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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2008-09-16 08:08:59 UTC
Update Date2019-05-22 17:22:10 UTC
HMDB IDHMDB0010346
Secondary Accession Numbers
  • HMDB0062203
  • HMDB10346
  • HMDB62203
Metabolite Identification
Common NameTriiodothyronine glucuronide
DescriptionTriiodothyronine glucuronide is a natural human metabolite of triiodothyronine generated in the liver by UDP glucuonyltransferase. Glucuronidation is used to assist in the excretion of toxic substances, drugs, or other substances that cannot be used as an energy source. Glucuronic acid is attached via a glycosidic bond to the substance, and the resulting glucuronide, which has a much higher water solubility than the original substance, is eventually excreted by the kidneys.
Structure
Data?1558545730
Synonyms
ValueSource
(S)-4-(4-(2-Amino-2-carboxyethyl)-2,6-diiodophenoxy)-2-iodophenyl-beta-D-glucopyranosiduronic acidHMDB
(S)-4-(4-(2-Amino-2-carboxyethyl)-2,6-diiodophenoxy)-2-iodophenyl-beta-delta-glucopyranosiduronic acidHMDB
Triiodothyronine glucuronosideHMDB
T3GHMDB
(2S,3S,4S,5R,6S)-6-(4-{4-[(2S)-2-amino-2-carboxyethyl]-2,6-diiodophenoxy}-2-iodophenoxy)-3,4,5-trihydroxyoxane-2-carboxylateGenerator
Triiodothyronine glucuronideMeSH
3,3',5-Triiodo-L-thyronine 4'-O-beta-D-glucuronideHMDB
3,3',5-Triiodo-L-thyronine 4'-O-β-D-glucuronideHMDB
3,3',5-Triiodo-L-thyronine O-beta-D-GlucuronideHMDB
3,3',5-Triiodothyronine O-beta-D-glucuronideHMDB
3,3',5-Triiodothyronine glucuronideHMDB
3,3,5-Triiodo-L-thyronine-beta-D-glucuronosideHMDB
3,3,5-Triiodo-L-thyronine-β-D-glucuronosideHMDB
3,3’,5-Triiodo-L-thyronine 4’-O-β-D-glucuronideHMDB
3,3’,5-Triiodo-L-thyronine O-β-D-GlucuronideHMDB
3,3’,5-Triiodothyronine O-β-D-glucuronideHMDB
3,3’,5-Triiodothyronine glucuronideHMDB
3,5,3'-Triiodothyronine glucuronideHMDB
3,5,3’-Triiodothyronine glucuronideHMDB
Triiodothyronine O-beta-D-glucuronideHMDB
Triiodothyronine O-β-D-glucuronideHMDB
Chemical FormulaC21H20I3NO10
Average Molecular Weight827.0976
Monoisotopic Molecular Weight826.822126125
IUPAC Name(2S,3S,4S,5R,6S)-6-(4-{4-[(2S)-2-amino-2-carboxyethyl]-2,6-diiodophenoxy}-2-iodophenoxy)-3,4,5-trihydroxyoxane-2-carboxylic acid
Traditional Nametriiodothyronine glucuronide
CAS Registry Number29919-72-0
SMILES
N[C@@H](CC1=CC(I)=C(OC2=CC(I)=C(O[C@@H]3O[C@@H]([C@@H](O)[C@H](O)[C@H]3O)C(O)=O)C=C2)C(I)=C1)C(O)=O
InChI Identifier
InChI=1S/C21H20I3NO10/c22-9-6-8(33-17-10(23)3-7(4-11(17)24)5-12(25)19(29)30)1-2-13(9)34-21-16(28)14(26)15(27)18(35-21)20(31)32/h1-4,6,12,14-16,18,21,26-28H,5,25H2,(H,29,30)(H,31,32)/t12-,14-,15-,16+,18-,21+/m0/s1
InChI KeyYYFGGGCINNGOLE-ZDXOGFQLSA-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
  • Phenolic glycoside
  • O-glucuronide
  • 1-o-glucuronide
  • Diphenylether
  • Glucuronic acid or derivatives
  • Hexose monosaccharide
  • 3-phenylpropanoic-acid
  • O-glycosyl compound
  • Glycosyl compound
  • Diaryl ether
  • Amphetamine or derivatives
  • L-alpha-amino acid
  • Alpha-amino acid
  • Phenoxy compound
  • Phenol ether
  • Halobenzene
  • Aralkylamine
  • Iodobenzene
  • Beta-hydroxy acid
  • Aryl halide
  • Aryl iodide
  • Monocyclic benzene moiety
  • Dicarboxylic acid or derivatives
  • Hydroxy acid
  • Benzenoid
  • Monosaccharide
  • Pyran
  • Oxane
  • Secondary alcohol
  • Amino acid
  • Acetal
  • Polyol
  • Carboxylic acid
  • Organoheterocyclic compound
  • Oxacycle
  • Ether
  • Primary aliphatic amine
  • Hydrocarbon derivative
  • Amine
  • Organic oxide
  • Organic oxygen compound
  • Carbonyl group
  • Organopnictogen compound
  • Alcohol
  • Primary amine
  • Organohalogen compound
  • Organoiodide
  • Organonitrogen compound
  • Organooxygen compound
  • Organic nitrogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Source:

Biological location:

Role

Biological role:

