FIMEPINOSTAT

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Synonyms
Status
Molecule Category Free-form
UNII 3S9RX35S5X
EPA CompTox DTXSID90712307

Structure

InChI Key JOWXJLIFIIOYMS-UHFFFAOYSA-N
Smiles COc1ccc(-c2nc(N3CCOCC3)c3sc(CN(C)c4ncc(C(=O)NO)cn4)cc3n2)cn1
InChI
InChI=1S/C23H24N8O4S/c1-30(23-25-11-15(12-26-23)22(32)29-33)13-16-9-17-19(36-16)21(31-5-7-35-8-6-31)28-20(27-17)14-3-4-18(34-2)24-10-14/h3-4,9-12,33H,5-8,13H2,1-2H3,(H,29,32)

Physicochemical Descriptors

Property Name Value
Molecular Formula C23H24N8O4S
Molecular Weight 508.56
AlogP 2.14
Hydrogen Bond Acceptor 12.0
Hydrogen Bond Donor 2.0
Number of Rotational Bond 7.0
Polar Surface Area 138.72
Molecular species NEUTRAL
Aromatic Rings 4.0
Heavy Atoms 36.0

Bioactivity

Mechanism of Action Action Reference
Histone deacetylase inhibitor INHIBITOR PubMed Other
Protein: PI3-kinase p110-delta subunit
Description: Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit delta isoform
Organism : Homo sapiens
O00329 ENSG00000171608
Protein: Histone deacetylase
Description: Histone deacetylase 3
Organism : Homo sapiens
O15379 ENSG00000171720
Protein: PI3-kinase p110-alpha subunit
Description: Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit alpha isoform
Organism : Homo sapiens
P42336 ENSG00000121879
Protein: PI3-kinase p110-beta subunit
Description: Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit beta isoform
Organism : Homo sapiens
P42338 ENSG00000051382
Protein: Histone deacetylase
Description: Histone deacetylase 1
Organism : Homo sapiens
Q13547 ENSG00000116478
Protein: Histone deacetylase
Description: Histone deacetylase 7
Organism : Homo sapiens
Q8WUI4 ENSG00000061273
Protein: Histone deacetylase
Description: Histone deacetylase 2
Organism : Homo sapiens
Q92769 ENSG00000196591
Protein: Histone deacetylase
Description: Polyamine deacetylase HDAC10
Organism : Homo sapiens
Q969S8 ENSG00000100429
Protein: Histone deacetylase
Description: Histone deacetylase 11
Organism : Homo sapiens
Q96DB2 ENSG00000163517
Protein: Histone deacetylase
Description: Histone deacetylase 8
Organism : Homo sapiens
Q9BY41 ENSG00000147099
Protein: Histone deacetylase
Description: Histone deacetylase 6
Organism : Homo sapiens
Q9UBN7 ENSG00000094631
Protein: Histone deacetylase
Description: Histone deacetylase 9
Organism : Homo sapiens
Q9UKV0 ENSG00000048052
Protein: Histone deacetylase
Description: Histone deacetylase 5
Organism : Homo sapiens
Q9UQL6 ENSG00000108840
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Enzyme Kinase Protein Kinase Atypical protein kinase group Atypical protein kinase PIKK family Atypical protein kinase FRAP subfamily
- 185-431 - - -
Enzyme Kinase Protein Kinase Atypical protein kinase group Atypical protein kinase PIKK family
- 185-431 - - -
Enzyme Transferase
- 39-359 - - -
Enzyme
- 39-359 - - -
Epigenetic regulator Eraser Histone deacetylase HDAC class I
126 2-8 - - -
Epigenetic regulator Eraser Histone deacetylase HDAC class IIa
- 191-479 - - -
Epigenetic regulator Eraser Histone deacetylase HDAC class IIb
222 8-674 - - -
Epigenetic regulator Eraser Histone deacetylase HDAC class IV
- 5-1267 - - -
Ion channel Voltage-gated ion channel Potassium channels Voltage-gated potassium channel
- 79500 - - -
Unclassified protein
- 2-3 - - -
Assay Description Organism Bioactivity Reference
Cytotoxicity against human Glioma cells (HF2303) after 72 hrs by CelltiterGlo assay Homo sapiens 0.7 nM
Cytotoxicity against human Glioma cells (HF2381) after 72 hrs by CelltiterGlo assay Homo sapiens 0.7 nM
Cytotoxicity against human Glioma cells (HF2476) after 72 hrs by CelltiterGlo assay Homo sapiens 0.7 nM
Cytotoxicity against human Glioma cells (HF2790) after 72 hrs by CelltiterGlo assay Homo sapiens 0.7 nM
Cytotoxicity against human Glioma cells (HF2876) after 72 hrs by CelltiterGlo assay Homo sapiens 0.7 nM
