ChemFOnt: Showing chemical card for Betavulgarin (CFc000282850)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-14 03:35:35 UTC

Chemfont ID

CFc000282850

Molecule Identification

Common Name

Betavulgarin

Definition

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.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
2'-Hydroxy-5-methoxy-6,7-methylenedioxyisoflavone	ChEBI
7-(2-Hydroxyphenyl)-9-methoxy-8H-(1,3)dioxolo(4,5-g)chromen-8-one	MeSH

Chemical Formula

C₁₇H₁₂O₆

Average Molecular Weight

312.2736

Monoisotopic Molecular Weight

312.063388116

IUPAC Name

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

Traditional Name

betavulgarin

CAS Registry Number

51068-94-1

SMILES

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

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

Chemical Taxonomy

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 )

Functional Ontology

Not Available

Exogenous (HMDB: HMDB0303334)

Food

Vegetable

Root vegetable

Red beetroot (FooDB: FOOD00264)

Leaf vegetable

Common beet (FooDB: FOOD00025)

Pulse

Pea

Chickpea (FooDB: FOOD00047)

Process

Not Available

Role

Industrial application

Agriculture

Pesticide (HMDB: HMDB0303334)

Biological role

Phytoalexin (HMDB: HMDB0303334)

Physical Properties

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