LENALIDOMIDE

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Trade Names
Synonyms
Status
Molecule Category UNKNOWN
ATC L04AX04
UNII F0P408N6V4
EPA CompTox DTXSID8046664

Structure

InChI Key GOTYRUGSSMKFNF-UHFFFAOYSA-N
Smiles Nc1cccc2c1CN(C1CCC(=O)NC1=O)C2=O
InChI
InChI=1S/C13H13N3O3/c14-9-3-1-2-7-8(9)6-16(13(7)19)10-4-5-11(17)15-12(10)18/h1-3,10H,4-6,14H2,(H,15,17,18)

Physicochemical Descriptors

Property Name Value
Molecular Formula C13H13N3O3
Molecular Weight 259.26
AlogP 0.03
Hydrogen Bond Acceptor 4.0
Hydrogen Bond Donor 2.0
Number of Rotational Bond 1.0
Polar Surface Area 92.5
Molecular species NEUTRAL
Aromatic Rings 1.0
Heavy Atoms 19.0

Bioactivity

Mechanism of Action Action Reference
CRL4(CRBN) E3 ubiquitin ligase inhibitor INHIBITOR PubMed PubMed
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Epigenetic regulator Reader Bromodomain
- 5190 - - -
Other cytosolic protein
- - - - 4-6
Transcription factor
- - - - 4-6
Unclassified protein
67 1500-37800 - 1490-16300 100
Assay Description Organism Bioactivity Reference
Inhibition of Phosphodiesterase 4 from U937 cells at 100 uM Homo sapiens 50.0 %
Inhibition of lipopolysaccharide stimulated TNF-alpha release in human whole blood Homo sapiens 480.0 nM
Inhibition of lipopolysaccharide stimulated TNF-alpha release in human whole blood Homo sapiens 100.0 nM
Inhibition of lipopolysaccharide stimulated TNF-alpha release in human PBMC at 100 uM Homo sapiens 74.0 %
Inhibitory activity in HUVEC tube formation assay at 100 uM Homo sapiens 32.0 %
Inhibition of IL-2 production in human T cells measured after 2 to 3 days by ELISA Homo sapiens 150.0 nM
Antiproliferative activity against human NAMALWA cells assessed as inhibition of [3H]thymidine incorporation after 72 hrs by scintillation counting Homo sapiens 360.0 nM
Inhibition of TNF-alpha production in LPS-stimulated human PBMC preincubated for 1 hr before LPS challenge measured after 28 to 20 hrs by ELISA Homo sapiens 100.0 nM
Inhibition of NFkappaB in human FRT-Jurkat cells expressing GFP assessed as reduction of TNF expression at 10 uM after 24 hrs by flow cytometry relative to control Homo sapiens 4.0 %
Inhibition of NFkappaB in human FRT-Jurkat cells expressing GFP assessed as reduction of TNF expression at 100 uM after 24 hrs by flow cytometry relative to control Homo sapiens 6.0 %
Inhibition of TNFalpha expression in human Jurkat cells containing GFP gene under control of TNF gene promoter at 100 uM incubated for 24 hrs Homo sapiens 14.0 %
Inhibition of TNFalpha expression in human Jurkat cells containing GFP gene under control of TNF gene promoter at 10 uM incubated for 24 hrs Homo sapiens 14.0 %
Antiinflammatory activity in human HT-29 cells assessed as inhibition of TNF-alpha induced BCECF-AM labeled human U937 cell adhesion at 1 uM preincubated for 1 hr followed by stimulation with TNF-alpha for 3 hrs followed by further co-incubation with BCECF-AM labeled human U937 cells for 1 hr by fluorescent/light microscopic analysis Homo sapiens 64.6 %
Antiproliferative activity against human EC9706 cells after 48 hrs by CCK-8 assay Homo sapiens 340.3 ug.mL-1
Induction of CRL4/CRBN ubiquitin ligase-mediated aiolos degradation in human DF15 cells expressing pLOC-ePL-tagged aiolos after 4 hrs by luminescence based beta-galactosidase enzyme fragmentation complementation assay Homo sapiens 53.0 nM
Induction of cereblon-mediated ikaros degradation in human DF15 cells expressing ePL-tagged ikaros after 4 hrs by luminometric analysis Homo sapiens 67.0 nM
Induction of cereblon-mediated aiolos degradation in human DF15 cells expressing ePL-tagged aiolos after 4 hrs by luminometric analysis Homo sapiens 87.0 nM
Inhibition of CRBN-mediated IKFZ3 degradation in human OPM2 cells at 100 uM measured after 24 hrs by Western blot analysis relative to control Homo sapiens 100.0 %
Antiproliferative activity against human MM1S cells measured after 168 hrs by CellTiter96 Aqueous non-radioactive cell proliferation assay Homo sapiens 50.0 nM
Antiinflammatory activity in human PBMC cells assessed as reduction in LPS-induced TNF-alpha production preincubated for 1 hr followed by LPS addition and measured after 18 to 20 hrs by ELISA Homo sapiens 100.0 nM
Binding affinity to human CRBN (1 to 442 residues)/N-terminal 6His-tagged human DDB1 (1 to 1140 residues) expressed in baculovirus infected BTI-TN-5B1-4 insect cells after 30 mins by cy5 probe based fluorescence polarization assay Homo sapiens 178.0 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 25.36 %
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 0.1 % 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 0.1 %
Antiproliferative activity against human MM1.S cells assessed as reduction in cell growth measured after 7 days culturing by CellTiter 96 Aqueous non-radioactive cell proliferation assay Homo sapiens 81.0 nM
Antitumor activity against human MM1.S cells xenografted in CB17-SCID mouse assessed as reduction in tumor weight at 60 mg/kg, po qd for 14 days and measured after 14 days Homo sapiens 62.59 %
Antimigratory activity against mouse BMOL-T cells assessed as inhibition of cell migration at 10 uM incubated for 16 hrs by scratch wound healing assay relative to control Mus musculus 20.0 %
Displacement of Cy5-O-Len probe from 6XHis-tagged CRBN/DDB1 (unknown origin) incubated in dark for 1 hr by fluorescence polarization assay Homo sapiens 286.0 nM

Related Entries

Cross References

Resources Reference
ChEBI 63791
ChEMBL CHEMBL848
DrugBank DB00480
DrugCentral 3317
FDA SRS F0P408N6V4
Human Metabolome Database HMDB0014623
Guide to Pharmacology 7331
PharmGKB PA162363968
PubChem 216326
SureChEMBL SCHEMBL32978
CONTENTS