Cytotoxicity against human Glioma cells (HF2885) after 72 hrs by CelltiterGlo assay Homo sapiens 0.7 nM
Cytotoxicity against human Glioma cells (HF3013) after 72 hrs by CelltiterGlo assay Homo sapiens 0.7 nM
Cytotoxicity against human MV4-11 cells assessed as growth inhibition after 24 hrs by MTT assay Homo sapiens 0.43 nM
Cytotoxicity against human A2780S cells assessed as growth inhibition after 24 hrs by MTT assay Homo sapiens 6.15 nM
Cytotoxicity against human HCT116 cells assessed as growth inhibition after 24 hrs by MTT assay Homo sapiens 7.34 nM
Inhibition of full length human recombinant HDAC2 expressed in baculovirus infected insect Sf9 cells using Ac-peptide-AMC as substrate assessed as release of AMC preincubated for 15 mins followed by substrate addition measured after 1 hr by fluorescence assay Homo sapiens 5.0 nM
Inhibition of full length C-terminal His-tagged human recombinant HDAC3/NCOR2 (395 to 489 residues) expressed in baculovirus infected insect Sf9 cells using Ac-peptide-AMC as substrate assessed as release of AMC preincubated for 15 mins followed by substrate addition measured after 1 hr by fluorescence assay Homo sapiens 1.8 nM
Inhibition of full length C-terminal His-tagged human recombinant HDAC8 expressed in baculovirus infected insect Sf9 cells using Ac-peptide-AMC as substrate assessed as release of AMC preincubated for 15 mins followed by substrate addition measured after 1 hr by fluorescence assay Homo sapiens 191.0 nM
Inhibition of N-terminal GST/C-terminal His-tagged human recombinant HDAC4 (627 to 1084 residues) expressed in baculovirus infected insect Sf9 cells using Ac-peptide-AMC as substrate assessed as release of AMC preincubated for 15 mins followed by substrate addition measured after 1 hr by fluorescence assay Homo sapiens 409.0 nM
Inhibition of human recombinant HDAC5 expressed in baculovirus infected insect Sf9 cells using Ac-peptide-AMC as substrate assessed as release of AMC preincubated for 15 mins followed by substrate addition measured after 1 hr by fluorescence assay Homo sapiens 674.0 nM
Inhibition of N-terminal GST-tagged human recombinant HDAC7 (518 to end residues) expressed in baculovirus infected insect Sf9 cells using Ac-peptide-AMC as substrate assessed as release of AMC preincubated for 15 mins followed by substrate addition measured after 1 hr by fluorescence assay Homo sapiens 426.0 nM
Inhibition of C-terminal His-tagged human recombinant HDAC9 (604 to 1066 residues) expressed in baculovirus infected insect Sf9 cells using Ac-peptide-AMC as substrate assessed as release of AMC preincubated for 15 mins followed by substrate addition measured after 1 hr by fluorescence assay Homo sapiens 554.0 nM
Inhibition of full length human recombinant HDAC6 expressed in baculovirus infected insect Sf9 cells using Ac-peptide-AMC as substrate assessed as release of AMC preincubated for 15 mins followed by substrate addition measured after 1 hr by fluorescence assay Homo sapiens 27.0 nM
Inhibition of human recombinant HDAC10 expressed in baculovirus infected insect Sf9 cells using Ac-peptide-AMC as substrate assessed as release of AMC preincubated for 15 mins followed by substrate addition measured after 1 hr by fluorescence assay Homo sapiens 2.8 nM
Inhibition of full length human recombinant HDAC11 expressed in baculovirus infected insect Sf9 cells using Ac-peptide-AMC as substrate assessed as release of AMC preincubated for 15 mins followed by substrate addition measured after 1 hr by fluorescence assay Homo sapiens 5.4 nM
Inhibition of human recombinant HDAC1 (482 residues) by Color-de-Lys assay Homo sapiens 1.7 nM
Inhibition of full length recombinant human N-terminal GST-tagged p110 alpha/untagged p85 alpha expressed in baculovirus infected insect Sf9 cells using PI:3PS as substrate incubated for 60 mins by ADP-Glo luminescence assay Homo sapiens 19.0 nM
