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Compound Detail

CHEMBL491960

CAMBINOL
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O=c1[nH]c(=S)[nH]c(-c2ccccc2)c1Cc1c(O)ccc2ccccc12
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL491960
Name CAMBINOL
Phase Preclinical
Structure Type MOL
InChI Key RVNSQVIUFZVNAU-UHFFFAOYSA-N
9
Targets
36
Activities
2
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

360.4
MW (Da)
4.55
ALogP
3
HBA
3
HBD
68.9
PSA (Ų)
0.47
QED
0
Ro5 Violations
3
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C21H16N2O2S
MW 360.44
Aromatic Rings 4
Heavy Atoms 26
NP-Likeness -0.27

Activity Summary

IC50 35 meas. best 5.3
Ki 1 meas. best 5.16

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Sphingomyelin phosphodiesterase 3
CHEMBL4523470
 IC50 5.3 5.3 5000.0 1
Unchecked
CHEMBL612545
 IC50 5.3 4.85 5000.0 2
Sphingomyelin phosphodiesterase 3
CHEMBL4523130
 IC50 5.22 5.22 6000.0 1
Sphingomyelin phosphodiesterase 3
CHEMBL4523470
 Ki 5.16 5.16 7000.0 1
NAD-dependent protein deacetylase sirtuin-1
CHEMBL4506
 IC50 5.05 4.3392 8850.0 12
NAD-dependent protein deacetylase sirtuin-2
CHEMBL4462
 IC50 4.96 4.3338 10900.0 13
NAD-dependent protein deacetylase sirtuin-3, mitochondrial
CHEMBL4461
 IC50 4.89 4.89 12900.0 1
RT-112
CHEMBL614145
 IC50 4.42 4.42 37900.0 1
NAD-dependent protein deacylase sirtuin-5, mitochondrial
CHEMBL2163183
 IC50 4.37 4.37 42500.0 1
EJ
CHEMBL614292
 IC50 4.02 4.02 95900.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Unchecked IC50 = 5000.0 nM 5.3 Inhibition of Bacillus cereus nSMase 33395289
Sphingomyelin phosphodiesterase 3 IC50 = 5000.0 nM 5.3 Inhibition of human recombinant nSMase expressed in HEK293 cells using sphingomy... 30921693
Sphingomyelin phosphodiesterase 3 IC50 = 6000.0 nM 5.22 Inhibition of rat nSMase2 33395289
Sphingomyelin phosphodiesterase 3 Ki = 7000.0 nM 5.16 Uncompetitive inhibition of nSMase2 (unknown origin) assessed as inhibition cons... 33395289
NAD-dependent protein deacetylase sirtuin-1 IC50 = 8850.0 nM 5.05 Inhibition of recombinant human GST or His6-tagged SIRT1 using H2N-HK-[Nepsilon-... 27707605
NAD-dependent protein deacetylase sirtuin-2 IC50 = 10900.0 nM 4.96 Inhibition of recombinant human His6-tagged SIRT2 using H2N-HK-[Nepsilon-acetyl-... 27707605
NAD-dependent protein deacetylase sirtuin-3, mitochondrial IC50 = 12900.0 nM 4.89 Inhibition of recombinant human His6-tagged SIRT3 using H2N-HK-[Nepsilon-acetyl-... 27707605
RT-112 IC50 = 37900.0 nM 4.42 Antiproliferative activity against human RT112 cells expressing p53 mutant asses... 30442421
Unchecked IC50 = 39900.0 nM 4.4 Cytotoxicity against human C3PV cells assessed as decrease in cell viability aft... 30442421
NAD-dependent protein deacetylase sirtuin-1 IC50 = 40700.0 nM 4.39 Inhibition of human recombinant SIRT1 19419202
NAD-dependent protein deacetylase sirtuin-2 IC50 = 40700.0 nM 4.39 Inhibition of human recombinant SIRT2 expressed in Escherichia coli incubated at... 21306905
NAD-dependent protein deacetylase sirtuin-2 IC50 = 42100.0 nM 4.38 Inhibition of human recombinant SIRT2 expressed in Escherichia coli cells using ... 22931526
NAD-dependent protein deacylase sirtuin-5, mitochondrial IC50 = 42500.0 nM 4.37 Inhibition of SIRT5 using ZK(suc)A substrate after 1 hr by homogeneous fluoresce... 24900427
NAD-dependent protein deacetylase sirtuin-2 IC50 = 45860.0 nM 4.34 Inhibition of human recombinant C-terminal His-tagged SIRT2 (13 to 319 amino aci... 24992072
NAD-dependent protein deacetylase sirtuin-1 IC50 = 47900.0 nM 4.32 Inhibition of human recombinant N-terminal GST-tagged SIRT1 (193 to 741) after 4... 24387981
NAD-dependent protein deacetylase sirtuin-1 IC50 = 47900.0 nM 4.32 Inhibition of human recombinant N-terminal GST-tagged SIRT1 (193 to 741 amino ac... 24992072
NAD-dependent protein deacetylase sirtuin-2 IC50 = 47900.0 nM 4.32 Inhibition of human recombinant SIRT2 19419202
NAD-dependent protein deacetylase sirtuin-2 IC50 = 51000.0 nM 4.29 Inhibition of SIRT2 (unknown origin) by luminescence assay 24697269
NAD-dependent protein deacetylase sirtuin-2 IC50 = 52890.0 nM 4.28 Inhibition of human recombinant C-terminal His-tagged SIRT2 (13 to 319) after 45... 24387981
NAD-dependent protein deacetylase sirtuin-1 IC50 = 56000.0 nM 4.25 Inhibition of SIRT1 21080630

Literature References

PubMed DOI Target Context # Activities
19419202 10.1021/jm8014298 MCF7 6
31812033 10.1016/j.ejmech.2019.111926 NAD-dependent protein deacetylase sirtuin-2 2
24387981 10.1016/j.bmc.2013.12.029 NAD-dependent protein deacetylase sirtuin-2 2
24387981 10.1016/j.bmc.2013.12.029 NAD-dependent protein deacetylase sirtuin-1 2
24992072 10.1016/j.ejmech.2014.06.060 NAD-dependent protein deacetylase sirtuin-2 2
27707605 10.1016/j.bmcl.2016.09.055 Unchecked 2
24697269 10.1021/jm4018064 NAD-dependent protein deacetylase sirtuin-1 2
24697269 10.1021/jm4018064 NAD-dependent protein deacetylase sirtuin-3, mitochondrial 2
24992072 10.1016/j.ejmech.2014.06.060 NAD-dependent protein deacetylase sirtuin-1 2
30442421 10.1016/j.bmcl.2018.11.006 RT-112 2
24697269 10.1021/jm4018064 NAD-dependent protein deacetylase sirtuin-2 2
21306905 10.1016/j.bmc.2011.01.025 U-937 2
21306905 10.1016/j.bmc.2011.01.025 NAD-dependent protein deacetylase sirtuin-2 2
21306905 10.1016/j.bmc.2011.01.025 NAD-dependent protein deacetylase sirtuin-1 2
30442421 10.1016/j.bmcl.2018.11.006 EJ 2
33395289 10.1021/acs.jmedchem.0c01664 Sphingomyelin phosphodiesterase 3 2
30442421 10.1016/j.bmcl.2018.11.006 Unchecked 2
19419202 10.1021/jm8014298 NAD-dependent protein deacetylase sirtuin-2 2
19419202 10.1021/jm8014298 NAD-dependent protein deacetylase sirtuin-1 2
22931526 10.1021/jm301115r NAD-dependent protein deacetylase sirtuin-2 1

Data from ChEMBL 36 via Core Engine