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Compound Detail

CHEMBL469444

BAVACHIN
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CC(C)=CCc1cc2c(cc1O)O[C@H](c1ccc(O)cc1)CC2=O
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL469444
Name BAVACHIN
Phase Preclinical
Structure Type MOL
InChI Key OAUREGNZECGNQS-IBGZPJMESA-N
5
Targets
6
Activities
1
Assay Types
0
PK Parameters
16
Publications
0
Known Names

Molecular Properties

324.4
MW (Da)
4.31
ALogP
4
HBA
2
HBD
66.8
PSA (Ų)
0.83
QED
0
Ro5 Violations
3
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

Natural Product First in Class Prodrug

Extended Properties

Molecular Formula C20H20O4
MW 324.38
Aromatic Rings 2
Heavy Atoms 24
NP-Likeness 1.97

Activity Summary

IC50 6 meas. best 5.57

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Unchecked
CHEMBL612545
 IC50 5.57 5.16 2700.0 2
MCF7
CHEMBL387
 IC50 4.71 4.71 19500.0 1
HCT-116
CHEMBL394
 IC50 4.68 4.68 20700.0 1
PC-3
CHEMBL390
 IC50 4.59 4.59 25400.0 1
A549
CHEMBL392
 IC50 4.52 4.52 30500.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Unchecked IC50 = 2700.0 nM 5.57 Inhibition of melanin synthesis in NHEM cells assessed as [14C]thiouracil incorp... 19132934
Unchecked IC50 = 18000.0 nM 4.75 Inhibition of melanin synthesis in NHEM after 24 hrs by liquid scintillation 19102656
MCF7 IC50 = 19500.0 nM 4.71 Cytotoxicity against human MCF7 cells assessed as growth inhibition after 48 hrs... 29335212
HCT-116 IC50 = 20700.0 nM 4.68 Cytotoxicity against human HCT116 cells assessed as growth inhibition after 48 h... 29335212
PC-3 IC50 = 25400.0 nM 4.59 Cytotoxicity against human PC3 cells assessed as growth inhibition after 48 hrs ... 29335212
A549 IC50 = 30500.0 nM 4.52 Cytotoxicity against human A549 cells assessed as growth inhibition after 48 hrs... 29335212

Literature References

PubMed DOI Target Context # Activities
3069957 10.1021/np50060a006 Salmonella typhimurium 11
8759164 10.1021/np960157y NON-PROTEIN TARGET 3
29335212 10.1016/j.ejmech.2018.01.006 PC-3 2
29335212 10.1016/j.ejmech.2018.01.006 A549 2
29335212 10.1016/j.ejmech.2018.01.006 MCF7 2
29335212 10.1016/j.ejmech.2018.01.006 HCT-116 2
11678652 10.1021/np010288l Aromatase 1
19132934 10.1021/np800395j Unchecked 1
19132934 10.1021/np800395j ADMET 1
19102656 10.1021/np800535g Unchecked 1
19102656 10.1021/np800535g ADMET 1
25710081 10.1021/np500834d K562 1
25710081 10.1021/np500834d A549 1
25710081 10.1021/np500834d NAD-dependent protein deacetylase sirtuin-1 1
33984802 10.1016/j.ejmech.2021.113492 Acetylcholinesterase 1
33984802 10.1016/j.ejmech.2021.113492 Beta-secretase 1 1

Data from ChEMBL 36 via Core Engine