Inhibition of recombinant human p110beta expressed in baculovirus infected insect Sf9 cells incubated for 1 hr by ADP-gloreagen assay Homo sapiens 54.0 nM
Inhibition of His-tagged full length recombinant human p110gamma expressed in baculovirus expression system incubated for 1 hr by ADP-gloreagen assay Homo sapiens 311.0 nM
Inhibition of N-terminal His6-tagged recombinant full-length human p110delta/untagged recombinant full length human p85alpha expressed in baculovirus infected insect Sf9 cells incubated for 2 hrs by kinase-glo assay Homo sapiens 39.0 nM
Inhibition of HDAC in human HeLa cell nuclear extract using Ac-Leu-Gly-Lys (Ac)-AMC as substrate after 30 mins by fluorescence assay Homo sapiens 6.8 nM
Inhibition of HDAC6 in human A2780S cells assessed as tubulin acetylation incubated for 6 hrs by cytoblot assay Homo sapiens 221.75 nM
Inhibition of HDAC1/2/3 in human A2780S cells assessed as histone H3 acetylation incubated for 6 hrs by cytoblot assay Homo sapiens 126.25 nM
Inhibition of recombinant full length human N-terminal GST-tagged PI3K p110alpha/untagged p85alpha expressed in baculovirus infected insect Sf9 cells by ADP-Glo luminescent assay Homo sapiens 19.0 nM
Inhibition of recombinant full length human N-terminal GST-tagged PI3K p110beta/untagged p85alpha expressed in baculovirus infected insect Sf9 cells by ADP-Glo luminescent assay Homo sapiens 54.0 nM
Inhibition of recombinant full length human N-terminal GST-tagged PI3K p110delta/untagged p85alpha expressed in baculovirus infected insect Sf9 cells by ADP-Glo luminescent assay Homo sapiens 39.0 nM
Inhibition of HDAC6 (unknown origin) using Color de lys as substrate by HTS assay Homo sapiens 27.0 nM
Inhibition of HDAC2 (unknown origin) using Color de lys as substrate by HTS assay Homo sapiens 5.0 nM
Inhibition of HDAC10 (unknown origin) using Color de lys as substrate by HTS assay Homo sapiens 2.8 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 37.12 %
Antiproliferative activity against human HCT116 cells after 96 hrs by MTT assay Homo sapiens 5.0 nM
Inhibition of recombinant C-terminal His/FLAG-tagged HDAC1 (unknown origin) expressed in baculovirus infected Sf9 insect cells using Ac-peptide as substrate preincubated for 15 mins followed by substrate addition and measured after 1 hr Homo sapiens 0.36 nM
Inhibition of recombinant human PI3Kalpha using PIP2 as substrate incubated for 1 hr by kinase-glo assay Homo sapiens 69.0 nM
Inhibition of recombinant human full length HDAC11 expressed in baculovirus infected Sf9 insect cells using Ac-peptide as substrate preincubated for 15 mins followed by substrate addition and measured after 1 hr Homo sapiens 132.0 nM
Inhibition of recombinant human full length C-terminal His-tagged HDAC8 expressed in baculovirus infected Sf9 insect cells using Ac-peptide as substrate preincubated for 15 mins followed by substrate addition and measured after 1 hr Homo sapiens 1.4 nM
Inhibition of HDAC6 (unknown origin) using Ac-peptide as substrate preincubated for 15 mins followed by substrate addition and measured after 1 hr Homo sapiens 8.0 nM
Inhibition of recombinant human full length HDAC4 expressed in baculovirus infected Sf9 insect cells using Ac-peptide as substrate preincubated for 15 mins followed by substrate addition and measured after 1 hr Homo sapiens 445.0 nM
Inhibition of recombinant human full length HDAC2 expressed in baculovirus infected Sf9 insect cells using Ac-peptide as substrate preincubated for 15 mins followed by substrate addition and measured after 1 hr Homo sapiens 1.6 nM
Inhibition of recombinant human His-tagged PIK3CG expressed in baculovirus expression system using PIP2 as substrate incubated for 1 hr by ADP-glo assay Homo sapiens 374.0 nM
Inhibition of recombinant human PIK3CB using PIP2 as substrate incubated for 1 hr by ADP-glo assay Homo sapiens 16.0 nM
