BIIB021

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Synonyms
Status
Molecule Category UNKNOWN
UNII 851B9FQ7Q0

Structure

InChI Key QULDDKSCVCJTPV-UHFFFAOYSA-N
Smiles COc1c(C)cnc(Cn2cnc3c(Cl)nc(N)nc32)c1C
InChI
InChI=1S/C14H15ClN6O/c1-7-4-17-9(8(2)11(7)22-3)5-21-6-18-10-12(15)19-14(16)20-13(10)21/h4,6H,5H2,1-3H3,(H2,16,19,20)

Physicochemical Descriptors

Property Name Value
Molecular Formula C14H15ClN6O
Molecular Weight 318.77
AlogP 2.13
Hydrogen Bond Acceptor 7.0
Hydrogen Bond Donor 1.0
Number of Rotational Bond 3.0
Polar Surface Area 91.74
Molecular species NEUTRAL
Aromatic Rings 3.0
Heavy Atoms 22.0

Bioactivity

Mechanism of Action Action Reference
Heat shock protein HSP90 inhibitor INHIBITOR PubMed PubMed PubMed
Protein: Heat shock protein HSP90
Description: Heat shock protein HSP 90-alpha
Organism : Homo sapiens
P07900 ENSG00000080824
Protein: Heat shock protein HSP90
Description: Heat shock protein HSP 90-beta
Organism : Homo sapiens
P08238 ENSG00000096384
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Enzyme Kinase Protein Kinase
- - - - 87
Other cytosolic protein
38 5-56800 2 2-26 96
Other membrane protein
- 124 - 176 -
Assay Description Organism Bioactivity Reference
Inhibition of Hsp90 assessed as Her2 degradation by cell based assay None 30.0 nM
Inhibition of HSP90-mediated client protein HER2 degradation in human MCF7 cells Homo sapiens 38.0 nM
Inhibition of HSP90-mediated client protein HER2 degradation None 7.0 nM
Binding affinity to HSP90 under reducing conditions in presence of TECP None 13.0 nM
Binding affinity to HSP90 by fluorescence polarization assay None 1.7 nM
Binding affinity to HSP90 under non-reducing conditions in absence of TECP None 26.0 nM
Inhibition of HSP90alpha None 1.7 nM
Binding affinity to Hsp90 nucleotide binding domain None 1.7 nM
Binding affinity to Hsp90 nucleotide binding domain in human BT474 cells Homo sapiens 140.0 nM
Inhibition of Hsp90alpha None 5.1 nM
Binding affinity at recombinant Hsp90alpha incubated for 16 hrs by fluorescence polarization competition assay None 1.7 nM
Inhibition of HSP90alpha in human MCF7 cells assessed as degradation of Her-2 Homo sapiens 38.0 nM
Displacement of 5-(3-(3-(6-amino-8-(6-iodobenzo[d][1,3]dioxol-5-ylthio)-9H-purin-9-yl)propyl)thioureido)-2-(6-hydroxy-3-oxo-3H-xanthen-9-yl)benzoic acid from recombinant human Trap-1 after 24 hrs by fluorescence polarization assay Homo sapiens 90.0 nM
Displacement of 5-(3-(3-(6-amino-8-(6-iodobenzo[d][1,3]dioxol-5-ylthio)-9H-purin-9-yl)propyl)thioureido)-2-(6-hydroxy-3-oxo-3H-xanthen-9-yl)benzoic acid from dog Grp94 after 24 hrs by fluorescence polarization assay Canis lupus familiaris 124.0 nM
Displacement of 5-(3-(3-(6-amino-8-(6-iodobenzo[d][1,3]dioxol-5-ylthio)-9H-purin-9-yl)propyl)thioureido)-2-(6-hydroxy-3-oxo-3H-xanthen-9-yl)benzoic acid from recombinant HSP90beta (unknown origin) after 24 hrs by fluorescence polarization assay Homo sapiens 17.0 nM
Displacement of 5-(3-(3-(6-amino-8-(6-iodobenzo[d][1,3]dioxol-5-ylthio)-9H-purin-9-yl)propyl)thioureido)-2-(6-hydroxy-3-oxo-3H-xanthen-9-yl)benzoic acid from HSP90alpha (unknown origin) after 24 hrs by fluorescence polarization assay Homo sapiens 19.0 nM
Binding affinity to human recombinant TRAP1 after 3 hrs by fluorescence polarization assay Homo sapiens 62.0 nM
Binding affinity to human N-terminal polyHis-tagged GRP94 (L69 to N337) expressed in Escherichia coli BL21(DE3) after 3 hrs by fluorescence polarization assay Homo sapiens 176.0 nM
Binding affinity to human N-terminal polyHis-tagged HSP90beta (D9 to E236) expressed in insect sf9 cells after 3 hrs by fluorescence polarization assay Homo sapiens 4.0 nM
Binding affinity to human N-terminal polyHis-tagged HSP90alpha (D9 to E236) alpha-helix conformation expressed in insect sf9 cells after 3 hrs by fluorescence polarization assay Homo sapiens 2.0 nM
Growth inhibition of human HFF1 cells at 10 uM after 72 hrs by MTT assay Homo sapiens 51.28 %
Growth inhibition of human HCT116 cells at 10 uM after 72 hrs by MTT assay Homo sapiens 71.94 %
Growth inhibition of human SKBR3 cells at 10 uM after 72 hrs by MTT assay Homo sapiens 86.2 %
Growth inhibition of human MCF7 cells at 10 uM after 72 hrs by MTT assay Homo sapiens 84.81 %
Inhibition of FITC-labeled geldanamycin binding to human Hsp90alpha by fluorescence polarization assay Homo sapiens 29.0 nM
Inhibition of FITC-labeled geldanamycin binding to human Hsp90alpha at 10 uM by fluorescence polarization assay Homo sapiens 96.1 %
Inhibition of FITC3-labeled PU-H71 binding to recombinant human N-terminal His6-tagged TRAP1 (60 to 561 residues) expressed in Escherichia coli BL21(DE3) after 24 hrs by fluorescence polarization assay Homo sapiens 535.0 nM
Inhibition of FITC3-labeled PU-H71 binding to recombinant HSP90alpha (unknown origin) after 24 hrs by fluorescence polarization assay Homo sapiens 52.0 nM
Inhibition of recombinant Caulobacter vibrioides cell cycle histidine kinase CckA deltaTM mutant DHp domain (70 to 691 residues) expressed in Escherichia coli at 250 uM in presence of varying levels of ATP measured every 60 secs for 2 hrs by PK/LDH enzyme coupled assay relative to control Caulobacter vibrioides 87.0 %
Inhibition of FITC-geldanamycin binding to HSP90alpha (unknown origin) after 3 hrs by fluorescence polarization assay Homo sapiens 65.7 nM
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 -6.36 %
Antiproliferative activity against human MCF7 cells Homo sapiens 310.0 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 17.72 % SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 28.11 %
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 0.04 % 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 16.68 % 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 16.68 % 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 0.04 %
Inhibition of recombinant His-tagged full length human HSP90 (9 to 236 residues) expressed in Escherichia coli BL21(DE3) cells after 18 hrs by fluorescence polarization displacement assay Homo sapiens 1.7 nM
Inhibition of HSP90a (unknown origin) Homo sapiens 65.7 nM

Cross References

Resources Reference
ChEBI 90687
ChEMBL CHEMBL467399
DrugBank DB12359
FDA SRS 851B9FQ7Q0
Guide to Pharmacology 9258
PDB 94M
PubChem 16736529
SureChEMBL SCHEMBL1791028
ZINC ZINC000014974583
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