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Compound Detail

CHEMBL420311

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NC(=O)C1CCCc2c1[nH]c1ccc(Cl)cc21
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL420311
Phase Preclinical
Structure Type MOL
InChI Key FUZYTVDVLBBXDL-UHFFFAOYSA-N
11
Targets
65
Activities
2
Assay Types
4
PK Parameters
20
Publications
0
Known Names

Molecular Properties

248.7
MW (Da)
2.73
ALogP
1
HBA
2
HBD
58.9
PSA (Ų)
0.80
QED
0
Ro5 Violations
1
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

Natural Product First in Class Prodrug

Extended Properties

Molecular Formula C13H13ClN2O
MW 248.71
Aromatic Rings 2
Heavy Atoms 17
NP-Likeness -0.50

Activity Summary

IC50 64 meas. best 8.22
Ki 1 meas. best 6.94

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
NAD-dependent protein deacetylase sirtuin-1
CHEMBL4506
 IC50 8.22 6.7052 6.0 27
NAD-dependent protein deacetylase sirtuin-2
CHEMBL4462
 IC50 7.01 5.2525 98.0 20
NAD-dependent protein deacetylase sirtuin-1
CHEMBL4506
 Ki 6.94 6.94 114.0 1
NAD-dependent protein deacetylase sirtuin-3, mitochondrial
CHEMBL4461
 IC50 5.19 4.3967 6400.0 6
HUVEC
CHEMBL613979
 IC50 4.82 4.82 15000.0 1
A549
CHEMBL392
 IC50 4.54 4.54 29000.0 1
MCF7
CHEMBL387
 IC50 4.43 4.43 37000.0 1
HCT-116
CHEMBL394
 IC50 4.43 4.43 37000.0 1
HepG2
CHEMBL395
 IC50 4.36 4.36 44000.0 1
NCI-H460
CHEMBL396
 IC50 4.32 4.32 48000.0 1
HEK-293T
CHEMBL3706568
 IC50 4.29 4.29 51000.0 1
K562
CHEMBL385
 IC50 4.22 4.22 60000.0 1

