AFCDB: Formononetin (FDB012219)

Record Information

Version

1.0

Creation date

2010-04-08 22:10:03 UTC

Update date

2019-11-26 03:06:25 UTC

Primary ID

FDB012219

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Formononetin

Description

Formononetin, also known as biochanin b, belongs to the class of organic compounds known as 4'-o-methylisoflavones. These are isoflavones with methoxy groups attached to the C4' atom of the isoflavone backbone. Thus, formononetin is considered to be a flavonoid. Formononetin is found, on average, in the highest concentration within a few different foods, such as milk (cow), soy beans (Glycine max), and sunflowers (Helianthus annuus) and in a lower concentration in soy sauce, soy milk, and tofu. Formononetin has also been detected, but not quantified in, several different foods, such as cupuaçus (Theobroma grandiflorum), saffrons (Crocus sativus), prairie turnips (Pediomelum esculentum), hazelnuts (Corylus), and broad beans (Vicia faba). This could make formononetin a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on Formononetin.

CAS Number

485-72-3

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	0.04 g/L	ALOGPS
logP	3.56	ALOGPS
logP	2.88	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	6.48	ChemAxon
pKa (Strongest Basic)	-4.7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	55.76 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	74.18 m³·mol⁻¹	ChemAxon
Polarizability	27.86 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

C16H12O4

IUPAC name

7-hydroxy-3-(4-methoxyphenyl)-4H-chromen-4-one

InChI Identifier

InChI=1S/C16H12O4/c1-19-12-5-2-10(3-6-12)14-9-20-15-8-11(17)4-7-13(15)16(14)18/h2-9,17H,1H3

InChI Key

HKQYGTCOTHHOMP-UHFFFAOYSA-N

Isomeric SMILES

COC1=CC=C(C=C1)C1=COC2=C(C=CC(O)=C2)C1=O

Average Molecular Weight

268.268

Monoisotopic Molecular Weight

268.073558866

Classification

Description

Belongs to the class of organic compounds known as 4'-o-methylisoflavones. These are isoflavones with methoxy groups attached to the C4' atom of the isoflavone backbone.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Isoflavonoids

Sub Class

O-methylated isoflavonoids

Direct Parent

4'-O-methylisoflavones

Alternative Parents

Substituents

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

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

methoxyisoflavone (CHEBI:18088 )
7-hydroxyisoflavones (CHEBI:18088 )
isoflavones (C00858 )
Isoflavonoids (C00858 )
Isoflavonoids (LMPK12050037 )
a 4'-methoxyisoflavone (FORMONONETIN )

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Food

Biological:

Animal

Plant:

Biological location:

Subcellular:

Biofluid and excreta:

Foods

Nuts and legumes:

Legumes:

