XANTHOHUMOL

Investigational

Details

Stereochemistry	ACHIRAL
Molecular Formula	C21H22O5
Molecular Weight	354.3964
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	1
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

COC1=C(C(=O)\C=C\C2=CC=C(O)C=C2)C(O)=C(CC=C(C)C)C(O)=C1

InChI

InChIKey=ORXQGKIUCDPEAJ-YRNVUSSQSA-N

InChI=1S/C21H22O5/c1-13(2)4-10-16-18(24)12-19(26-3)20(21(16)25)17(23)11-7-14-5-8-15(22)9-6-14/h4-9,11-12,22,24-25H,10H2,1-3H3/b11-7+

HIDE SMILES / InChI

Molecular Formula	C21H22O5
Molecular Weight	354.3964
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	1
Optical Activity	NONE

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/25574819 | https://www.ncbi.nlm.nih.gov/pubmed/26840505 | https://www.ncbi.nlm.nih.gov/pubmed/29121426 | https://www.pharmacodia.com/yaodu/html/v1/chemicals/9f68494b83211ff09f2918a8f14510e6.html

Xanthohumol is a prenylated flavonoid most abundant in hops. It is found in beers and refreshment drinks. It can attenuate several factors of the metabolic syndrome. It has been reported to inhibit adipogenesis or increase cell apoptosis and therefore can be used in preventing obesity. Xanthohumol inhibited angiogenesis by suppressing NF-κB activity in pancreatic cancer. Xanthohumol may represent a novel therapeutic agent for the management of pancreatic cancer. Moreover, it is in phase I clinical trials for preventing many types of cancer. It has a range of other biological properties: antiviral, antimalarial, antibacterial and as an osteoporosis preventing agent.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Butyrylcholinesterase 46 Target ID: CHEMBL5077 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20387235	Inhibitor 8297	44.57 µM [IC50]
Beta-secretase 1 21 Target ID: CHEMBL4822 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20387235	Inhibitor 8297	7.19 µM [IC50]
Oxidative Stress 160 Target ID: WP408 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26840505 \| http://www.raysahelian.com/xanthohumol.html	Inhibitor 8297

Conditions

Condition	Modality	Highest Phase	Product
Cancer 592 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27923802 https://www.ncbi.nlm.nih.gov/pubmed/26840505	Primary	Phase I 428	Unknown Approved Use Unknown
Metabolic syndrome 32 Sources: https://www.ncbi.nlm.nih.gov/pubmed/29048380 https://www.ncbi.nlm.nih.gov/pubmed/26976708 https://www.ncbi.nlm.nih.gov/pubmed/26140926 https://www.ncbi.nlm.nih.gov/pubmed/22640929	Primary	Phase I 428	Unknown Approved Use Unknown
Alzheimer’s disease 272 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20387235 https://www.ncbi.nlm.nih.gov/pubmed/25574819	Primary	Basic research	Unknown Approved Use Unknown

C_max

Value	Dose	Analyte	Population
9.3 μg/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/24038952	60 mg single, oral dose: 60 mg route of administration: Oral experiment type: SINGLE co-administered:	ISOXANTHOHUMOL plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: UNKNOWN
25 μg/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/24038952	180 mg single, oral dose: 180 mg route of administration: Oral experiment type: SINGLE co-administered:	ISOXANTHOHUMOL plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
37 μg/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/24038952	180 mg single, oral dose: 180 mg route of administration: Oral experiment type: SINGLE co-administered:	ISOXANTHOHUMOL plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: UNKNOWN
9.7 μg/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/24038952	60 mg single, oral dose: 60 mg route of administration: Oral experiment type: SINGLE co-administered:	ISOXANTHOHUMOL plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
63 μg/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/24038952	60 mg single, oral dose: 60 mg route of administration: Oral experiment type: SINGLE co-administered:	XANTHOHUMOL plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
70 μg/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/24038952	60 mg single, oral dose: 60 mg route of administration: Oral experiment type: SINGLE co-administered:	XANTHOHUMOL plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: UNKNOWN
83 μg/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/24038952	180 mg single, oral dose: 180 mg route of administration: Oral experiment type: SINGLE co-administered:	XANTHOHUMOL plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
178 μg/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/24038952	180 mg single, oral dose: 180 mg route of administration: Oral experiment type: SINGLE co-administered:	XANTHOHUMOL plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: UNKNOWN

