PU-H71

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Synonyms
Status
Molecule Category UNKNOWN
UNII 06IVK87M04
EPA CompTox DTXSID20236288

Structure

InChI Key SUPVGFZUWFMATN-UHFFFAOYSA-N
Smiles CC(C)NCCCn1c(Sc2cc3c(cc2I)OCO3)nc2c(N)ncnc21
InChI
InChI=1S/C18H21IN6O2S/c1-10(2)21-4-3-5-25-17-15(16(20)22-8-23-17)24-18(25)28-14-7-13-12(6-11(14)19)26-9-27-13/h6-8,10,21H,3-5,9H2,1-2H3,(H2,20,22,23)

Physicochemical Descriptors

Property Name Value
Molecular Formula C18H21IN6O2S
Molecular Weight 512.38
AlogP 3.28
Hydrogen Bond Acceptor 9.0
Hydrogen Bond Donor 2.0
Number of Rotational Bond 7.0
Polar Surface Area 100.11
Molecular species BASE
Aromatic Rings 3.0
Heavy Atoms 28.0
Assay Description Organism Bioactivity Reference
Inhibitory activity against Hsp90 in human breast cancer SKBr3 cell line Homo sapiens 16.1 nM
Growth inhibition in human breast cancer SKBr3 cell line using SRB Homo sapiens 50.0 nM
Inhibition of Her2 degradation in human breast cancer SKBr3 cell line Homo sapiens 50.0 nM
Inhibitory activity against Hsp90 in human breast cancer MDA-MB-468 cell line Homo sapiens 10.2 nM
Growth inhibition in human breast cancer MDA-MB-468 cell line using SRB Homo sapiens 58.0 nM
Antimitotic activity in human breast cancer MDA-MB-468 cell line Homo sapiens 70.0 nM
Displacement of cy3B-GM from Hsp90alpha Homo sapiens 59.6 nM
Inhibition of Hsp90 in human MCF7 cell lysates assessed as interaction with Cy3b-conjugated geldanamycin by FP assay Homo sapiens 43.0 nM
Inhibition of Hsp90 in human MCF7 cells assessed as Her2 level after 24 hrs by Western blot Homo sapiens 60.0 nM
Inhibition of Hsp90 None 16.0 nM
Inhibition of Hsp90 in human SKBR3 cells assessed as Her2 degradation Homo sapiens 50.0 nM
Inhibition of HSP90-mediated proliferation of human NCI-H526 cells at 0.3 to 0.5 uM after 72 to 96 hrs by sulforhodamine B assay Homo sapiens 50.0 %
Inhibition of HSP90-mediated proliferation of human NCI-N417 cells at 0.3 to 0.5 uM after 72 to 96 hrs by sulforhodamine B assay Homo sapiens 50.0 %
Inhibition of HSP90-mediated proliferation of human NCI-H146 cells at 0.3 to 0.5 uM after 72 to 96 hrs by sulforhodamine B assay Homo sapiens 50.0 %
Inhibition of HSP90-mediated proliferation of human NCI-H187 cells at 0.3 to 0.5 uM after 72 to 96 hrs by sulforhodamine B assay Homo sapiens 50.0 %
Inhibition of HSP90-mediated proliferation of human NCI-H209 cells at 0.3 to 0.5 uM after 72 to 96 hrs by sulforhodamine B assay Homo sapiens 50.0 %
Inhibition of HSP90-mediated proliferation of human NCI-H510 cells at 0.3 to 0.5 uM after 72 to 96 hrs by sulforhodamine B assay Homo sapiens 50.0 %
Inhibition of HSP90-mediated proliferation of human NCI-H69 cells at 0.3 to 0.5 uM after 72 to 96 hrs by sulforhodamine B assay Homo sapiens 50.0 %
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 205.0 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 30.0 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 42.0 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 43.0 nM
Displacement of Cy3B-GM from recombinant Hsp90alpha (unknown origin) after 24 hrs by fluorescence polarization assay Homo sapiens 43.0 nM
Displacement of Cy3B-GM from recombinant Hsp90beta (unknown origin) after 24 hrs by fluorescence polarization assay Homo sapiens 42.0 nM
Displacement of Cy3B-GM from recombinant Grp94 (unknown origin) after 24 hrs by fluorescence polarization assay Homo sapiens 26.0 nM
Displacement of PU-FITC3 from recombinant TRAP-1 (unknown origin) after 24 hrs by fluorescence polarization assay Homo sapiens 205.0 nM
Growth inhibition of human HCT116 cells at 10 uM after 72 hrs by MTT assay Homo sapiens 78.43 %
Growth inhibition of human SKBR3 cells at 10 uM after 72 hrs by MTT assay Homo sapiens 65.34 %
Growth inhibition of human MCF7 cells at 10 uM after 72 hrs by MTT assay Homo sapiens 70.55 %
Inhibition of FITC-labeled geldanamycin binding to human Hsp90alpha by fluorescence polarization assay Homo sapiens 51.0 nM
Inhibition of FITC-labeled geldanamycin binding to human Hsp90alpha at 10 uM by fluorescence polarization assay Homo sapiens 106.2 %
Recombinant Hsp90 [His-Tev-huHsp90-alpha (9-236)] was immobilized on a Biacore CM5 chip at 25 degrees C and a flow rate of 30 uL/min using amine coupling at pH 4.50 according to Biacore standard protocol. Hsp90 was applied at a concentration of 20 ug/mL with 50uM 17-DMAG.Data sets were processed and analyzed using the software Biacore 4000 Evaluation. Solvent corrected and double-referenced association and dissociation phase data were fitted to a simple 1:1 interaction model with mass transport limitations Homo sapiens 7.62 nM
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 257.0 nM
Inhibition of FITC3-labeled PU-H71 binding to recombinant HSP90alpha (unknown origin) after 24 hrs by fluorescence polarization assay Homo sapiens 89.0 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 61.0 %
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 57.4 %
Antiproliferative activity against human MCF7 cells Homo sapiens 90.0 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 10.55 %
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 2.26 % 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 2.26 %
Inhibition of PU-H71-FITC binding to recombinant wild-type human TRAP1 expressed in Escherichia coli BL21 (DE3) measured after 2 hrs by fluorescence polarization assay Homo sapiens 675.0 nM
Inhibition of recombinant HSP90alpha (unknown origin) incubated for 24 hrs in presence of 1-FITC3 probe by fluorescence polarization assay Homo sapiens 126.2 nM
Inhibition of TRAP1 (unknown origin) Homo sapiens 330.6 nM
Inhibition of GRP94 (unknown origin) Homo sapiens 300.6 nM
Antiproliferative activity against human HeLa cells by MTT assay Homo sapiens 226.5 nM
Antiproliferative activity against human PC3 cells by MTT assay Homo sapiens 363.0 nM
Inhibition of PU-H71-FITC3 binding to recombinant full length TRAP1 (unknown origin) incubated for 2 hrs by fluorescence polarization assay Homo sapiens 192.0 nM
Inhibition of PU-H71-FITC3 binding to recombinant N-terminal HSP90alpha (unknown origin) incubated for 2 hrs by fluorescence polarization assay Homo sapiens 72.9 nM
Inhibition of PU-H71-FITC3 binding to recombinant N-terminal Grp94 (unknown origin) incubated for 2 hrs by fluorescence polarization assay Homo sapiens 132.0 nM

Cross References

Resources Reference
ChEMBL CHEMBL200102
DrugBank DB12638
FDA SRS 06IVK87M04
PDB H71
SureChEMBL SCHEMBL1857579
ZINC ZINC000013679213
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