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

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

Description

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 45	Inhibitor 8,504	44.57 µM [IC50]
Beta-secretase 1 21	Inhibitor 8,504	7.19 µM [IC50]
Oxidative Stress 162	Inhibitor 8,504

Conditions

Condition	Modality	Highest Phase	Product
Cancer 609	Primary	Phase I 438	Unknown
Metabolic syndrome 34	Primary	Phase I 438	Unknown
Alzheimer’s disease 278	Primary	Basic research	Unknown

C_max

Value	Dose	Analyte	Population
63 μg/L	60 mg single, oral	XANTHOHUMOL plasma	Homo sapiens
178 μg/L	180 mg single, oral	XANTHOHUMOL plasma	Homo sapiens
83 μg/L	180 mg single, oral	XANTHOHUMOL plasma	Homo sapiens
70 μg/L	60 mg single, oral	XANTHOHUMOL plasma	Homo sapiens
25 μg/L	180 mg single, oral	ISOXANTHOHUMOL plasma	Homo sapiens
9.7 μg/L	60 mg single, oral	ISOXANTHOHUMOL plasma	Homo sapiens
9.3 μg/L	60 mg single, oral	ISOXANTHOHUMOL plasma	Homo sapiens
37 μg/L	180 mg single, oral	ISOXANTHOHUMOL plasma	Homo sapiens

AUC

Value	Dose	Analyte	Population
286.99 μg × h/L	60 mg single, oral	XANTHOHUMOL plasma	Homo sapiens
996 μg × h/L	180 mg single, oral	XANTHOHUMOL plasma	Homo sapiens
712 μg × h/L	180 mg single, oral	XANTHOHUMOL plasma	Homo sapiens
354 μg × h/L	60 mg single, oral	XANTHOHUMOL plasma	Homo sapiens
511 μg × h/L	180 mg single, oral	ISOXANTHOHUMOL plasma	Homo sapiens
216 μg × h/L	60 mg single, oral	ISOXANTHOHUMOL plasma	Homo sapiens
342 μg × h/L	60 mg single, oral	ISOXANTHOHUMOL plasma	Homo sapiens
982 μg × h/L	180 mg single, oral	ISOXANTHOHUMOL plasma	Homo sapiens

T_1/2

Value	Dose	Analyte	Population
20 h	60 mg single, oral	XANTHOHUMOL plasma	Homo sapiens
19 h	180 mg single, oral	XANTHOHUMOL plasma	Homo sapiens
16 h	180 mg single, oral	XANTHOHUMOL plasma	Homo sapiens
19 h	60 mg single, oral	XANTHOHUMOL plasma	Homo sapiens
22 h	180 mg single, oral	ISOXANTHOHUMOL plasma	Homo sapiens
21.6 h	60 mg single, oral	ISOXANTHOHUMOL plasma	Homo sapiens
30 h	60 mg single, oral	ISOXANTHOHUMOL plasma	Homo sapiens
24 h	180 mg single, oral	ISOXANTHOHUMOL plasma	Homo sapiens

Sourcing

Sourcing

Show entries

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

Showing 1 to 5 of 38 entries

Previous1 2 3 4 5…8Next

PubMed

Show entries

Title	Date	PubMed
Xanthohumol induces phase II enzymes via Nrf2 in human hepatocytes in vitro.	2013 Feb	23085367
2-Hydroxychalcone and xanthohumol inhibit invasion of triple negative breast cancer cells.	2013 May 25	23562496

Showing 1 to 2 of 2 entries

Previous1Next

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.

Show entries

Name

Type

Language

XANTHOHUMOL

Official Name

English

XANTHO-FLAV

Preferred 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

Showing 1 to 5 of 5 entries

Previous1Next

Show entries

Classification Tree

Code System

Code

Pharmacologic Substance

NCI_THESAURUS

C274

chemical

DSLD

3469 (Number of products:3)

Showing 1 to 2 of 2 entries

Previous1Next

Show entries

Code System

Code

Type

Description

PUBCHEM

639665

PRIMARY

DRUG BANK

DB15359

PRIMARY

WIKIPEDIA

XANTHOHUMOL

PRIMARY

NCI_THESAURUS

C121950

PRIMARY

CAS

6754-58-1

PRIMARY

Showing 1 to 5 of 9 entries

Previous1 2Next

ACTIVE MOIETY


					T4467YT1NT

XANTHOHUMOL

SMILES

InChI

CNS Activity

Originator

Approval Year

Targets

Conditions

Cmax

AUC

T1/2

Sourcing

PubMed

Patents

Sample Use Guides

C_max

T_1/2