Pharmacokinetic Data

Parameter Value Units Species
T1/2 1.0 hr Rattus norvegicus
T1/2 2.267 hr Mus musculus
T1/2 3.233 hr Mus musculus
T1/2 2.0 hr Mus musculus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
NAD-dependent protein deacetylase sirtuin-1 IC50 = 6.0 nM 8.22 Inhibition of human N-terminal His-tagged SIRT1 (183 to 664 residues) expressed ... 32163813
NAD-dependent protein deacetylase sirtuin-1 IC50 = 38.0 nM 7.42 Inhibition of human recombinant GST-tagged SIRT1 expressed in 293T cells by Fluo... 21306906
NAD-dependent protein deacetylase sirtuin-1 IC50 = 48.0 nM 7.32 Inhibition of His6-tagged SIRT1 (unknown origin) expressed in Escherichia coli B... 33876629
NAD-dependent protein deacetylase sirtuin-1 IC50 = 85.0 nM 7.07 Inhibition of human SIRT1 deacetylase activity using acetylated H3K9 as substrat... 30986062
NAD-dependent protein deacetylase sirtuin-1 IC50 = 98.0 nM 7.01 Inhibitory activity against recombinant human SIRT1 expressed in Escherichia col... 16335928
NAD-dependent protein deacetylase sirtuin-1 IC50 = 98.0 nM 7.01 Inhibition of SIRT1 21080630
NAD-dependent protein deacetylase sirtuin-2 IC50 = 98.0 nM 7.01 Inhibition of recombinant human N-terminal His6-tagged SIRT-2 expressed in Esche... -
NAD-dependent protein deacetylase sirtuin-1 IC50 = 100.0 nM 7.0 Inhibition of SIRT1 using Ac-His-Arg-Lys-Lys(Ac)-AMC as substrate 21080630
NAD-dependent protein deacetylase sirtuin-1 IC50 = 100.0 nM 7.0 Inhibition of recombinant SIRT1 using ZMAL substrate after 4 hrs by homogeneous ... 24900427
NAD-dependent protein deacetylase sirtuin-1 IC50 = 100.0 nM 7.0 Inhibition of N-terminal His-tagged recombinant human SIRT-1 expressed in Escher... 28475330
NAD-dependent protein deacetylase sirtuin-1 Ki = 114.0 nM 6.94 Uncompetitive inhibition of His6-tagged SIRT1 (unknown origin) expressed in Esch... 33876629
NAD-dependent protein deacetylase sirtuin-1 IC50 = 123.0 nM 6.91 Inhibitory activity against recombinant human SIRT1 expressed in Escherichia col... 16335928
NAD-dependent protein deacetylase sirtuin-1 IC50 = 130.0 nM 6.89 Inhibition of SIRT1 (unknown origin) 28415012
NAD-dependent protein deacetylase sirtuin-1 IC50 = 140.0 nM 6.85 Inhibition of human N-terminal His-tagged SIRT1 (183 to 664 residues) expressed ... 32163813
NAD-dependent protein deacetylase sirtuin-1 IC50 = 160.0 nM 6.8 Inhibition of human recombinant SIRT1 expressed in Escherichia coli cells using ... 22931526
NAD-dependent protein deacetylase sirtuin-1 IC50 = 210.0 nM 6.68 Inhibition of full length human SIRT1 expressed in Escherichia coli BL21 (DE3) c... 25275824
NAD-dependent protein deacetylase sirtuin-1 IC50 = 250.0 nM 6.6 Inhibition of recombinant human N-terminal GST-tagged SIRT1 (193 to 741 residues... -
NAD-dependent protein deacetylase sirtuin-1 IC50 = 260.0 nM 6.58 Inhibition of His-tagged SIRT1 (1 to 747) (unknown origin)-mediated deacetylatio... 23570514
NAD-dependent protein deacetylase sirtuin-1 IC50 = 280.0 nM 6.55 Inhibition of recombinant SIRT1 preincubated for 5 mins before addition of subst... 19296597
NAD-dependent protein deacetylase sirtuin-1 IC50 = 280.0 nM 6.55 Inhibition of SIRT1 17329104

Literature References

PubMed DOI Target Context # Activities
33876629 10.1021/acs.jmedchem.1c00017 NAD-dependent protein deacetylase sirtuin-1 12
- 10.6019/CHEMBL5303304 U2OS 7
- 10.6019/CHEMBL5303304 HEK-293T 6
24340169 10.1039/c2md00290f MCF7 5
22931526 10.1021/jm301115r NON-PROTEIN TARGET 4
28437106 10.1021/acs.jmedchem.7b00147 Ubiquitin-conjugating enzyme E2 T 4
21080630 10.1021/jm100861p NAD-dependent protein deacetylase sirtuin-1 4
16335928 10.1021/jm050522v NAD-dependent protein deacetylase sirtuin-1 4
23189967 10.1021/jm3011614 NON-PROTEIN TARGET 4
33691794 10.1186/s13148-021-01037-1 A549 4
- 10.6019/CHEMBL5303304 Fibroblast 3
28475330 10.1021/acs.jmedchem.7b00533 Hs 683 3
23189967 10.1021/jm3011614 U-937 3
30986062 10.1021/acs.jmedchem.9b00191 NAD-dependent protein deacetylase sirtuin-1 2
17329104 10.1016/j.bmcl.2007.02.023 NAD-dependent protein deacetylase sirtuin-2 2
17329104 10.1016/j.bmcl.2007.02.023 NAD-dependent protein deacetylase sirtuin-1 2
16335928 10.1021/jm050522v Liver microsomes 2
28475330 10.1021/acs.jmedchem.7b00533 Unchecked 2
- 10.6019/CHEMBL4495565 SARS-CoV-2 2
32163813 10.1016/j.ejmech.2020.112201 NAD-dependent protein deacetylase sirtuin-1 2

Data from ChEMBL 36 via Core Engine