Milk Composition Database: Showing metabocard for Daidzein (BMDB0003312)

Identification Taxonomy Physical properties Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-09-30 23:03:30 UTC

Update Date

2020-06-04 20:48:12 UTC

MCDB ID

BMDB0003312

Secondary Accession Numbers

BMDB03312

Metabolite Identification

Common Name

Daidzein

Description

Daidzein, also known as daidzeol or isoaurostatin, 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. Thus, daidzein is considered to be a flavonoid lipid molecule. Daidzein exists as a solid, very hydrophobic, practically insoluble (in water), and relatively neutral molecule. Daidzein is a potentially toxic compound.

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Value	Source
4',7-Dihydroxyisoflavone	ChEBI
7,4'-Dihydroxyisoflavone	ChEBI
7-Hydroxy-3-(4-hydroxyphenyl)-4-benzopyrone	ChEBI
7-Hydroxy-3-(4-hydroxyphenyl)-4H-1-benzopyran-4-one	ChEBI
Daidzeol	ChEBI
Isoaurostatin	ChEBI
Diadzein	MeSH
4',7-Dihydroxy-isoflavone	HMDB

Chemical Formula

C₁₅H₁₀O₄

Average Molecular Weight

254.241

Monoisotopic Molecular Weight

254.057908802

IUPAC Name

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

Traditional Name

daidzein

CAS Registry Number

486-66-8

SMILES

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

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

Chemical Taxonomy

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 )

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	323 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
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	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-001j-1928000000-f956e5fd0e616ef96161	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (2 TMS)	splash10-000t-1619000000-eb2f87cd7d535b4d0446	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-001j-1928000000-f956e5fd0e616ef96161	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-000t-1619000000-eb2f87cd7d535b4d0446	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-001j-1927000000-87f11afa0cde5b353147	2017-09-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-004i-1390000000-0ff8f0de4d2d339f9357	2017-07-27	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-00gi-4229000000-71c73470904ad7b680ee	2017-10-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-0udi-0090000000-20d2c8ade6aac1f46e8a	2012-07-25	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-0udi-0970000000-a2349152106bd9da1257	2012-07-25	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-0006-9100000000-691c394958fd19d47510	2012-07-25	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-APPI-QQ (API2000) , Positive	splash10-0f7x-4900000000-5acb56232432597c00e5	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-APPI-QQ (API2000) , Positive	splash10-0pej-1930000000-89bedfb39603a12f3c75	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-APPI-QQ (API2000) , Positive	splash10-0a4i-0490000000-c633d3449d8bb0206fc2	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-APPI-QQ (API2000) , Positive	splash10-0a4i-0190000000-3a5de741e814e47d5cbe	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-APPI-QQ (API2000) , Positive	splash10-0a4i-0090000000-fb84819005f7f65b4fc8	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-APPI-QQ (API2000) , Positive	splash10-0a4i-0090000000-b3ae695d217c756a5f8f	2012-08-31	View Spectrum
LC-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
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative	splash10-0udi-0190000000-a9b6c8c416cb482a5dc1	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative	splash10-0089-1970000000-f6070acf0fd663c4ae6f	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive	splash10-0uem-1900000000-fa199caebb806e9eb0f9	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive	splash10-0a4i-0490000000-3defe1cbaf29e0cd2d1f	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive	splash10-0a4i-1790000000-2502633932fc66220039	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative	splash10-0udi-0290000000-56b4c039a64ab57d3e70	2012-08-31	View Spectrum
LC-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 LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-0090000000-7dcbed418d38de120895	2015-04-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-0090000000-c522d590074eabe8c4c4	2015-04-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-002r-6950000000-7b85969731514bf2d0bc	2015-04-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0090000000-388d21c85a84d4e0988a	2015-04-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0udi-0090000000-cc8371583b5ba50a4f0d	2015-04-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0gbi-3950000000-cb120c48a579b9363f74	2015-04-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-0090000000-7dcbed418d38de120895	2015-05-26	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-0090000000-c522d590074eabe8c4c4	2015-05-26	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, 100%_DMSO, experimental)	Not Available	2012-12-05	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, DMSO, experimental)	Not Available	2021-10-10	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, 100%_DMSO, experimental)	Not Available	2012-12-05	View Spectrum

Concentrations

Status	Value	Reference	Details
Detected and Quantified	0.000393 - 0.00787 uM	PMID: 12811748	details
Detected and Quantified	7.2 uM	PMID: 18565930	details
Detected and Quantified	30 uM	PMID: 18565930	details
Detected and Quantified	2.64 uM	PMID: 18565930	details
Detected and Quantified	0.905 uM	PMID: 18565930	details
Detected and Quantified	0.00118 - 0.0224 uM	PMID: 19679050	details

External Links

HMDB ID

HMDB0003312

DrugBank ID

DB13182

Phenol Explorer Compound ID

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Daidzein

METLIN ID

Not Available

PubChem Compound

5281708

PDB ID

Not Available

ChEBI ID

28197

References

Synthesis Reference

Baker, Wilson; Robinson, Robert; Simpson, N. M. Synthetical experiments in the isoflavone group. VII. Synthesis of daidzein. Journal of the Chemical Society (1933), 274-5.

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Antignac JP, Cariou R, Le Bizec B, Cravedi JP, Andre F: Identification of phytoestrogens in bovine milk using liquid chromatography/electrospray tandem mass spectrometry. Rapid Commun Mass Spectrom. 2003;17(12):1256-64. doi: 10.1002/rcm.1052. [PubMed:12811748 ]
Steinshamn H, Purup S, Thuen E, Hansen-Moller J: Effects of clover-grass silages and concentrate supplementation on the content of phytoestrogens in dairy cow milk. J Dairy Sci. 2008 Jul;91(7):2715-25. doi: 10.3168/jds.2007-0857. [PubMed:18565930 ]
Nielsen TS, Norgaard JV, Purup S, Frette XC, Bonefeld-Jorgensen EC: Estrogenic activity of bovine milk high or low in equol using immature mouse uterotrophic responses and an estrogen receptor transactivation assay. Cancer Epidemiol. 2009 Jul;33(1):61-8. doi: 10.1016/j.canep.2009.04.003. Epub 2009 May 31. [PubMed:19679050 ]

Showing metabocard for Daidzein (BMDB0003312)

Structure for BMDB0003312 (Daidzein)