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Compound Detail

CHEMBL371562

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CC(C)=CCc1c(O)cc(O)c2c(=O)cc(-c3ccc(O)cc3)oc12
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL371562
Phase Preclinical
Structure Type MOL
InChI Key MEHHCBRCXIDGKZ-UHFFFAOYSA-N
5
Targets
5
Activities
2
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

338.4
MW (Da)
4.09
ALogP
5
HBA
3
HBD
90.9
PSA (Ų)
0.63
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 C20H18O5
MW 338.36
Aromatic Rings 3
Heavy Atoms 25
NP-Likeness 1.88

Activity Summary

IC50 3 meas. best 6.2
EC50 2 meas. best 8.46

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Estrogen receptor beta
CHEMBL242
 EC50 8.46 8.46 3.5 1
Estrogen receptor
CHEMBL206
 EC50 7.3 7.3 50.0 1
3',5'-cyclic-AMP phosphodiesterase 4D
CHEMBL288
 IC50 6.2 6.2 630.0 1
cGMP-specific 3',5'-cyclic phosphodiesterase
CHEMBL1827
 IC50 5.89 5.89 1290.0 1
RAW264.7
CHEMBL612557
 IC50 5.42 5.42 3830.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Estrogen receptor beta EC50 = 3.5 nM 8.46 Estrogenic activity at ERbeta (unknown origin) expressed in human MDA-MB-231/bet... 29641206
Estrogen receptor EC50 = 50.0 nM 7.3 Estrogenic activity at ERalpha in human Ishikawa cells assessed as induction of ... 29641206
3',5'-cyclic-AMP phosphodiesterase 4D IC50 = 630.0 nM 6.2 Inhibition of human PDE4D2 catalytic domain (86 to 413 residues) expressed in Es... 29291443
cGMP-specific 3',5'-cyclic phosphodiesterase IC50 = 1290.0 nM 5.89 Inhibition of human recombinant PDE5A1 expressed in COS7 cells 18778098
RAW264.7 IC50 = 3830.0 nM 5.42 Antiinflammatory activity in mouse RAW264.7 cells assessed as inhibition of LPS-... 28522265

Literature References

PubMed DOI Target Context # Activities
29641206 10.1021/acs.jnatprod.7b01070 Estrogen receptor 2
29641206 10.1021/acs.jnatprod.7b01070 Estrogen receptor beta 2
28522265 10.1016/j.bmc.2017.05.009 RAW264.7 2
15828817 10.1021/jm040770b HT-29 2
28522265 10.1016/j.bmc.2017.05.009 Mushroom tyrosinase 1
33609662 10.1016/j.bmcl.2021.127859 NCI-H460 1
31427220 10.1016/j.bmcl.2019.07.048 Nakaseomyces glabratus 1
31427220 10.1016/j.bmcl.2019.07.048 Candida albicans 1
29641206 10.1021/acs.jnatprod.7b01070 Unchecked 1
29641206 10.1021/acs.jnatprod.7b01070 Ishikawa 1
29641206 10.1021/acs.jnatprod.7b01070 MDA-MB-231 1
29291443 10.1016/j.ejmech.2017.12.057 3',5'-cyclic-AMP phosphodiesterase 4D 1
28835349 10.1016/j.bmc.2017.08.018 Nuclear factor erythroid 2-related factor 2 1
28522265 10.1016/j.bmc.2017.05.009 Tyrosine-protein phosphatase non-receptor type 1 1
28522265 10.1016/j.bmc.2017.05.009 Unchecked 1
28522265 10.1016/j.bmc.2017.05.009 HEK-293T 1
28522265 10.1016/j.bmc.2017.05.009 L02 1
28522265 10.1016/j.bmc.2017.05.009 HepG2 1
28522265 10.1016/j.bmc.2017.05.009 SW480 1
28522265 10.1016/j.bmc.2017.05.009 MCF7 1

Data from ChEMBL 36 via Core Engine