AFCDB: Daidzein (FDB002608)

Record Information

Version

1.0

Creation date

2010-04-08 22:05:27 UTC

Update date

2019-11-26 02:57:41 UTC

Primary ID

FDB002608

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Daidzein

Description

Widespread isoflavone in the Leguminosae, especies Phaseolus subspecies (broad beans, lima beans); also found in soy and soy products (tofu, miso), chick peas (Cicer arietinum) and peanuts (Arachis hypogaea). Nutriceutical with anticancer and bone protective props. Daidzein is one of several known isoflavones. Isoflavones compounds are found in a number of plants, but soybeans and soy products like tofu and textured vegetable protein are the primary food source. Up until recently, daidzein was considered to be one of the most important and most studied isoflavones, however more recently attention has shifted to isoflavone metabolites. Equol represents the main active product of daidzein metabolism, produced via specific microflora in the gut. The clinical effectiveness of soy isoflavones may be a function of the ability to biotransform soy isoflavones to the more potent estrogenic metabolite, equol, which may enhance the actions of soy isoflavones, owing to its greater affinity for estrogen receptors, unique antiandrogenic properties, and superior antioxidant activity. However, not all individuals consuming daidzein produce equol. Only approximately one-third to one-half of the population is able to metabolize daidzein to equol. This high variability in equol production is presumably attributable to interindividual differences in the composition of the intestinal microflora, which may play an important role in the mechanisms of action of isoflavones. But, the specific bacterial species in the colon involved in the production of equol are yet to be discovered. (PMID: 18045128, 17579894, Curr Med Chem. 2007;14(26):2824-30., Mol Nutr Food Res. 2007 Jul;51(7):765-81.) Daidzein is a biomarker for the consumption of soy beans and other soy products. .

CAS Number

486-66-8

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	0.085 g/L	ALOGPS
logP	3.3	ALOGPS
logP	2.73	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Acidic)	6.48	ChemAxon
pKa (Strongest Basic)	-5.3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	66.76 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	69.7 m³·mol⁻¹	ChemAxon
Polarizability	25.75 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

C15H10O4

IUPAC name

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

InChI Identifier

InChI=1S/C15H10O4/c16-10-3-1-9(2-4-10)13-8-19-14-7-11(17)5-6-12(14)15(13)18/h1-8,16-17H

InChI Key

ZQSIJRDFPHDXIC-UHFFFAOYSA-N

Isomeric SMILES

OC1=CC=C(C=C1)C1=COC2=C(C=CC(O)=C2)C1=O

Average Molecular Weight

254.241

Monoisotopic Molecular Weight

254.057908802

Classification

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

Isoflavone
Hydroxyisoflavonoid
Chromone
Benzopyran
1-benzopyran
Pyranone
Phenol
1-hydroxy-2-unsubstituted benzenoid
Benzenoid
Monocyclic benzene moiety
Pyran
Heteroaromatic compound
Oxacycle
Organoheterocyclic compound
Organooxygen compound
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

7-hydroxyisoflavones (CHEBI:28197 )
isoflavones (C10208 )
Isoflavonoids (C10208 )
Isoflavonoids (LMPK12050038 )
an isoflavone (DAIDZEIN )
a 4'-hydroxyisoflavone (DAIDZEIN )

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Food

Biological:

Animal

Plant:

Biological location:

Subcellular:

Biofluid and excreta:

Role

Industrial application:

Pharmaceutical industry:

Pharmaceutical

Antineoplastic agent:

Antitumor

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 70.86%; H 3.96%; O 25.17%	DFC
Melting Point	Mp 330° (323°)	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	[neutral] lmax 252 (e 25400) (MeOH) (Derep)	DFC
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
GC-MS	Daidzein, non-derivatized, GC-MS Spectrum	splash10-001j-1928000000-f956e5fd0e616ef96161	Spectrum
GC-MS	Daidzein, 2 TMS, GC-MS Spectrum	splash10-000t-1619000000-eb2f87cd7d535b4d0446	Spectrum
GC-MS	Daidzein, non-derivatized, GC-MS Spectrum	splash10-001j-1928000000-f956e5fd0e616ef96161	Spectrum
GC-MS	Daidzein, non-derivatized, GC-MS Spectrum	splash10-000t-1619000000-eb2f87cd7d535b4d0446	Spectrum
GC-MS	Daidzein, non-derivatized, GC-MS Spectrum	splash10-001j-1927000000-87f11afa0cde5b353147	Spectrum
Predicted GC-MS	Daidzein, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-004i-1390000000-0ff8f0de4d2d339f9357	Spectrum
Predicted GC-MS	Daidzein, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-00gi-4229000000-71c73470904ad7b680ee	Spectrum
Predicted GC-MS	Daidzein, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-0udi-0090000000-20d2c8ade6aac1f46e8a	2012-07-25	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-0udi-0970000000-a2349152106bd9da1257	2012-07-25	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-0006-9100000000-691c394958fd19d47510	2012-07-25	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-APPI-QQ (API2000) , Positive	splash10-0f7x-4900000000-5acb56232432597c00e5	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-APPI-QQ (API2000) , Positive	splash10-0pej-1930000000-89bedfb39603a12f3c75	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-APPI-QQ (API2000) , Positive	splash10-0a4i-0490000000-c633d3449d8bb0206fc2	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-APPI-QQ (API2000) , Positive	splash10-0a4i-0190000000-3a5de741e814e47d5cbe	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-APPI-QQ (API2000) , Positive	splash10-0a4i-0090000000-fb84819005f7f65b4fc8	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-APPI-QQ (API2000) , Positive	splash10-0a4i-0090000000-b3ae695d217c756a5f8f	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 5V, Positive	splash10-0a4i-0090000000-d25bba2f5a1ac12e3d86	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative	splash10-0udi-0190000000-a9b6c8c416cb482a5dc1	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative	splash10-0089-1970000000-f6070acf0fd663c4ae6f	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive	splash10-0uem-1900000000-fa199caebb806e9eb0f9	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive	splash10-0a4i-0490000000-3defe1cbaf29e0cd2d1f	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive	splash10-0a4i-1790000000-2502633932fc66220039	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative	splash10-0udi-0290000000-56b4c039a64ab57d3e70	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Negative	splash10-0089-2970000000-f32e85ba94cb6621d4f1	2012-08-31	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-0090000000-7dcbed418d38de120895	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-0090000000-c522d590074eabe8c4c4	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-002r-6950000000-7b85969731514bf2d0bc	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0090000000-388d21c85a84d4e0988a	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0udi-0090000000-cc8371583b5ba50a4f0d	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0gbi-3950000000-cb120c48a579b9363f74	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-0090000000-7dcbed418d38de120895	2015-05-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-0090000000-c522d590074eabe8c4c4	2015-05-26	View Spectrum

