ISOXANTHOHUMOL

Details

Stereochemistry	ACHIRAL
Molecular Formula	C21H22O4
Molecular Weight	338.397
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	1
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

COC1=CC(O)=C(C(=O)\C=C\C2=CC=CC=C2)C(O)=C1CC=C(C)C

InChI

InChIKey=VNKGJUSYZMFRJX-ZRDIBKRKSA-N

InChI=1S/C21H22O4/c1-14(2)9-11-16-19(25-3)13-18(23)20(21(16)24)17(22)12-10-15-7-5-4-6-8-15/h4-10,12-13,23-24H,11H2,1-3H3/b12-10+

HIDE SMILES / InChI

Molecular Formula	C21H22O4
Molecular Weight	338.397
Charge	0
Count

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

Approval Year

Targets

Primary Target	Pharmacology	Potency
reactive oxygen species biosynthetic process 41 Target ID: GO:1903409 Sources: https://www.ncbi.nlm.nih.gov/pubmed/31010128	Activator 1447
Apoptosis 156 Target ID: map04210 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25771121	Activator 1447
Cytochrome P450 2C8 18 Target ID: CHEMBL3721 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25771121	Inhibitor 8504	0.2 µM [IC50]

PubMed

Title	Date	PubMed
The hop-derived prenylflavonoid isoxanthohumol inhibits the formation of lung metastasis in B16-F10 murine melanoma model.	2019-07	31034931
Positive allosteric modulation of native and recombinant GABAA receptors by hops prenylflavonoids.	2019-06-05	30797788
Potent inhibition of human carbonyl reductase 1 (CBR1) by the prenylated chalconoid xanthohumol and its related prenylflavonoids isoxanthohumol and 8-prenylnaringenin.	2019-05-25	30849340
Antiproliferative Effects of Hop-derived Prenylflavonoids and Their Influence on the Efficacy of Oxaliplatine, 5-fluorouracil and Irinotecan in Human ColorectalC Cells.	2019-04-19	31010128
The Multiple Biological Targets of Hops and Bioactive Compounds.	2019-02-18	30608650
Biotransformed Metabolites of the Hop Prenylflavanone Isoxanthohumol.	2019-01-22	30678278
Reductive Metabolism of Xanthohumol and 8-Prenylnaringenin by the Intestinal Bacterium Eubacterium ramulus.	2019-01	30471194
Simultaneous Optimization for Ultrasound-Assisted Extraction and Antioxidant Activity of Flavonoids from Sophora flavescens Using Response Surface Methodology.	2018-12-29	30597974
Biotransformation of a major beer prenylflavonoid - isoxanthohumol.	2018-12-19	30864390
The hop-derived compounds xanthohumol, isoxanthohumol and 8-prenylnaringenin are tight-binding inhibitors of human aldo-keto reductases 1B1 and 1B10.	2018-12	29532688
Highly Cancer Selective Antiproliferative Activity of Natural Prenylated Flavonoids.	2018-11-09	30423918
Chiral separation of isoxanthohumol and 8-prenylnaringenin in beer, hop pellets and hops by HPLC with chiral columns.	2018-10	29768665
Effect-directed classification of biological, biochemical and chemical profiles of 50 German beers.	2018-09-15	29699678
Isoxanthohumol stimulates ubiquitin-proteasome-dependent degradation of precursor forms of sterol regulatory element-binding proteins.	2018-09	29804513
Rice Protein Matrix Enhances Circulating Levels of Xanthohumol Following Acute Oral Intake of Spent Hops in Humans.	2018-03	29322620

Substance Class	Chemical Created by `admin` on `Wed Apr 02 09:14:55 GMT 2025` Edited by `admin` on `Wed Apr 02 09:14:55 GMT 2025`
Record UNII	B3BXQ4EZD6
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ISOXANTHOHUMOL

Common Name

English

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

Preferred Name

English

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

Systematic Name

English

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

Systematic Name

English

Code System Code Type Description

CAS

72247-79-1

Created by admin on Wed Apr 02 09:14:55 GMT 2025 , Edited by admin on Wed Apr 02 09:14:55 GMT 2025

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FDA UNII

B3BXQ4EZD6

Created by admin on Wed Apr 02 09:14:55 GMT 2025 , Edited by admin on Wed Apr 02 09:14:55 GMT 2025

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PUBCHEM

15410693

Created by admin on Wed Apr 02 09:14:55 GMT 2025 , Edited by admin on Wed Apr 02 09:14:55 GMT 2025

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