ChemFOnt: Showing chemical card for Thyroxine glucuronide (CFc000006334)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:52:17 UTC

Chemfont ID

CFc000006334

Molecule Identification

Common Name

Thyroxine glucuronide

Definition

Thyroxine glucuronide is a natural human metabolite of thyroxine 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

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(S)-4-[4-(2-Amino-2-carboxyethyl)-2,6-diiodophenoxy]-2,6-diiodophenyl beta-D-glucopyranosiduronic acid	HMDB
(S)-4-[4-(2-Amino-2-carboxyethyl)-2,6-diiodophenoxy]-2,6-diiodophenyl beta-delta-glucopyranosiduronate	HMDB
(S)-4-[4-(2-Amino-2-carboxyethyl)-2,6-diiodophenoxy]-2,6-diiodophenyl beta-delta-glucopyranosiduronic acid	HMDB
beta-D 4-[4-(L-2-Amino-2-carboxyethyl)-2,6-diiodophenoxy]-2,6-diiodophenyl glucopyranosiduronate	HMDB
beta-D 4-[4-(L-2-Amino-2-carboxyethyl)-2,6-diiodophenoxy]-2,6-diiodophenyl glucopyranosiduronic acid	HMDB
L-Thyroxine glucuronide	HMDB
T4G	HMDB
(2S,3S,4S,5R)-6-(4-{4-[(2S)-2-amino-2-carboxyethyl]-2,6-diiodophenoxy}-2,6-diiodophenoxy)-3,4,5-trihydroxyoxane-2-carboxylate	HMDB
Thyroxine glucuronide	MeSH

Chemical Formula

C₂₁H₁₉I₄NO₁₀

Average Molecular Weight

952.9941

Monoisotopic Molecular Weight

952.718769513

IUPAC Name

(2S,3S,4S,5R)-6-(4-{4-[(2S)-2-amino-2-carboxyethyl]-2,6-diiodophenoxy}-2,6-diiodophenoxy)-3,4,5-trihydroxyoxane-2-carboxylic acid

Traditional Name

thyroxine glucuronide

CAS Registry Number

21462-56-6

SMILES

N[C@@H](CC1=CC(I)=C(OC2=CC(I)=C(OC3O[C@@H]([C@@H](O)[C@H](O)[C@H]3O)C(O)=O)C(I)=C2)C(I)=C1)C(O)=O

InChI Identifier

InChI=1S/C21H19I4NO10/c22-8-1-6(3-12(26)19(30)31)2-9(23)16(8)34-7-4-10(24)17(11(25)5-7)35-21-15(29)13(27)14(28)18(36-21)20(32)33/h1-2,4-5,12-15,18,21,27-29H,3,26H2,(H,30,31)(H,32,33)/t12-,13-,14-,15+,18-,21?/m0/s1

InChI Key

RGHRJBIKIYUHEV-SGPDEFQSSA-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.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Phenylalanine 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 Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (HMDB: HMDB0010326)

Organ

Liver (HMDB: HMDB0010326)
Kidney (HMDB: HMDB0010326)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0010326)

Cellular substructure

Cytoplasm (HMDB: HMDB0010326)

Source

Endogenous

Endogenous (HMDB: HMDB0010326)

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Process

Not Available

Role

Biological role

Drug metabolite (HMDB: HMDB0010326)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.073 g/L	ALOGPS
logP	0.58	ALOGPS
logP	1.69	ChemAxon
logS	-4.1	ALOGPS
pKa (Strongest Acidic)	0.26	ChemAxon
pKa (Strongest Basic)	9.43	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	189 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	158.8 m³·mol⁻¹	ChemAxon
Polarizability	63.82 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

HMDB0010326

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB027478

KNApSAcK ID

Not Available

Chemspider ID

134339

KEGG Compound ID

Not Available

BioCyc ID

Beta-D-Glucuronides

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

152424

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for Thyroxine glucuronide (CFc000006334)

MOL for CFc000006334 (Thyroxine glucuronide)

3D MOL for CFc000006334 (Thyroxine glucuronide)

3D SDF for CFc000006334 (Thyroxine glucuronide)

3D-SDF for CFc000006334 (Thyroxine glucuronide)

PDB for CFc000006334 (Thyroxine glucuronide)

3D PDB for CFc000006334 (Thyroxine glucuronide)

SMILES for CFc000006334 (Thyroxine glucuronide)

INCHI for CFc000006334 (Thyroxine glucuronide)

Structure for CFc000006334 (Thyroxine glucuronide)

3D Structure for CFc000006334 (Thyroxine glucuronide)