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Compound Detail

CHEMBL245412

ZERUMBONE
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C/C1=C\CC(C)(C)/C=C/C(=O)/C(C)=C/CC1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL245412
Name ZERUMBONE
Phase Preclinical
Structure Type MOL
InChI Key GIHNTRQPEMKFKO-SKTNYSRSSA-N
6
Targets
7
Activities
1
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

218.3
MW (Da)
4.21
ALogP
1
HBA
0
HBD
17.1
PSA (Ų)
0.56
QED
0
Ro5 Violations
0
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

Natural Product First in Class Prodrug

Extended Properties

Molecular Formula C15H22O
MW 218.34
Aromatic Rings 0
Heavy Atoms 16
NP-Likeness 2.84

Activity Summary

IC50 7 meas. best 8.26

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
DU-145
CHEMBL613508
 IC50 8.26 6.71 5.5 2
Zinc finger protein GLI2
CHEMBL5119
 IC50 6.04 6.04 910.0 1
Zinc finger protein GLI1
CHEMBL5461
 IC50 5.15 5.15 7100.0 1
PC-3
CHEMBL390
 IC50 5.04 5.04 9100.0 1
RAW264.7
CHEMBL612557
 IC50 4.87 4.87 13600.0 1
Cytochrome P450 3A4
CHEMBL340
 IC50 4.66 4.66 21800.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
DU-145 IC50 = 5.5 nM 8.26 Potentiation of PTX-induced anticancer activity in human DU145 cells assessed as... 31336310
Zinc finger protein GLI2 IC50 = 910.0 nM 6.04 Inhibition of Gli2-mediated transcription expressed in human PANC1 cells 19309080
DU-145 IC50 = 6900.0 nM 5.16 Cytotoxicity against human DU145 cells 31336310
Zinc finger protein GLI1 IC50 = 7100.0 nM 5.15 Inhibition of Gli1-mediated transcription expressed in human PANC1 cells 19309080
PC-3 IC50 = 9100.0 nM 5.04 Cytotoxicity against human PC3 cells 31336310
RAW264.7 IC50 = 13600.0 nM 4.87 Antiinflammatory activity against mouse RAW264.7 cells assessed as inhibition of... 30024153
Cytochrome P450 3A4 IC50 = 21800.0 nM 4.66 Inhibition of human CYP3A4 by radiometric assay 15270556

Literature References

PubMed DOI Target Context # Activities
26681550 10.1021/acs.jnatprod.5b00796 A549 9
20541293 10.1016/j.ejmech.2010.05.029 NON-PROTEIN TARGET 5
26681550 10.1021/acs.jnatprod.5b00796 Molecular identity unknown 5
30024153 10.1021/acs.jnatprod.7b01071 RAW264.7 3
31336310 10.1016/j.ejmech.2019.07.034 DU-145 2
23062825 10.1016/j.bmc.2012.09.040 Cholinesterase 1
17157007 10.1016/j.bmcl.2006.11.015 Staphylococcus aureus 1
17157007 10.1016/j.bmcl.2006.11.015 Enterococcus faecalis 1
39026645 10.1039/d4md00224e B16-F10 1
26459207 10.1016/j.bmcl.2015.09.069 NON-PROTEIN TARGET 1
26459207 10.1016/j.bmcl.2015.09.069 HepG2 1
26459207 10.1016/j.bmcl.2015.09.069 MCF7 1
15270556 10.1021/np030556a Cytochrome P450 3A4 1
23062825 10.1016/j.bmc.2012.09.040 Acetylcholinesterase 1
17157007 10.1016/j.bmcl.2006.11.015 Sensor histidine kinase WalK 1
10514305 10.1021/np990092+ Polyunsaturated fatty acid 5-lipoxygenase 1
10514305 10.1021/np990092+ Unchecked 1
19309080 10.1021/jm801420y Unchecked 1
19309080 10.1021/jm801420y Zinc finger protein GLI2 1
19309080 10.1021/jm801420y Zinc finger protein GLI1 1

Data from ChEMBL 36 via Core Engine