LIOTHYRONINE

/static/temp/default.svg Search structure
Synonyms
Status
Molecule Category Free-form
UNII 06LU7C9H1V
EPA CompTox DTXSID8023216

Structure

InChI Key AUYYCJSJGJYCDS-LBPRGKRZSA-N
Smiles N[C@@H](Cc1cc(I)c(Oc2ccc(O)c(I)c2)c(I)c1)C(=O)O
InChI
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

Physicochemical Descriptors

Property Name Value
Molecular Formula C15H12I3NO4
Molecular Weight 650.98
AlogP 3.95
Hydrogen Bond Acceptor 4.0
Hydrogen Bond Donor 3.0
Number of Rotational Bond 5.0
Polar Surface Area 92.78
Molecular species ZWITTERION
Aromatic Rings 2.0
Heavy Atoms 23.0

Bioactivity

Mechanism of Action Action Reference
Thyroid hormone receptor agonist AGONIST DailyMed Wikipedia Wikipedia
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Enzyme Protease Serine protease Serine protease PA clan Serine protease S1A subfamily
1-6 - - - -
Ion channel Ligand-gated ion channel GABA-A receptor
7000 23000 - - -
Other nuclear protein
- 3600 - - -
Transcription factor Nuclear receptor Nuclear hormone receptor subfamily 1 Nuclear hormone receptor subfamily 1 group A Nuclear hormone receptor subfamily 1 group A member 1
0-10 0-3 0-0 0-2 -
Transcription factor Nuclear receptor Nuclear hormone receptor subfamily 1 Nuclear hormone receptor subfamily 1 group A Nuclear hormone receptor subfamily 1 group A member 2
2-15 0-3 0-0 0-2 -
Transcription factor Nuclear receptor Nuclear hormone receptor subfamily 1 Nuclear hormone receptor subfamily 1 group C Nuclear hormone receptor subfamily 1 group C member 3
5800 - 710 - -
Transcription factor Nuclear receptor Nuclear hormone receptor subfamily 3 Nuclear hormone receptor subfamily 3 group C Nuclear hormone receptor subfamily 3 group C member 4
- - - - 24
Transporter Primary active transporter ATP-binding cassette ABCB subfamily
- 11270 - - -
Assay Description Organism Bioactivity Reference
Inhibition of [125I]L-T3 binding to rat hepatic 3,5,3''-triiodo-L-thyronine receptor Rattus norvegicus 1.1 nM
In vitro inhibition of the bound [125I]L-T3 rat liver nuclear L-triiodothyronine receptor None 4.4 nM In vitro inhibition of the bound [125I]L-T3 rat liver nuclear L-triiodothyronine receptor None 1.8 nM
In vitro inhibition of bound [125I]L-T3 rat plasma membrane 3,5,3'' L-triiodothyronine receptor None 500.0 nM In vitro inhibition of bound [125I]L-T3 rat plasma membrane 3,5,3'' L-triiodothyronine receptor None 100.0 nM
Binding affinity towards thyroid hormone receptor (hTR alpha 1) Homo sapiens 0.17 nM
Effective concentration binding towards TRalpha in E25B2 cells (agonistic activity) None 2.0 nM
Half-maximum activation of human Thyroid hormone receptor alpha-1 (hTRalpha1) None 2.0 nM
Binding affinity against human Thyroid hormone receptor alpha-1 (hTRalpha1) using radiolabeled T3 Homo sapiens 0.1 nM
Binding affinity of compound was determined against Thyroid hormone receptor alpha1 None 0.06 nM
Binding affinity towards thyroid hormone receptor (hTR beta 1) Homo sapiens 0.14 nM
Effective concentration binding towards TR-beta-1 in E25B2 cells (agonistic activity) None 2.0 nM
Half-maximum activation of human Thyroid hormone receptor beta 1 (hTRbeta1) Homo sapiens 2.0 nM
Binding affinity against human Thyroid hormone receptor beta 1 (hTRbeta1) using radiolabeled T3 Homo sapiens 0.1 nM
Binding affinity of compound was determined against thyroid hormone receptor beta 1 None 0.087 nM
Inhibitory activity against [125I]T3 binding to human TRbeta1 receptor None 0.08 nM
In vitro concentration required to displace [125I]L-T3 from rat hepatic nuclei. None 1.56 nM
Inhibitory concentration against cloned human thyroid hormone receptor beta 1 Homo sapiens 0.26 nM
Inhibitory concentration against cloned human thyroid hormone receptor alpha 1 Homo sapiens 0.24 nM
Binding affinity at human thyroid hormone receptor alpha 1 expressed in CHOK1 cells Homo sapiens 0.24 nM
Binding affinity at human thyroid hormone receptor beta-1 expressed in CHOK1 cells Homo sapiens 0.26 nM
Inhibition of human thyroid hormone receptor beta 1 Homo sapiens 0.257 nM
Displacement of [125I]T3 from human TRalpha receptor Homo sapiens 0.058 nM
Displacement of [125I]T3 from human TRbeta receptor Homo sapiens 0.081 nM
Effect on human TRalpha transactivation activity in U2OS cells by luciferase reporter assay Homo sapiens 2.4 nM
Effect on human TRbeta transactivation activity in U2OS cells by luciferase reporter assay Homo sapiens 11.0 nM
Effect on human TRalpha transactivation activity in HeLa cells by luciferase reporter assay Homo sapiens 2.4 nM
Effect on human TRbeta transactivation activity in HeLa cells by luciferase reporter assay Homo sapiens 2.4 nM
Activity at androgen receptor ligand binding domain assessed as inhibition of SRC2-3 interaction at 50 uM after 2 hrs by fluorescence polarization assay None 24.0 %
Displacement of [125I]3,5,3'-triiodo-L-thyronine from His-tagged human recombinant TRalpha1 by scintillation proximity assay Homo sapiens 0.33 nM