Inhibition of recombinant human His-tagged PIK3CD/PIK3R1 expressed in baculovirus expression system using PIP2 as substrate incubated for 1 hr by ADP-glo assay Homo sapiens 359.0 nM
Inhibition of recombinant human N-terminal FLAG-tagged mTOR (1362 to end amino acids) using ULight-4E-BP1 as substrate incubated for 1 hr by LANCE Ultra assay Homo sapiens 431.0 nM
Antiproliferative activity against human K562 cells after 96 hrs by MTT assay Homo sapiens 280.0 nM
Antiproliferative activity against human MCF7 cells after 96 hrs by MTT assay Homo sapiens 41.0 nM
Antiproliferative activity against human MDA-MB-453 cells after 96 hrs by MTT assay Homo sapiens 9.0 nM
Antiproliferative activity against human HCT8 cells after 96 hrs by MTT assay Homo sapiens 5.0 nM
Antiproliferative activity against human U87 cells after 96 hrs by MTT assay Homo sapiens 7.0 nM
Antiproliferative activity against human NCI-H460 cells after 96 hrs by MTT assay Homo sapiens 150.0 nM
Antiproliferative activity against human NCI-H1299 cells after 96 hrs by MTT assay Homo sapiens 25.0 nM
Antiproliferative activity against human Capan2 cells after 96 hrs by MTT assay Homo sapiens 7.0 nM
Antiproliferative activity against human SW1990 cells after 96 hrs by MTT assay Homo sapiens 180.0 nM
Antiproliferative activity against human DU145 cells after 96 hrs by MTT assay Homo sapiens 560.0 nM
Antiproliferative activity against human HGC27 cells after 96 hrs by MTT assay Homo sapiens 41.0 nM
Antiproliferative activity against human HepG2 cells after 96 hrs by MTT assay Homo sapiens 15.0 nM
Antiproliferative activity against human HuH7 cells after 96 hrs by MTT assay Homo sapiens 560.0 nM
Antiproliferative activity against human Bel7402 cells after 96 hrs by MTT assay Homo sapiens 13.0 nM
Inhibition of HDAC1 (unknown origin) Homo sapiens 1.7 nM
Inhibition of HDAC2 (unknown origin) Homo sapiens 5.0 nM
Inhibition of HDAC3 (unknown origin) Homo sapiens 1.8 nM
Inhibition of HDAC4 (unknown origin) Homo sapiens 191.0 nM
Inhibition of HDAC5 (unknown origin) Homo sapiens 406.0 nM
Inhibition of HDAC6 (unknown origin) Homo sapiens 674.0 nM
Inhibition of HDAC7 (unknown origin) Homo sapiens 27.0 nM
Inhibition of HDAC8 (unknown origin) Homo sapiens 426.0 nM
Inhibition of HDAC9 (unknown origin) Homo sapiens 554.0 nM
Inhibition of HDAC10 (unknown origin) Homo sapiens 2.8 nM
Inhibition of HDAC11 (unknown origin) Homo sapiens 5.4 nM
Inhibition of recombinant human full-length N-terminal GST-tagged p110alpha/untagged full-length p85alpha expressed in baculovirus infected Sf9 cells using PIP2 as substrate by ADP-glo luminescence assay Homo sapiens 19.0 nM
Inhibition of recombinant human full-length N-terminal GST-tagged p110beta/untagged full-length p85alpha expressed in baculovirus infected Sf9 cells using PIP2 as substrate by ADP-glo luminescence assay Homo sapiens 54.0 nM
Inhibition of recombinant human full-length N-terminal GST-tagged p110delta/untagged full-length p85alpha expressed in baculovirus infected Sf9 cells using PIP2 as substrate by ADP-glo luminescence assay Homo sapiens 39.0 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 17.07 % SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 11.93 %
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 4.34 % 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 2.55 % 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 2.55 % 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 4.34 %
Inhibition of human PI3Kdelta incubated for 1 hr by ADP-Glo kinase assay Homo sapiens 6.3 nM
Inhibition of full length recombinant human C-terminal FLAG/His-tagged HDAC1 (1 to 482 end residues) expressed in baculovirus infected Sf9 cells using fluorogenic HDAC substrate 3 measured after 30 mins by fluorescence based assay Homo sapiens 2.0 nM
