LEVOTHYROXINE

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Synonyms
Status
Molecule Category Free-form
UNII Q51BO43MG4
EPA CompTox DTXSID8023214

Structure

InChI Key XUIIKFGFIJCVMT-LBPRGKRZSA-N
Smiles N[C@@H](Cc1cc(I)c(Oc2cc(I)c(O)c(I)c2)c(I)c1)C(=O)O
InChI
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

Physicochemical Descriptors

Property Name Value
Molecular Formula C15H11I4NO4
Molecular Weight 776.87
AlogP 4.56
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 24.0
Assay Description Organism Bioactivity Reference
Inhibition of 4-(4-(dimethylamino)styryl)-N-methylpyridinium uptake at human OCT1 expressed in HEK293 cells at 100 uM by confocal microscopy Homo sapiens 12.7 %
Inhibition of human liver OATP1B1 expressed in HEK293 Flp-In cells assessed as reduction in E17-betaG uptake at 20 uM by scintillation counting Homo sapiens -13.1 %
Inhibition of human liver OATP1B3 expressed in HEK293 Flp-In cells assessed as reduction in [3H]E17-betaG uptake at 20 uM incubated for 5 mins by scintillation counting Homo sapiens 11.4 %
Inhibition of human liver OATP2B1 expressed in HEK293 Flp-In cells assessed as reduction in [3H]E3S uptake at 20 uM incubated for 5 mins by scintillation counting Homo sapiens 63.7 %
Antagonist activity at human GTS-tagged FXR at 15 uM after 20 mins by TR-FRET assay Homo sapiens 58.2 %
Inhibition of human recombinant TTR Y78F mutant-mediated fibrillogenesis at 40 uM after 30 mins by turbidimetric assay relative to control Homo sapiens 80.0 %
Antibacterial activity against Staphylococcus aureus MRSA ATCC 43300 (CO-ADD:GP_020); MIC in CAMBH media, using NBS plates, by OD(600) Staphylococcus aureus subsp. aureus -5.39 %
Antibacterial activity against Escherichia coli ATCC 25922 (CO-ADD:GN_001); MIC in CAMBH media using NBS plates, by OD(600) Escherichia coli -12.96 %
Antibacterial activity against Klebsiella pneumoniae MDR ATCC 70063 (CO-ADD:GN_003); MIC in CAMBH media using NBS plates, by OD(600) Klebsiella pneumoniae 0.79 %
Antibacterial activity against Pseudomonas aeruginosa ATCC 27853 (CO-ADD:GN_042); MIC in CAMBH media using NBS plates, by OD(600) Pseudomonas aeruginosa -9.42 %
Antibacterial activity against Acinetobacter baumannii ATCC 19606 (CO-ADD:GN_034); MIC in CAMBH media using NBS plates, by OD600 Acinetobacter baumannii 5.92 %
Antifungal activity against Candida albicans ATCC 90028 (CO-ADD:FG_001); MIC in YNB media using NBS plates, by OD630 Candida albicans 21.06 %
Antifungal activity against Cryptococcus neoformans H99 ATCC 208821 (CO-ADD:FG_002); MIC in YNB media using NBS plates, by Resazurin OD(600-570) Cryptococcus neoformans -5.43 %
Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of Caco-2 cells at 10 uM after 48 hours by high content imaging Homo sapiens 5.73 %
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 -0.15 % SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 -3.004 %
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 -0.05 % 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 -0.14 % 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 -0.05 % 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 -0.14 %
Binding affinity to recombinant PPARgamma LBD (unknown origin) by isothermal titration calorimetry Homo sapiens 400.0 nM
Binding affinity to RXRalpha LBD (unknown origin) by isothermal titration calorimetry Homo sapiens 930.0 nM
Agonist activity at THRalpha (unknown origin) incubated for 14 to 16 hrs by dual glo luciferase reporter gene assay Homo sapiens 19.0 nM
Agonist activity at THRbeta (unknown origin) incubated for 14 to 16 hrs by dual glo luciferase reporter gene assay Homo sapiens 240.0 nM

Related Entries

Cross References

Resources Reference
ChEBI 18332
ChEMBL CHEMBL1624
DrugBank DB00451
DrugCentral 2646
FDA SRS Q51BO43MG4
Human Metabolome Database HMDB0000248
Guide to Pharmacology 2635
KEGG C01829
PDB T44
PharmGKB PA450221
PubChem 5819
SureChEMBL SCHEMBL23098
ZINC ZINC000003830993
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