PRACINOSTAT

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Synonyms
Status
Molecule Category UNKNOWN
UNII GPO2JN4UON
EPA CompTox DTXSID00239196

Structure

InChI Key JHDKZFFAIZKUCU-ZRDIBKRKSA-N
Smiles CCCCc1nc2cc(/C=C/C(=O)NO)ccc2n1CCN(CC)CC
InChI
InChI=1S/C20H30N4O2/c1-4-7-8-19-21-17-15-16(10-12-20(25)22-26)9-11-18(17)24(19)14-13-23(5-2)6-3/h9-12,15,26H,4-8,13-14H2,1-3H3,(H,22,25)/b12-10+

Physicochemical Descriptors

Property Name Value
Molecular Formula C20H30N4O2
Molecular Weight 358.49
AlogP 3.24
Hydrogen Bond Acceptor 5.0
Hydrogen Bond Donor 2.0
Number of Rotational Bond 10.0
Polar Surface Area 70.39
Molecular species BASE
Aromatic Rings 2.0
Heavy Atoms 26.0
Assay Description Organism Bioactivity Reference
Inhibition of HDAC in human HeLa cell nuclear extracts using Fluor de Lys as substrate by fluorescence assay Homo sapiens 126.0 nM
Inhibition of HDAC in human HeLa cell nuclear extracts using Fluor de Lys as substrate at 1 uM by fluorescence assay Homo sapiens 92.6 %
Antimalarial activity against Plasmodium falciparum infected in human erythrocytes after 72 hrs Plasmodium falciparum 80.0 nM
Cytotoxicity against human mammalian cells after 72 to 96 hrs by MTT assay Homo sapiens 800.0 nM
Antimalarial activity against exo-erythrocytic form of Plasmodium berghei infected in human HepG2 cells Plasmodium berghei 150.0 nM
Inhibition of recombinant human HDAC-1 expressed in baculovirus infected insect Sf9 cells using Fluor de Lys as substrate preincubated for 2 hrs followed by substrate addition measured after 10 mins by fluorescence assay Homo sapiens 16.0 nM
Inhibition of recombinant human HDAC-2 expressed in baculovirus infected insect Sf9 cells using Fluor de Lys as substrate preincubated for 2 hrs followed by substrate addition measured after 10 mins by fluorescence assay Homo sapiens 16.0 nM
Inhibition of recombinant human HDAC-8 expressed in HEK293-F cells using Fluor de Lys as substrate preincubated for 2 hrs followed by substrate addition measured after 10 mins by fluorescence assay Homo sapiens 16.0 nM
Inhibition of human HDAC1 Homo sapiens 28.0 nM
Inhibition of human HDAC2 Homo sapiens 27.0 nM
Inhibition of human HDAC3 Homo sapiens 19.0 nM
Inhibition of human HDAC8 Homo sapiens 48.0 nM
Inhibition of human HDAC4 Homo sapiens 16.0 nM
Inhibition of human HDAC5 Homo sapiens 21.0 nM
Inhibition of human HDAC7 Homo sapiens 107.0 nM
Inhibition of human HDAC9 Homo sapiens 24.0 nM
Inhibition of human HDAC6 Homo sapiens 247.0 nM
Inhibition of human HDAC10 Homo sapiens 23.0 nM
Inhibition of human HDAC11 Homo sapiens 43.0 nM
Inhibition of recombinant human LTA4H aminopeptidase activity expressed in Escherichia coli BL21 (DE3) pLysS assessed as formation of p-NA from Ala-p-NA at 10 uM preincubated for 10 mins followed by substrate addition measured after 10 mins Homo sapiens 50.0 %
Inhibition of recombinant human LTA4H Epoxide Hydrolase expressed in Escherichia coli BL21 (DE3) pLysS at 10 uM preincubated for 10 mins followed by addition of LTA4 as substrate measured after 15 mins by reverse-phase HPLC analysis Homo sapiens 50.0 %
Antimalarial activity against Plasmodium falciparum infected in human erythrocytes after 24 hrs by microbeta scintillation counting-based [3H]-hypoxanthine incorporation assay Plasmodium falciparum 80.0 nM
Antiplasmodial activity against exoerythrocytic-stage of Plasmodium berghei ANKA infected in human HepG2 cells after 53 hrs by DAPI staining-based method Plasmodium berghei ANKA 150.0 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 -8.99 %
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 23.36 % SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 4.276 %
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 5.37 % 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 2.63 % 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 2.63 % 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 5.37 %
Inhibition of HDAC8 (unknown origin) Homo sapiens 140.0 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 50.0 nM
Inhibition of HDAC2 (unknown origin) using fluorogenic HDAC substrate 3 incubated for 30 mins by fluorescence based assay Homo sapiens 290.0 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 70.0 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 93.0 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 82.0 nM

Cross References

Resources Reference
ChEBI 95071
ChEMBL CHEMBL1851943
DrugBank DB05223
FDA SRS GPO2JN4UON
Guide to Pharmacology 8365
PubChem 49855250
SureChEMBL SCHEMBL833105
ZINC ZINC000043152558
CONTENTS