AFCDB: Betavulgarin (FDB011161)

Record Information

Version

1.0

Creation date

2010-04-08 22:09:30 UTC

Update date

2019-11-26 03:04:38 UTC

Primary ID

FDB011161

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Betavulgarin

Description

Betavulgarin, also known as 2'-hydroxy-5-methoxy-6,7-methylenedioxyisoflavone, is a member of the class of compounds known as isoflavones. Isoflavones are polycyclic compounds containing a 2-isoflavene skeleton which bears a ketone group at the C4 carbon atom. Thus, betavulgarin is considered to be a flavonoid lipid molecule. Betavulgarin is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Betavulgarin can be found in chickpea, common beet, and red beetroot, which makes betavulgarin a potential biomarker for the consumption of these food products.

CAS Number

51068-94-1

Structure

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

Synonyms

Synonym	Source
Not Available	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.11 g/L	ALOGPS
logP	2.67	ALOGPS
logP	2.5	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	8.66	ChemAxon
pKa (Strongest Basic)	-4.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	74.22 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	79.95 m³·mol⁻¹	ChemAxon
Polarizability	30.73 Å³	ChemAxon
Number of Rings	4	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

C17H12O6

IUPAC name

7-(2-hydroxyphenyl)-9-methoxy-2H,8H-[1,3]dioxolo[4,5-g]chromen-8-one

InChI Identifier

InChI=1S/C17H12O6/c1-20-17-14-12(6-13-16(17)23-8-22-13)21-7-10(15(14)19)9-4-2-3-5-11(9)18/h2-7,18H,8H2,1H3

InChI Key

NDVRQFZUJRMKKP-UHFFFAOYSA-N

Isomeric SMILES

COC1=C2OCOC2=CC2=C1C(=O)C(=CO2)C1=CC=CC=C1O

Average Molecular Weight

312.2736

Monoisotopic Molecular Weight

312.063388116

Classification

Description

Belongs to the class of organic compounds known as isoflavones. These are polycyclic compounds containing a 2-isoflavene skeleton which bears a ketone group at the C4 carbon atom.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Isoflavonoids

Sub Class

Isoflav-2-enes

Direct Parent

Isoflavones

Alternative Parents

Substituents

Hydroxyisoflavonoid
Isoflavone
Chromone
Benzopyran
1-benzopyran
Benzodioxole
Anisole
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Phenol
Pyranone
Monocyclic benzene moiety
Benzenoid
Pyran
Heteroaromatic compound
Vinylogous ester
Organoheterocyclic compound
Ether
Oxacycle
Acetal
Organooxygen compound
Hydrocarbon derivative
Organic oxygen compound
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

hydroxyisoflavone (CHEBI:3081 )
methoxyisoflavone (CHEBI:3081 )
isoflavones (C10201 )
Isoflavonoids (C10201 )
Isoflavonoids (LMPK12050361 )

Ontology

No ontology term

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Not Available
Physical Description	Not Available
Mass Composition	C 65.39%; H 3.87%; O 30.74%	DFC
Melting Point	Mp 162-163° (147-150°)	DFC
Boiling Point	Not Available
Experimental Water Solubility	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	Not Available
Spectroscopic UV Data	317 (e 17230) (MeOH) (Berdy)	DFC
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Not Available

MS/MS

Type	Description	Splash Key	View
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03di-0019000000-cf27b403f1f851b39b9f	2016-08-02	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03di-4069000000-f1d7b7941835d870a2e2	2016-08-02	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0udi-2490000000-aab1ca8d9f6100083838	2016-08-02	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-0019000000-de6d144144be5a77bc85	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-02t9-0094000000-77bc55cee1f6540e4fd3	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0007-5590000000-8688b3faaffe0c937687	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03di-0009000000-fbd933023572de11abf0	2021-10-21	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03di-0009000000-fbd933023572de11abf0	2021-10-21	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-03e9-0197000000-bebe7428ab51ab6a912d	2021-10-21	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-0009000000-b504eaff11e6208b17b1	2021-10-21	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03di-0029000000-7a303f5b7aea5212b45a	2021-10-21	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0gc3-0090000000-c27fdffadd025e7fd9ab	2021-10-21	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

Not Available

ChEMBL ID

Not Available

KEGG Compound ID

C10201

Pubchem Compound ID

442668

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

Not Available

CRC / DFC (Dictionary of Food Compounds) ID

GNB65-A:GBW78-B

EAFUS ID

Not Available

Dr. Duke ID

BETAVULGARIN

BIGG ID

Not Available

KNApSAcK ID

C00002509

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

Food	Content Range	Average	Reference
Food			Reference

Biological Effects and Interactions

Health Effects / Bioactivities

Descriptor	ID	Definition	Reference
pesticide	25944	Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.	DUKE
phytoalexin	26115	A toxin made by a plant that acts against an organism attacking it.	DUKE

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

— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.
— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).

Betavulgarin (FDB011161)

Structure for FDB011161 (Betavulgarin)