Compound Detail

CHEMBL63354

AMENTOFLAVONE

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O=c1cc(-c2ccc(O)c(-c3c(O)cc(O)c4c(=O)cc(-c5ccc(O)cc5)oc34)c2)oc2cc(O)cc(O)c12

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL63354
Name	AMENTOFLAVONE
Phase	Preclinical
Structure Type	MOL
InChI Key	YUSWMAULDXZHPY-UHFFFAOYSA-N

Targets

Activities

Assay Types

PK Parameters

Publications

Known Names

Molecular Properties

538.5

MW (Da)

5.13

ALogP

HBA

HBD

181.8

PSA (Å²)

0.18

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	C30H18O10
MW	538.46
Aromatic Rings	6
Heavy Atoms	40
NP-Likeness	1.23

Activity Summary

IC50 46 meas. best 9.7

Ki 10 meas. best 8.22

EC50 5 meas. best 5.78

Kd 3 meas. best 8.09

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Poly [ADP-ribose] polymerase 1 CHEMBL3105	IC50	9.7	7.5125	0.2	4
GABA-A receptor; anion channel CHEMBL2093872	Ki	8.22	8.22	6.0	2
Placenta growth factor CHEMBL1697671	Kd	8.09	8.09	8.2	1
GABA-A receptor; anion channel CHEMBL1907607	IC50	7.83	7.83	14.9	1
Vascular endothelial growth factor A, long form CHEMBL1783	Kd	7.78	7.78	16.5	1
Delta-type opioid receptor CHEMBL4103	Ki	7.44	7.44	36.5	1
Delta-type opioid receptor CHEMBL236	Ki	7.44	7.44	36.0	2
Unchecked CHEMBL612545	IC50	6.57	5.31	270.0	4
Neutrophil CHEMBL5314326	IC50	6.12	6.06	750.0	2
D(3) dopamine receptor CHEMBL234	Ki	5.91	5.91	1241.0	1
Neutrophil elastase CHEMBL248	IC50	5.9	5.9	1270.0	1
Beta-secretase 1 CHEMBL4822	IC50	5.81	5.81	1540.0	1
Induced myeloid leukemia cell differentiation protein Mcl-1 CHEMBL4361	IC50	5.79	5.79	1634.1	1
Streptococcus sp. 'group A' CHEMBL612389	EC50	5.78	5.78	1678.0	1
Fibroblast CHEMBL613838	IC50	5.75	5.75	1800.0	1
Matrix metalloproteinase-9 CHEMBL321	Kd	5.66	5.66	2180.0	1
Streptokinase A CHEMBL1293228	EC50	5.64	5.64	2298.0	1
Matrix metalloproteinase-9 CHEMBL321	IC50	5.59	5.59	2580.0	1
5-hydroxytryptamine receptor 2C CHEMBL225	Ki	5.59	5.59	2555.0	1
Monocyte CHEMBL614076	IC50	5.52	5.52	3000.0	1
GABA-A receptor; alpha-1/beta-2/gamma-2 CHEMBL2095172	EC50	5.44	5.44	3600.0	1
5-hydroxytryptamine receptor 1D CHEMBL4105	Ki	5.39	5.39	4094.0	1
Amyloid-beta precursor protein CHEMBL2487	IC50	5.32	5.32	4800.0	1
HeLa CHEMBL399	IC50	5.28	4.805	5300.0	2
Tyrosine-protein phosphatase non-receptor type 1 CHEMBL335	IC50	5.13	5.13	7400.0	1
Tyrosine-protein phosphatase non-receptor type 1 CHEMBL335	Ki	5.11	5.11	7800.0	1
Replicase polyprotein 1ab CHEMBL5118	IC50	5.08	5.08	8300.0	1
Human immunodeficiency virus 1 CHEMBL378	EC50	5.08	4.555	8300.0	2
A549 CHEMBL392	IC50	5.08	5.08	8360.0	1
Transitional endoplasmic reticulum ATPase CHEMBL1075145	IC50	5.05	5.05	8984.0	1
HepG2 CHEMBL395	IC50	5.04	5.04	9130.0	1
NIH3T3 CHEMBL614822	IC50	5.04	5.04	9200.0	1
MGC-803 CHEMBL3706566	IC50	5.01	5.01	9860.0	1
Poly [ADP-ribose] polymerase 2 CHEMBL5366	IC50	4.99	4.99	10300.0	3
T-24 CHEMBL614774	IC50	4.97	4.97	10670.0	1
Replicase polyprotein 1ab CHEMBL5118	Ki	4.86	4.86	13800.0	1
Plasmodium falciparum CHEMBL364	IC50	4.72	4.66	19000.0	2
Phospholipase A2, membrane associated CHEMBL3474	IC50	4.62	4.62	23800.0	1
1-phosphatidylinositol 4,5-bisphosphate phosphodiesterase gamma-1 CHEMBL5566	IC50	4.54	4.54	29000.0	1
1-phosphatidylinositol 4,5-bisphosphate phosphodiesterase gamma-1 CHEMBL3964	IC50	4.54	4.54	29000.0	1
72 kDa type IV collagenase CHEMBL333	IC50	4.52	4.52	30310.0	1
PBMC CHEMBL613107	IC50	4.46	4.46	35000.0	1
Xanthine dehydrogenase/oxidase CHEMBL3649	IC50	4.45	4.45	35300.0	1
HL-60 CHEMBL383	IC50	4.29	4.29	51200.0	1
MCF7 CHEMBL387	IC50	4.12	4.12	75400.0	1

