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Compound Detail

CHEMBL257991

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O=C(Nc1ccccc1-c1cn2c(CN3CCNCC3)csc2n1)c1cnc2ccccc2n1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL257991
Phase Preclinical
Structure Type MOL
InChI Key IASPBORHOMBZMY-UHFFFAOYSA-N
9
Targets
12
Activities
2
Assay Types
14
PK Parameters
20
Publications
0
Known Names

Molecular Properties

469.6
MW (Da)
3.66
ALogP
8
HBA
2
HBD
87.5
PSA (Ų)
0.41
QED
0
Ro5 Violations
5
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C25H23N7OS
MW 469.57
Aromatic Rings 5
Heavy Atoms 34
NP-Likeness -1.91

Activity Summary

EC50 6 meas. best 6.8
IC50 6 meas. best 6.07

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
NAD-dependent protein deacetylase sirtuin-2
CHEMBL4462
 EC50 6.8 5.615 160.0 2
NAD-dependent protein deacetylase sirtuin-1
CHEMBL4506
 EC50 6.8 6.8 160.0 3
NAD-dependent protein deacetylase sirtuin-3, mitochondrial
CHEMBL4461
 IC50 6.07 6.07 850.0 1
Trypanosoma brucei brucei
CHEMBL612851
 EC50 6.05 6.05 892.0 1
Sodium-dependent noradrenaline transporter
CHEMBL222
 IC50 5.61 5.61 2470.0 1
Alpha-2A adrenergic receptor
CHEMBL1867
 IC50 5.55 5.55 2830.0 1
Unchecked
CHEMBL612545
 IC50 5.47 5.47 3370.0 1
Muscarinic acetylcholine receptor M2
CHEMBL211
 IC50 5.2 5.2 6280.0 1
Muscarinic acetylcholine receptor M1
CHEMBL216
 IC50 5.1 5.1 8020.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 7892.0 ng.hr.mL-1 Mus musculus
AUC 3714.0 ng.hr.mL-1 Rattus norvegicus
AUC 7900.0 ng.hr.mL-1 Mus musculus
AUC 3700.0 ng.hr.mL-1 Rattus norvegicus
Cmax 1000.0 nM Mus musculus
Cmax 320.0 nM Rattus norvegicus
F 50.0 % Mus musculus
F 25.0 % Rattus norvegicus
F 50.0 % Mus musculus
F 25.0 % Rattus norvegicus
T1/2 5.0 hr Mus musculus
T1/2 8.4 hr Rattus norvegicus
T1/2 5.0 hr Mus musculus
T1/2 8.4 hr Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
NAD-dependent protein deacetylase sirtuin-1 EC50 = 160.0 nM 6.8 Activation of human SIRT1 expressed in Escherichia coli BL21 by mass spectrometr... 18046409
NAD-dependent protein deacetylase sirtuin-2 EC50 = 160.0 nM 6.8 Activation of human SirT2 protein fluorescence polarization assay 18800048
NAD-dependent protein deacetylase sirtuin-1 EC50 = 160.0 nM 6.8 Activation of N-terminal His6-tagged SIRT1 (156 to 664 amino acid residues) (unk... 23316803
NAD-dependent protein deacetylase sirtuin-1 EC50 = 160.0 nM 6.8 Inhibition of SIRT1 (unknown origin) 34607244
NAD-dependent protein deacetylase sirtuin-3, mitochondrial IC50 = 850.0 nM 6.07 Inhibition of SIRT3 (unknown origin) 28415012
Trypanosoma brucei brucei EC50 = 892.0 nM 6.05 Antitrypanosomal activity against Trypanosoma brucei brucei 427 assessed as inhi... 25637120
Sodium-dependent noradrenaline transporter IC50 = 2470.0 nM 5.61 Inhibition of norepinephrine transporter 19199480
Alpha-2A adrenergic receptor IC50 = 2830.0 nM 5.55 Inhibition of adrenergic alpha2A receptor 19199480
Unchecked IC50 = 3370.0 nM 5.47 Inhibition of sodium channel site 2 19199480
Muscarinic acetylcholine receptor M2 IC50 = 6280.0 nM 5.2 Inhibition of muscarinic M2 receptor 19199480
Muscarinic acetylcholine receptor M1 IC50 = 8020.0 nM 5.1 Inhibition of muscarinic M1 receptor 19199480
NAD-dependent protein deacetylase sirtuin-2 EC50 = 37000.0 nM 4.43 Activation of SIRT2 by mass spectrometry assay 18046409

Literature References

PubMed DOI Target Context # Activities
19199480 10.1021/jm8012954 Mus musculus 16
18046409 10.1038/nature06261 Rattus norvegicus 13
18046409 10.1038/nature06261 NAD-dependent protein deacetylase sirtuin-1 12
18046409 10.1038/nature06261 Mus musculus 10
19199480 10.1021/jm8012954 Rattus norvegicus 8
19199480 10.1021/jm8012954 Salmonella typhimurium 4
- 10.6019/CHEMBL4495565 SARS-CoV-2 4
23195732 10.1016/j.bmcl.2012.10.136 NAD-dependent protein deacylase sirtuin-5, mitochondrial 2
19199480 10.1021/jm8012954 NAD-dependent protein deacetylase sirtuin-1 2
36265019 10.1021/acs.jmedchem.2c01291 NAD-dependent protein deacetylase sirtuin-1 2
26689352 10.1021/acs.jmedchem.5b01117 NAD-dependent protein deacetylase sirtuin-1 2
23316803 10.1021/jm301032j NAD-dependent protein deacetylase sirtuin-1 2
- 10.6019/CHEMBL4808148 Histone deacetylase 6 2
23876989 10.1016/j.bmcl.2013.06.070 NAD-dependent protein deacetylase sirtuin-1 2
- 10.6019/CHEMBL4495564 Replicase polyprotein 1ab 2
19199480 10.1021/jm8012954 Cytochrome P450 2C19 1
19199480 10.1021/jm8012954 Cytochrome P450 3A4 1
19199480 10.1021/jm8012954 Cytochrome P450 2D6 1
19199480 10.1021/jm8012954 Cytochrome P450 2C9 1
34607244 10.1016/j.ejmech.2021.113867 NAD-dependent protein deacetylase sirtuin-1 1

Data from ChEMBL 36 via Core Engine