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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2006-05-22 15:12:06 UTC
Update Date2021-09-14 15:20:03 UTC
HMDB IDHMDB0002728
Secondary Accession Numbers
  • HMDB02728
Metabolite Identification
Common NameThyroxine sulfate
DescriptionThyroxine Sulfate (abbreviated T4) is a major Thyroid hormone metabolite secreted by follicular cells of the Thyroid gland. T4 is transported in blood, with 99.95% of the secreted T4 being protein bound, principally to thyroxine binding globulin (TBG) and to a lesser extent to thyroxine binding pre-albumin (TBPA) and serum albumin. T4 is involved in controlling the rate of metabolic processes in the body and influencing physical development. T4 is considered a prohormone and a reservoir for the active thyroid hormone triiodothyronine (T3), T4 being converted as required in the tissues by deiodinases.
Structure
Data?1582752255
Synonyms
ValueSource
Thyroxine sulfuric acidGenerator
Thyroxine sulphateGenerator
Thyroxine sulphuric acidGenerator
3,5,3',5'-Tetraiodo-L-thyronine 4'-O-sulfateHMDB
3,5,3',5'-Tetraiodo-L-thyronine 4'-O-sulphateHMDB
3,5,3',5'-Tetraiodo-L-thyronine 4-O-sulfateHMDB
3,5,3',5'-Tetraiodo-L-thyronine 4-O-sulphateHMDB
3-[4-(4-Hydroxy-3,5-diiodophenoxy-4-O-sulfate)-3,5-diiodophenyl]-L-alanineHMDB
3-[4-(4-Hydroxy-3,5-diiodophenoxy-4-O-sulphate)-3,5-diiodophenyl]-L-alanineHMDB
L-Thyroxine 4'-O-sulfateHMDB
L-Thyroxine 4'-O-sulphateHMDB
O-(4-Hydroxy-3,5-diiodophenyl-4-O-sulfate)-3,5-diiodo-L-tyrosineHMDB
O-(4-Hydroxy-3,5-diiodophenyl-4-O-sulphate)-3,5-diiodo-L-tyrosineHMDB
T4SHMDB
Thyroxine-4-sulfateHMDB
T4 SulfateHMDB
(2S)-2-Amino-3-{4-[3,5-diiodo-4-(sulfooxy)phenoxy]-3,5-diiodophenyl}propanoateHMDB
(2S)-2-Amino-3-{4-[3,5-diiodo-4-(sulphooxy)phenoxy]-3,5-diiodophenyl}propanoateHMDB
(2S)-2-Amino-3-{4-[3,5-diiodo-4-(sulphooxy)phenoxy]-3,5-diiodophenyl}propanoic acidHMDB
Thyroxine sulfateMeSH
Chemical FormulaC15H11I4NO7S
Average Molecular Weight856.933
Monoisotopic Molecular Weight856.643496081
IUPAC Name(2S)-2-amino-3-{4-[3,5-diiodo-4-(sulfooxy)phenoxy]-3,5-diiodophenyl}propanoic acid
Traditional Namethyroxine sulfic acid
CAS Registry Number77074-49-8
SMILES
N[C@@H](CC1=CC(I)=C(OC2=CC(I)=C(OS(O)(=O)=O)C(I)=C2)C(I)=C1)C(O)=O
InChI Identifier
InChI=1S/C15H11I4NO7S/c16-8-1-6(3-12(20)15(21)22)2-9(17)13(8)26-7-4-10(18)14(11(19)5-7)27-28(23,24)25/h1-2,4-5,12H,3,20H2,(H,21,22)(H,23,24,25)/t12-/m0/s1
InChI KeyQYXIJUZWSSQICT-LBPRGKRZSA-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
  • 3-phenylpropanoic-acid
  • Phenylsulfate
  • Diaryl ether
  • Alpha-amino acid
  • Amphetamine or derivatives
  • L-alpha-amino acid
  • Arylsulfate
  • Phenoxy compound
  • Phenol ether
  • Halobenzene
  • Aralkylamine
  • Iodobenzene
  • Monocyclic benzene moiety
  • Benzenoid
  • Sulfuric acid ester
  • Sulfate-ester
  • Sulfuric acid monoester
  • Aryl halide
  • Aryl iodide
  • Organic sulfuric acid or derivatives
  • Amino acid
  • Carboxylic acid
  • Ether
  • Monocarboxylic acid or derivatives
  • Primary aliphatic amine
  • Organonitrogen compound
  • Organooxygen compound
  • Amine
  • Primary amine
  • Organic nitrogen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Organohalogen compound
  • Organoiodide
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Physiological effect

Adverse health effect

Disposition

Biological location

Source

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Spectral PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.0047 g/LALOGPS
logP10(0.81) g/LALOGPS
logP10(4.31) g/LChemAxon
logS10(-5.3) g/LALOGPS
pKa (Strongest Acidic)-3ChemAxon
pKa (Strongest Basic)9.43ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area136.15 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity136.78 m³·mol⁻¹ChemAxon
Polarizability54.41 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Spectral Properties

