Showing Compound Liothyronine (FDB021810)

Record Information

Version

1.0

Creation date

2011-04-11 17:01:41 UTC

Update date

2019-11-26 03:20:54 UTC

Primary ID

FDB021810

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Liothyronine

Description

Liothyronine is a T3 thyroid hormone normally synthesized and secreted by the thyroid gland in much smaller quantities than thyroxine (T4). Most T3 is derived from peripheral monodeiodination of T4 at the 5' position of the outer ring of the iodothyronine nucleus. The hormone finally delivered and used by the tissues is mainly T3. Mildly toxic by ingestion. An experimental teratogen. Experimental reproductive effects. When heated to decomposition it emits toxic fumes of NOx, I(-), and Cl(-). (Sax's Dangerous Properties of Industrial Materials) [HMDB]

CAS Number

6893-02-3

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

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Synonym	Source
3,3',5'-Triiodo-L-thyronine	HMDB
3,3',5'-Triiodothyronine	HMDB
3,3',5-Triiodo-L-thyronine	HMDB
3,3',5-Triiodothyronine	HMDB
3,5,3'-Triiodo-L-thyronine	ChEBI
3,5,3'-Triiodothyronine	ChEBI
3,5,3'TRIIODOTHYRONINE	ChEBI
4-(4-Hydroxy-3-iodophenoxy)-3,5-diiodo-L-phenylalanine	ChEBI
4-(4-Hydroxy-3-iodophenoxy)-3,5-diiodophenylalanine	HMDB
Cyronine	HMDB

Showing 1 to 10 of 26 entries

Predicted Properties

Property	Value	Source
Water Solubility	0.02 g/L	ALOGPS
logP	0.82	ALOGPS
logP	2.8	ChemAxon
logS	-4.5	ALOGPS
pKa (Strongest Acidic)	0.3	ChemAxon
pKa (Strongest Basic)	9.48	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	113.43 m³·mol⁻¹	ChemAxon
Polarizability	44.13 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

Chemical Formula

C15H12I3NO4

IUPAC name

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

InChI Identifier

InChI=1S/C15H12I3NO4/c16-9-6-8(1-2-13(9)20)23-14-10(17)3-7(4-11(14)18)5-12(19)15(21)22/h1-4,6,12,20H,5,19H2,(H,21,22)

InChI Key

AUYYCJSJGJYCDS-UHFFFAOYSA-N

Isomeric SMILES

NC(CC1=CC(I)=C(OC2=CC(I)=C(O)C=C2)C(I)=C1)C(O)=O

Average Molecular Weight

650.9735

Monoisotopic Molecular Weight

650.790038137

Classification

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
Phenoxy compound
2-iodophenol
2-halophenol
Phenol ether
1-hydroxy-2-unsubstituted benzenoid
Iodobenzene
Halobenzene
Aralkylamine
Phenol
Aryl halide
Aryl iodide
Monocyclic benzene moiety
Benzenoid
Amino acid
Monocarboxylic acid or derivatives
Ether
Carboxylic acid
Organic nitrogen compound
Primary aliphatic amine
Organohalogen compound
Organoiodide
Organonitrogen compound
Organooxygen compound
Primary amine
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Amine
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

No ontology term

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

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Property	Value	Reference
Boiling Point	Not Available
Charge	Not Available
Density	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Experimental Water Solubility	Not Available
Isoelectric point	Not Available
Mass Composition	Not Available
Melting Point	Not Available
Optical Rotation	Not Available

Showing 1 to 10 of 14 entries

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	Liothyronine, TMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Liothyronine, TMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Liothyronine, TMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Liothyronine, TMS_2_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Liothyronine, TMS_2_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Liothyronine, TMS_2_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Liothyronine, TMS_2_4, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Liothyronine, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Liothyronine, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Liothyronine, TBDMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Liothyronine, TBDMS_2_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Liothyronine, TBDMS_2_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Liothyronine, TBDMS_2_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Liothyronine, TBDMS_2_4, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0pc0-0000019000-ce6501f45cc1be8e04bf	2018-04-06	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-0000169000-994e0bd9f52b612be5a7	2018-04-06	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00or-0019020000-7a249e4b1229f4851cac	2018-04-06	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-0000009000-4b86ec8520a3e5dfdd18	2018-04-06	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001i-0040029000-a0cdc3663027d8214797	2018-04-06	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00e9-9252420000-89230d2bff335f11c510	2018-04-06	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-0000009000-9044a59ba63b511399cd	2021-10-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-0000019000-9a3ced9d360ca4bb7172	2021-10-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a6r-0032629000-227cf95eb5064b9a6105	2021-10-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-0000009000-f8e74b77f02e17e351b1	2021-10-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004j-1700029000-9e90bebe08cced3041e1	2021-10-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-0900000000-0dba40d354fa6a5575e0	2021-10-12	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

ChEMBL ID

KEGG Compound ID

Pubchem Compound ID

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

Not Available

DrugBank ID

DB00279

HMDB ID

HMDB00265

CRC / DFC (Dictionary of Food Compounds) ID

BDQ38-W:BDQ43-U

EAFUS ID

Not Available

Dr. Duke ID

Not Available

BIGG ID

39878

KNApSAcK ID

Not Available

HET ID

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

Not Available

SuperScent ID

Not Available

Wikipedia ID

Not Available

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

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Food	Content Range	Average	Reference

Processing...

Biological Effects and Interactions

Health Effects / Bioactivities

Not Available

Enzymes

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Name	Gene Name	UniProt ID
Thyroid hormone receptor beta	THRB	P10828
Thyroxine-binding globulin	SERPINA7	P05543
Transthyretin	TTR	P02766
Type I iodothyronine deiodinase	DIO1	P49895
Type II iodothyronine deiodinase	DIO2	Q92813
Type III iodothyronine deiodinase	DIO3	P55073