Daidzein
(right click,save link as to download,it is a temp file,please download as soon as possible, you can also use CTRL+S to save the whole html page)
Basic Info
| Common Name | Daidzein(F05165) |
| 2D Structure | |
| Description | 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. (A3191, A3189). |
| FRCD ID | F05165 |
| CAS Number | 486-66-8 |
| PubChem CID | 5281708 |
| Formula | C15H10O4 |
| IUPAC Name | 7-hydroxy-3-(4-hydroxyphenyl)chromen-4-one |
| InChI Key | ZQSIJRDFPHDXIC-UHFFFAOYSA-N |
| InChI | 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 |
| Canonical SMILES | C1=CC(=CC=C1C2=COC3=C(C2=O)C=CC(=C3)O)O |
| Isomeric SMILES | C1=CC(=CC=C1C2=COC3=C(C2=O)C=CC(=C3)O)O |
| Synonyms |
daidzein
486-66-8
4',7-Dihydroxyisoflavone
Daidzeol
7,4'-Dihydroxyisoflavone
7-hydroxy-3-(4-hydroxyphenyl)-4H-chromen-4-one
Diadzein
7-Hydroxy-3-(4-hydroxyphenyl)-4H-1-benzopyran-4-one
4H-1-Benzopyran-4-one, 7-hydroxy-3-(4-hydroxyphenyl)-
7-hydroxy-3-(4-hydroxyphenyl)chromen-4-one
|
| Classifies |
Plant Toxin
|
| Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
| Kingdom | Organic compounds |
| Superclass | Phenylpropanoids and polyketides |
| Class | Isoflavonoids |
| Subclass | Isoflav-2-enes |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Isoflavones |
| Alternative Parents | |
| Molecular Framework | Aromatic heteropolycyclic compounds |
| 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 |
| Description | This compound 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. |
Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 254.241 |
| Hydrogen Bond Donor Count | 2 |
| Hydrogen Bond Acceptor Count | 4 |
| Rotatable Bond Count | 1 |
| Complexity | 382 |
| Monoisotopic Mass | 254.058 |
| Exact Mass | 254.058 |
| XLogP | 2.5 |
| Formal Charge | 0 |
| Heavy Atom Count | 19 |
| Defined Atom Stereocenter Count | 0 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| Isotope Atom Count | 0 |
| Covalently-Bonded Unit Count | 1 |
ADMET
| Model | Result | Probability |
|---|---|---|
| Absorption | ||
| Blood-Brain Barrier | BBB+ | 0.7448 |
| Human Intestinal Absorption | HIA+ | 0.9942 |
| Caco-2 Permeability | Caco2+ | 0.7270 |
| P-glycoprotein Substrate | Non-substrate | 0.5151 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.9040 |
| Non-inhibitor | 0.7657 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.8982 |
| Distribution | ||
| Subcellular localization | Mitochondria | 0.8516 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.7878 |
| CYP450 2D6 Substrate | Non-substrate | 0.9113 |
| CYP450 3A4 Substrate | Non-substrate | 0.6927 |
| CYP450 1A2 Inhibitor | Inhibitor | 0.9108 |
| CYP450 2C9 Inhibitor | Inhibitor | 0.9757 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.9199 |
| CYP450 2C19 Inhibitor | Inhibitor | 0.8994 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.6261 |
| CYP Inhibitory Promiscuity | High CYP Inhibitory Promiscuity | 0.6929 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.9556 |
| Non-inhibitor | 0.9065 | |
| AMES Toxicity | Non AMES toxic | 0.9211 |
| Carcinogens | Non-carcinogens | 0.9203 |
| Fish Toxicity | High FHMT | 0.9427 |
| Tetrahymena Pyriformis Toxicity | High TPT | 0.9881 |
| Honey Bee Toxicity | High HBT | 0.6719 |
| Biodegradation | Not ready biodegradable | 0.8811 |
| Acute Oral Toxicity | II | 0.5629 |
| Carcinogenicity (Three-class) | Non-required | 0.6163 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -3.2055 | LogS |
| Caco-2 Permeability | 1.1564 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 3.5363 | LD50, mol/kg |
| Fish Toxicity | 0.1688 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | 0.9241 | pIGC50, ug/L |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| Toxicity and non-harmful effects of the soya isoflavones, genistein and daidzein, in embryos of the zebrafish, Danio rerio. | Comp Biochem Physiol C Toxicol Pharmacol | 2018 Sep | 29870789 |
| PKCι is a target of 7,8,4'-trihydroxyisoflavone for the suppression ofUVB-induced MMP-1 expression. | Exp Dermatol | 2018 May | 28453925 |
| Isoflavones from green vegetable soya beans and their antimicrobial andantioxidant activities. | J Sci Food Agric | 2018 Mar | 28885710 |