Inhibition of HDAC2 (unknown origin) using fluorogenic HDAC substrate 3 incubated for 30 mins by fluorescence based assay Homo sapiens 8.0 nM
Inhibition of recombinant human C-terminal His-tagged HDAC3 (1 to 428 end residues)/N-terminal GST-tagged recombinant human NCoR2 (395 to 489 residues) expressed in baculovirus infected Sf9 cells using fluorogenic HDAC substrate 3 measured after 30 mins by fluorescence based assay Homo sapiens 3.2 nM
Inhibition of recombinant human N-terminal GST-tagged and C-terminal His-tagged HDAC4 (627 to 1084 end residues) expressed in baculovirus infected Sf9 cells using fluorogenic HDAC class2a as substrate measured after 30 mins by fluorescence based assay Homo sapiens 479.0 nM
Inhibition of HDAC5 (unknown origin) using fluorogenic HDAC class2a as substrate measured after 30 mins by fluorescence based assay Homo sapiens 581.0 nM
Inhibition of recombinant human N-terminal GST-tagged HDAC6 expressed in baculovirus infected Sf9 cells using fluorogenic HDAC substrate 3 measured after 30 mins by fluorescence based assay Homo sapiens 34.0 nM
Inhibition of N-terminal GST-tagged human HDAC7 (518 to end residues) expressed in baculovirus infected Sf9 cells using fluorogenic HDAC class2a as substrate measured after 30 mins by fluorescence based assay Homo sapiens 528.0 nM
Inhibition of recombinant human full length C-terminal His-tagged HDAC8 expressed in baculovirus infected Sf9 cells using fluorogenic HDAC class2a as substrate measured after 30 mins by fluorescence based assay Homo sapiens 54.0 nM
Inhibition of C-terminal His-tagged human HDAC9 (604 to 1066 residues) expressed in baculovirus infected Sf9 cells using fluorogenic HDAC class2a as substrate measured after 30 mins by fluorescence based assay Homo sapiens 639.0 nM
Inhibition of N-terminal FLAG-tagged human HDAC10 (2 to 631 residues) expressed in baculovirus infected Sf9 cells using fluorogenic HDAC substrate 3 measured after 30 mins by fluorescence based assay Homo sapiens 4.1 nM
Inhibition of human PI3Kalpha incubated for 1 hr by ADP-Glo kinase assay Homo sapiens 7.9 nM
Inhibition of human PI3Kbeta incubated for 1 hr by ADP-Glo kinase assay Homo sapiens 21.0 nM
Inhibition of human PI3Kgamma incubated for 1 hr by ADP-Glo kinase assay Homo sapiens 112.0 nM
Inhibition of human mTOR Homo sapiens 185.0 nM
Inhibition of HDAC1 (unknown origin) by color de Lys colorimetric assay Homo sapiens 2.0 nM
Inhibition of HDAC2 (unknown origin) by color de Lys colorimetric assay Homo sapiens 5.0 nM
Inhibition of HDAC3 (unknown origin) by color de Lys colorimetric assay Homo sapiens 2.0 nM
Inhibition of HDAC8 (unknown origin) by color de Lys colorimetric assay Homo sapiens 191.0 nM
Inhibition of HDAC4 (unknown origin) by color de Lys colorimetric assay Homo sapiens 409.0 nM
Inhibition of HDAC5 (unknown origin) by color de Lys colorimetric assay Homo sapiens 674.0 nM
Inhibition of HDAC7 (unknown origin) by color de Lys colorimetric assay Homo sapiens 426.0 nM
Inhibition of HDAC9 (unknown origin) by color de Lys colorimetric assay Homo sapiens 554.0 nM
Inhibition of HDAC6 (unknown origin) by color de Lys colorimetric assay Homo sapiens 27.0 nM
Inhibition of HDAC10 (unknown origin) by color de Lys colorimetric assay Homo sapiens 3.0 nM
Inhibition of HDAC11 (unknown origin) by color de Lys colorimetric assay Homo sapiens 5.0 nM
Inhibition of human PI3K alpha by ADP-Glo luminescent kinase assay Homo sapiens 19.0 nM
Inhibition of human PI3K beta by ADP-Glo luminescent kinase assay Homo sapiens 54.0 nM
Inhibition of human PI3K delta by ADP-Glo luminescent kinase assay None 39.0 nM
Inhibition of HDAC1 (unknown origin) by color-de-lys assay Homo sapiens 1.7 nM

Cross References

Resources Reference
ChEMBL CHEMBL3622533
DrugBank DB11891
FDA SRS 3S9RX35S5X
Guide to Pharmacology 8952
PubChem 54575456
SureChEMBL SCHEMBL1284705
ZINC ZINC000073488511
CONTENTS