ChemFOnt: Showing chemical card for 2-amino-3-[4-(4-hydroxy-3,5-diiodophenoxy)-3,5-diiodophenyl]propanoic acid (CFc000165283)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 23:57:33 UTC

Chemfont ID

CFc000165283

Molecule Identification

Common Name

2-amino-3-[4-(4-hydroxy-3,5-diiodophenoxy)-3,5-diiodophenyl]propanoic acid

Definition

Thyroxine, also known as T4 or levothyroxin, 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. Thyroxine is a very strong basic compound (based on its pKa). Thyroxine exists in all living organisms, ranging from bacteria to humans. In humans, thyroxine is involved in thyroid hormone synthesis.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
3,3',5,5'-Tetraiodo-L-thyronine	ChEBI
3,5,3',5'-TETRAIODO-L-thyronine	ChEBI
4-(4-Hydroxy-3,5-diiodophenoxy)-3,5-diiodo-L-phenylalanine	ChEBI
L-T4	ChEBI
Levothyroxin	ChEBI
Levothyroxine	ChEBI
LT4	ChEBI
O-(4-Hydroxy-3,5-diiodophenyl)-3,5-diiodo-L-tyrosine	ChEBI
T4	ChEBI
L-Thyroxine	Kegg
O-(4-Hydroxy-3,5-diidophenyl)-3,5-diiodo-L-tyrosine	Kegg
3,5,3'5'-Tetraiodo-L-thyronine	Kegg
Forthyron	Kegg
(-)-Thyroxine	HMDB
3,3',5,5''-tetraiodo-L-Thyronine	HMDB
3,5,3',5'-Tetraiodothyronine	HMDB, MeSH
D-Thyroxine	HMDB
DL-Thyroxin	HMDB
Henning	HMDB
L-3,5,3',5'-Tetraiodothyronine	HMDB, MeSH
L-Thyroxin	HMDB
Laevothyroxinum	HMDB
Levothroid	HMDB, MeSH
Levothyroxine sodium	HMDB, MeSH
Levothyroxinum	HMDB
Levoxyl	HMDB, MeSH
Prestwick_548	HMDB
Synthroid	HMDB, MeSH
Tetraiodothyronine	HMDB
Tetramet	HMDB
THX	HMDB
Thyratabs	HMDB
Thyrax	HMDB, MeSH
Thyreoideum	HMDB
Thyroxin	HMDB, MeSH
Thyroxinal	HMDB
Thyroxine I 125	HMDB
Thyroxine iodine	HMDB
Allphar brand OF levothyroxine sodium	MeSH, HMDB
Berlthyrox	MeSH, HMDB
Delalande, levothyroxin	MeSH, HMDB
Dexnon	MeSH, HMDB
Eferox	MeSH, HMDB
Eltroxin	MeSH, HMDB
Kern brand OF levothyroxine sodium	MeSH, HMDB
L-Thyrox	MeSH, HMDB
L-Thyroxin henning	MeSH, HMDB
L-Thyroxin beta	MeSH, HMDB
L-Thyroxine roche	MeSH, HMDB
Levothyroxin deladande	MeSH, HMDB
Lévothyrox	MeSH, HMDB
Merck lipha santé brand OF levothyroxine sodium	MeSH, HMDB
Nourypharma brand OF levothyroxine sodium	MeSH, HMDB
Oroxine	MeSH, HMDB
Aventis brand OF levothyroxine sodium	MeSH, HMDB
Euthyrox	MeSH, HMDB
Eutirox	MeSH, HMDB
Forest brand OF levothyroxine sodium	MeSH, HMDB
Genpharm brand OF levothyroxine sodium	MeSH, HMDB
GlaxoSmithKline brand OF levothyroxine sodium	MeSH, HMDB
Goldshield brand OF levothyroxine sodium	MeSH, HMDB
LThyroxin henning	MeSH, HMDB
levo-T	MeSH, HMDB
Sanofi synthelabo brand OF levothyroxine sodium	MeSH, HMDB
Sigma brand OF levothyroxine sodium	MeSH, HMDB
Synthrox	MeSH, HMDB
Thevier	MeSH, HMDB
Watson brand OF levothyroxine sodium	MeSH, HMDB
Berlin chemie brand OF levothyroxine sodium	MeSH, HMDB
Delalande brand OF levothyroxine sodium	MeSH, HMDB
Eltroxine	MeSH, HMDB
Hexal brand 2 OF levothyroxine sodium	MeSH, HMDB
L Thyroxine roche	MeSH, HMDB
Novothyral	MeSH, HMDB
Tiroidine	MeSH, HMDB
Vortex brand OF levothyroxine sodium	MeSH, HMDB
Abbot brand OF levothyroxine sodium	MeSH, HMDB
Berlin-chemie brand OF levothyroxine sodium	MeSH, HMDB
Byk brand OF levothyroxine sodium	MeSH, HMDB
Deladande, levothyroxin	MeSH, HMDB
GlaxoWellcome brand OF levothyroxine sodium	MeSH, HMDB
Henning berlin brand OF levothyroxine sodium	MeSH, HMDB
Hexal brand 1 OF levothyroxine sodium	MeSH, HMDB
L Thyrox	MeSH, HMDB
L Thyroxin henning	MeSH, HMDB
L Thyroxin beta	MeSH, HMDB
L Thyroxine	MeSH, HMDB
LThyroxin beta	MeSH, HMDB
leo, Tiroxina	MeSH, HMDB
levo T	MeSH, HMDB
LevoT	MeSH, HMDB
Levothyroid	MeSH, HMDB
Levothyroxin delalande	MeSH, HMDB
Levoxine	MeSH, HMDB
Merck brand OF levothyroxine sodium	MeSH, HMDB
Monarch brand OF levothyroxine sodium	MeSH, HMDB
Mova brand OF levothyroxine sodium	MeSH, HMDB
Novothyrox	MeSH, HMDB
O-(4-Hydroxy-3,5-diiodophenyl) 3,5-diiodo-L-tyrosine	MeSH, HMDB
O-(4-Hydroxy-3,5-diiodophenyl)-3,5-diiodotyrosine	MeSH, HMDB
Roche brand OF levothyroxine sodium	MeSH, HMDB
Rudefsa brand OF levothyroxine sodium	MeSH, HMDB
Sodium levothyroxine	MeSH, HMDB
T4 Thyroid hormone	MeSH, HMDB
Thyroid hormone, T4	MeSH, HMDB
Tiroxina leo	MeSH, HMDB
Unithroid	MeSH, HMDB
Betapharm brand OF levothyroxine sodium	MeSH, HMDB

