Compound Detail

CHEMBL9352

NARINGENIN

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O=C1C[C@@H](c2ccc(O)cc2)Oc2cc(O)cc(O)c21

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL9352
Name	NARINGENIN
Phase	Preclinical
Structure Type	MOL
InChI Key	FTVWIRXFELQLPI-ZDUSSCGKSA-N

Targets

Activities

Assay Types

PK Parameters

Publications

Known Names

Molecular Properties

272.3

MW (Da)

2.51

ALogP

HBA

HBD

87.0

PSA (Å²)

0.74

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	C15H12O5
MW	272.26
Aromatic Rings	2
Heavy Atoms	20
NP-Likeness	1.76

Activity Summary

IC50 60 meas. best 8.54

EC50 8 meas. best 4.87

Ki 8 meas. best 8.37

Kd 4 meas. best 6.02

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Aromatase CHEMBL1978	IC50	8.54	6.184	2.9	10
Carbonic anhydrase 7 CHEMBL2326	Ki	8.37	8.37	4.3	1
Carbonic anhydrase 12 CHEMBL3242	Ki	7.35	7.35	44.3	1
Carbonic anhydrase 4 CHEMBL3729	Ki	7.1	7.1	79.5	1
Dipeptidyl peptidase 4 CHEMBL284	IC50	6.62	6.62	240.0	1
MCF7 CHEMBL387	IC50	6.52	6.52	300.0	1
Unchecked CHEMBL612545	Ki	6.16	6.16	685.0	1
Sex hormone-binding globulin CHEMBL3305	Kd	6.02	5.285	955.0	2
No relevant target CHEMBL2362975	IC50	5.98	5.1633	1050.0	3
Mus musculus CHEMBL375	IC50	5.88	5.88	1310.0	1
Transthyretin CHEMBL3194	Kd	5.79	5.79	1630.0	1
Human immunodeficiency virus type 1 integrase CHEMBL3471	IC50	5.77	5.77	1700.0	1
Unchecked CHEMBL612545	IC50	5.75	4.678	1800.0	5
Multidrug resistance-associated protein 1 CHEMBL3004	Ki	5.62	5.15	2400.0	2
Neutrophil CHEMBL5314326	IC50	5.48	5.38	3300.0	2
Carbonyl reductase [NADPH] 1 CHEMBL5586	Ki	5.46	5.46	3430.0	1
Cytochrome P450 1B1 CHEMBL4878	IC50	5.44	5.44	3656.0	1
17-beta-hydroxysteroid dehydrogenase type 1 CHEMBL3181	IC50	5.3	5.3	4960.0	1
Estrogen receptor beta CHEMBL242	IC50	4.87	4.87	13473.0	1
NON-PROTEIN TARGET CHEMBL3879801	EC50	4.87	4.87	13480.0	1
17-beta-hydroxysteroid dehydrogenase type 2 CHEMBL2789	IC50	4.84	4.84	14400.0	2
Cytochrome P450 1A1 CHEMBL2231	IC50	4.82	4.82	15167.0	1
Lactoylglutathione lyase CHEMBL2424	Ki	4.76	4.76	17378.0	1
Solute carrier organic anion transporter family member 2B1 CHEMBL1743124	IC50	4.68	4.68	20893.0	2
Carbonyl reductase [NADPH] 1 CHEMBL5586	IC50	4.67	4.67	21480.0	1
Calmodulin-1 CHEMBL6093	IC50	4.66	4.66	22010.0	1
Cytochrome P450 1A2 CHEMBL3356	IC50	4.58	4.58	26339.0	1
Aldo-keto reductase family 1 member B1 CHEMBL1900	IC50	4.54	4.54	28870.0	1
ATP-dependent translocase ABCB1 CHEMBL2573	Kd	4.54	4.54	28500.0	1
dengue virus type 3 CHEMBL612717	EC50	4.45	4.45	35810.0	1
dengue virus type 1 CHEMBL613360	EC50	4.45	4.45	35810.0	1
dengue virus type 4 CHEMBL613728	EC50	4.45	4.45	35810.0	1
dengue virus type 2 CHEMBL613966	EC50	4.45	4.45	35810.0	1
Proteasome Macropain subunit MB1 CHEMBL4662	IC50	4.38	4.345	41600.0	2
Glycogen synthase kinase-3 beta CHEMBL262	IC50	4.34	4.34	45700.0	1
RAW264.7 CHEMBL612557	IC50	4.22	4.22	60000.0	1
Radical scavenging activity CHEMBL613712	EC50	4.14	4.14	72330.0	1
Estrogen receptor CHEMBL206	IC50	4.12	4.12	75302.0	1
Human immunodeficiency virus 1 CHEMBL378	EC50	4.04	4.04	92000.0	1
Alpha amylase CHEMBL6066863	IC50	2.75	2.75	1800000.0	1

