ChemFOnt: Showing chemical card for Irigenin (CFc000282675)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-14 03:35:15 UTC

Chemfont ID

CFc000282675

Molecule Identification

Common Name

Irigenin

Definition

Irigenin, also known as 5,7,3'-trihydroxy-6,4',5'-trimethoxyisoflavone, is a member of the class of compounds known as 3'-hydroxy,4'-methoxyisoflavonoids. 3'-hydroxy,4'-methoxyisoflavonoids are isoflavonoids carrying a methoxy group attached to the C4' atom, as well as a hydroxyl group at the C3'-position of the isoflavonoid backbone. Thus, irigenin is considered to be a flavonoid lipid molecule. Irigenin is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Irigenin can be synthesized from isoflavone. Irigenin can also be synthesized into iridin. Irigenin can be found in lima bean, which makes irigenin a potential biomarker for the consumption of this food product. Irigenin is an O-methylated isoflavone, a type of flavonoid. It can be isolated from the rhizomes of the leopard lily (Belamcanda chinensis), and Iris kemaonensis .

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
5,7,3'-Trihydroxy-6,4',5'-trimethoxyisoflavone	ChEBI

Chemical Formula

C₁₈H₁₆O₈

Average Molecular Weight

360.3148

Monoisotopic Molecular Weight

360.084517488

IUPAC Name

5,7-dihydroxy-3-(3-hydroxy-4,5-dimethoxyphenyl)-6-methoxy-4H-chromen-4-one

Traditional Name

irigenin

CAS Registry Number

548-76-5

SMILES

COC1=CC(=CC(O)=C1OC)C1=COC2=CC(O)=C(OC)C(O)=C2C1=O

InChI Identifier

InChI=1S/C18H16O8/c1-23-13-5-8(4-10(19)17(13)24-2)9-7-26-12-6-11(20)18(25-3)16(22)14(12)15(9)21/h4-7,19-20,22H,1-3H3

InChI Key

TUGWPJJTQNLKCL-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 3'-hydroxy,4'-methoxyisoflavonoids. These are isoflavonoids carrying a methoxy group attached to the C4' atom, as well as a hydroxyl group at the C3'-position of the isoflavonoid backbone.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Isoflavonoids

Sub Class

O-methylated isoflavonoids

Direct Parent

3'-hydroxy,4'-methoxyisoflavonoids

Alternative Parents

Substituents

3p-methoxyisoflavone
4p-o-methylisoflavone
3'-hydroxy,4'-methoxyisoflavonoid
Isoflavone
Hydroxyisoflavonoid
Chromone
Methoxyphenol
Benzopyran
O-dimethoxybenzene
Dimethoxybenzene
1-benzopyran
Phenoxy compound
Anisole
Methoxybenzene
Phenol ether
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Phenol
Pyranone
Monocyclic benzene moiety
Pyran
Benzenoid
Heteroaromatic compound
Vinylogous acid
Oxacycle
Organoheterocyclic compound
Ether
Organic oxygen compound
Organic oxide
Organooxygen compound
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

hydroxyisoflavone (CHEBI:81409 )
methoxyisoflavone (CHEBI:81409 )
Isoflavonoids (C17957 )
Isoflavonoids (LMPK12050417 )

Functional Ontology

Not Available

Exogenous (HMDB: HMDB0303159)

Food

Pulse

Bean

Lima bean (FooDB: FOOD00133)

Not Available

CAMP-phosphodiesterase inhibitor (HMDB: HMDB0303159)

Cholinergic (HMDB: HMDB0303159)
RNA-genic (HMDB: HMDB0303159)

Industrial application

Pharmaceutical industry

Hepatoprotective (HMDB: HMDB0303159)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.066 g/L	ALOGPS
logP	2.74	ALOGPS
logP	2.6	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	7.12	ChemAxon
pKa (Strongest Basic)	-4.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	114.68 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	91.07 m³·mol⁻¹	ChemAxon
Polarizability	35.6 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