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Showing Compound Levothyroxine (FDB021829)

Record Information
Version1.0
Creation date2011-04-11 17:18:27 UTC
Update date2015-10-09 22:30:38 UTC
Primary IDFDB021829
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameLevothyroxine
DescriptionThe 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 [HMDB]
CAS Number51-48-9
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
SynonymSource
2-Amino-3-[4-(4-hydroxy-3,5-diiodophenoxy)-3,5-diiodophenyl]propanoic acidChEBI
DL-ThyroxineChEBI
O-(4-Hydroxy-3,5-diiodophenyl)-3,5-diiodo-DL-tyrosineChEBI
ThxChEBI
2-Amino-3-[4-(4-hydroxy-3,5-diiodophenoxy)-3,5-diiodophenyl]propanoateGenerator
EltroxineMeSH
3,5,3',5'-TetraiodothyronineMeSH
EltroxinMeSH
Levo TMeSH
O-(4-Hydroxy-3,5-diiodophenyl)-3,5-diiodotyrosineMeSH
L Thyroxine rocheMeSH
L-Thyroxin betaMeSH
Levothyroxine sodiumMeSH
SynthroxMeSH
EutiroxMeSH
O-(4-Hydroxy-3,5-diiodophenyl) 3,5-diiodo-L-tyrosineMeSH
Sodium levothyroxineMeSH
Tiroxina leoMeSH
Levothyroxin delalandeMeSH
LevoxineMeSH
TiroidineMeSH
L-ThyroxineMeSH
EuthyroxMeSH
BerlthyroxMeSH
DexnonMeSH
L-ThyroxMeSH
ThevierMeSH
ThyroxinMeSH
NovothyralMeSH
L ThyroxineMeSH
Levothyroxin deladandeMeSH
L-3,5,3',5'-TetraiodothyronineMeSH
T4 Thyroid hormoneMeSH
UnithroidMeSH
L Thyroxin henningMeSH
ThyraxMeSH
Thyroid hormone, T4MeSH
L-Thyroxin henningMeSH
OroxineMeSH
L ThyroxMeSH
L Thyroxin betaMeSH
LevoxylMeSH
L-Thyroxine rocheMeSH
LevothyroidMeSH
SynthroidMeSH
ThyroxineMeSH
NovothyroxMeSH
Levo-TMeSH
LévothyroxMeSH
EferoxMeSH
LevothroidMeSH
(-)-ThyroxineHMDB
3,3',5,5'-Tetraiodo-L-thyronineChEBI
3,3',5,5''-tetraiodo-L-thyronineHMDB
3,5,3',5'-TETRAIODO-L-thyronineChEBI
3,5,3'5'-Tetraiodo-L-thyronineHMDB
4-(4-Hydroxy-3,5-diiodophenoxy)-3,5-diiodo-L-phenylalanineChEBI
D-ThyroxineHMDB
DL-ThyroxinHMDB
HenningHMDB
L-T4ChEBI
L-ThyroxinHMDB
LaevothyroxinumHMDB
LevothyroxinChEBI
LevothyroxinumHMDB
LT4ChEBI
O-(4-Hydroxy-3,5-diiodophenyl)-3,5-diiodo-L-tyrosineChEBI
Prestwick_548HMDB
S-Thyroxinemanual
T4ChEBI
TetraiodothyronineHMDB
TetrametHMDB
THXHMDB
ThyratabsHMDB
ThyreoideumHMDB
ThyroxinalHMDB
Thyroxine I 125HMDB
Thyroxine iodineHMDB
Predicted Properties
PropertyValueSource
Water Solubility0.009 g/LALOGPS
logP1.15ALOGPS
logP3.73ChemAxon
logS-4.9ALOGPS
pKa (Strongest Acidic)0.27ChemAxon
pKa (Strongest Basic)9.43ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area92.78 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity126.79 m³·mol⁻¹ChemAxon
Polarizability49.62 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC15H11I4NO4
IUPAC name2-amino-3-[4-(4-hydroxy-3,5-diiodophenoxy)-3,5-diiodophenyl]propanoic acid
InChI IdentifierInChI=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)
InChI KeyXUIIKFGFIJCVMT-UHFFFAOYSA-N
Isomeric SMILESNC(CC1=CC(I)=C(OC2=CC(I)=C(O)C(I)=C2)C(I)=C1)C(O)=O
Average Molecular Weight776.87
Monoisotopic Molecular Weight776.686681525
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.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentPhenylalanine 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
  • 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 FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
OntologyNo ontology term
Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MSNot Available
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01si-0000000900-044da621c91c6b84c16d2018-04-05View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0f89-0000001900-34a76db480c71499866b2018-04-05View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-016u-0009001000-2f7c573ddd8db95ad6632018-04-05View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0000000900-fa4c16f40dc921b003752018-04-06View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-08i0-0004000900-78b9cd7513d1c7d552c72018-04-06View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0h9u-6029105200-130f64d248c3516bf4602018-04-06View Spectrum
NMRNot Available
ChemSpider ID5614
ChEMBL IDCHEMBL1624
KEGG Compound IDC01829
Pubchem Compound ID5819
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDDB00451
HMDB IDHMDB00248
CRC / DFC (Dictionary of Food Compounds) IDBCK11-Y:BCJ81-O
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG ID38499
KNApSAcK IDNot Available
HET IDT44
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDThyroxine
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
Enzymes
NameGene NameUniProt ID
Type I iodothyronine deiodinaseDIO1P49895
Type II iodothyronine deiodinaseDIO2Q92813
TransthyretinTTRP02766
Thyroxine-binding globulinSERPINA7P05543
Type III iodothyronine deiodinaseDIO3P55073
Pathways
NameSMPDB LinkKEGG Link
Tyrosine MetabolismSMP00006 map00350
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference