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Details

Stereochemistry ACHIRAL
Molecular Formula C15H10O4
Molecular Weight 254.2375
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of DAIDZEIN

SMILES

OC1=CC=C(C=C1)C2=COC3=C(C=CC(O)=C3)C2=O

InChI

InChIKey=ZQSIJRDFPHDXIC-UHFFFAOYSA-N
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

HIDE SMILES / InChI
Molecular Formula C15H10O4
Molecular Weight 254.2375
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

Daidzein, an isoflavonoid phytoestrogenic compound found in soybeans, possesses various biological properties. It may induce apoptosis of choriocarcinoma cells in a dose-dependent manner via the mitochondrial apoptotic pathway, in addition, it promotes proliferation and differentiation in osteoblastic OCT1 cells via activation of the BMP-2/Smads pathway. Daidzein exerts neuroprotective effects through the novel extranuclear GPR30 and the classical transcriptionally acting ERβ.

Approval Year

Unknown
149124
Targets

Targets

Primary TargetPharmacologyConditionPotency
G-protein coupled estrogen receptor 1
3
Target ID: Q99527|||Q99981
Gene ID: 2852.0
Gene Symbol: GPER1
Target Organism: Homo sapiens (Human)
Agonist
2752
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
0.31 μM
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/12540402/
0.4 mg/kg bw single, oral
dose: 0.4 mg/kg bw
route of administration: Oral
experiment type: SINGLE
co-administered:
DAIDZEIN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE
food status: FASTED
0.71 μM
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/12540402/
0.8 mg/kg bw single, oral
dose: 0.8 mg/kg bw
route of administration: Oral
experiment type: SINGLE
co-administered:
DAIDZEIN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE
food status: FASTED
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
3.96 μM × h
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/12540402/
0.4 mg/kg bw single, oral
dose: 0.4 mg/kg bw
route of administration: Oral
experiment type: SINGLE
co-administered:
DAIDZEIN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE
food status: FASTED
3.96 μM × h
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/12540402/
0.8 mg/kg bw single, oral
dose: 0.8 mg/kg bw
route of administration: Oral
experiment type: SINGLE
co-administered:
DAIDZEIN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE
food status: FASTED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
8.17 h
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/12540402/
0.4 mg/kg bw single, oral
dose: 0.4 mg/kg bw
route of administration: Oral
experiment type: SINGLE
co-administered:
DAIDZEIN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE
food status: FASTED
8.7 h
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/12540402/
0.8 mg/kg bw single, oral
dose: 0.8 mg/kg bw
route of administration: Oral
experiment type: SINGLE
co-administered:
DAIDZEIN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE
food status: FASTED
PubMed

PubMed

TitleDatePubMed
Regulation of an ERG K+ current by Src tyrosine kinase.
2002-04-19
Dietary soy isoflavones and bone mineral density: results from the study of women's health across the nation.
2002-04-15
Down-regulation of osteoclast differentiation by daidzein via caspase 3.
2002-04
Detection of phytoestrogens in samples of second trimester human amniotic fluid.
2002-03-28
Structure-activity relationships for inhibition of human 5alpha-reductases by polyphenols.
2002-03-15
Isoflavone aglycon and glucoconjugate content of high- and low-soy U.K. foods used in nutritional studies.
2002-03-13
Estrogenic isoflavones in rodent diets.
2002-03-10
Relationships of urinary phyto-oestrogen excretion to BMD in postmenopausal women.
2002-03
Overnight urinary isoflavone excretion in a population of women living in the United States, and its relationship to isoflavone intake.
2002-03
Usual dietary isoflavone intake, bone mineral density, and bone metabolism in postmenopausal women.
2002-02-28
Tyrosine kinases act directly on the alpha1 subunit to modulate Ca(v)2.2 calcium channels.
2002-02-01
Transplacental transfer of the phytoestrogen daidzein in DA/Han rats.
2002-02
Oestrogenic activity of the hop phyto-oestrogen, 8-prenylnaringenin.
2002-02
Effects of naturally occurring isoflavones on prostaglandin E2 production.
2002-02
Identification and concentration of soy isoflavones in commercial cat foods.
2002-02
Lysophosphatidylcholine potentiates vascular contractile responses in rat aorta via activation of tyrosine kinase.
2002-02
Daidzein: bioavailability, potential for reproductive toxicity, and breast cancer chemoprevention in female rats.
2002-02
The correlation between dietary soy phytoestrogens and neuropathic pain behavior in rats after partial denervation.
2002-02
Monitoring of MRP-like activity in human erythrocytes: inhibitory effect of isoflavones.
2002-01-11
Determination of isoflavones in soy and selected foods containing soy by extraction, saponification, and liquid chromatography: collaborative study.
2002-01-05
Inhibitory effect of isoflavones on peroxynitrite-mediated low-density lipoprotein oxidation.
2002-01
Phytoestrogens and thyroid cancer risk: the San Francisco Bay Area thyroid cancer study.
2002-01
Mammographic breast density as a biomarker of effects of isoflavones on the female breast.
2002
Anticarcinogenic effects of isoflavones may be mediated by genistein in mouse mammary tumor virus-induced breast cancer.
2002
The effect of dietary soy daidzein on pig growth and viral replication during a viral challenge.
2001-12
Effects of phytoestrogens on DNA synthesis and creatine kinase activity in vascular cells.
2001-12
Elicitor-induced association of isoflavone O-methyltransferase with endomembranes prevents the formation and 7-O-methylation of daidzein during isoflavonoid phytoalexin biosynthesis.
2001-12
Partial purification and characterization of a soybean beta-glucosidase with high specific activity towards isoflavone conjugates.
2001-12
Dietary soy phytoestrogen effects on brain structure and aromatase in Long-Evans rats.
2001-11-16
Dependence of delta1-opioid receptor-induced cardioprotection on a tyrosine kinase-dependent but not a Src-dependent pathway.
2001-11
Determination of BRCA2 oncosuppressor protein expression in human mammary cells by affinity perfusion high-performance chromatography.
2001-10-30
Effect of soy isoflavone supplementation on markers of oxidative stress in men and women.
2001-10-22
Dietary soy isoflavone intake in older Japanese American women.
2001-10
The presence of three isoflavonoid compounds in Psoralea corylifolia.
2001-10
Regulation of phenobarbital-mediated induction of CYP102 (cytochrome P450(BM-3)) in Bacillus megaterium by phytochemicals from soy and green tea.
2001-10
Neuronal apoptosis resulting from high doses of the isoflavone genistein: role for calcium and p42/44 mitogen-activated protein kinase.
2001-10
Synthesis of potential antidipsotropic isoflavones: inhibitors of the mitochondrial monoamine oxidase-aldehyde dehydrogenase pathway.
2001-09-27
Assaying the estrogenicity of phytoestrogens in cells of different estrogen sensitive tissues.
2001-09-22
Separation and purification of isoflavones from a crude soybean extract by high-speed counter-current chromatography.
2001-09-14
Contractile effects of angiotensin peptides in rat aorta are differentially dependent on tyrosine kinase activity.
2001-09
Chemoprevention of DMBA-induced mammary cancer in rats by dietary soy.
2001-09
Effects of phytoestrogens on acetylcholine- and isoprenaline-induced vasodilation in rat aorta.
2001-09
Isoflavonoid compounds from red clover (Trifolium pratense) protect from inflammation and immune suppression induced by UV radiation.
2001-09
Transdermal absorption of phytoestrogens.
2001-09
Effects of soy phytoestrogens genistein and daidzein on breast cancer growth.
2001-09
Soya intake and plasma concentrations of daidzein and genistein: validity of dietary assessment among eighty British women (Oxford arm of the European Prospective Investigation into Cancer and Nutrition).
2001-09
Genistein, a soybean isoflavone, inhibits inward rectifier K(+) channels in rat osteoclasts.
2001-08
Manipulation of prenatal hormones and dietary phytoestrogens during adulthood alter the sexually dimorphic expression of visual spatial memory.
2001
Visual spatial memory is enhanced in female rats (but inhibited in males) by dietary soy phytoestrogens.
2001
Pilot study of a specific dietary supplement in tumor-bearing mice and in stage IIIB and IV non-small cell lung cancer patients.
2001
Patents

Patents

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JP2008222622A
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JP2009507547A
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JP2010104241A
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JP2010187647A
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JP2010515695A
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JP2011506455A
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JP2011512798A
9
JP2013538187A
2

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Unknown
In Vitro Use Guide
In the presence of either 1 μM of daidzein or equol, the number of cells in S-phase, which was determined by detecting bromodeoxyuridine incorporated into replicated DNA, almost doubled. The total amounts of MCM7 protein and chromatin-bound MCM7 protein increased in the presence of daidzein. The data suggest that phytoestrogens facilitate cell cycle progression in G1-phase by increasing the level of MCM proteins.
Substance Class Chemical
Created
by admin
on Mon Mar 31 18:11:53 GMT 2025
Edited
by admin
on Mon Mar 31 18:11:53 GMT 2025
Record UNII
6287WC5J2L
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
DAIDZEIN
INCI   MART.   MI   USP-RS   WHO-DD  
INCI  
Official Name English
4',7-DIHYDROXYISOFLAVONE
Preferred Name English
DAIDZEIN (CONSTITUENT OF SOY ISOFLAVONES) [DSC]
Common Name English
DAIDZEIN [MI]
Common Name English
Daidzein [WHO-DD]
Common Name English
DAIDZEIN (CONSTITUENT OF RED CLOVER) [DSC]
Common Name English
7-HYDROXY-3-(4-HYDROXYPHENYL)-4H-1-BENZOPYRAN-4-ONE
Systematic Name English
DAIDZEIN [MART.]
Common Name English
DAIDZEIN (CONSTITUENT OF ASTRAGALUS) [DSC]
Common Name English
DAIDZEIN [USP-RS]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C599
Created by admin on Mon Mar 31 18:11:53 GMT 2025 , Edited by admin on Mon Mar 31 18:11:53 GMT 2025
DSLD 2780 (Number of products:39)
Created by admin on Mon Mar 31 18:11:53 GMT 2025 , Edited by admin on Mon Mar 31 18:11:53 GMT 2025
NCI_THESAURUS C1967
Created by admin on Mon Mar 31 18:11:53 GMT 2025 , Edited by admin on Mon Mar 31 18:11:53 GMT 2025
Code System Code Type Description
PUBCHEM
5281708
Created by admin on Mon Mar 31 18:11:53 GMT 2025 , Edited by admin on Mon Mar 31 18:11:53 GMT 2025
PRIMARY
EPA CompTox
DTXSID9022310
Created by admin on Mon Mar 31 18:11:53 GMT 2025 , Edited by admin on Mon Mar 31 18:11:53 GMT 2025
PRIMARY
FDA UNII
6287WC5J2L
Created by admin on Mon Mar 31 18:11:53 GMT 2025 , Edited by admin on Mon Mar 31 18:11:53 GMT 2025
PRIMARY
MESH
C004742
Created by admin on Mon Mar 31 18:11:53 GMT 2025 , Edited by admin on Mon Mar 31 18:11:53 GMT 2025
PRIMARY
DRUG BANK
DB13182
Created by admin on Mon Mar 31 18:11:53 GMT 2025 , Edited by admin on Mon Mar 31 18:11:53 GMT 2025
PRIMARY
RS_ITEM_NUM
1162421
Created by admin on Mon Mar 31 18:11:53 GMT 2025 , Edited by admin on Mon Mar 31 18:11:53 GMT 2025
PRIMARY
NCI_THESAURUS
C1060
Created by admin on Mon Mar 31 18:11:53 GMT 2025 , Edited by admin on Mon Mar 31 18:11:53 GMT 2025
PRIMARY
SMS_ID
100000079515
Created by admin on Mon Mar 31 18:11:53 GMT 2025 , Edited by admin on Mon Mar 31 18:11:53 GMT 2025
PRIMARY
CAS
486-66-8
Created by admin on Mon Mar 31 18:11:53 GMT 2025 , Edited by admin on Mon Mar 31 18:11:53 GMT 2025
PRIMARY
EVMPD
SUB13529MIG
Created by admin on Mon Mar 31 18:11:53 GMT 2025 , Edited by admin on Mon Mar 31 18:11:53 GMT 2025
PRIMARY
CHEBI
77764
Created by admin on Mon Mar 31 18:11:53 GMT 2025 , Edited by admin on Mon Mar 31 18:11:53 GMT 2025
PRIMARY
MERCK INDEX
m4068
Created by admin on Mon Mar 31 18:11:53 GMT 2025 , Edited by admin on Mon Mar 31 18:11:53 GMT 2025
PRIMARY Merck Index
ECHA (EC/EINECS)
207-635-4
Created by admin on Mon Mar 31 18:11:53 GMT 2025 , Edited by admin on Mon Mar 31 18:11:53 GMT 2025
PRIMARY
WIKIPEDIA
DAIDZEIN
Created by admin on Mon Mar 31 18:11:53 GMT 2025 , Edited by admin on Mon Mar 31 18:11:53 GMT 2025
PRIMARY
CHEBI
28197
Created by admin on Mon Mar 31 18:11:53 GMT 2025 , Edited by admin on Mon Mar 31 18:11:53 GMT 2025
PRIMARY
Related Record Type Details
TRIFOLIUM PRATENSE FLOWER
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PARENT -> CONSTITUENT ALWAYS PRESENT
Related Record Type Details
Structure of EQUOL
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Produced by intestinal microbiota. Similar activity as estrodiol
NIH
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