Showing Compound 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
4'-O-Methyldaidzein	ChEBI
7-Hydroxy-3-(4-methoxyphenyl)-4-benzopyrone	ChEBI
7-Hydroxy-3-(4-methoxyphenyl)-4H-benzopyran-4-one	ChEBI
7-Hydroxy-3-(4-methoxyphenyl)-4H-chromen-4-one	ChEBI
7-Hydroxy-4'-methoxyisoflavone	ChEBI
Biochanin b	ChEBI
Formononetol	ChEBI
Formononetin, 4-(14)C-labeled	MeSH
7-Hydroxy-3-(4-methoxyphenyl)-4H-benzopyran-4-one(9ci)	HMDB
7-Hydroxy-4'-methoxy-isoflavone	HMDB
7-Hydroxy-4'-methoxy-isoflavone (8ci)	HMDB
4H-1-Benzopyran-4-one, 7-hydroxy-3-(4-methoxyphenyl)-	biospider
7-Hydroxy-3-(4-methoxyphenyl)-4H-1-benzopyran-4-one, 9CI	db_source
7-hydroxy-3-(4-methoxyphenyl)-4H-benzopyran-4-one	biospider
7-hydroxy-3-(4-methoxyphenyl)-4H-chromen-4-one	biospider
7-Hydroxy-3-(4-methoxyphenyl)chromone	biospider
Biochanin B	db_source
Daidzein 4-methyl ether	biospider
Formononetin	db_source
Formoononetin	db_source
Neochanin	db_source
Pratol	db_source

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	An agent that induces abortion, disrupting pregnancy by blocking progesterone or causing uterine contractions. Therapeutically, it's used to terminate early pregnancies, manage ectopic pregnancies, or treat miscarriages. Key medical uses include medical abortion, pregnancy termination, and menstrual regulation.	DUKE
Anti cephalagic	52217	An agent that relieves headache symptoms, commonly used in managing migraines and other cephalalgias. Its biological role involves inhibiting pain pathways, and its therapeutic applications include reducing inflammation and alleviating vascular headaches, making it a key medical use in neurology and pain management.	DUKE
Anti feedant		A substance that inhibits normal feeding behavior, found in certain plants, deterring insects and animals from consuming them. Its therapeutic applications include pest control, while key medical uses involve managing insect-borne diseases and reducing crop damage.	DUKE
Anti ulcer	49201	An agent that reduces stomach acid and protects the mucous lining, preventing ulcer formation. It is used to treat conditions like gastroesophageal reflux disease (GERD), peptic ulcers, and Zollinger-Ellison syndrome, promoting healing and relieving symptoms.	DUKE
Cancer preventive	35610	An agent that inhibits the development and progression of cancer, reducing tumor formation and growth. It plays a biological role in blocking carcinogenic pathways, and has therapeutic applications in chemoprevention. Key medical uses include reducing the risk of cancer in high-risk individuals and preventing cancer recurrence.	DUKE
Estrogenic		An agent that mimics the effects of estrogen, regulating female reproductive processes and development. Therapeutically, estrogenic agents are used in hormone replacement therapy, contraception, and treating menopausal symptoms, as well as certain cases of osteoporosis and infertility.	DUKE
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
Herbicide	24527	A chemical agent that kills or inhibits plant growth, used in agriculture to control weeds and pests. It has no direct biological role or therapeutic applications in human medicine, but its development has led to the creation of related compounds with potential medical uses, such as anticancer agents.	DUKE
Hypocholesterolemic		An agent that lowers cholesterol levels in the blood, playing a crucial role in preventing cardiovascular disease. Therapeutically, it is used to manage hyperlipidemia and reduce the risk of heart disease, with key medical applications including the treatment of high cholesterol, atherosclerosis, and coronary artery disease.	DUKE
Hypolipidemic		An agent that lowers lipid levels, treating hyperlipidemias by reducing cholesterol and triglyceride production, with therapeutic applications in managing cardiovascular disease, atherosclerosis, and stroke, commonly used to prevent heart attacks and improve overall cardiovascular health.	DUKE
Myorelaxant		An agent that reduces muscle contractility by blocking nerve impulses or decreasing motor end plate excitability, used therapeutically to relieve muscle spasms, tension, and pain, commonly in managing musculoskeletal disorders, anxiety, and insomnia.	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
Topoisomerase-I inhibitor	50276	An agent that blocks the activity of topoisomerase I, an enzyme involved in DNA replication. It is used therapeutically in cancer treatment, particularly for solid tumors, by inducing DNA damage and inhibiting cancer cell growth, with key medical uses in colorectal, lung, and breast cancers.	DUKE
VAM stimulant		A agent that stimulates vasopressin, a hormone regulating water balance, increasing its release. Therapeutically, it treats central diabetes insipidus, nocturnal enuresis, and bleeding disorders by enhancing blood clotting, and is also used to manage postpartum hemorrhage and abdominal distension.	DUKE