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Compound Detail

CHEMBL133046

ASCOFURANONE
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C/C(=C\Cc1c(O)c(Cl)c(C)c(C=O)c1O)CC/C=C(\C)[C@@H]1CC(=O)C(C)(C)O1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL133046
Name ASCOFURANONE
Phase Preclinical
Structure Type MOL
InChI Key VGYPZLGWVQQOST-JUERRSSISA-N
8
Targets
13
Activities
2
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

420.9
MW (Da)
5.22
ALogP
5
HBA
2
HBD
83.8
PSA (Ų)
0.47
QED
1
Ro5 Violations
7
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

Natural Product First in Class Prodrug

Extended Properties

Molecular Formula C23H29ClO5
MW 420.93
Aromatic Rings 1
Heavy Atoms 29
NP-Likeness 1.94

Activity Summary

IC50 11 meas. best 8.7
Ki 2 meas. best 9.89

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Alternative oxidase, mitochondrial
CHEMBL4295594
 Ki 9.89 9.89 0.1 1
Alternative oxidase, mitochondrial
CHEMBL4295594
 IC50 8.7 8.7 2.0 1
Unchecked
CHEMBL612545
 IC50 8.7 7.2433 2.0 3
Unchecked
CHEMBL612545
 Ki 8.62 8.62 2.4 1
Dihydroorotate dehydrogenase (quinone), mitochondrial
CHEMBL1966
 IC50 7.43 6.35 37.5 2
A549
CHEMBL392
 IC50 6.05 6.05 900.0 1
HepG2
CHEMBL395
 IC50 6.05 6.05 900.0 1
C3H 10T1/2
CHEMBL614531
 IC50 5.5 5.5 3200.0 1
MDA-MB-231
CHEMBL400
 IC50 5.28 5.28 5200.0 1
MDA-MB-468
CHEMBL614335
 IC50 5.15 5.15 7100.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Alternative oxidase, mitochondrial Ki = 0.13 nM 9.89 Inhibition of Trypanosoma brucei alternative oxidase expressed in Escherichia co... 29107420
Alternative oxidase, mitochondrial IC50 = 2.0 nM 8.7 Inhibition of recombinant Trypanosoma brucei brucei alternative oxidase using ub... 30258542
Unchecked IC50 = 2.0 nM 8.7 Inhibition of recombinant N-terminal His6 tagged SUMO-fused Trypanosoma brucei b... 29544150
Unchecked Ki = 2.38 nM 8.62 Non-competitive inhibition of Trypanosoma brucei brucei TC221 TAO expressed in E... 29544150
Dihydroorotate dehydrogenase (quinone), mitochondrial IC50 = 37.5 nM 7.43 Inhibition of human recombinant DHODH expressed in Escherichia coli BL21(DE3) ce... 32652407
Unchecked IC50 = 187.0 nM 6.73 Inhibitory Effects on Recombinant AOX Protein: Table 1 summarises the concentrat... -
Unchecked IC50 = 500.0 nM 6.3 Inhibitory Effects on Recombinant AOX Protein: Table 1 summarises the concentrat... -
A549 IC50 = 900.0 nM 6.05 Cytotoxicity against human A549 cells assessed as reduction in cell viability in... 34781681
HepG2 IC50 = 900.0 nM 6.05 Cytotoxicity against human HepG2 cells assessed as reduction in cell viability i... 34781681
C3H 10T1/2 IC50 = 3200.0 nM 5.5 Concentration required for inhibition of C3H10T1/2 progenitor cell growth 12954063
MDA-MB-231 IC50 = 5200.0 nM 5.28 Cytotoxicity against human MDA-MB-231 cells assessed as reduction in cell viabil... 34516133
Dihydroorotate dehydrogenase (quinone), mitochondrial IC50 = 5400.0 nM 5.27 Inhibition of recombinant N-terminal His-tagged human DHODH (31 to 395 residues)... 34516133
MDA-MB-468 IC50 = 7100.0 nM 5.15 Cytotoxicity against human MDA-MB-468 cells assessed as reduction in cell viabil... 34516133

Literature References

PubMed DOI Target Context # Activities
34781681 10.1021/acs.jnatprod.1c00834 Staphylococcus aureus 3
19199645 10.1021/np8006793 RAW264.7 2
30258542 10.1021/acsmedchemlett.8b00282 Trypanosoma brucei brucei 2
29544150 10.1016/j.ejmech.2018.02.075 Unchecked 2
29544150 10.1016/j.ejmech.2018.02.075 Trypanosoma brucei brucei 2
30258542 10.1021/acsmedchemlett.8b00282 Alternative oxidase, mitochondrial 1
32652407 10.1016/j.ejmech.2020.112502 Dihydroorotate dehydrogenase (quinone), mitochondrial 1
34781681 10.1021/acs.jnatprod.1c00834 Pseudomonas aeruginosa 1
34781681 10.1021/acs.jnatprod.1c00834 Escherichia coli 1
34781681 10.1021/acs.jnatprod.1c00834 Enterococcus faecalis 1
34781681 10.1021/acs.jnatprod.1c00834 Bacillus subtilis 1
34781681 10.1021/acs.jnatprod.1c00834 Staphylococcus epidermidis 1
29107420 10.1016/j.ejmech.2017.09.067 Alternative oxidase, mitochondrial 1
12954063 10.1021/jm0205649 C3H 10T1/2 1
20303767 10.1016/j.bmc.2010.02.034 Trypanosoma brucei brucei 1
12954063 10.1021/jm0205649 Androgen receptor 1
12954063 10.1021/jm0205649 Estrogen receptor beta 1
12954063 10.1021/jm0205649 Estrogen receptor 1
12954063 10.1021/jm0205649 Nuclear receptor subfamily 1 group I member 2 1
12954063 10.1021/jm0205649 Peroxisome proliferator-activated receptor alpha 1

Data from ChEMBL 36 via Core Engine