Compound Detail

CHEMBL253896

XANTHOHUMOL

🧪 Phase II

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🧪 Phase II

COc1cc(O)c(CC=C(C)C)c(O)c1C(=O)/C=C/c1ccc(O)cc1

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL253896
Name	XANTHOHUMOL
Phase	Phase II
Structure Type	MOL
InChI Key	ORXQGKIUCDPEAJ-YRNVUSSQSA-N

Known Names

Xantho-flav Xanthohumol

Targets

Activities

Assay Types

PK Parameters

Publications

Known Names

Indications

Molecular Properties

354.4

MW (Da)

4.22

ALogP

HBA

HBD

87.0

PSA (Å²)

0.41

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Small molecule
Chirality	Achiral

Flags

Natural Product

Extended Properties

Molecular Formula	C21H22O5
MW	354.40
Aromatic Rings	2
Heavy Atoms	26
NP-Likeness	1.63

Indications

Crohn Disease

Activity Summary

IC50 38 meas. best 5.7

Kd 2 meas. best 4.92

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Radical scavenging activity CHEMBL613712	IC50	5.7	5.7	1980.0	1
NON-PROTEIN TARGET CHEMBL3879801	IC50	5.7	5.1	1980.0	4
Polyunsaturated fatty acid 5-lipoxygenase CHEMBL215	IC50	5.68	5.61	2100.0	2
MCF7 CHEMBL387	IC50	5.46	5.065	3470.0	4
VSMC CHEMBL4296522	IC50	5.46	5.46	3490.0	1
Unchecked CHEMBL612545	IC50	5.45	4.9325	3550.0	4
Ishikawa CHEMBL614649	IC50	5.38	5.38	4200.0	1
3-phosphoinositide-dependent protein kinase 1 CHEMBL2534	IC50	5.18	5.18	6600.0	1
NCI-H460 CHEMBL396	IC50	5.16	5.14	6900.0	2
BGC-823 CHEMBL614526	IC50	5.11	5.11	7800.0	1
BV-2 CHEMBL614781	IC50	5.1	5.1	7920.0	1
Plasmodium falciparum CHEMBL364	IC50	5.09	4.855	8200.0	2
RAW264.7 CHEMBL612557	IC50	5.08	5.08	8300.0	1
HeLa CHEMBL399	IC50	5.03	4.87	9400.0	4
SGC-7901 CHEMBL614909	IC50	5.0	5.0	10000.0	1
PC-3 CHEMBL390	IC50	4.97	4.97	10670.0	2
A549 CHEMBL392	IC50	4.92	4.72	11900.0	2
Transthyretin CHEMBL3194	Kd	4.92	4.92	12000.0	1
NCI-H1975 CHEMBL614348	IC50	4.89	4.89	13000.0	1
HepG2 CHEMBL395	IC50	4.46	4.46	35000.0	1
HT-29 CHEMBL384	IC50	4.04	4.04	91310.0	2