| Isoflavones Production and Possible Mechanism of Their Exudation in <i>Genista tinctoria</i> L. Suspension Culture after Treatment with Vanadium Compounds. | Molecules | 2018 Jul 3 | 29970854 |
| Vertical Leaching of Allelochemicals Affecting Their Bioactivity and theMicrobial Community of Soil. | J Agric Food Chem | 2017 Sep 13 | 28800227 |
| Genistein Binding to Copper(II)-Solvent Dependence and Effects on RadicalScavenging. | Molecules | 2017 Oct 18 | 29057848 |
| Multiresidue determination of estrogens in different dairy products by ultra-high-performance liquid chromatography triple quadrupole mass spectrometry. | J Chromatogr A | 2017 May 5 | 28363417 |
| MIL-101(Cr) as matrix for sensitive detection of quercetin by matrix-assistedlaser desorption/ionization mass spectrometry. | Talanta | 2017 Mar 1 | 28107941 |
| Inhibitory mechanism of five natural flavonoids against murine norovirus. | Phytomedicine | 2017 Jul 1 | 28545670 |
| Safety evaluation of daidzein in laying hens: Effects on laying performance,hatchability, egg quality, clinical blood parameters, and organ development. | Poult Sci | 2017 Jul 1 | 28520935 |
| Phytoestrogens in milk: Overestimations caused by contamination of the hydrolytic enzyme used during sample extraction. | J Dairy Sci | 2016 Sep | 27394955 |
| Urine and serum biomonitoring of exposure to environmental estrogens II: Soy isoflavones and zearalenone in pregnant women. | Food Chem Toxicol | 2016 Sep | 27255803 |
| Anthropogenic pressure in a Portuguese river: Endocrine-disrupting compounds, trace elements and nutrients. | J Environ Sci Health A Tox Hazard Subst Environ Eng | 2016 Oct 14 | 27411033 |
| Bovine and soybean milk bioactive compounds: Effects on inflammatory response of human intestinal Caco-2 cells. | Food Chem | 2016 Nov 1 | 27211648 |
| NMR Study on the Inclusion Complexes of β-Cyclodextrin with Isoflavones. | Molecules | 2016 Mar 28 | 27043500 |
| Equol inhibits growth, induces atresia, and inhibits steroidogenesis of mouseantral follicles in vitro. | Toxicol Appl Pharmacol | 2016 Mar 15 | 26876617 |
| Kanamycin inhibits daidzein metabolism and abilities of the metabolites toprevent bone loss in ovariectomized mice. | BMC Res Notes | 2016 Jul 7 | 27388904 |
| Impact of equol-producing capacity and soy-isoflavone profiles of supplements on bone calcium retention in postmenopausal women: a randomized crossover trial. | Am J Clin Nutr | 2015 Sep | 26245807 |
| Latifolicinin A from a Fermented Soymilk Product and the Structure-Activity Relationship of Synthetic Analogues as Inhibitors of Breast Cancer Cell Growth. | J Agric Food Chem | 2015 Nov 11 | 26499209 |
| Isoflavones in food supplements: chemical profile, label accordance andpermeability study in Caco-2 cells. | Food Funct | 2015 Mar | 25653232 |
Targets
- General Function:
- Zinc ion binding
- Specific Function:
- Nuclear hormone receptor. Binds estrogens with an affinity similar to that of ESR1, and activates expression of reporter genes containing estrogen response elements (ERE) in an estrogen-dependent manner (PubMed:20074560). Isoform beta-cx lacks ligand binding ability and has no or only very low ere binding activity resulting in the loss of ligand-dependent transactivation ability. DNA-binding by ESR1 and ESR2 is rapidly lost at 37 degrees Celsius in the absence of ligand while in the presence of 17 beta-estradiol and 4-hydroxy-tamoxifen loss in DNA-binding at elevated temperature is more gradual.
- Gene Name:
- ESR2
- Uniprot ID:
- Q92731
- Molecular Weight:
- 59215.765 Da
References
- Matsuda H, Shimoda H, Morikawa T, Yoshikawa M: Phytoestrogens from the roots of Polygonum cuspidatum (Polygonaceae): structure-requirement of hydroxyanthraquinones for estrogenic activity. Bioorg Med Chem Lett. 2001 Jul 23;11(14):1839-42. [11459643 ]
- General Function:
- Electron carrier activity
- Gene Name:
- ALDH2
- Uniprot ID:
- P05091
- Molecular Weight:
- 56380.93 Da
References
- Rooke N, Li DJ, Li J, Keung WM: The mitochondrial monoamine oxidase-aldehyde dehydrogenase pathway: a potential site of action of daidzin. J Med Chem. 2000 Nov 2;43(22):4169-79. [11063613 ]
- General Function:
- Oxygen binding
- Specific Function:
- Catalyzes the formation of aromatic C18 estrogens from C19 androgens.
