Livestock Metabolome Database: Showing metabocard for Thyroxine (LMDB00114)

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-07-13 19:42:40 UTC

Update Date

2016-07-19 23:09:42 UTC

Lmdb

LMDB00114

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Thyroxine

Description

The thyronamines function via some unknown mechanism to inhibit neuronal activity; this plays an important role in the hibernation cycles of mammals. One effect of administering the thyronamines is a severe drop in body temperature. Iodide is actively absorbed from the bloodstream and concentrated in the thyroid follicles. (If there is a deficiency of dietary iodine, the thyroid enlarges in an attempt to trap more iodine, resulting in goitre.) Via a reaction with the enzyme thyroperoxidase, iodine is covalently bound to tyrosine residues in the thyroglobulin molecules, forming monoiodotyrosine (MIT) and diiodotyrosine (DIT). Linking two moieties of DIT produces thyroxine. Combining one particle of MIT and one particle of DIT produces triiodothyronine. Both T3 and T4 are used to treat thyroid hormone deficiency (hypothyroidism). They are both absorbed well by the gut, so can be given orally. Levothyroxine, the most commonly used synthetic thyroxine form, is a stereoisomer of physiological thyroxine, which is metabolized more slowly and hence usually only needs once-daily administration. Natural desiccated thyroid hormones, which are derived from pig thyroid glands, are a "natural" hypothyroid treatment containing 20% T3 and traces of T2, T1 and calcitonin. this plays an important role in the hibernation cycles of mammals. One effect of administering the thyronamines is a severe drop in body temperature. The major hormone derived from the thyroid gland. Thyroxine is synthesized via the iodination of tyrosines (monoiodotyrosine) and the coupling of iodotyrosines (diiodotyrosine) in the thyroglobulin. Thyroxine is released from thyroglobulin by proteolysis and secreted into the blood. Thyroxine is peripherally deiodinated to form triiodothyronine which exerts a broad spectrum of stimulatory effects on cell metabolism. The thyronamines function via some unknown mechanism to inhibit neuronal activity.

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 )

Ontology

Status

Detected and Quantified

Origin

Not Available

Biofunction

Not Available

Application

Not Available

Cellular locations

Not Available

Physical Properties

State

Not Available

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	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	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0f89-4002002900-0d489fed1cb888a2d9d0	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-0ac9-0591664310-c9b7aec3184ebb20a2da	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-014i-2566449540-35bb942c7bcbcfe41af7	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-00xr-3375497520-9dee3cb0c153e6c6df9e	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-0059-0001001900-83ff4aafed0b73c6c7b7	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-004i-0900000000-6e0a640216afcce0837e	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 45V, Negative	splash10-004i-0900000000-9223d3d63e3db43052a7	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 60V, Negative	splash10-004i-0900000000-1e8e674422aa4d820da7	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-001i-0132219000-42259b5a596f74aec76f	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-0udi-0019217000-baafc92556cb18d71b3a	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Negative	splash10-004i-0900000000-bb154453510a75ca822c	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 15V, Negative	splash10-004i-0900000000-f785346765de92765afd	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-001i-0000119000-af7b1e923ec5750514af	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-0f8j-1248309000-68eea5695ceb400ea5b0	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-0udi-0029337000-a85b59c3575dc95d36fd	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-001i-0003109000-480d647f8d49feeec28c	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-01si-0000000900-524d052a32c1fe4b904d	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-001i-0000001900-553f6a4045ef2241fd85	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-014i-0009000000-d2431d885a79bb80b7a5	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-0000000900-137b5f8f48031bc9aa4f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03fr-0004001900-db1d8cdb93785d786382	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0h9u-7029014300-3bd9620b0c6a8dd20c93	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-0000000900-95266ab7e52b7d3cb322	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-1700000900-195c16ab7434b857e712	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-0900000000-0dba40d354fa6a5575e0	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004i-0000000900-d76aec17d3d890cb64c1	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	Spectrum

Biological Properties

Cellular Locations

Not Available

Biofluid Locations and Tissue Locations

Plasma
Serum

Concentrations

Biofluid	Status	Value	Condition	Species	Reference	Details
Plasma	Detected and Quantified	0.0768 +/- 0.00193-0.0847+/-0.00399 uM	Not Available	Porcine	22513987	details
Plasma	Detected and Quantified	0.0824 +/- 0.00451-0.0862+/-0.00438 uM	Not Available	Porcine	22513987	details
Plasma	Detected and Quantified	0.0848 +/- 0.00348-0.0843+/-0.00425 uM	Not Available	Porcine	22513987	details
Serum	Detected and Quantified	12.5 +/- 2.8 uM	Not Available	Porcine	21429726	details
Serum	Detected and Quantified	10.9 +/- 2.6 uM	Not Available	Porcine	21429726	details