Compound Detail

CHEMBL491820

AMORFRUTIN A

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COc1cc(CCc2ccccc2)c(C(=O)O)c(O)c1CC=C(C)C

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL491820
Name	AMORFRUTIN A
Phase	Preclinical
Structure Type	MOL
InChI Key	CTNFTPUIYFUXBE-UHFFFAOYSA-N

Targets

Activities

Assay Types

PK Parameters

Publications

Known Names

Molecular Properties

340.4

MW (Da)

4.39

ALogP

HBA

HBD

66.8

PSA (Å²)

0.73

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Small molecule
Availability	Unknown
Chirality	Unknown

Flags

Natural Product First in Class Prodrug

Extended Properties

Molecular Formula	C21H24O4
MW	340.42
Aromatic Rings	2
Heavy Atoms	25
NP-Likeness	1.45

Activity Summary

IC50 5 meas. best 6.08

EC50 4 meas. best 6.34

Kd 3 meas. best 6.63

Ki 1 meas. best 6.63

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Peroxisome proliferator-activated receptor gamma CHEMBL235	Kd	6.63	6.63	236.0	1
Peroxisome proliferator-activated receptor gamma CHEMBL235	Ki	6.63	6.63	236.0	1
Peroxisome proliferator-activated receptor gamma CHEMBL235	EC50	6.34	6.34	458.0	2
Unchecked CHEMBL612545	IC50	6.08	5.73	840.0	2
Unchecked CHEMBL612545	EC50	5.78	5.78	1680.0	1
Corticotropin-releasing factor receptor 2/Corticotropin-releasing factor-binding protein CHEMBL3885546	IC50	5.1	5.1	7930.0	1
Peroxisome proliferator-activated receptor alpha CHEMBL239	Kd	4.57	4.57	27000.0	1
Peroxisome proliferator-activated receptor delta CHEMBL3979	Kd	4.57	4.57	27000.0	1
Corticotropin-releasing factor receptor 2/Corticotropin-releasing factor-binding protein CHEMBL3885546	EC50	4.45	4.45	35200.0	1
THP-1 CHEMBL614245	IC50	4.3	4.3	50000.0	1
HT-29 CHEMBL384	IC50	4.29	4.29	50800.0	1

Pharmacokinetic Data

Parameter	Value	Units	Species
Cmax	124552.02	nM	Mus musculus
T1/2	2.0	hr	Mus musculus

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
Peroxisome proliferator-activated receptor gamma	Kd	=	236.0	nM	6.63	Binding affinity to human PPARgamma (unknown origin) by competitive TR-FRET assa...	23286787
Peroxisome proliferator-activated receptor gamma	Ki	=	236.0	nM	6.63	Binding affinity to PPARgamma (unknown origin)	33992930
Peroxisome proliferator-activated receptor gamma	EC50	=	458.0	nM	6.34	Agonist at human PPARgamma LBD expressed in human HEK293 cells cotransfected wit...	23286787
Peroxisome proliferator-activated receptor gamma	EC50	=	458.0	nM	6.34	Activity at human PPARgamma transfected in HEK293 cells assessed as transactivat...	25734377
Unchecked	IC50	=	840.0	nM	6.08	Inhibition of TNF-alpha-induced NF-kappaB activation in human HeLa cells by SEAP...	18841906
Unchecked	EC50	=	1680.0	nM	5.78	Antiviral activity against HCV subtype 2a J6/JFH/JC1 infected in human Huh7.5 ce...	27783522
Unchecked	IC50	=	4170.0	nM	5.38	Inhibition of LPS-induced NF-kappaB activation in mouse RAW264.7 cells by SEAP r...	18841906
Corticotropin-releasing factor receptor 2/Corticotropin-releasing factor-binding protein	IC50	=	7930.0	nM	5.1	PUBCHEM_BIOASSAY: Dose Response confirmation of uHTS hits for small molecule ant...	-
Peroxisome proliferator-activated receptor delta	Kd	=	27000.0	nM	4.57	Binding affinity to human PPARdelta (unknown origin) by competitive TR-FRET assa...	23286787
Peroxisome proliferator-activated receptor alpha	Kd	=	27000.0	nM	4.57	Binding affinity to human PPARalpha (unknown origin) by competitive TR-FRET assa...	23286787
Corticotropin-releasing factor receptor 2/Corticotropin-releasing factor-binding protein	EC50	=	35200.0	nM	4.45	PUBCHEM_BIOASSAY: Dose Response confirmation of uHTS hits for small molecule ago...	-
THP-1	IC50	=	50000.0	nM	4.3	Cytotoxicity against human THP1 cells after 48 hrs by resazurin dye-based fluore...	28075580
HT-29	IC50	=	50800.0	nM	4.29	Reduction in TNFalpha-induced PPARgamma expression in human HT-29 cells after 48...	25938459

Literature References

PubMed	DOI	Target Context	# Activities
25938459	10.1021/np500747y	Peroxisome proliferator-activated receptor gamma	14
23286787	10.1021/jm3013272	Peroxisome proliferator-activated receptor gamma	3
27783522	10.1021/acs.jmedchem.6b01301	Unchecked	3
18841906	10.1021/np800383q	Unchecked	3
28075580	10.1021/acs.jnatprod.6b00809	Enterococcus faecium	2
37940359	10.1021/acs.jnatprod.3c00509	Peroxisome proliferator-activated receptor gamma	2
33992930	10.1016/j.ejmech.2021.113535	ADMET	2
33992930	10.1016/j.ejmech.2021.113535	Peroxisome proliferator-activated receptor gamma	2
28075580	10.1021/acs.jnatprod.6b00809	Enterococcus faecalis	2
28075580	10.1021/acs.jnatprod.6b00809	Staphylococcus aureus	2
25734377	10.1021/jm501155f	Peroxisome proliferator-activated receptor gamma	2
25938459	10.1021/np500747y	HT-29	2
18841906	10.1021/np800383q	MCF7	2
28075580	10.1021/acs.jnatprod.6b00809	Mycobacterium tuberculosis	1
28075580	10.1021/acs.jnatprod.6b00809	Acinetobacter baumannii	1
28075580	10.1021/acs.jnatprod.6b00809	THP-1	1
28075580	10.1021/acs.jnatprod.6b00809	L5178Y	1
30444360	10.1021/acs.jnatprod.8b00315	Pseudomonas aeruginosa	1
23286787	10.1021/jm3013272	Peroxisome proliferator-activated receptor alpha	1
23286787	10.1021/jm3013272	Peroxisome proliferator-activated receptor delta	1

Data from ChEMBL 36 via Core Engine