AUC

Value	Dose	Analyte	Population
342 μg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/24038952	60 mg single, oral dose: 60 mg route of administration: Oral experiment type: SINGLE co-administered:	ISOXANTHOHUMOL plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: UNKNOWN
511 μg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/24038952	180 mg single, oral dose: 180 mg route of administration: Oral experiment type: SINGLE co-administered:	ISOXANTHOHUMOL plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
982 μg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/24038952	180 mg single, oral dose: 180 mg route of administration: Oral experiment type: SINGLE co-administered:	ISOXANTHOHUMOL plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: UNKNOWN
216 μg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/24038952	60 mg single, oral dose: 60 mg route of administration: Oral experiment type: SINGLE co-administered:	ISOXANTHOHUMOL plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
286.99 μg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/24038952	60 mg single, oral dose: 60 mg route of administration: Oral experiment type: SINGLE co-administered:	XANTHOHUMOL plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
354 μg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/24038952	60 mg single, oral dose: 60 mg route of administration: Oral experiment type: SINGLE co-administered:	XANTHOHUMOL plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: UNKNOWN
712 μg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/24038952	180 mg single, oral dose: 180 mg route of administration: Oral experiment type: SINGLE co-administered:	XANTHOHUMOL plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
996 μg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/24038952	180 mg single, oral dose: 180 mg route of administration: Oral experiment type: SINGLE co-administered:	XANTHOHUMOL plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: UNKNOWN

T_1/2

Value	Dose	Analyte	Population
30 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/24038952	60 mg single, oral dose: 60 mg route of administration: Oral experiment type: SINGLE co-administered:	ISOXANTHOHUMOL plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: UNKNOWN
22 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/24038952	180 mg single, oral dose: 180 mg route of administration: Oral experiment type: SINGLE co-administered:	ISOXANTHOHUMOL plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
24 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/24038952	180 mg single, oral dose: 180 mg route of administration: Oral experiment type: SINGLE co-administered:	ISOXANTHOHUMOL plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: UNKNOWN
21.6 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/24038952	60 mg single, oral dose: 60 mg route of administration: Oral experiment type: SINGLE co-administered:	ISOXANTHOHUMOL plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
20 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/24038952	60 mg single, oral dose: 60 mg route of administration: Oral experiment type: SINGLE co-administered:	XANTHOHUMOL plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
19 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/24038952	60 mg single, oral dose: 60 mg route of administration: Oral experiment type: SINGLE co-administered:	XANTHOHUMOL plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: UNKNOWN
16 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/24038952	180 mg single, oral dose: 180 mg route of administration: Oral experiment type: SINGLE co-administered:	XANTHOHUMOL plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
19 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/24038952	180 mg single, oral dose: 180 mg route of administration: Oral experiment type: SINGLE co-administered:	XANTHOHUMOL plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: UNKNOWN

Sourcing

Vendor/Aggregator	ID	URL
001 Chemical	DY100745	https://www.001chemical.com/chem/search?q=DY100745
1PlusChem LLC	1P003D9I	https://www.1pchem.com/search?query=1P003D9I
AK Scientific	0397AC	https://aksci.com/item_detail.php?cat=0397AC
AK Scientific	W2672	https://aksci.com/item_detail.php?cat=W2672
Ambeed	A139015	http://www.ambeed.com/search/Search.html?keyword=A139015
ApexBio Technology	A8630	https://www.apexbt.com/catalogsearch/result/?q=A8630
AstaTech	44367	http://astatechinc.com/CPSResult.php?CRNO=44367
BOC Sciences	569-83-5	http://www.bocsci.com/description.asp?cas=569-83-5
BOC Sciences	6754-58-1	http://www.bocsci.com/description.asp?cas=6754-58-1
Biopurify Phytochemicals	BP1458	https://www.phytopurify.com/search.do?a=s&searchtype=3&psize=10&q=BP1458&searchhtmp=simplesearch&t=1
Cayman Chemical	15399	http://www.caymanchem.com/app/template/Product.vm/catalog/15399
Chem Scene	CS-6024	http://www.chemscene.com/goproductList/searchProductList?productObj=CS-6024
ChemShuttle	152113	https://www.chemshuttle.com/catalogsearch/result/?q=152113
Combi-Blocks	QW-5748	http://www.combi-blocks.com/cgi-bin/find.cgi?QW-5748
EndoTherm	ENO074	https://endotherm-lsm.com/en/component/finder/search.html?q=ENO074
Lab Network	LN00200293	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN00200293
Lab Seeker	SC-11144	http://www.labseeker.com/search.php?keywords=SC-11144&category=0
LabSeeker	SC-11144	http://www.labseeker.com/search.php?keywords=SC-11144&category=0
Matrix Scientific	99290	http://www.matrixscientific.com/099290.html
MedChem Express	HY-N1067	https://www.medchemexpress.com/search.html?q=HY-N1067&ft=&fa=&fp=
MolPort	MolPort-001-740-284	https://www.molport.com/shop/molecule-link/MolPort-001-740-284
MolPort	MolPort-046-417-455	https://www.molport.com/shop/molecule-link/MolPort-046-417-455
Molcore	MC100745	http://www.molcore.com/CatMC100745.html
Molnova	M17566	https://www.molnova.com/en/serch-list.html?keywords=M17566
MuseChem	I004540	https://www.musechem.com/product/I004540.html
Selleck Chemicals	S7889	http://www.selleckchem.com/search.html?searchDTO.searchParam=S7889
ShangHai Biochempartner	BCP18498	http://www.biochempartner.com/search_BCP18498
TargetMol	BBP60029	https://www.targetmol.com/search?keyword=BBP60029
TargetMol	T3342	https://www.targetmol.com/search?keyword=T3342
Tetrahedron	TS66112	http://www.thsci.com/search.do?q=TS66112
Tocris	4686	https://www.tocris.com/search.php?Type=QuickSearch&Value=4686
W&J PharmaChem	50C901699	http://wjpharmachem.com/new/searcht.php?keyword=50C901699
eMolecules	110118790	https://orderbb.emolecules.com/search/#?query=110118790
eMolecules	26757710	https://orderbb.emolecules.com/search/#?query=26757710
eMolecules	43443150	https://orderbb.emolecules.com/search/#?query=43443150
eNovation Chemicals	D659894	https://www.enovationchem.com/Products.asp?SEARCHTEXT=D659894&searchbtn.x=0&searchbtn.y=0
mcule	MCULE-1443775561	https://mcule.com/MCULE-1443775561/
mcule	MCULE-7307777782	https://mcule.com/MCULE-7307777782/