Pharmacokinetic Data

Parameter	Value	Units	Species
Ka	0.68	10'5/M	Homo sapiens
Ke	2300.0	nM	Homo sapiens
Ke	3680.0	nM	Homo sapiens
Ke	1700.0	nM	Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
Aromatase	IC50	=	2.9	nM	8.54	Inhibition of human placental microsome CYP19	20413308
Carbonic anhydrase 7	Ki	=	4.3	nM	8.37	Inhibition of human recombinant carbonic anhydrase 7 preincubated for 15 mins at...	26498393
Carbonic anhydrase 12	Ki	=	44.3	nM	7.35	Inhibition of human recombinant carbonic anhydrase 12 preincubated for 15 mins a...	26498393
Carbonic anhydrase 4	Ki	=	79.5	nM	7.1	Inhibition of human recombinant carbonic anhydrase 4 preincubated for 15 mins at...	26498393
Aromatase	IC50	=	230.0	nM	6.64	Inhibition of aromatase after 10 mins preincubation by plate reader relative to ...	21978950
Aromatase	IC50	=	230.0	nM	6.64	Inhibition of human aromatase using dibenzylfluorescein as substrate preincubate...	22115839
Aromatase	IC50	=	230.0	nM	6.64	Inhibition of human aromatase activity after 30 mins by fluorescence analysis	23142320
Dipeptidyl peptidase 4	IC50	=	240.0	nM	6.62	Inhibition of DPP4 (unknown origin) using Gly-Pro-AMC as substrate preincubated ...	29609120
MCF7	IC50	=	300.0	nM	6.52	Antiproliferative activity against human MCF7 cells assessed as inhibition of ce...	33257172
Unchecked	Ki	=	685.0	nM	6.16	Binding affinity to Chikungunya virus NS3	28689975
Sex hormone-binding globulin	Kd	=	954.99	nM	6.02	Displacement of [3H]5alpha dihydrotestosterone from human sex hormone binding gl...	18330978
Aromatase	IC50	=	1000.0	nM	6.0	Inhibition of aromatase (unknown origin) preincubated for 10 mins in presence of...	27155469
No relevant target	IC50	=	1050.0	nM	5.98	Antioxidant activity assessed as hydroxyl radical scavenging activity	34391893
Aromatase	IC50	=	1200.0	nM	5.92	Inhibition of aromatase (unknown origin) using dibenzylfluorscein as substrate i...	23994869
Aromatase	IC50	=	1200.0	nM	5.92	Inhibition of aromatase (unknown origin) using dibenzylfluorescein substrate aft...	24992702
Mus musculus	IC50	=	1310.0	nM	5.88	Antiinflammatory activity against TPA-induced CD-1 mouse ear edema model assesse...	37683361
Transthyretin	Kd	=	1630.0	nM	5.79	Binding affinity to TTR V30M mutant (unknown origin) expressed in Escherichia co...	36472374
Human immunodeficiency virus type 1 integrase	IC50	=	1700.0	nM	5.77	Inhibition of His6-tagged HIV-1 integrase assessed as decrease in integrase-Flag...	24794743
Unchecked	IC50	=	1800.0	nM	5.75	Inhibition of rat liver mitochondrial ATPase assessed per mg of protein	2959755
Multidrug resistance-associated protein 1	Ki	=	2400.0	nM	5.62	Inhibition of MRP1 transfected in human HeLa cells assessed as inhibition of [3H...	19725578

Literature References

PubMed	DOI	Target Context	# Activities
30688453	10.1021/acs.jnatprod.8b00366	Mus musculus	11
26517554	10.1021/acs.jnatprod.5b00075	ADMET	9
18682327	10.1016/j.bmc.2008.07.052	Prenyltransferase homolog	6
19097799	10.1016/j.bmc.2008.11.076	Carbonyl reductase [NADPH] 1	6
18249545	10.1016/j.bmc.2008.01.028	No relevant target	5
18249545	10.1016/j.bmc.2008.01.028	Caco-2	5
36472374	10.1021/acs.jmedchem.2c00511	Transthyretin	5
33530021	10.1016/j.bmc.2021.116043	Cytochrome c	4
21129983	10.1016/j.bmc.2010.10.063	Aorta	4
2959755	10.1021/np50051a014	Unchecked	4
34391893	10.1016/j.bmcl.2021.128316	No relevant target	4
37252098	10.1039/d3md00078h	Solute carrier organic anion transporter family member 2B1	4
20189399	10.1016/j.bmc.2010.01.046	Unchecked	4
9287415	10.1021/np960581z	L929	4
19928832	10.1021/np900676y	T47D	4
19928832	10.1021/np900676y	MCF7	4
12643908	10.1016/s0960-894x(03)00088-x	Mus musculus	4
19097799	10.1016/j.bmc.2008.11.076	Carbonyl reductase [NADPH] 3	3
18440233	10.1016/j.bmc.2008.04.016	NON-PROTEIN TARGET	3
22578462	10.1016/j.bmcl.2012.04.081	Unchecked	3

Data from ChEMBL 36 via Core Engine