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Compound Detail

CHEMBL452483

GUTTIFERONE A
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CC(C)=CCC[C@]1(C)[C@@H](CC=C(C)C)C[C@]2(CC=C(C)C)C(=O)[C@@]1(CC=C(C)C)C(=O)C(C(=O)c1ccc(O)c(O)c1)=C2O
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL452483
Name GUTTIFERONE A
Phase Preclinical
Structure Type MOL
InChI Key QKKRBNPMUBNTPA-GHCWVHGPSA-N
12
Targets
12
Activities
2
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

602.8
MW (Da)
9.06
ALogP
6
HBA
3
HBD
111.9
PSA (Ų)
0.08
QED
2
Ro5 Violations
11
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

Natural Product First in Class Prodrug

Extended Properties

Molecular Formula C38H50O6
MW 602.81
Aromatic Rings 1
Heavy Atoms 44
NP-Likeness 2.28

Activity Summary

IC50 11 meas. best 5.72
EC50 1 meas. best 5.1

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Papain
CHEMBL4779
 IC50 5.72 5.72 1900.0 1
Cathepsin B
CHEMBL4072
 IC50 5.68 5.68 2100.0 1
Cathepsin G
CHEMBL4071
 IC50 5.57 5.57 2700.0 1
Trypanosoma brucei brucei
CHEMBL612851
 IC50 5.53 5.53 2950.0 1
Plasmodium falciparum
CHEMBL364
 IC50 5.48 5.48 3320.0 1
Leishmania donovani
CHEMBL367
 IC50 5.23 5.23 5830.0 1
HCT-116
CHEMBL394
 IC50 5.22 5.22 6000.0 1
Vero
CHEMBL391
 IC50 5.15 5.15 7050.0 1
Human immunodeficiency virus 1
CHEMBL378
 EC50 5.1 5.1 8000.0 1
Unchecked
CHEMBL612545
 IC50 5.03 5.03 9400.0 1
NON-PROTEIN TARGET
CHEMBL3879801
 IC50 4.9 4.9 12530.0 1
Radical scavenging activity
CHEMBL613712
 IC50 4.51 4.51 30990.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Papain IC50 = 1900.0 nM 5.72 Inhibition of Carica papaya papain by spectrofluorimetry 18995931
Cathepsin B IC50 = 2100.0 nM 5.68 Inhibition of cathepsin B by spectrofluorimetry 18995931
Cathepsin G IC50 = 2700.0 nM 5.57 Inhibition of cathepsin G by spectrofluorimetry 18995931
Trypanosoma brucei brucei IC50 = 2950.0 nM 5.53 Antitrypanosomal activity against bloodstream stage of Trypanosoma brucei brucei... 23727538
Plasmodium falciparum IC50 = 3320.0 nM 5.48 Antiplasmodial activity against chloroquine-resistant Plasmodium falciparum FcB1... 23727538
Leishmania donovani IC50 = 5830.0 nM 5.23 Leishmanicidal activity against promastigote stage of Leishmania donovani LV9 as... 23727538
HCT-116 IC50 = 6000.0 nM 5.22 Cytotoxicity against human HCT116 cells after 72 hrs by MTS assay 26221771
Vero IC50 = 7050.0 nM 5.15 Cytotoxicity against african green monkey Vero cells assessed as growth inhibiti... 23727538
Human immunodeficiency virus 1 EC50 = 8000.0 nM 5.1 Antiviral activity against HIV1 in human CEM-SS cells assessed as inhibition of ... 11430019
Unchecked IC50 = 9400.0 nM 5.03 Inhibition of trypsin by spectrofluorimetry 18995931
NON-PROTEIN TARGET IC50 = 12530.0 nM 4.9 Antioxidant activity assessed as ABTS radical scavenging activity 21028890
Radical scavenging activity IC50 = 30990.0 nM 4.51 Antioxidant activity assessed as DPPH radical scavenging activity 21028890

Literature References

PubMed DOI Target Context # Activities
27669815 10.1021/acs.jmedchem.6b01182 No relevant target 16
27669815 10.1021/acs.jmedchem.6b01182 NAD-dependent protein deacetylase sirtuin-1 15
23727538 10.1016/j.ejmech.2013.04.066 Trypanosoma brucei brucei 4
18995931 10.1016/j.ejmech.2008.09.018 Papain 4
23727538 10.1016/j.ejmech.2013.04.066 Plasmodium falciparum 4
18995931 10.1016/j.ejmech.2008.09.018 Unchecked 3
22401914 10.1016/j.bmc.2012.02.023 Staphylococcus aureus 3
22401914 10.1016/j.bmc.2012.02.023 Cryptococcus neoformans 2
23727538 10.1016/j.ejmech.2013.04.066 Vero 2
22401914 10.1016/j.bmc.2012.02.023 Candida tropicalis 2
22401914 10.1016/j.bmc.2012.02.023 Nakaseomyces glabratus 2
22401914 10.1016/j.bmc.2012.02.023 Candida parapsilosis 2
22401914 10.1016/j.bmc.2012.02.023 Candida albicans 2
22401914 10.1016/j.bmc.2012.02.023 Proteus mirabilis 2
22401914 10.1016/j.bmc.2012.02.023 Escherichia coli 2
22401914 10.1016/j.bmc.2012.02.023 Salmonella typhimurium 2
22401914 10.1016/j.bmc.2012.02.023 Pseudomonas aeruginosa 2
22401914 10.1016/j.bmc.2012.02.023 Bacillus cereus 2
22401914 10.1016/j.bmc.2012.02.023 Staphylococcus epidermidis 2
23727538 10.1016/j.ejmech.2013.04.066 NON-PROTEIN TARGET 2

Data from ChEMBL 36 via Core Engine