PubMed

Title	Date	PubMed
Xanthohumol, a novel anti-HIV-1 agent purified from Hops Humulus lupulus.	2004 Dec	15550272
Antiviral activity of hop constituents against a series of DNA and RNA viruses.	2004 Jan	14670594
Regulation of osteoblastic phenotype and gene expression by hop-derived phytoestrogens.	2005 Sep	16019205
Xanthohumol induces apoptosis in cultured 40-16 human colon cancer cells by activation of the death receptor- and mitochondrial pathway.	2005 Sep	15995977
Protective effects of xanthohumol against the genotoxicity of benzo(a)pyrene (BaP), 2-amino-3-methylimidazo[4,5-f]quinoline (IQ) and tert-butyl hydroperoxide (t-BOOH) in HepG2 human hepatoma cells.	2007 Aug 15	17590382
Discovery of sulfated sterols from marine invertebrates as a new class of marine natural antagonists of farnesoid-X-receptor.	2011 Mar 10	21309576
Protective effects of xanthohumol against the genotoxicity of heterocyclic aromatic amines MeIQx and PhIP in bacteria and in human hepatoma (HepG2) cells.	2012 Mar	22138251
Xanthohumol modulates the expression of osteoclast-specific genes during osteoclastogenesis in RAW264.7 cells.	2013 Dec	23994090
Curcumin analogue identified as hyaluronan export inhibitor by virtual docking to the ABC transporter MRP5.	2013 Dec	23978416
Xanthohumol induces phase II enzymes via Nrf2 in human hepatocytes in vitro.	2013 Feb	23085367
Xanthohumol attenuates tumour cell-mediated breaching of the lymphendothelial barrier and prevents intravasation and metastasis.	2013 Jul	23503627
2-Hydroxychalcone and xanthohumol inhibit invasion of triple negative breast cancer cells.	2013 May 25	23562496
Induction of NAD(P)H:Quinone Oxidoreductase 1 (NQO1) by Glycyrrhiza Species Used for Women's Health: Differential Effects of the Michael Acceptors Isoliquiritigenin and Licochalcone A.	2015 Nov 16	26473469
Xanthohumol inhibits cell cycle progression and proliferation of larynx cancer cells in vitro.	2015 Oct 5	26297991

Patents

Sample Use Guides

In Vivo Use Guide

Single dose of 20 mg, 60mg, or 180 mg over a course of six days

Route of Administration: Oral

In Vitro Use Guide

Xanthohumol showed strong antimicrobial effects with MIC and MBC values of 15-107 ug/mL, which are close to those of conventional antibiotics in the strains of Clostridium difficile bacteria with increased resistance.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 18:59:00 UTC 2023` Edited by `admin` on `Fri Dec 15 18:59:00 UTC 2023`
Record UNII	T4467YT1NT
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

XANTHOHUMOL

Official Name

English

XANTHO-FLAV

Brand Name

English

XANTHOHUMOL [INCI]

Common Name

English

(2E)-1-(2,4-DIHYDROXY-6-METHOXY-3-(3-METHYL-2-BUTEN-1-YL)PHENYL)-3-(4-HYDROXYPHENYL)-2-PROPEN-1-ONE

Systematic Name

English

(E)-1-(2,4-DIHYDROXY-6-METHOXY-3-(3-METHYLBUT-2-ENYL)PHENYL)-3-(4-HYDROXYPHENYL)PROP-2-EN-1-ONE

Systematic Name

English

2-PROPEN-1-ONE, 1-(2,4-HYDROXY-6-METHOXY-3-(3-METHYL-2-BUTENYL)PHENYL)-3-(4-HYDROXYPHENYL)-, (E)-

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C274