Compound Detail

CHEMBL117

CHRYSIN

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O=c1cc(-c2ccccc2)oc2cc(O)cc(O)c12

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL117
Name	CHRYSIN
Phase	Preclinical
Structure Type	MOL
InChI Key	RTIXKCRFFJGDFG-UHFFFAOYSA-N

Targets

146

Activities

Assay Types

PK Parameters

Publications

Known Names

Molecular Properties

254.2

MW (Da)

2.87

ALogP

HBA

HBD

70.7

PSA (Å²)

0.70

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	C15H10O4
MW	254.24
Aromatic Rings	3
Heavy Atoms	19
NP-Likeness	1.23

Activity Summary

IC50 113 meas. best 9.0

Ki 23 meas. best 7.8

EC50 8 meas. best 5.3

Kd 2 meas. best 5.05

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Aromatase CHEMBL1978	IC50	9.0	6.676	1.0	5
Cytochrome P450 1B1 CHEMBL4878	Ki	7.8	7.8	16.0	2
Cytochrome P450 1B1 CHEMBL4878	IC50	7.62	7.085	24.0	2
Carbonic anhydrase 12 CHEMBL3242	Ki	7.46	5.85	34.7	3
Cytochrome P450 1A1 CHEMBL2231	Ki	7.38	7.38	42.0	1
MCF7 CHEMBL387	IC50	7.3	5.19	50.0	4
Cytochrome P450 1A2 CHEMBL3356	IC50	7.27	6.8633	54.0	3
Carbonyl reductase [NADPH] 1 CHEMBL5586	Ki	6.96	6.96	110.0	1
Cytochrome P450 1A1 CHEMBL2231	IC50	6.82	6.355	153.0	2
Carbonic anhydrase 7 CHEMBL2326	Ki	6.77	6.77	171.4	1
Unchecked CHEMBL612545	IC50	6.6	5.0529	250.0	7
Cytochrome P450 1A2 CHEMBL3356	Ki	6.3	6.3	500.0	1
Carbonic anhydrase 4 CHEMBL3729	Ki	6.27	6.27	537.8	1
Histone deacetylase 6 CHEMBL1865	IC50	6.27	6.27	534.0	1
Carbonyl reductase [NADPH] 1 CHEMBL5586	IC50	6.17	6.17	670.0	1
Xanthine dehydrogenase/oxidase CHEMBL1929	IC50	6.08	5.99	840.0	2
GABA-A receptor; anion channel CHEMBL1907607	Ki	6.04	6.04	920.0	1
Xanthine dehydrogenase/oxidase CHEMBL3649	IC50	5.9	5.9	1260.0	1
Human immunodeficiency virus type 1 integrase CHEMBL3471	IC50	5.85	5.85	1400.0	1
Broad substrate specificity ATP-binding cassette transporter ABCG2 CHEMBL5393	IC50	5.82	5.7	1500.0	2
Monoamine oxidase CHEMBL2095205	IC50	5.8	5.8	1600.0	1
NON-PROTEIN TARGET CHEMBL3879801	IC50	5.73	4.6117	1870.0	6
Neutrophil CHEMBL5314326	IC50	5.65	5.65	2250.0	1
Monocyte CHEMBL614076	IC50	5.62	5.62	2400.0	1
Aromatase CHEMBL1978	Ki	5.58	5.58	2600.0	1
Carbonic anhydrase 9 CHEMBL3594	Ki	5.58	5.575	2650.0	2
GABA-A receptor; anion channel CHEMBL2093872	Ki	5.52	5.52	3019.9	1
HT-29 CHEMBL384	IC50	5.51	5.11	3100.0	2
Cyclin-dependent kinase 5/CDK5 activator 1 CHEMBL1907600	IC50	5.51	5.51	3100.0	1
Carbonic anhydrase 2 CHEMBL205	Ki	5.37	5.365	4310.0	2
Proteasome Macropain subunit MB1 CHEMBL4662	IC50	5.31	5.26	4900.0	2
Human immunodeficiency virus 1 CHEMBL378	EC50	5.3	5.3	5000.0	1
Cytochrome P450 2C9 CHEMBL3397	IC50	5.28	5.28	5225.0	1
Carbonic anhydrase 1 CHEMBL261	Ki	5.27	5.265	5420.0	2
SGC-7901 CHEMBL614909	IC50	5.24	5.24	5800.0	1
Cyclin-dependent kinase 6 CHEMBL2508	IC50	5.22	5.22	6000.0	2
Cyclin-dependent kinase 1/cyclin B CHEMBL2094127	IC50	5.15	5.15	7100.0	1
Glycogen synthase kinase-3 CHEMBL2095188	IC50	5.14	5.14	7200.0	1
Aldo-keto reductase family 1 member B1 CHEMBL1900	IC50	5.11	5.09	7780.0	2
Aldo-keto reductase family 1 member B1 CHEMBL3081	IC50	5.11	5.11	7790.0	1
Peroxisome proliferator-activated receptor gamma CHEMBL235	Ki	5.11	4.905	7860.0	2
Casein kinase 2 CHEMBL3832943	IC50	5.05	5.05	9000.0	1
ATP-dependent translocase ABCB1 CHEMBL4302	Kd	5.05	5.05	8912.5	1
Casein kinase 2 CHEMBL3988629	IC50	5.05	5.05	9000.0	1
Neutrophil CHEMBL613710	IC50	5.02	4.65	9590.0	2
Caco-2 CHEMBL614058	IC50	5.02	5.02	9500.0	1
DU-145 CHEMBL613508	IC50	5.01	5.01	9810.0	1
3-oxoacyl-acyl-carrier protein reductase CHEMBL4513	IC50	5.0	5.0	10000.0	1
ADMET CHEMBL612558	Kd	4.88	4.88	13100.0	1
HeLa CHEMBL399	IC50	4.85	4.59	14200.0	4

