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Compound Detail

CHEMBL270361

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COc1cc(/C=C2\CC/C(=C\c3ccc(O)c(OC)c3)C2=O)ccc1O
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL270361
Phase Preclinical
Structure Type MOL
InChI Key NZSRSKNDCCSSGY-KAVGSWPWSA-N
11
Targets
14
Activities
2
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

352.4
MW (Da)
3.94
ALogP
5
HBA
2
HBD
76.0
PSA (Ų)
0.82
QED
0
Ro5 Violations
4
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

Natural Product First in Class Prodrug

Extended Properties

Molecular Formula C21H20O5
MW 352.39
Aromatic Rings 2
Heavy Atoms 26
NP-Likeness 0.19

Activity Summary

IC50 13 meas. best 5.55
EC50 1 meas. best 5.23

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Cytochrome P450 2C9
CHEMBL3397
 IC50 5.55 5.55 2800.0 1
Molecular identity unknown
CHEMBL612546
 EC50 5.23 5.23 5900.0 1
HT-29
CHEMBL384
 IC50 5.01 5.01 9700.0 1
RAW264.7
CHEMBL612557
 IC50 4.86 4.86 13940.0 1
PC-3
CHEMBL390
 IC50 4.81 4.81 15540.0 1
PANC-1
CHEMBL614139
 IC50 4.81 4.81 15490.0 1
Cytochrome P450 1A2
CHEMBL3356
 IC50 4.41 4.41 38900.0 1
HeLa
CHEMBL399
 IC50 4.38 4.38 42000.0 1
HepG2
CHEMBL395
 IC50 4.36 4.36 44000.0 1
Cytochrome P450 3A4
CHEMBL340
 IC50 4.19 4.19 64900.0 1
NON-PROTEIN TARGET
CHEMBL3879801
 IC50 4.12 4.12 74960.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Cytochrome P450 2C9 IC50 = 2800.0 nM 5.55 Inhibition of human recombinant CYP2C9 18249473
Molecular identity unknown EC50 = 5900.0 nM 5.23 Inhibition of Wnt3A/beta-catenin signaling in HEK293 cells after 24 hrs by firef... 24275249
HT-29 IC50 = 9700.0 nM 5.01 Cytotoxicity against human HT-29 cells after 72 hrs by MTT assay 22551677
RAW264.7 IC50 = 13940.0 nM 4.86 Anti-inflammatory activity in Mus musculus (mouse) RAW264.7 cells assessed as in... -
PC-3 IC50 = 15540.0 nM 4.81 Cytotoxicity against human PC3 cells after 72 hrs by MTT assay 22551677
PANC-1 IC50 = 15490.0 nM 4.81 Cytotoxicity against human PANC1 cells after 72 hrs by MTT assay 22551677
Cytochrome P450 1A2 IC50 = 38900.0 nM 4.41 Inhibition of human recombinant CYP1A2 18249473
HeLa IC50 = 42000.0 nM 4.38 Antiproliferative activity against Homo sapiens (human) HeLa cells after 48 hr b... -
HepG2 IC50 = 44000.0 nM 4.36 Antiproliferative activity against Homo sapiens (human) HepG2 cells after 48 hr ... -
Cytochrome P450 3A4 IC50 = 64900.0 nM 4.19 Inhibition of human recombinant CYP3A4 18249473
NON-PROTEIN TARGET IC50 = 74960.0 nM 4.12 Antioxidant activity assessed as DPPH scavenging activity after 30 min by spectr... -

Literature References

PubMed DOI Target Context # Activities
- 10.1007/s00044-012-0237-1 Rattus norvegicus 9
24275249 10.1016/j.ejmech.2013.10.073 Molecular identity unknown 7
23800686 10.1016/j.bmcl.2013.05.080 11-beta-hydroxysteroid dehydrogenase 1 4
18249473 10.1016/j.ejmech.2007.10.034 Cytochrome P450 1A2 3
18249473 10.1016/j.ejmech.2007.10.034 Cytochrome P450 3A4 3
18249473 10.1016/j.ejmech.2007.10.034 Cytochrome P450 2C9 3
- 10.1007/s00044-011-9551-2 NON-PROTEIN TARGET 3
- 10.1007/s00044-010-9521-0 RAW264.7 3
23800686 10.1016/j.bmcl.2013.05.080 11-beta-hydroxysteroid dehydrogenase type 2 2
18336957 10.1016/j.ejmech.2008.01.031 J774.A1 2
18234497 10.1016/j.bmcl.2007.12.068 J774.A1 2
- 10.1007/s00044-011-9551-2 HepG2 2
- 10.1007/s00044-011-9551-2 Unchecked 2
22551677 10.1016/j.ejmech.2012.04.005 HT-29 1
1255669 10.1021/jm00225a022 Sarcoma-180 1
- 10.1007/s00044-010-9521-0 NON-PROTEIN TARGET 1
22551677 10.1016/j.ejmech.2012.04.005 PANC-1 1
22551677 10.1016/j.ejmech.2012.04.005 PC-3 1
18249473 10.1016/j.ejmech.2007.10.034 Cytochrome P450 2B6 1
18249473 10.1016/j.ejmech.2007.10.034 Cytochrome P450 2D6 1

Data from ChEMBL 36 via Core Engine