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 Solubility0.067 g/LALOGPS
logP-0.15ALOGPS
logP0.77ChemAxon
logS-4.1ALOGPS
pKa (Strongest Acidic)0.29ChemAxon
pKa (Strongest Basic)9.43ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area189 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity145.44 m³·mol⁻¹ChemAxon
Polarizability59.63 ųChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0pc0-0000009660-4b8db75411fb4ad3840bJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0zgi-0000009100-ae2bd193ecb19a0b6425JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0uxr-0133159000-b987c4874aea3d80ebd5JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-005a-2200006490-37ebd7b467add975a4c4JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000t-2200009210-1fc55e521a5e081aca43JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-007k-5100119000-cea3decba2c3578e5a88JSpectraViewer | MoNA
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Urine
Tissue Locations
  • Kidney
  • Liver
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableNormal
    details
    UrineExpected but not Quantified Not AvailableNot AvailableNormal
      details
      Abnormal Concentrations
      Not Available
      Associated Disorders and Diseases
      Disease ReferencesNone
      Associated OMIM IDsNone
      DrugBank IDNot Available
      Phenol Explorer Compound IDNot Available
      FoodDB IDFDB027498
      KNApSAcK IDNot Available
      Chemspider ID2338495
      KEGG Compound IDNot Available
      BioCyc IDNot Available
      BiGG IDNot Available
      Wikipedia LinkNot Available
      METLIN IDNot Available
      PubChem Compound3080759
      PDB IDNot Available
      ChEBI IDNot Available
      References
      Synthesis ReferenceNot Available
      Material Safety Data Sheet (MSDS)Not Available
      General ReferencesNot Available

      Only showing the first 10 proteins. There are 18 proteins in total.

      Enzymes

      General function:
      Involved in transferase activity, transferring hexosyl groups
      Specific function:
      UDPGTs are of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isozyme has glucuronidating capacity with steroid substrates such as 5-beta-androstane 3-alpha,17-beta-diol, estradiol, ADT, eugenol and bile acids. Only isoform 1 seems to be active.
      Gene Name:
      UGT2B28
      Uniprot ID:
      Q9BY64
      Molecular weight:
      38742.9
      General function:
      Involved in transferase activity, transferring hexosyl groups
      Specific function:
      UDPGTs are of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isozyme is active on polyhydroxylated estrogens (such as estriol, 4-hydroxyestrone and 2-hydroxyestriol) and xenobiotics (such as 4-methylumbelliferone, 1-naphthol, 4-nitrophenol, 2-aminophenol, 4-hydroxybiphenyl and menthol). It is capable of 6 alpha-hydroxyglucuronidation of hyodeoxycholic acid.
      Gene Name:
      UGT2B4
      Uniprot ID:
      P06133
      Molecular weight:
      60512.035
      General function:
      Involved in transferase activity, transferring hexosyl groups
      Specific function:
      UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate.
      Gene Name:
      UGT1A4
      Uniprot ID:
      P22310
      Molecular weight:
      60024.535
      General function:
      Involved in transferase activity, transferring hexosyl groups
      Specific function:
      UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. Its unique specificity for 3,4-catechol estrogens and estriol suggests it may play an important role in regulating the level and activity of these potent and active estrogen metabolites. Is also active with androsterone, hyodeoxycholic acid and tetrachlorocatechol (in vitro).
      Gene Name:
      UGT2B7
      Uniprot ID:
      P16662
      Molecular weight:
      60720.15
      General function:
      Involved in transferase activity, transferring hexosyl groups
      Specific function:
      UDPGTs are of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isozyme displays activity toward several classes of xenobiotic substrates, including simple phenolic compounds, 7-hydroxylated coumarins, flavonoids, anthraquinones, and certain drugs and their hydroxylated metabolites. It also catalyzes the glucuronidation of endogenous estrogens and androgens.
      Gene Name:
      UGT2B15
      Uniprot ID:
      P54855
      Molecular weight:
      61035.815
      General function:
      Involved in transferase activity, transferring hexosyl groups
      Specific function:
      UDP-glucuronosyltransferases catalyze phase II biotransformation reactions in which lipophilic substrates are conjugated with glucuronic acid to increase water solubility and enhance excretion. They are of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. Active on odorants and seems to be involved in olfaction; it could help clear lipophilic odorant molecules from the sensory epithelium.
      Gene Name:
      UGT2A1
      Uniprot ID:
      Q9Y4X1
      Molecular weight:
      60771.605
      General function:
      Involved in transferase activity, transferring hexosyl groups
      Specific function:
      UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
      Gene Name:
      UGT1A1
      Uniprot ID:
      P22309
      Molecular weight:
      59590.91
      General function:
      Involved in transferase activity, transferring hexosyl groups
      Specific function:
      UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform has specificity for phenols.
      Gene Name:
      UGT1A9
      Uniprot ID:
      O60656
      Molecular weight:
      59940.495
      General function:
      Involved in transferase activity, transferring hexosyl groups
      Specific function:
      UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds.
      Gene Name:
      UGT1A3
      Uniprot ID:
      P35503
      Molecular weight:
      60337.835
      General function:
      Involved in transferase activity, transferring hexosyl groups
      Specific function:
      UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. The major substrates of this isozyme are eugenol > 4-methylumbelliferone > dihydrotestosterone (DHT) > androstane-3-alpha,17-beta-diol (3-alpha-diol) > testosterone > androsterone (ADT).
      Gene Name:
      UGT2B17
      Uniprot ID:
      O75795
      Molecular weight:
      61094.915

      Only showing the first 10 proteins. There are 18 proteins in total.