Pharmacokinetic Data

Parameter	Value	Units	Species
AUC	110.0	nM hr ml	-
Tmax	1.0	hr	-

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
Aromatase	IC50	=	1.0	nM	9.0	Inhibition of human placental microsome CYP19	20413308
Cytochrome P450 1B1	Ki	=	16.0	nM	7.8	Inhibition of CYP1B1 EROD activity assessed as inhibition of deethylation of 7-e...	21482471
Cytochrome P450 1B1	Ki	=	16.0	nM	7.8	Inhibition of CYP1B1 (unknown origin)	28458135
Cytochrome P450 1B1	IC50	=	24.0	nM	7.62	Inhibition of human CYP1B1 by EROD assay	20696580
Carbonic anhydrase 12	Ki	=	34.7	nM	7.46	Inhibition of human recombinant carbonic anhydrase 12 preincubated for 15 mins a...	26498393
Cytochrome P450 1A1	Ki	=	42.0	nM	7.38	Inhibition of CYP1A1 EROD activity assessed as inhibition of deethylation of 7-e...	21482471
MCF7	IC50	=	50.0	nM	7.3	Antiproliferative activity against human MCF7 cells assessed as inhibition of ce...	33257172
Cytochrome P450 1A2	IC50	=	54.0	nM	7.27	Inhibition of human CYP1A2	20832301
Cytochrome P450 1A2	IC50	=	84.0	nM	7.08	Inhibition of human CYP1A2 by EROD assay	20696580
Carbonyl reductase [NADPH] 1	Ki	=	110.0	nM	6.96	Binding affinity to human recombinant carbonyl reductase 1 expressed in Escheric...	19097799
Cytochrome P450 1A1	IC50	=	153.0	nM	6.82	Inhibition of human CYP1A1 by EROD assay	20696580
Carbonic anhydrase 7	Ki	=	171.41	nM	6.77	Inhibition of human recombinant carbonic anhydrase 7 preincubated for 15 mins at...	26498393
Unchecked	IC50	=	250.0	nM	6.6	Inhibition of beef heart mitochondrial NADH oxidase assessed per mg of protein	2959755
Cytochrome P450 1B1	IC50	=	280.0	nM	6.55	Inhibition of recombinant human CYP1B1 expressed in supersomes using ethoxyresor...	28458135
Cytochrome P450 1A2	Ki	=	500.0	nM	6.3	Inhibition of recombinant human CYP1A2 expressed in Escherichia coli DH5alpha co...	28458135
Aromatase	IC50	=	500.0	nM	6.3	Inhibition of aromatase (unknown origin)	26301554
Histone deacetylase 6	IC50	=	534.0	nM	6.27	Determination of IC50 values for inhibition of enzymatic assay of human HDAC6 wi...	-
Carbonic anhydrase 4	Ki	=	537.75	nM	6.27	Inhibition of human recombinant carbonic anhydrase 4 preincubated for 15 mins at...	26498393
Cytochrome P450 1A2	IC50	=	570.0	nM	6.24	Inhibition of CYP1A2 (unknown origin)-mediated demethylation of resorufin methyl...	23600958
Carbonyl reductase [NADPH] 1	IC50	=	670.0	nM	6.17	Binding affinity to human recombinant carbonyl reductase 1 expressed in Escheric...	19097799

Literature References

PubMed	DOI	Target Context	# Activities
20346546	10.1016/j.ejmech.2010.02.049	Rattus norvegicus	13
24793879	10.1016/j.ejmech.2014.04.054	Lipid bilayer	11
25906385	10.1021/acs.jmedchem.5b00230	HEK293	8
31708277	10.1016/j.bmc.2019.115163	Unchecked	7
17624791	10.1016/j.bmc.2007.06.046	Unchecked	7
28325635	10.1016/j.bmc.2017.03.023	Unchecked	6
19097799	10.1016/j.bmc.2008.11.076	Carbonyl reductase [NADPH] 1	6
21129983	10.1016/j.bmc.2010.10.063	Aorta	6
24368208	10.1016/j.ejmech.2013.11.030	Seed linoleate 13S-lipoxygenase-1	6
11063613	10.1021/jm990614i	Monoamine oxidase	5
37077388	10.1021/acsmedchemlett.2c00511	Unchecked	5
1338212	10.1021/np50090a003	Human alphaherpesvirus 1	5
24007917	10.1016/j.bmcl.2013.08.055	HepG2	5
24007917	10.1016/j.bmcl.2013.08.055	MCF7	5
11063613	10.1021/jm990614i	Aldehyde dehydrogenase, mitochondrial	5
24007917	10.1016/j.bmcl.2013.08.055	COLO 205	5
39089002	10.1016/j.ejmech.2024.116728	Peroxisome proliferator-activated receptor gamma	5
19948405	10.1016/j.bmcl.2009.11.024	Rattus norvegicus	4
24556144	10.1016/j.ejmech.2013.12.044	H22	4
2959755	10.1021/np50051a014	Unchecked	4

Data from ChEMBL 36 via Core Engine