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Compound Detail

CHEMBL380797

SIRTINOL
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CC(NC(=O)c1ccccc1/N=C/c1c(O)ccc2ccccc12)c1ccccc1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL380797
Name SIRTINOL
Phase Preclinical
Structure Type MOL
InChI Key UXJFDYIHRJGPFS-WPWMEQJKSA-N
10
Targets
47
Activities
1
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

394.5
MW (Da)
5.79
ALogP
3
HBA
2
HBD
61.7
PSA (Ų)
0.42
QED
1
Ro5 Violations
5
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C26H22N2O2
MW 394.47
Aromatic Rings 4
Heavy Atoms 30
NP-Likeness -0.77

Activity Summary

IC50 47 meas. best 5.72

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Unchecked
CHEMBL612545
 IC50 5.72 5.065 1920.0 2
NAD-dependent protein deacetylase sirtuin-2
CHEMBL4462
 IC50 5.12 4.3806 7620.0 17
Plasmodium falciparum
CHEMBL364
 IC50 5.05 4.9933 9000.0 3
Neutrophil elastase
CHEMBL248
 IC50 4.61 4.61 24500.0 1
Leishmania infantum
CHEMBL612848
 IC50 4.52 4.52 30000.0 2
Hs 683
CHEMBL612596
 IC50 4.47 4.47 33900.0 1
NAD-dependent protein deacetylase sirtuin-1
CHEMBL4506
 IC50 4.43 4.2971 37000.0 7
NAD-dependent histone deacetylase SIR2
CHEMBL3275
 IC50 4.32 4.245 48000.0 2
NAD-dependent protein deacetylase HST2
CHEMBL5933
 IC50 4.32 4.32 48000.0 1
NAD-dependent protein deacylase sirtuin-5, mitochondrial
CHEMBL2163183
 IC50 4.31 4.31 48900.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Unchecked IC50 = 1920.0 nM 5.72 Inhibition of elastase release in fMLP/CB-induced human neutrophils by cell base... 37939864
NAD-dependent protein deacetylase sirtuin-2 IC50 = 7620.0 nM 5.12 Inhibition of SIRT2 (unknown origin) activity 37939864
Plasmodium falciparum IC50 = 9000.0 nM 5.05 Antiplasmodial activity against Plasmodium falciparum 3D7 assessed as growth inh... 28241112
Plasmodium falciparum IC50 = 9100.0 nM 5.04 Antimalarial activity against chloroquine-resistant Plasmodium falciparum Dd2 in... 18212103
Plasmodium falciparum IC50 = 12900.0 nM 4.89 Antimalarial activity against chloroquine-sensitive Plasmodium falciparum 3D7 in... 18212103
Neutrophil elastase IC50 = 24500.0 nM 4.61 Inhibition of human neutrophil elastase by enzymatic assay 37939864
Leishmania infantum IC50 = 30000.0 nM 4.52 Antiproliferative activity against amastigote stage of Leishmania infantum measu... 28241112
Leishmania infantum IC50 = 30000.0 nM 4.52 Antileishmanial activity against amastigote stage of Leishmania infantum MHOM/MA... 28241112
Hs 683 IC50 = 33900.0 nM 4.47 Antiproliferative activity against human Hs683 cells after 72 hrs by MTT assay 28475330
NAD-dependent protein deacetylase sirtuin-1 IC50 = 37000.0 nM 4.43 Inhibition of recombinant SIRT1 using ZMAL substrate after 4 hrs by homogeneous ... 24900427
NAD-dependent protein deacetylase sirtuin-2 IC50 = 38000.0 nM 4.42 Inhibition of human recombinant GST-tagged SIRT2 using acetylated HeLa histones ... 21306906
NAD-dependent protein deacetylase sirtuin-1 IC50 = 38000.0 nM 4.42 Inhibition of SIRT1 (unknown origin) 28135086
NAD-dependent protein deacetylase sirtuin-2 IC50 = 38000.0 nM 4.42 Inhibition of human GST-tagged SIRT1 (18 to 340 residues) expressed in Escherich... 27153347
NAD-dependent protein deacetylase sirtuin-2 IC50 = 38000.0 nM 4.42 Inhibition of human GST-tagged SIRT-2 (18 to 340 amino acids) using [3H]-acetyl ... -
NAD-dependent protein deacetylase sirtuin-1 IC50 = 38000.0 nM 4.42 Inhibition of recombinant human N-tagged GST-SIRT1 fusion protein using fluoresc... 24340169
NAD-dependent protein deacetylase sirtuin-2 IC50 = 38000.0 nM 4.42 Inhibition of recombinant SIRT2 using ZMAL substrate after 4 hrs by homogeneous ... 24900427
Unchecked IC50 = 39300.0 nM 4.41 Antiproliferative activity against human U373 cells after 72 hrs by MTT assay 28475330
NAD-dependent protein deacetylase sirtuin-1 IC50 = 40100.0 nM 4.4 Inhibition of human recombinant SIRT1 using Arg-His-Lys-Lys(epsilon-acetyl)-AMC ... 23167691
NAD-dependent protein deacetylase sirtuin-2 IC50 = 45100.0 nM 4.35 Inhibition of SIRT2 17181175
NAD-dependent protein deacetylase sirtuin-2 IC50 = 45100.0 nM 4.35 Inhibition of human recombinant GST-tagged SIRT2 by histone deacetylase assay 15566299

Literature References

PubMed DOI Target Context # Activities
24340169 10.1039/c2md00290f MCF7 5
28475330 10.1021/acs.jmedchem.7b00533 Hs 683 4
33691794 10.1186/s13148-021-01037-1 A549 4
23189967 10.1021/jm3011614 U-937 3
24340169 10.1039/c2md00290f NAD-dependent protein deacetylase sirtuin-1 3
28241112 10.1021/acs.jmedchem.6b01595 Leishmania infantum 3
28241112 10.1021/acs.jmedchem.6b01595 Schistosoma mansoni 3
28475330 10.1021/acs.jmedchem.7b00533 Unchecked 3
16302818 10.1021/jm050100l NAD-dependent protein deacetylase sirtuin-1 2
23195732 10.1016/j.bmcl.2012.10.136 NAD-dependent protein deacylase sirtuin-5, mitochondrial 2
18212103 10.1128/aac.00757-07 Unchecked 2
18212103 10.1128/aac.00757-07 Plasmodium falciparum 2
24340169 10.1039/c2md00290f NAD-dependent protein deacetylase sirtuin-2 2
- 10.6019/CHEMBL4808148 Histone deacetylase 6 2
20041717 10.1021/jm9013345 Caenorhabditis elegans 2
25818461 10.1016/j.bmcl.2015.03.018 NAD-dependent protein deacylase sirtuin-5, mitochondrial 2
18348515 10.1021/jm701595q U-937 2
16302818 10.1021/jm050100l NAD-dependent protein deacetylase sirtuin-2 2
16302818 10.1021/jm050100l NAD-dependent histone deacetylase SIR2 2
19734050 10.1016/j.bmc.2009.07.073 NAD-dependent protein deacetylase HST2 1

Data from ChEMBL 36 via Core Engine