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Compound Detail

CHEMBL464748

DICENTRINE
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COc1cc2c(cc1OC)-c1c3c(cc4c1[C@H](C2)N(C)CC4)OCO3
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL464748
Name DICENTRINE
Phase Preclinical
Structure Type MOL
InChI Key YJWBWQWUHVXPNC-AWEZNQCLSA-N
5
Targets
5
Activities
1
Assay Types
0
PK Parameters
19
Publications
0
Known Names

Molecular Properties

339.4
MW (Da)
3.18
ALogP
5
HBA
0
HBD
40.2
PSA (Ų)
0.84
QED
0
Ro5 Violations
2
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

Natural Product First in Class Prodrug

Extended Properties

Molecular Formula C20H21NO4
MW 339.39
Aromatic Rings 2
Heavy Atoms 25
NP-Likeness 1.48

Activity Summary

IC50 5 meas. best 7.1

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Aorta
CHEMBL613606
 IC50 7.1 7.1 80.0 1
HL-60
CHEMBL383
 IC50 5.43 5.43 3700.0 1
Acetylcholinesterase
CHEMBL4078
 IC50 5.21 5.21 6110.0 1
HCT-116
CHEMBL394
 IC50 5.06 5.06 8800.0 1
Cholinesterase
CHEMBL5763
 IC50 4.58 4.58 26410.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Aorta IC50 = 80.0 nM 7.1 Vasorelaxation activity in Sprague-Dawley rat aortic assessed as inhibition of p... 18217715
HL-60 IC50 = 3700.0 nM 5.43 Cytotoxicity against human HL60 cells assessed as cell growth inhibition after 7... 31403289
Acetylcholinesterase IC50 = 6110.0 nM 5.21 Inhibition of Electrophorus electricus AChE using ATCI as substrate pre-incubate... 37172474
HCT-116 IC50 = 8800.0 nM 5.06 Cytotoxicity against human HCT116 cells assessed as cell growth inhibition after... 31403289
Cholinesterase IC50 = 26410.0 nM 4.58 Inhibition of equine serum BuChE using BTCI as substrate pre-incubated for 10 mi... 37172474

Literature References

PubMed DOI Target Context # Activities
9214740 10.1021/np9700735 NON-PROTEIN TARGET 8
10691712 10.1021/np990442s Saccharomyces cerevisiae 3
- 10.1021/np50123a013 Platelet 2
- 10.1021/np50123a013 Aorta 2
37172474 10.1016/j.ejmech.2023.115414 Alpha-1D adrenergic receptor 1
18217715 10.1021/np070564h Aorta 1
37172474 10.1016/j.ejmech.2023.115414 Alpha-1B adrenergic receptor 1
37172474 10.1016/j.ejmech.2023.115414 Alpha-1A adrenergic receptor 1
37172474 10.1016/j.ejmech.2023.115414 5-hydroxytryptamine receptor 2C 1
37172474 10.1016/j.ejmech.2023.115414 5-hydroxytryptamine receptor 2B 1
37172474 10.1016/j.ejmech.2023.115414 5-hydroxytryptamine receptor 2A 1
37172474 10.1016/j.ejmech.2023.115414 Cholinesterase 1
37172474 10.1016/j.ejmech.2023.115414 Acetylcholinesterase 1
31403289 10.1021/acs.jnatprod.9b00287 MRC5 1
31403289 10.1021/acs.jnatprod.9b00287 HL-60 1
31403289 10.1021/acs.jnatprod.9b00287 HepG2 1
31403289 10.1021/acs.jnatprod.9b00287 HCT-116 1
31403289 10.1021/acs.jnatprod.9b00287 MCF7 1
20097066 10.1016/j.bmcl.2010.01.007 Cyclin-dependent kinase 2 1

Data from ChEMBL 36 via Core Engine