Pharmacokinetic Data

Parameter	Value	Units	Species
T1/2	20.0	hr	Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
Radical scavenging activity	IC50	=	1980.0	nM	5.7	Antioxidant activity assessed as DPPH radical scavenging activity by by UV-vis s...	23466227
NON-PROTEIN TARGET	IC50	=	1980.0	nM	5.7	Antioxidant activity assessed as concentration required for 50 % inhibition of m...	23434138
Polyunsaturated fatty acid 5-lipoxygenase	IC50	=	2100.0	nM	5.68	Inhibition of recombinant human 5-LO expressed in Escherichia coli MV1190 cells ...	26918635
Polyunsaturated fatty acid 5-lipoxygenase	IC50	=	2900.0	nM	5.54	Inhibition of 5-LO in human polymorphonuclear leukocytes preincubated for 10 min...	26918635
VSMC	IC50	=	3490.0	nM	5.46	Inhibition of PDGF-BB-induced rat VSMC proliferation preincubated for 30 mins fo...	28627872
MCF7	IC50	=	3470.0	nM	5.46	Antiproliferative activity against human MCF7 cells assessed as inhibition of ce...	33257172
Unchecked	IC50	=	3550.0	nM	5.45	Non-competitive inhibition of glucose transporter in HTR-8/SVneo cells assessed ...	28042452
Ishikawa	IC50	=	4200.0	nM	5.38	Cytotoxicity against human Ishikawa cells after 96 hrs by SRB assay	28812892
3-phosphoinositide-dependent protein kinase 1	IC50	=	6600.0	nM	5.18	Inhibition of human PDK1 assessed as inhibition of [33P] incorporation into subs...	22537682
NCI-H460	IC50	=	6900.0	nM	5.16	Cytotoxicity against human NCI-H460 cells assessed as cell growth inhibition aft...	29288946
NCI-H460	IC50	=	7500.0	nM	5.12	Antiproliferative activity against human NCI-H460 cells after 72 hrs by MTT assa...	30196062
BGC-823	IC50	=	7800.0	nM	5.11	Cytotoxicity against human BGC823 cells assessed as cell growth inhibition after...	29288946
BV-2	IC50	=	7920.0	nM	5.1	Antineuroinflammatory activity in mouse BV2 cells assessed as inhibition of LPS-...	29154541
Plasmodium falciparum	IC50	=	8200.0	nM	5.09	Antiplasmodial activity against chloroquine-sensitive Plasmodium falciparum poW ...	17112640
RAW264.7	IC50	=	8300.0	nM	5.08	Inhibition of LPS/IFN-gamma-induced NO production in mouse RAW264.7 cells after ...	15679315
Unchecked	IC50	=	8800.0	nM	5.06	Non-competitive inhibition of alpha-glucosidase (unknown origin)	25638569
HeLa	IC50	=	9400.0	nM	5.03	Cytotoxicity against human HeLa cells by MTT assay	18343123
HeLa	IC50	=	9400.0	nM	5.03	Cytotoxicity against human HeLa cells by MTT assay after 72 hrs	18611049
HeLa	IC50	=	9400.0	nM	5.03	Cytotoxicity against human HeLa cells after 72 hrs by MTT assay	20153559
SGC-7901	IC50	=	10000.0	nM	5.0	Cytotoxicity against human SGC7901 cells assessed as cell growth inhibition afte...	29288946

Literature References

PubMed	DOI	Target Context	# Activities
22111577	10.1021/np200390x	T98G	32
36584344	10.1021/acs.jmedchem.2c01793	Staphylococcus aureus	14
24200239	10.1021/np4002898	Rattus norvegicus	13
39126694	10.1021/acs.jnatprod.4c00532	Unchecked	11
28234482	10.1021/acs.jnatprod.6b00869	Caco-2	7
19757857	10.1021/np900230p	Liver	6
28750311	10.1016/j.ejmech.2017.07.024	HUVEC	5
22111577	10.1021/np200390x	U-87 MG	4
22111577	10.1021/np200390x	Mitogen-activated protein kinase; ERK1/ERK2	4
29288946	10.1016/j.ejmech.2017.12.043	NCI-H460	4
28627872	10.1021/acs.jnatprod.7b00268	VSMC	4
32088124	10.1016/j.bmc.2020.115372	Histone-lysine N-methyltransferase SETD7	3
22111577	10.1021/np200390x	MAP kinase p38	3
19757857	10.1021/np900230p	HEK293	3
17112640	10.1016/j.ejmech.2006.09.019	Human immunodeficiency virus 1	3
28812892	10.1021/acs.jnatprod.7b00284	Estrogen receptor	2
17112640	10.1016/j.ejmech.2006.09.019	Plasmodium falciparum	2
19757857	10.1021/np900230p	Unchecked	2
15679315	10.1021/np0499113	RAW264.7	2
31539776	10.1016/j.ejmech.2019.111687	MCF7	2

Data from ChEMBL 36 via Core Engine