Showing Compound Xanthohumol B (FDB013439)

Record Information

Version

1.0

Creation date

2010-04-08 22:10:42 UTC

Update date

2019-11-26 03:08:25 UTC

Primary ID

FDB013439

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Xanthohumol B

Description

Xanthohumol B belongs to the class of organic compounds known as 2'-hydroxychalcones. These are organic compounds containing chalcone skeleton that carries a hydroxyl group at the 2'-position. Thus, xanthohumol b is considered to be a flavonoid. Xanthohumol B has been detected, but not quantified in, a few different foods, such as alcoholic beverages, breakfast cereal, and cereals and cereal products. This could make xanthohumol b a potential biomarker for the consumption of these foods. Based on a literature review a small amount of articles have been published on Xanthohumol B.

CAS Number

189308-10-9

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

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Synonym	Source
6'',6''-Dimethyl-5''-hydroxy-4'',5''-dihydropyrano[2'',3'':4',3']-4,2'-dihydroxy-6'-methoxychalcone	HMDB
Dehydrocycloxanthohumol hydrate	ChEBI
Dehydrocycloxanthohumol hydric acid	Generator
rac-(e)-1-(3,5-Dihydroxy-7-methoxy-2,2-dimethyl-3,4-dihydrochromen-6-yl)-3-(4-hydroxyphenyl)prop-2-en-1-one	ChEBI
rac-6'',6''-Dimethyl-5''-hydroxy-4'',5''-dihydropyrano[2'',3'':4',3']-4,2'-dihydroxy-6'-methoxychalcone	ChEBI
rac-6-[3,4-Dihydro-3,5-dihydroxy-7-methoxy-2,2-dimethyl-2H-benzo[b]pyrano]-3-(4-hydroxyphenyl)-2-propen-1-one	ChEBI
Xanthohumol B	db_source

Showing 1 to 7 of 7 entries

Predicted Properties

Property	Value	Source
Water Solubility	0.013 g/L	ALOGPS
logP	3.21	ALOGPS
logP	3.72	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Acidic)	8.27	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	96.22 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	102.09 m³·mol⁻¹	ChemAxon
Polarizability	39.71 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C21H22O6

IUPAC name

(2E)-1-(3,5-dihydroxy-7-methoxy-2,2-dimethyl-3,4-dihydro-2H-1-benzopyran-6-yl)-3-(4-hydroxyphenyl)prop-2-en-1-one

InChI Identifier

InChI=1S/C21H22O6/c1-21(2)18(24)10-14-16(27-21)11-17(26-3)19(20(14)25)15(23)9-6-12-4-7-13(22)8-5-12/h4-9,11,18,22,24-25H,10H2,1-3H3/b9-6+

InChI Key

GUQGMEWOCKDLDE-RMKNXTFCSA-N

Isomeric SMILES

COC1=C(C(=O)\C=C\C2=CC=C(O)C=C2)C(O)=C2CC(O)C(C)(C)OC2=C1

Average Molecular Weight

370.3958

Monoisotopic Molecular Weight

370.141638436

Classification

Description

Belongs to the class of organic compounds known as 2'-hydroxychalcones. These are organic compounds containing chalcone skeleton that carries a hydroxyl group at the 2'-position.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Linear 1,3-diarylpropanoids

Sub Class

Chalcones and dihydrochalcones

Direct Parent

2'-Hydroxychalcones

Alternative Parents

Substituents

2'-hydroxychalcone
Hydroxycinnamic acid or derivatives
2,2-dimethyl-1-benzopyran
Chromane
Benzopyran
1-benzopyran
Anisole
Styrene
Aryl ketone
Alkyl aryl ether
Phenol
1-hydroxy-2-unsubstituted benzenoid
1-hydroxy-4-unsubstituted benzenoid
Benzenoid
Monocyclic benzene moiety
Vinylogous acid
Alpha,beta-unsaturated ketone
Acryloyl-group
Enone
Secondary alcohol
Ketone
Oxacycle
Organoheterocyclic compound
Ether
Hydrocarbon derivative
Organic oxygen compound
Organooxygen compound
Alcohol
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

aromatic ether (CHEBI:66334 )
polyphenol (CHEBI:66334 )
chalcones (CHEBI:66334 )
Chalcones and dihydrochalcones (LMPK12120299 )

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Biological location:

Subcellular:

Source:

Food

Biological:

Plant:

Poaceae

Role

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 68.10%; H 5.99%; O 25.92%	DFC
Melting Point	Not Available
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 B, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0udl-0229000000-b811f90951d1a0a835d1	Spectrum
Predicted GC-MS	Xanthohumol B, 3 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-00di-6040190000-bdc2a7531e971d5f1a9d	Spectrum
Predicted GC-MS	Xanthohumol B, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-0179000000-e2301b1431f4b57e5b7a	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0002-0493000000-6468906cb55db17ec732	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-014i-2940000000-8c2ed436d015fefe3a4b	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0149000000-423b4abd708a051724ef	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00xs-6594000000-22d370d3f79419763d48	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-014i-3590000000-430efc544d480953d59b	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0029000000-0be4f2f0792fa82b11b5	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-014i-0898000000-a197e8c9c81ccea5ceca	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-014i-1930000000-bf324f554727d9051fa0	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-0019000000-7b119b59c36247b7ed5e	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0f89-1391000000-92e5e602575e67980af7	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00su-4962000000-6aa1110047dcb2f70570	2021-09-22	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

7975271

ChEMBL ID

Not Available

KEGG Compound ID

Not Available

Pubchem Compound ID

9799506

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB34867

CRC / DFC (Dictionary of Food Compounds) ID

KQQ61-G:JBT25-B

EAFUS ID

Not Available

Dr. Duke ID

Not Available

BIGG ID

Not Available

KNApSAcK ID

C00014478

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

Processing...

Biological Effects and Interactions

Health Effects / Bioactivities

Not Available

Enzymes

Not Available

Pathways

Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Not Available

Files

MSDS

Not Available

References

Synthesis Reference

Not Available

General Reference

Not Available

Content Reference

Showing Compound Xanthohumol B (FDB013439)

Structure for FDB013439 (Xanthohumol B)