Chemical Formula

C₁₅H₁₁I₄NO₄

Average Molecular Weight

776.87

Monoisotopic Molecular Weight

776.686681525

IUPAC Name

(2S)-2-amino-3-[4-(4-hydroxy-3,5-diiodophenoxy)-3,5-diiodophenyl]propanoic acid

Traditional Name

levothyroxine

CAS Registry Number

51-48-9

SMILES

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

InChI Identifier

InChI=1S/C15H11I4NO4/c16-8-4-7(5-9(17)13(8)21)24-14-10(18)1-6(2-11(14)19)3-12(20)15(22)23/h1-2,4-5,12,21H,3,20H2,(H,22,23)/t12-/m0/s1

InChI Key

XUIIKFGFIJCVMT-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.

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
Diphenylether
Diaryl ether
3-phenylpropanoic-acid
Alpha-amino acid
Amphetamine or derivatives
L-alpha-amino acid
Phenoxy compound
Phenol ether
2-halophenol
2-iodophenol
Aralkylamine
Phenol
Halobenzene
Iodobenzene
Aryl halide
Aryl iodide
Benzenoid
Monocyclic benzene moiety
Amino acid
Carboxylic acid
Ether
Monocarboxylic acid or derivatives
Organoiodide
Organonitrogen compound
Organooxygen compound
Organopnictogen compound
Organic nitrogen compound
Organic oxide
Carbonyl group
Primary amine
Amine
Hydrocarbon derivative
Primary aliphatic amine
Organic oxygen compound
Organohalogen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

non-proteinogenic L-alpha-amino acid (CHEBI:18332 )
L-phenylalanine derivative (CHEBI:18332 )
iodophenol (CHEBI:18332 )
2-halophenol (CHEBI:18332 )
thyroxine (CHEBI:18332 )
thyroxine (C01829 )
Other amino acids (C01829 )
Biogenic amines (C01829 )

Functional Ontology

Not Available

Not Available

Not Available

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.009 g/L	ALOGPS
logP	1.15	ALOGPS
logP	3.73	ChemAxon
logS	-4.9	ALOGPS
pKa (Strongest Acidic)	0.27	ChemAxon
pKa (Strongest Basic)	9.43	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	92.78 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	126.79 m³·mol⁻¹	ChemAxon
Polarizability	49.4 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0000248

DrugBank ID

DB00451

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

5614

KEGG Compound ID

C01829

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Levothyroxine

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

18332

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for 2-amino-3-[4-(4-hydroxy-3,5-diiodophenoxy)-3,5-diiodophenyl]propanoic acid (CFc000165283)

MOL for CFc000165283 (2-amino-3-[4-(4-hydroxy-3,5-diiodophenoxy)-3,5-diiodophenyl]propanoic acid)

3D MOL for CFc000165283 (2-amino-3-[4-(4-hydroxy-3,5-diiodophenoxy)-3,5-diiodophenyl]propanoic acid)

3D SDF for CFc000165283 (2-amino-3-[4-(4-hydroxy-3,5-diiodophenoxy)-3,5-diiodophenyl]propanoic acid)

3D-SDF for CFc000165283 (2-amino-3-[4-(4-hydroxy-3,5-diiodophenoxy)-3,5-diiodophenyl]propanoic acid)

PDB for CFc000165283 (2-amino-3-[4-(4-hydroxy-3,5-diiodophenoxy)-3,5-diiodophenyl]propanoic acid)

3D PDB for CFc000165283 (2-amino-3-[4-(4-hydroxy-3,5-diiodophenoxy)-3,5-diiodophenyl]propanoic acid)

SMILES for CFc000165283 (2-amino-3-[4-(4-hydroxy-3,5-diiodophenoxy)-3,5-diiodophenyl]propanoic acid)

INCHI for CFc000165283 (2-amino-3-[4-(4-hydroxy-3,5-diiodophenoxy)-3,5-diiodophenyl]propanoic acid)

Structure for CFc000165283 (2-amino-3-[4-(4-hydroxy-3,5-diiodophenoxy)-3,5-diiodophenyl]propanoic acid)

3D Structure for CFc000165283 (2-amino-3-[4-(4-hydroxy-3,5-diiodophenoxy)-3,5-diiodophenyl]propanoic acid)