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Record Information
Version4.0
Creation Date2006-05-22 15:12:06 UTC
Update Date2017-09-27 08:24:18 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
Thumb
Synonyms
ValueSource
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 sulphateHMDB
Thyroxine-4-sulfateMeSH
T4 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
DescriptionThis compound belongs to the class of chemical entities known as phenylalanine and derivatives. These 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.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganic acids and derivatives
Sub ClassCarboxylic acids and derivatives
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

Health effect:

  Health condition:

    Endocrine disorders:

Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

  Organ and components:

Source:

Role

Biological role:

  Molecular messenger:

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 Solubility0.0047 g/LALOGPS
logP0.81ALOGPS
logP4.31ChemAxon
logS-5.3ALOGPS
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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MSNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane (predicted from logP)
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Liver
PathwaysNot Available
NameSMPDB/PathwhizKEGG
No entries found
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
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 Quantified Not AvailableNot AvailableNormal
    details
    Abnormal Concentrations
    BiofluidStatusValueAgeSexConditionReferenceDetails
    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 IDs
    DrugBank IDNot Available
    DrugBank Metabolite IDDBMET00555
    Phenol Explorer Compound IDNot Available
    Phenol Explorer Metabolite IDNot Available
    FoodDB 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
    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