Pharmacokinetic Data

Parameter	Value	Units	Species
Ke	490.0	nM	Homo sapiens
Ke	6000.0	nM	Homo sapiens
Ke	10000.0	nM	Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
Poly [ADP-ribose] polymerase 1	IC50	=	0.2	nM	9.7	Inhibition of PARP-1 (unknown origin)	34404206
GABA-A receptor; anion channel	Ki	=	6.0	nM	8.22	Binding affinity for GABA-A benzodiazepine receptor	12824018
GABA-A receptor; anion channel	Ki	=	6.0	nM	8.22	Binding affinity for human cloned GABA-A benzodiazepine receptor	12824018
Placenta growth factor	Kd	=	8.2	nM	8.09	Binding affinity to recombinant PIGF1 (unknown origin) measured for 60 seconds b...	23268742
GABA-A receptor; anion channel	IC50	=	14.9	nM	7.83	Inhibition of [3H]flunitrazepam binding to rat brain GABA-A benzodiazepine recep...	12824018
Vascular endothelial growth factor A, long form	Kd	=	16.5	nM	7.78	Binding affinity to recombinant VEGFA (unknown origin) measured for 60 seconds b...	23268742
Delta-type opioid receptor	Ki	=	36.5	nM	7.44	Binding affinity to delta opioid receptor	20408551
Delta-type opioid receptor	Ki	=	36.0	nM	7.44	Binding affinity to delta opioid receptor	17685652
Delta-type opioid receptor	Ki	=	36.5	nM	7.44	Binding affinity (in vitro) against Opioid receptor delta 1 using radio-ligand b...	12824018
Poly [ADP-ribose] polymerase 1	IC50	=	120.0	nM	6.92	Inhibition of PARP1 (unknown origin)	34843914
Poly [ADP-ribose] polymerase 1	IC50	=	186.6	nM	6.73	Inhibition of recombinant human full-length PARP-1 using biotinylated substrate	34404206
Poly [ADP-ribose] polymerase 1	IC50	=	198.0	nM	6.7	Inhibition of PARP1 (unknown origin)	36512711
Unchecked	IC50	=	270.0	nM	6.57	Inhibition of PDE in Sprague-Dawley rat epididymal adipose tissue assessed as [1...	9834158
Neutrophil	IC50	=	750.0	nM	6.12	Antiinflammatory activity in human neutrophils assessed as inhibition of fMLP/CB...	29381070
Neutrophil	IC50	=	1010.0	nM	6.0	Anti-inflammatory activity in human neutrophils assessed as inhibition of fMLP/C...	29381070
D(3) dopamine receptor	Ki	=	1241.0	nM	5.91	Binding affinity (in vitro) against Dopamine receptor D3 using radio-ligand bind...	12824018
Neutrophil elastase	IC50	=	1270.0	nM	5.9	Inhibition of human neutrophil elastase using N-Methoxysuccinyl-Ala-Ala-Pro-Val-...	29381070
Beta-secretase 1	IC50	=	1540.0	nM	5.81	Inhibition of BACE1 after 60 mins by FRET assay	20598535
Induced myeloid leukemia cell differentiation protein Mcl-1	IC50	=	1634.07	nM	5.79	PUBCHEM_BIOASSAY: Dose Response Confirmation for Mcl-1/Noxa Interaction Inhibito...	-
Streptococcus sp. 'group A'	EC50	=	1678.0	nM	5.78	PUBCHEM_BIOASSAY: Luminescence Microorganism-Based Dose Confirmation HTS to Iden...	-

Literature References

PubMed	DOI	Target Context	# Activities
29921475	10.1016/j.bmcl.2018.06.024	A549	17
29381070	10.1021/acs.jnatprod.7b00476	RBL-2H3	11
21917453	10.1016/j.bmcl.2011.08.067	NON-PROTEIN TARGET	5
25907369	10.1016/j.bmc.2015.04.007	Tyrosine-protein phosphatase non-receptor type 1	4
29381070	10.1021/acs.jnatprod.7b00476	Neutrophil	4
22578462	10.1016/j.bmcl.2012.04.081	Unchecked	4
38864383	10.1021/acs.jmedchem.4c00597	Unchecked	3
18029185	10.1016/j.bmc.2007.10.036	Fibroblast	3
17027271	10.1016/j.bmcl.2006.09.042	ADMET	3
12824018	10.1016/s0960-894x(03)00434-7	GABA-A receptor; anion channel	3
17685652	10.1021/np070194x	Delta-type opioid receptor	3
34843914	10.1016/j.bmcl.2021.128480	A549	3
12824018	10.1016/s0960-894x(03)00434-7	GABA-A receptor; alpha-1/beta-2/gamma-2	2
26722868	10.1021/acs.jnatprod.5b00874	Plasmodium falciparum	2
26722868	10.1021/acs.jnatprod.5b00874	ADMET	2
23206866	10.1016/j.bmcl.2012.10.127	ADMET	2
20934345	10.1016/j.bmc.2010.09.035	Replicase polyprotein 1ab	2
9322359	10.1021/np9700275	Human immunodeficiency virus type 1 reverse transcriptase	2
23206866	10.1016/j.bmcl.2012.10.127	HL-60	2
17685652	10.1021/np070194x	Unchecked	2

Data from ChEMBL 36 via Core Engine