NMR

Type	Description	View
1D NMR	¹H NMR Spectrum (1D, 600 MHz, 100%_DMSO, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, DMSO, experimental)	Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, 100%_DMSO, experimental)	Spectrum

External Links

ChemSpider ID

ChEMBL ID

KEGG Compound ID

Pubchem Compound ID

Pubchem Substance ID

Not Available

ChEBI ID

28197

Phenol-Explorer ID

394

DrugBank ID

Not Available

HMDB ID

HMDB03312

CRC / DFC (Dictionary of Food Compounds) ID

CMR01-H:CMR01-H

EAFUS ID

Not Available

Dr. Duke ID

TATOIN|DAIDZEIN

BIGG ID

Not Available

KNApSAcK ID

C00009380

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

Daidzein

Phenol-Explorer Metabolite ID

394

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
anti alcoholic	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti arrhythmic	38070	A drug used for the treatment or prevention of cardiac arrhythmias. Anti-arrhythmia drugs may affect the polarisation-repolarisation phase of the action potential, its excitability or refractoriness, or impulse conduction or membrane responsiveness within cardiac fibres.	DUKE
anti cancer	35610	A substance that inhibits or prevents the proliferation of neoplasms.	DUKE
anti cephalagic	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti dipsomanic			DUKE
anti estrogenic	35222	A substance that diminishes the rate of a chemical reaction.	DUKE
anti hemolytic	50248	Drug that acts on blood and blood-forming organs and those that affect the hemostatic system.	DUKE
anti inflammatory	35472	A substance that reduces or suppresses inflammation.	DUKE
anti leukemic	35610	A substance that inhibits or prevents the proliferation of neoplasms.	DUKE
anti melanomic	35610	A substance that inhibits or prevents the proliferation of neoplasms.	DUKE
anti microbial	33281	A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.	DUKE
anti mutagenic			DUKE
anti osteoporotic	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
antioxidant	22586	A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides. In European countries, E-numbers for permitted antioxidant food additives are from E 300 to E 324.	DUKE
anti proliferative			DUKE
anti radicular			DUKE
anti spasmodic	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
antitumor promoter	35610	A substance that inhibits or prevents the proliferation of neoplasms.	DUKE
anti viral	22587	A substance that destroys or inhibits replication of viruses.	DUKE
aromatase inhibitor	50790	An EC 1.14.14.* (oxidoreductase acting on paired donors, incorporating of 1 atom of oxygen, with reduced flavin or flavoprotein as one donor) inhibitor which interferes with the action of aromatase (EC 1.14.14.14) and so reduces production of estrogenic steroid hormones.	DUKE
cancer preventive	35610	A substance that inhibits or prevents the proliferation of neoplasms.	DUKE
coronarydilator			DUKE
estrogen agonist	63951	An agonist at the estrogen receptor.	DUKE
estrogenic			DUKE
fungicide	24127	A substance used to destroy fungal pests.	DUKE
hypotensive			DUKE
lipase inhibitor	23924	A compound or agent that combines with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction.	DUKE
quinone-reductase inducer			DUKE
topoisomerase-II inhibitor	50750	A topoisomerase inhibitor that inhibits DNA topoisomerase (ATP-hydrolysing), EC 5.99.1.3 (topoisomerase II), which catalyses ATP-dependent breakage of both strands of DNA, passage of the unbroken strands through the breaks, and rejoining of the broken strands.	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
utero trophic	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
VEGF inhibitor	35222	A substance that diminishes the rate of a chemical reaction.	DUKE

Enzymes

Not Available

Pathways

Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Flavor	Citations
bitter	Ayana Wiener, Marina Shudler, Anat Levit, Masha Y. Niv. BitterDB: a database of bitter compounds. Nucleic Acids Res 2012, 40(Database issue):D413-419. DOI:10.1093/nar/gkr755

Files

MSDS

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References

Synthesis Reference

Not Available

General Reference

Not Available

Content Reference

— 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.
— U.S. Department of Agriculture, Agricultural Research Service. 2008. USDA National Nutrient Database for Standard Reference, Release 21. Nutrient Data Laboratory Home Page.
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.
— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).

Daidzein (FDB002608)

Structure for FDB002608 (Daidzein)