Displacement of [125I]3,5,3'-triiodo-L-thyronine His-tagged human recombinant TRbeta1 by scintillation proximity assay Homo sapiens 0.68 nM
Displacement of [125I]T3 from recombinant thyroid hormone receptor alpha expressed in sf9 cells by scintillation proximity assay None 0.22 nM
Displacement of [125I]T3 from recombinant thyroid hormone receptor beta expressed in sf9 cells by scintillation proximity assay None 0.55 nM
Inhibition of rat thyroid hormone receptor Rattus norvegicus 0.38 nM
DRUGMATRIX: Adenosine A1 radioligand binding (ligand: DPCPX) None 410.9 nM DRUGMATRIX: Adenosine A1 radioligand binding (ligand: DPCPX) None 239.7 nM
Displacement of [125I]T3 from human recombinant thyroid harmone receptor beta after 16 to 48 hrs by gamma-ray detection Homo sapiens 2.29 nM
Displacement of [125I]T3 from human recombinant thyroid harmone receptor alpha after 16 to 48 hrs by gamma-ray detection Homo sapiens 2.33 nM
Displacement of [125I]-T3 from human TRbeta expressed in insect cells after 16 to 48 hrs by gamma-counting Homo sapiens 2.29 nM
Displacement of [125I]-T3 from human TRalpha expressed in insect cells after 16 to 48 hrs by gamma-counting Homo sapiens 2.33 nM
Displacement of [125I]Triiodothyronine from thyroid hormone receptor in Wistar rat liver after 18 hrs Rattus norvegicus 0.018 nM Displacement of [125I]Triiodothyronine from thyroid hormone receptor in Wistar rat liver after 18 hrs Rattus norvegicus 0.034 nM
Displacement of [125I]Triiodothyronine from thyroid hormone receptor in Wistar rat liver at 10 uM after 18 hrs relative to control Rattus norvegicus 6.0 %
Agonist activity at human recombinant TRbeta1 transfected in CV-1 cells after 8 to 10 hrs by alkaline phosphatase reporter gene assay Homo sapiens 2.0 nM
Agonist activity at human recombinant TRalpha1 transfected in CV-1 cells after 8 to 10 hrs by alkaline phosphatase reporter gene assay Homo sapiens 2.1 nM
Displacement of [125I]-Triiodothyronine from human recombinant TRbeta1 ligand binding domain after 2 to 3 hrs by beta counting Homo sapiens 2.9 nM
Displacement of [125I]-Triiodothyronine from human recombinant TRalpha1 ligand binding domain after 2 to 3 hrs by beta counting Homo sapiens 3.2 nM
Agonist activity at recombinant His6-tagged THR-beta (unknown origin) expressed in Escherichia coli BL21(DE3) co-expressing RXR preincubated for 30 mins assessed as biotin-GRIP1 peptide recruitment by HTRF assay Homo sapiens 15.0 nM
Agonist activity at recombinant His6-tagged THR-alpha (unknown origin) expressed in Escherichia coli BL21(DE3) co-expressing RXR preincubated for 30 mins assessed as biotin-GRIP1 peptide recruitment by HTRF assay Homo sapiens 10.0 nM
Agonist activity at human thyroid hormone receptor alpha expressed in HEK293 cells by luciferase reporter gene assay Homo sapiens 0.41 nM
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 2.74 %
Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging Chlorocebus sabaeus -0.2 % Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging Chlorocebus sabaeus -0.2 %
Binding affinity to recombinant PPARgamma LBD (unknown origin) by isothermal titration calorimetry Homo sapiens 710.0 nM
Agonist activity at Xenopus laevis THRalpha transfected in green monkey CV1 cells after 48 hrs by reporter gene assay Xenopus laevis 0.5 nM
Agonist activity at GST-labelled THRbeta ( 202 to 461 residues) (unknown origin) incubated for 2 hrs in presence SRC1-2 co-activator peptide by Alphascreen assay Homo sapiens 1.2 nM
Agonist activity at human THRalpha expressed in CHO cells after 24 hrs by luciferase assay Homo sapiens 3.4 nM
Agonist activity at human THRbeta expressed in CHO cells after 24 hrs by luciferase assay Homo sapiens 6.2 nM
Agonist activity at human THRalpha expressed in baculovirus infected SF9 cells after 15 mins by gel electrophoresis Homo sapiens 0.5 nM
Agonist activity at human THRbeta expressed in green monkey CV1 cells after 24 hrs by luciferase assay Homo sapiens 1.2 nM
Agonist activity at recombinant hexa-His-tagged THRalpha LBD (202 to 461 residues) (unknown origin)/recombinant human EE-tagged RXRalpha LBD (225 to 462 residues) assessed as increase in biotinylated GRIP1 peptide recruitment preincubated for 30 mins followed by peptide addition and measured after 30 mins by HTRF assay Homo sapiens 30.0 nM
Agonist activity at recombinant hexa-His-tagged THRbeta LBD (148 to 410 residues) (unknown origin)/recombinant human EE-tagged RXRalpha LBD (225 to 462 residues) assessed as increase in biotinylated GRIP1 peptide recruitment preincubated for 30 mins followed by peptide addition and measured after 30 mins by HTRF assay Homo sapiens 26.0 nM

Related Entries

Cross References

Resources Reference
ChEBI 18258
ChEMBL CHEMBL1544
DrugBank DB00279
DrugCentral 1585
FDA SRS 06LU7C9H1V
Human Metabolome Database HMDB0000265
Guide to Pharmacology 2634
KEGG C02465
PDB T3
PharmGKB PA164778866
PubChem 5920
SureChEMBL SCHEMBL8300
ZINC ZINC000003830999
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