Showing Compound Homoferreirin (FDB001912)

Record Information

Version

1.0

Creation date

2010-04-08 22:05:10 UTC

Update date

2025-11-18 22:33:38 UTC

Primary ID

FDB001912

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Homoferreirin

Description

Homoferreirin belongs to the class of organic compounds known as 4'-o-methylated isoflavonoids. These are isoflavonoids with methoxy groups attached to the C4' atom of the isoflavonoid backbone. Isoflavonoids are natural products derived from 3-phenylchromen-4-one. Thus, homoferreirin is considered to be a flavonoid. Homoferreirin has been detected, but not quantified in, chickpeas (Cicer arietinum) and pulses. This could make homoferreirin a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Homoferreirin.

CAS Number

482-01-9

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
5,7-Dihydroxy-2',4'-dimethoxyisoflavanone	ChEBI
Homoferreirin	db_source

Predicted Properties

Property	Value	Source
Water Solubility	0.075 g/L	ALOGPS
logP	2.79	ALOGPS
logP	2.72	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	7.91	ChemAxon
pKa (Strongest Basic)	-3.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	85.22 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	82.62 m³·mol⁻¹	ChemAxon
Polarizability	31.55 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

C17H16O6

IUPAC name

3-(2,4-dimethoxyphenyl)-5,7-dihydroxy-3,4-dihydro-2H-1-benzopyran-4-one

InChI Identifier

InChI=1S/C17H16O6/c1-21-10-3-4-11(14(7-10)22-2)12-8-23-15-6-9(18)5-13(19)16(15)17(12)20/h3-7,12,18-19H,8H2,1-2H3

InChI Key

LMLDNMHDNFCNCW-UHFFFAOYSA-N

Isomeric SMILES

COC1=CC(OC)=C(C=C1)C1COC2=CC(O)=CC(O)=C2C1=O

Average Molecular Weight

316.3053

Monoisotopic Molecular Weight

316.094688244

Classification

Description

Belongs to the class of organic compounds known as 4'-o-methylated isoflavonoids. These are isoflavonoids with methoxy groups attached to the C4' atom of the isoflavonoid backbone. Isoflavonoids are natural products derived from 3-phenylchromen-4-one.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Isoflavonoids

Sub Class

O-methylated isoflavonoids

Direct Parent

4'-O-methylated isoflavonoids

Alternative Parents

Substituents

2p-methoxyisoflavonoid-skeleton
4p-methoxyisoflavonoid
Isoflavanol
Isoflavanone
Hydroxyisoflavonoid
Isoflavan
Chromone
Chromane
Benzopyran
1-benzopyran
Dimethoxybenzene
M-dimethoxybenzene
Methoxybenzene
Aryl alkyl ketone
Aryl ketone
Anisole
Phenol ether
Phenoxy compound
Alkyl aryl ether
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Benzenoid
Monocyclic benzene moiety
Vinylogous acid
Ketone
Ether
Organoheterocyclic compound
Oxacycle
Hydrocarbon derivative
Organooxygen compound
Organic oxygen compound
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

dimethoxyflavanone (CHEBI:5754 )
dihydroxyflavanone (CHEBI:5754 )
Isoflavonoids (C10457 )
Isoflavonoids (LMPK12050502 )

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Fabaceae

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Not Available
Physical Description	Not Available
Mass Composition	C 64.55%; H 5.10%; O 30.35%	DFC
Melting Point	Mp 168-169°	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	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	Homoferreirin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0f79-0972000000-bfa02d0e32278d468d89	Spectrum
Predicted GC-MS	Homoferreirin, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-01vt-2934500000-7a4fdfeb18c01d5ea7fc	Spectrum
Predicted GC-MS	Homoferreirin, 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	splash10-014i-0339000000-346adbec090026b60fb2	2016-08-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0gb9-0965000000-a080c8063d4336811742	2016-08-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0udr-1910000000-acafbcb1364ca94d420c	2016-08-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0019000000-a7359d4c2115c453ca7d	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-014j-0796000000-c62eb664a6f0f81108f6	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a5i-6940000000-6d81a8f3c9ef6685c79b	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0109000000-509124d16308cc2ca18f	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-016s-0698000000-029dec21dabef44de6b7	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0gk9-1490000000-650847b22ef19db39cc4	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-0309000000-eed2ffdf6fb812f81994	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0gc9-0902000000-27a42f57801763de67af	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0udi-0910000000-217f6e98d9210e7a3ed5	2021-09-24	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

391121

ChEMBL ID

Not Available

KEGG Compound ID

C10457

Pubchem Compound ID

442788

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB30111

CRC / DFC (Dictionary of Food Compounds) ID

FMC58-N:CBB97-N

EAFUS ID

Not Available

Dr. Duke ID

HOMOFERREIRIN

BIGG ID

Not Available

KNApSAcK ID

C00002535

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
Fungicide	24127	An agent that kills or inhibits the growth of fungi, playing a biological role in preventing fungal infections. Therapeutically, it is used to treat fungal diseases, with key medical applications including athlete's foot, ringworm, and candidiasis, as well as agricultural uses to protect crops from fungal damage.	DUKE
Pesticide	25944	An agent that kills or repels pests, playing a biological role in controlling insect, weed, and fungal populations. Therapeutically, pesticides have limited applications, but some are used to treat ectoparasitic infestations, such as lice and scabies. Key medical uses include topical treatments for head lice and scabies, highlighting their role in managing parasitic infections.	DUKE
Phytoalexin	26115	A plant-derived compound that plays a biological role in defense against pathogens. It has therapeutic applications as an antimicrobial, antioxidant, and anti-inflammatory agent, with key medical uses in managing infections, cancer, and neurodegenerative diseases.	DUKE