 20V, Positive-QTOFsplash10-004i-0000920000-c6b727eb99ca0e5a19922021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,5-Diiodothyronine 40V, Positive-QTOFsplash10-004i-4203900000-460478b6a64a00caf41a2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,5-Diiodothyronine 10V, Negative-QTOFsplash10-00di-0000090000-2c48801ad2bd401ad2c32021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,5-Diiodothyronine 20V, Negative-QTOFsplash10-00fr-1800290000-803aa569bbb8878983f92021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,5-Diiodothyronine 40V, Negative-QTOFsplash10-004i-0900000000-0dba40d354fa6a5575e02021-09-24Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CD3OD, experimental)2012-12-05Wishart LabView Spectrum
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)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 ]
  13. Senese R, de Lange P, Petito G, Moreno M, Goglia F, Lanni A: 3,5-Diiodothyronine: A Novel Thyroid Hormone Metabolite and Potent Modulator of Energy Metabolism. Front Endocrinol (Lausanne). 2018 Jul 25;9:427. doi: 10.3389/fendo.2018.00427. eCollection 2018. [PubMed:30090086 ]
  14. Antonelli A, Fallahi P, Ferrari SM, Di Domenicantonio A, Moreno M, Lanni A, Goglia F: 3,5-diiodo-L-thyronine increases resting metabolic rate and reduces body weight without undesirable side effects. J Biol Regul Homeost Agents. 2011 Oct-Dec;25(4):655-60. [PubMed:22217997 ]