Predicted Kovats Retention Indices

Not Available
Spectra

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Thyroxine sulfate 10V, Positive-QTOFsplash10-08fu-0000000190-60a2d3c20ec6cb9d1c692016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Thyroxine sulfate 20V, Positive-QTOFsplash10-03ec-0000000960-1acc6f8ba4fa640eea142016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Thyroxine sulfate 40V, Positive-QTOFsplash10-016r-0009201200-f3a8fb5f5d259b4a08de2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Thyroxine sulfate 10V, Negative-QTOFsplash10-0a4i-0000000190-dcd5150fd64eb9666b362016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Thyroxine sulfate 20V, Negative-QTOFsplash10-056r-1001200930-81382d7ac99b1b2065042016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Thyroxine sulfate 40V, Negative-QTOFsplash10-00am-9004204800-333dbdf28ab736330d4a2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Thyroxine sulfate 10V, Negative-QTOFsplash10-0a4i-0000000090-d55170c46c67ae342e9e2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Thyroxine sulfate 20V, Negative-QTOFsplash10-056r-2800000190-20c0887d6c545eb80a282021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Thyroxine sulfate 40V, Negative-QTOFsplash10-004i-0900000000-0dba40d354fa6a5575e02021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Thyroxine sulfate 10V, Positive-QTOFsplash10-0a4i-0000000090-0f9cdad016a751aa1ba62021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Thyroxine sulfate 20V, Positive-QTOFsplash10-03di-0000000290-c5f42e3c3ab1663956b82021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Thyroxine sulfate 40V, Positive-QTOFsplash10-0fai-0000000900-4ef5f51f90403aad561a2021-09-25Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane (predicted from logP)
Biospecimen Locations
  • Blood
  • Urine
Tissue Locations
  • Kidney
  • Liver
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.000019 +/- 0.0000012 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.000021 +/- 0.0000043 uMAdult (>18 years old)FemaleNormal details
BloodDetected and Quantified0.000245 +/- 0.000026 uMNewborn (0-30 days old)Both
Normal
details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableNormal
      Not Available
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.000033 +/- 0.000010 uMAdult (>18 years old)Both
Hyperthyroidism
details
BloodDetected and Quantified0.000042 +/- 0.000015 uMAdult (>18 years old)BothHypothyroidism details
BloodDetected and Quantified0.000034 +/- 0.0000069 uMAdult (>18 years old)Both
Euthyroidism
details
Associated Disorders and Diseases
Disease References
Hyperthyroidism
  1. Chopra IJ, Santini F, Hurd RE, Chua Teco GN: A radioimmunoassay for measurement of thyroxine sulfate. J Clin Endocrinol Metab. 1993 Jan;76(1):145-50. [PubMed:8421080 ]
Hypothyroidism
  1. Chopra IJ, Santini F, Hurd RE, Chua Teco GN: A radioimmunoassay for measurement of thyroxine sulfate. J Clin Endocrinol Metab. 1993 Jan;76(1):145-50. [PubMed:8421080 ]
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB023056
KNApSAcK IDNot Available
Chemspider ID116397
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID988
PubChem Compound131742
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDMDB00000400
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Chopra IJ, Santini F, Hurd RE, Chua Teco GN: A radioimmunoassay for measurement of thyroxine sulfate. J Clin Endocrinol Metab. 1993 Jan;76(1):145-50. [PubMed:8421080 ]
  2. Wu SY, Huang WS, Polk D, Florsheim WH, Green WL, Fisher DA: Identification of thyroxine-sulfate (T4S) in human serum and amniotic fluid by a novel T4S radioimmunoassay. Thyroid. 1992 Summer;2(2):101-5. [PubMed:1525576 ]
  3. Peeters RP, Kester MH, Wouters PJ, Kaptein E, van Toor H, Visser TJ, Van den Berghe G: Increased thyroxine sulfate levels in critically ill patients as a result of a decreased hepatic type I deiodinase activity. J Clin Endocrinol Metab. 2005 Dec;90(12):6460-5. Epub 2005 Sep 27. [PubMed:16189257 ]
  4. Wu S, Polk D, Wong S, Reviczky A, Vu R, Fisher DA: Thyroxine sulfate is a major thyroid hormone metabolite and a potential intermediate in the monodeiodination pathways in fetal sheep. Endocrinology. 1992 Oct;131(4):1751-6. [PubMed:1396320 ]
  5. Huang WS, Cherng SC, Wang CH, Shih BF, Kuo SW, Wu SY: Increased urinary thyroxine sulfate excretion in thyroxine therapy. Endocr J. 1997 Aug;44(4):467-72. [PubMed:9447277 ]

Enzymes

General function:
Involved in thyroxine 5'-deiodinase activity
Specific function:
Responsible for the deiodination of T4 (3,5,3',5'-tetraiodothyronine) into T3 (3,5,3'-triiodothyronine) and of T3 into T2 (3,3'-diiodothyronine). Plays a role in providing a source of plasma T3 by deiodination of T4 in peripheral tissues such as liver and kidney.
Gene Name:
DIO1
Uniprot ID:
P49895
Molecular weight:
28924.21
General function:
Involved in thyroxine 5'-deiodinase activity
Specific function:
Responsible for the deiodination of T4 (3,5,3',5'-tetraiodothyronine) into T3 (3,5,3'-triiodothyronine). Essential for providing the brain with appropriate levels of T3 during the critical period of development.
Gene Name:
DIO2
Uniprot ID:
Q92813
Molecular weight:
30551.48
General function:
Involved in thyroxine 5'-deiodinase activity
Specific function:
Responsible for the deiodination of T4 (3,5,3',5'-tetraiodothyronine) into RT3 (3,3',5'-triiodothyronine) and of T3 (3,5,3'-triiodothyronine) into T2 (3,3'-diiodothyronine). RT3 and T2 are inactive metabolites. May play a role in preventing premature exposure of developing fetal tissues to adult levels of thyroid hormones. Can regulate circulating fetal thyroid hormone concentrations throughout gestation. Essential role for regulation of thyroid hormone inactivation during embryological development.
Gene Name:
DIO3
Uniprot ID:
P55073
Molecular weight:
33947.175