Bovine Metabolome Database: Showing metabocard for Liothyronine (BMDB0000265)

Identification Taxonomy Physical properties Pathways Spectra Concentrations Links References enzymes (1) Show 1 protein XML

Record Information

Version

1.0

Creation Date

2016-09-30 22:27:36 UTC

Update Date

2020-06-04 20:57:12 UTC

BMDB ID

BMDB0000265

Secondary Accession Numbers

BMDB00265

Metabolite Identification

Common Name

Liothyronine

Description

Liothyronine, also known as T3 or liotironina, 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. Liothyronine is a drug which is used as replacement or supplemental therapy in patients with hypothyroidism of any etiology, except transient hypothyrodism during the recovery phase of subacute thyroiditis. Liothyronine is possibly soluble (in water) and a very strong basic compound (based on its pKa). Liothyronine exists in all living organisms, ranging from bacteria to humans. In cattle, liothyronine is involved in the metabolic pathway called thyroid hormone synthesis pathway. Liothyronine is a potentially toxic compound.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
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
L-3,5,3'-Triiodothyronine	ChEBI
L-T3	ChEBI
Liothyroninum	ChEBI
Liotironina	ChEBI
O-(4-Hydroxy-3-iodophenyl)-3,5-diiodo-L-tyrosine	ChEBI
T3	ChEBI
Tertroxin	ChEBI
Tresitope	ChEBI
Triiodothyronine	ChEBI
3,3',5-Triiodo-L-thyronine	Kegg
Thyrolar	Kegg
3,3',5-Triiodothyronine	HMDB
Cytomel	HMDB
T3 Thyroid hormone	HMDB
Thyroid hormone, T3	HMDB
Liothyronine sodium	HMDB
3,3',5'-Triiodo-L-thyronine	HMDB
3,3',5'-Triiodothyronine	HMDB
4-(4-Hydroxy-3-iodophenoxy)-3,5-diiodophenylalanine	HMDB
Cyronine	HMDB
L-3,3',5-Triiodo-thyronine	HMDB
L-3,3',5-Triiodothyronine	HMDB
L-3-[4-(4-Hydroxy-3-iodophenoxy)-3,5-diiodophenyl]-alanine	HMDB
L-Liothyronine	HMDB
L-Triiodothyronine	HMDB
Liothyronin	HMDB
Triiodo-L-thyronine	HMDB

Chemical Formula

C₁₅H₁₂I₃NO₄

Average Molecular Weight

650.9735

Monoisotopic Molecular Weight

650.790038137

IUPAC Name

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

Traditional Name

liothyronine

CAS Registry Number

6893-02-3

SMILES

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

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)/t12-/m0/s1

InChI Key

AUYYCJSJGJYCDS-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
2-iodophenol
2-halophenol
Phenol ether
Iodobenzene
1-hydroxy-2-unsubstituted benzenoid
Halobenzene
Phenol
Aralkylamine
Aryl iodide
Aryl halide
Monocyclic benzene moiety
Benzenoid
Amino acid
Ether
Carboxylic acid
Monocarboxylic acid or derivatives
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

iodothyronine (CHEBI:18258 )
iodophenol (CHEBI:18258 )
2-halophenol (CHEBI:18258 )
thyroxine (C02465 )
Other amino acids (C02465 )

Ontology

Status

Detected and Quantified

Origin

Endogenous

Biofunction

Not Available

Application

Not Available

Cellular locations

Cell membrane
Cytoplasm
Membrane

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
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	43.92 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-05a9-5090378000-014ef55558b58a3d38f2	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_4) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_2) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_3) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_4) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS ("Liothyronine,1TMS,#1" TMS) - 70eV, Positive	Not Available	View in JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, N/A (Annotated)	splash10-000i-0009001000-1d47041336da63b556e4	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, N/A (Annotated)	splash10-000i-1009001000-15f70073b9018f013c9c	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, N/A (Annotated)	splash10-000i-0009000000-71c231d7a3ab505815ff	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-0udi-0000009000-f932659d1e6d8a622985	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-0udi-0000009000-6506a7a71dab928abfb0	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-0fc0-0700119000-1df6db0e3031eb2739fa	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative	splash10-004i-0900000000-973fc871534b19242cc8	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative	splash10-004i-0900000000-ac3c4a198bb017dc7ccc	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive	splash10-0udi-0000009000-2770ece749a9fa1042f4	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive	splash10-0udi-0000009000-881174c66da97022d645	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive	splash10-0a4i-0000019000-6f798ae76702a3053339	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive	splash10-0a4i-0000219000-d2ca9f0cc3c1b47176b5	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive	splash10-056r-0021915000-6f3810619f383bce651a	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0udi-0000009000-f932659d1e6d8a622985	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0udi-0000009000-6506a7a71dab928abfb0	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0fc0-0700119000-1df6db0e3031eb2739fa	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-004i-0900000000-973fc871534b19242cc8	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-004i-0900000000-ac3c4a198bb017dc7ccc	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-0udi-0000009000-2770ece749a9fa1042f4	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0pb9-0000009000-4d60e144164273111464	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-0000149000-87babecf610c68223da5	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-016r-0039010000-b57f6dd23e6456cf7c1e	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-0010009000-50e441d89395debe176b	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001j-0050139000-a259e39ad1204b60b373	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00e9-9262431000-bcc1f7554c4e309cef17	View in MoNA
1D NMR	¹H NMR Spectrum (1D, 600 MHz, 100%_DMSO, experimental)	Not Available	View in JSpectraViewer
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, 100%_DMSO, experimental)	Not Available	View in JSpectraViewer

Biological Properties

Cellular Locations

Cell membrane
Cytoplasm
Membrane

Biospecimen Locations

Adipose Tissue
Adrenal Gland
Epidermis
Fibroblasts
Intestine
Milk
Neuron
Placenta
Platelet
Skeletal Muscle
Testis
Thyroid Gland

Pathways

Name	SMPDB/Pathwhiz	KEGG
Thyroid Hormone Synthesis		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Adipose Tissue	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Adrenal Gland	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Epidermis	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Fibroblasts	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Intestine	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Milk	Detected and Quantified	500 uM	Not Specified	Not Specified	Normal	PMID: 3530717	details
Neuron	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Placenta	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Platelet	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Skeletal Muscle	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Testis	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Thyroid Gland	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details

Abnormal Concentrations

Not Available

External Links

HMDB ID

HMDB0000265

DrugBank ID

DB00279

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

C02465

BioCyc ID

CPD-10813

BiGG ID

Not Available

Wikipedia Link

Triiodothyronine

METLIN ID

Not Available

PubChem Compound

5920

PDB ID

Not Available

ChEBI ID

18258

References

Synthesis Reference

Salamonczyk, Grzegorz M.; Oza, Vibha B.; Sih, Charles J. A concise synthesis of thyroxine (T4) and 3,5,3'-triiodo-L-thyronine (T3). Tetrahedron Letters (1997), 38(40), 6965-69

Material Safety Data Sheet (MSDS)

Not Available

General References

Slebodzinski AB, Nowak J, Gawecka H, Sechman A: Thyroid hormones and insulin in milk; a comparative study. Endocrinol Exp. 1986 Aug;20(2-3):247-55. [PubMed:3530717 ]

Enzymes

Enzyme Details

1. Thyroxine 5-deiodinase

General function:: Involved in selenium binding
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:: Q5I3B1
Molecular weight:: 33888.0

Showing metabocard for Liothyronine (BMDB0000265)

Structure for BMDB0000265 (Liothyronine)

Enzymes