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Solid
Physical Description	Not Available
Mass Composition	C 71.64%; H 4.51%; O 23.86%	DFC
Melting Point	Mp 265-266° (257-258°)	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	340 () (MeOH/NaOH) (Berdy)	DFC
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
GC-MS	Formononetin, non-derivatized, GC-MS Spectrum	splash10-0016-2914000000-92598f879b703e3e34be	Spectrum
GC-MS	Formononetin, non-derivatized, GC-MS Spectrum	splash10-0016-2914000000-92598f879b703e3e34be	Spectrum
Predicted GC-MS	Formononetin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-000f-0490000000-e26e3143b0047535b40c	Spectrum
Predicted GC-MS	Formononetin, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-02or-3897000000-5e35eab52b4bd3010fa5	Spectrum
Predicted GC-MS	Formononetin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - ESI-TOF 50V, Negative	splash10-006t-0960000000-882facb1d6090879f469	2017-08-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF 30V, Negative	splash10-006t-0960000000-882facb1d6090879f469	2017-08-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF 10V, Negative	splash10-006t-0960000000-882facb1d6090879f469	2017-08-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF 40V, Negative	splash10-0fk9-0390000000-60bac2bf99a8a69fbfa0	2017-08-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF 20V, Negative	splash10-0fk9-0390000000-60bac2bf99a8a69fbfa0	2017-08-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF , Negative	splash10-0fk9-0390000000-60bac2bf99a8a69fbfa0	2017-08-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF 50V, Negative	splash10-006t-0960000000-882facb1d6090879f469	2017-09-12	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF 30V, Negative	splash10-0udi-0090000000-c85f2c5d083aef27307a	2017-09-12	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF 10V, Negative	splash10-014i-0090000000-1c961341bd2d8a5a1789	2017-09-12	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF 40V, Negative	splash10-0fk9-0390000000-60bac2bf99a8a69fbfa0	2017-09-12	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF 20V, Negative	splash10-0uxr-0090000000-0755787b026efa8867b7	2017-09-12	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF , Negative	splash10-014i-0090000000-9e7db78f88f3bcea3676	2017-09-12	View Spectrum
MS/MS	LC-MS/MS Spectrum - DI-ESI-qTof , Positive	splash10-0fvj-0590000000-7aa92270f764672f14e0	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - DI-ESI-qTof , Negative	splash10-0fka-0590000000-9b048aa233ab295b38b6	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-qTof , Positive	splash10-0ftb-3960000000-589c4d2db0e1616f048e	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-0uxr-0290000000-14118223ff7a3a92da15	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-014i-0090000000-641b16fcdf1e38d31ff3	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-0udi-0090000000-b0f1307bbe6403a8d785	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-0fl1-0970000000-c5c59bf872295bb5bd11	2017-09-14	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-0090000000-4e62264d96d83f1006b4	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-014i-0090000000-594ebd436c98639ce817	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000i-4960000000-5532b99421a0a70d5ff2	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0090000000-620f35334e7fd7404576	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-014i-0090000000-263722926d00078660ba	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00kr-4970000000-6aab7e0d78fd4ac98c77	2015-05-27	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

ChEMBL ID

KEGG Compound ID

Pubchem Compound ID

Pubchem Substance ID

Not Available

ChEBI ID

18088

Phenol-Explorer ID

395

DrugBank ID

Not Available

HMDB ID

HMDB05808

CRC / DFC (Dictionary of Food Compounds) ID

HFF84-G:HFF84-G

EAFUS ID

Not Available

Dr. Duke ID

FORMONONETIN

BIGG ID

Not Available

KNApSAcK ID

C00002525

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

Formononetin

Phenol-Explorer Metabolite ID

395

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
abortifacient	50691	A chemical substance that interrupts pregnancy after implantation.	DUKE
anti cephalagic	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti feedant			DUKE
anti ulcer	49201	One of various classes of drugs with different action mechanisms used to treat or ameliorate peptic ulcer or irritation of the gastrointestinal tract.	DUKE
cancer preventive	35610	A substance that inhibits or prevents the proliferation of neoplasms.	DUKE
estrogenic			DUKE
fungicide	24127	A substance used to destroy fungal pests.	DUKE
herbicide	24527	A substance used to destroy plant pests.	DUKE
hypocholesterolemic			DUKE
hypolipidemic			DUKE
myorelaxant			DUKE
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
topoisomerase-I inhibitor	50276	A topoisomerase inhibitor that inhibits the bacterial enzymes of the DNA topoisomerases, Type I class (EC 5.99.1.2) that catalyze ATP-independent breakage of one of the two strands of DNA, passage of the unbroken strand through the break, and rejoining of the broken strand. These bacterial enzymes reduce the topological stress in the DNA structure by relaxing negatively, but not positively, supercoiled DNA.	DUKE
VAM stimulant			DUKE

Enzymes

Not Available

Pathways

Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Not Available

Files

MSDS

show

References

Synthesis Reference

Not Available

General Reference

Not Available

Content Reference

— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.
— Rothwell JA, Pérez-Jiménez J, Neveu V, Medina-Ramon A, M'Hiri N, Garcia Lobato P, Manach C, Knox K, Eisner R, Wishart D, Scalbert A. (2013) Phenol-Explorer 3.0: a major update of the Phenol-Explorer database to incorporate data on the effects of food processing on polyphenol content. Database, 10.1093/database/bat070.

Formononetin (FDB012219)

Structure for FDB012219 (Formononetin)