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Compound Detail

CHEMBL157844

PUUPEHENONE
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CC1(C)CCC[C@]2(C)[C@H]3C=C4C=C(O)C(=O)C=C4O[C@@]3(C)CC[C@@H]12
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL157844
Name PUUPEHENONE
Phase Preclinical
Structure Type MOL
InChI Key LOCMLXSTDCXZFJ-YHELAOLJSA-N
9
Targets
14
Activities
2
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

328.4
MW (Da)
4.85
ALogP
3
HBA
1
HBD
46.5
PSA (Ų)
0.69
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 C21H28O3
MW 328.45
Aromatic Rings 0
Heavy Atoms 24
NP-Likeness 3.21

Activity Summary

IC50 13 meas. best 6.17
EC50 1 meas. best 5.48

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Polyunsaturated fatty acid 5-lipoxygenase
CHEMBL215
 IC50 6.17 6.17 680.0 1
Polyunsaturated fatty acid lipoxygenase ALOX15
CHEMBL2903
 IC50 6.12 5.67 760.0 2
Polyunsaturated fatty acid lipoxygenase ALOX12
CHEMBL3687
 IC50 5.62 5.14 2400.0 2
Endothelial PAS domain-containing protein 1
CHEMBL1744522
 EC50 5.48 5.48 3300.0 1
Cholesteryl ester transfer protein
CHEMBL3572
 IC50 5.22 5.22 6000.0 1
Unchecked
CHEMBL612545
 IC50 5.08 4.8767 8300.0 3
NON-PROTEIN TARGET
CHEMBL3879801
 IC50 4.81 4.78 15500.0 2
786-0
CHEMBL613102
 IC50 4.75 4.75 17700.0 1
HL-60
CHEMBL383
 IC50 4.57 4.57 27000.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Polyunsaturated fatty acid 5-lipoxygenase IC50 = 680.0 nM 6.17 Inhibition of human N-terminal His6-tagged 5-lipoxygenase arachidonic acid by UV... 19848434
Polyunsaturated fatty acid lipoxygenase ALOX15 IC50 = 760.0 nM 6.12 Inhibition of His-tagged human reticulocyte 15-lipoxygenase 12608855
Polyunsaturated fatty acid lipoxygenase ALOX12 IC50 = 2400.0 nM 5.62 Inhibition of His-tagged human platelet 12-lipoxygenase 12608855
Endothelial PAS domain-containing protein 1 EC50 = 3300.0 nM 5.48 Inhibition of HIF2alpha in human 786-0 cells expressing truncated HIF1alpha asse... 22928967
Cholesteryl ester transfer protein IC50 = 6000.0 nM 5.22 Compound was tested for Cholesteryl ester transfer protein (CETP) inhibition by ... -
Polyunsaturated fatty acid lipoxygenase ALOX15 IC50 = 6000.0 nM 5.22 Inhibition of human reticulocyte N-terminal His6-tagged 15-lipoxygenase by UV-vi... 19848434
Unchecked IC50 = 8300.0 nM 5.08 Inhibition of soybean 15-lipoxygenase 12608855
Unchecked IC50 = 9000.0 nM 5.05 Selectivity ratio of IC50 for human reticulocyte 15-lipoxygenase to IC50 for hum... 19848434
NON-PROTEIN TARGET IC50 = 15500.0 nM 4.81 Cytotoxicity against human SK-RC-28 cells expressing HIF1alpha after 2 days by X... 22928967
NON-PROTEIN TARGET IC50 = 18000.0 nM 4.75 Cytotoxicity against human RCC4 cells expressing HIF2alpha and HIF1alpha after 2... 22928967
786-0 IC50 = 17700.0 nM 4.75 Cytotoxicity against human 786-0 cells expressing HIF2alpha after 2 days by XTT ... 22928967
Polyunsaturated fatty acid lipoxygenase ALOX12 IC50 = 22000.0 nM 4.66 Inhibition of human platelet N-terminal His6-tagged 12-lipoxygenase by UV-vis sp... 19848434
HL-60 IC50 = 27000.0 nM 4.57 Antioxidant activity against TPA-induced ROS production in human HL60 cells by 2... 12762791
Unchecked IC50 = 32000.0 nM 4.5 Selectivity ratio of IC50 for human platelet 12-lipoxygenase to IC50 for human 5... 19848434

Literature References

PubMed DOI Target Context # Activities
22928967 10.1021/np300211x Endothelial PAS domain-containing protein 1 8
22928967 10.1021/np300211x Molecular identity unknown 7
22928967 10.1021/np300211x 786-0 4
12608855 10.1021/np020462l Unchecked 4
19783432 10.1016/j.bmcl.2009.09.015 Pichia kudriavzevii 3
19783432 10.1016/j.bmcl.2009.09.015 Nakaseomyces glabratus 3
19783432 10.1016/j.bmcl.2009.09.015 Aspergillus fumigatus 3
19783432 10.1016/j.bmcl.2009.09.015 Candida albicans 3
22928967 10.1021/np300211x Hypoxia-inducible factor 1-alpha 3
19783432 10.1016/j.bmcl.2009.09.015 Cryptococcus neoformans 3
10514320 10.1021/np9900829 Plasmodium falciparum 3
19848434 10.1021/np900465e Unchecked 3
3655802 10.1021/np50050a064 P388 2
22928967 10.1021/np300211x NON-PROTEIN TARGET 2
12608855 10.1021/np020462l Polyunsaturated fatty acid lipoxygenase ALOX15 1
12762791 10.1021/np0204038 Radical scavenging activity 1
12762791 10.1021/np0204038 HL-60 1
30685527 10.1016/j.ejmech.2019.01.026 Mycobacterium tuberculosis 1
3655802 10.1021/np50050a064 Candida albicans 1
3655802 10.1021/np50050a064 MCF7 1

Data from ChEMBL 36 via Core Engine