Showing Compound Xanthohumol (FDB016545)

Record Information

Version

1.0

Creation date

2010-04-08 22:12:30 UTC

Update date

2019-11-26 03:13:25 UTC

Primary ID

FDB016545

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Xanthohumol

Description

Xanthohumol belongs to the class of organic compounds known as 3-prenylated chalcones. These are chalcones featuring a C5-isoprenoid unit at the 3-position. Thus, xanthohumol is considered to be a flavonoid. Xanthohumol is a bitter tasting compound. Xanthohumol is found, on average, in the highest concentration within beer. Xanthohumol has also been detected, but not quantified in, alcoholic beverages. This could make xanthohumol a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on Xanthohumol.

CAS Number

6754-58-1

Structure

MOL SDF PDB SMILES InChI

Synonyms

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Synonym	Source
(2E)-1-[2,4-Dihydroxy-6-methoxy-3-(3-methylbut-2-en-1-yl)phenyl]-3-(4-hydroxyphenyl)prop-2-en-1-one	Kegg
1-(2,4-Dihydroxy-6-methoxy-3-(3-methyl-2-butenyl)phenyl)-3-(4-hydroxyphenyl)-2-propen-1-one	MeSH
2',4,4'-Trihydroxy-6'-methoxy-3'-prenylchalcone	ChEBI
Desmethylxanthohumol	MeSH
Xanthohumol	db_source

Showing 1 to 5 of 5 entries

Predicted Properties

Property	Value	Source
Water Solubility	0.0056 g/L	ALOGPS
logP	3.91	ALOGPS
logP	5.2	ChemAxon
logS	-4.8	ALOGPS
pKa (Strongest Acidic)	7.65	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	86.99 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	103.53 m³·mol⁻¹	ChemAxon
Polarizability	38.55 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C21H22O5

IUPAC name

(2E)-1-[2,4-dihydroxy-6-methoxy-3-(3-methylbut-2-en-1-yl)phenyl]-3-(4-hydroxyphenyl)prop-2-en-1-one

InChI Identifier

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+

InChI Key

ORXQGKIUCDPEAJ-YRNVUSSQSA-N

Isomeric SMILES

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

Average Molecular Weight

354.3964

Monoisotopic Molecular Weight

354.146723814

Classification

Description

Belongs to the class of organic compounds known as 3-prenylated chalcones. These are chalcones featuring a C5-isoprenoid unit at the 3-position.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Linear 1,3-diarylpropanoids

Sub Class

Chalcones and dihydrochalcones

Direct Parent

3-prenylated chalcones

Alternative Parents

Substituents

3-prenylated chalcone
2'-hydroxychalcone
Cinnamylphenol
Hydroxycinnamic acid or derivatives
Methoxyphenol
Phenoxy compound
Phenol ether
Resorcinol
Styrene
Aryl ketone
Anisole
Methoxybenzene
Benzoyl
Phenol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Benzenoid
Monocyclic benzene moiety
Acryloyl-group
Vinylogous acid
Enone
Alpha,beta-unsaturated ketone
Ketone
Ether
Organic oxide
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

aromatic ether (CHEBI:66331 )
polyphenol (CHEBI:66331 )
chalcones (CHEBI:66331 )
chalcones (C16417 )
Chalcones and dihydrochalcones (C16417 )
Chalcones and dihydrochalcones (LMPK12120294 )

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Biological location:

Subcellular:

Source:

Food

Biological:

Plant

Role

Industrial application:

Pharmaceutical industry:

Antiviral

Biological role:

Nutrient

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

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Property	Value	Reference
Boiling Point	Not Available
Charge	Not Available
Density	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Experimental Water Solubility	Not Available
Isoelectric point	Not Available
Mass Composition	C 71.17%; H 6.26%; O 22.57%	DFC
Melting Point	Mp 172°	DFC
Optical Rotation	Not Available

Showing 1 to 10 of 14 entries

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	Xanthohumol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-000l-3359000000-513a171f819b95432ac8	Spectrum
Predicted GC-MS	Xanthohumol, 3 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0a4i-2131390000-01a52cd1365880409310	Spectrum
Predicted GC-MS	Xanthohumol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Xanthohumol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - ESI-TOF , Negative	splash10-014i-0940000000-46dc70d70ca70dcf01b4	2017-08-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF 20V, Negative	splash10-014i-0940000000-46dc70d70ca70dcf01b4	2017-08-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF , Negative	splash10-0udi-0009000000-adffe3727a9d190af9ea	2017-09-12	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF 20V, Negative	splash10-0ue9-0159000000-89390bf396bc026f25db	2017-09-12	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0udi-0029000000-5292b3ba1142d29c7386	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0ue9-0497000000-dec7e1db8ee3c405c5da	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0159-0981000000-c78fd55b14d98033f180	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-TOF , negative	splash10-0ue9-0159000000-89390bf396bc026f25db	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - , negative	splash10-0uxr-0978000000-bb0b197988e97a4a05ca	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-004j-0970000000-179d5086107c87523593	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-004i-0910000000-2dea6c7222209825ac37	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-004i-0900000000-4e1106c364aad0846401	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-0002-0293000000-07b3d1d40f210eb9247b	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-004i-0940000000-6983981e47a0f6af296b	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-004i-0900000000-cee69c093feb8d9b8aa3	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-0002-0190000000-ec80f253f42d34e79be9	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-0002-0190000000-c3d920598c6526bdb0ba	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-0002-0290000000-a3b357466ef6c20fc37d	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-0002-0290000000-a6fb7803116d7827f288	2017-09-14	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-0129000000-6cc3dfff7ce5ef42566f	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-05mt-3596000000-0fb44a4b969d525ddeb1	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-014i-4910000000-c8ee4088761d3e104636	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0129000000-d3c87e511f6c42141ff1	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0pbd-0965000000-856a6ce55c4795d014f8	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0aba-1920000000-72db9ec75d5e130d0a45	2016-08-03	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

ChEMBL ID

KEGG Compound ID

Pubchem Compound ID

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

105

DrugBank ID

Not Available

HMDB ID

HMDB37479

CRC / DFC (Dictionary of Food Compounds) ID

CMD59-M:KRM94-F

EAFUS ID

Not Available

Dr. Duke ID

Not Available

BIGG ID

Not Available

KNApSAcK ID

Not Available

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

Not Available

SuperScent ID

Not Available

Wikipedia ID

Not Available

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

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Food	Content Range	Average	Reference

Beer	0.00030 - 0.03450 mg/100 g	0.01405 mg/100 g	PHENOL EXPLORER, PHYTOHUB

Showing 1 to 1 of 1 entries

Biological Effects and Interactions

Health Effects / Bioactivities

Not Available

Enzymes

Not Available

Pathways

Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

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Showing 1 to 1 of 1 entries

Files

MSDS

Not Available

References

Synthesis Reference

Not Available

General Reference

Not Available

Content Reference

— Rothwell JA, Pérez-Jiménez J, Neveu V, Medina-Ramon A, M'Hiri N, Garcia Lobato P, Manach C, Knox K, Eisner R, Wishart D, Scalbert A. (2013) Phenol-Explorer 3.0: a major update of the Phenol-Explorer database to incorporate data on the effects of food processing on polyphenol content. Database, 10.1093/database/bat070.

Showing Compound Xanthohumol (FDB016545)

Structure for FDB016545 (Xanthohumol)