- Gene Name:
- CYP19A1
- Uniprot ID:
- P11511
- Molecular Weight:
- 57882.48 Da
References
- Paoletta S, Steventon GB, Wildeboer D, Ehrman TM, Hylands PJ, Barlow DJ: Screening of herbal constituents for aromatase inhibitory activity. Bioorg Med Chem. 2008 Sep 15;16(18):8466-70. doi: 10.1016/j.bmc.2008.08.034. Epub 2008 Aug 19. [18778944 ]
- General Function:
- Zinc ion binding
- Specific Function:
- Nuclear receptor that binds and is activated by variety of endogenous and xenobiotic compounds. Transcription factor that activates the transcription of multiple genes involved in the metabolism and secretion of potentially harmful xenobiotics, drugs and endogenous compounds. Activated by the antibiotic rifampicin and various plant metabolites, such as hyperforin, guggulipid, colupulone, and isoflavones. Response to specific ligands is species-specific. Activated by naturally occurring steroids, such as pregnenolone and progesterone. Binds to a response element in the promoters of the CYP3A4 and ABCB1/MDR1 genes.
- Gene Name:
- NR1I2
- Uniprot ID:
- O75469
- Molecular Weight:
- 49761.245 Da
References
- Kretschmer XC, Baldwin WS: CAR and PXR: xenosensors of endocrine disrupters? Chem Biol Interact. 2005 Aug 15;155(3):111-28. [16054614 ]
- General Function:
- Zinc ion binding
- Specific Function:
- Binds to an ERR-alpha response element (ERRE) containing a single consensus half-site, 5'-TNAAGGTCA-3'. Can bind to the medium-chain acyl coenzyme A dehydrogenase (MCAD) response element NRRE-1 and may act as an important regulator of MCAD promoter. Binds to the C1 region of the lactoferrin gene promoter. Requires dimerization and the coactivator, PGC-1A, for full activity. The ERRalpha/PGC1alpha complex is a regulator of energy metabolism. Induces the expression of PERM1 in the skeletal muscle.
- Gene Name:
- ESRRA
- Uniprot ID:
- P11474
- Molecular Weight:
- 45509.11 Da
References
- Suetsugi M, Su L, Karlsberg K, Yuan YC, Chen S: Flavone and isoflavone phytoestrogens are agonists of estrogen-related receptors. Mol Cancer Res. 2003 Nov;1(13):981-91. [14638870 ]
- General Function:
- Zinc ion binding
- Specific Function:
- Nuclear receptor, may regulate ESR1 transcriptional activity. Induces the expression of PERM1 in the skeletal muscle.
- Gene Name:
- ESRRB
- Uniprot ID:
- O95718
- Molecular Weight:
- 56207.085 Da
References
- Suetsugi M, Su L, Karlsberg K, Yuan YC, Chen S: Flavone and isoflavone phytoestrogens are agonists of estrogen-related receptors. Mol Cancer Res. 2003 Nov;1(13):981-91. [14638870 ]
- General Function:
- Xanthine oxidase activity
- Specific Function:
- Key enzyme in purine degradation. Catalyzes the oxidation of hypoxanthine to xanthine. Catalyzes the oxidation of xanthine to uric acid. Contributes to the generation of reactive oxygen species. Has also low oxidase activity towards aldehydes (in vitro).
- Gene Name:
- XDH
- Uniprot ID:
- P47989
- Molecular Weight:
- 146422.99 Da
References
- Park JS, Park HY, Kim DH, Kim DH, Kim HK: ortho-dihydroxyisoflavone derivatives from aged Doenjang (Korean fermented soypaste) and its radical scavenging activity. Bioorg Med Chem Lett. 2008 Sep 15;18(18):5006-9. doi: 10.1016/j.bmcl.2008.08.016. Epub 2008 Aug 9. [18722771 ]
- General Function:
- Zinc ion binding
- Specific Function:
- Ligand-activated transcription factor. Receptor for bile acids such as chenodeoxycholic acid, lithocholic acid and deoxycholic acid. Represses the transcription of the cholesterol 7-alpha-hydroxylase gene (CYP7A1) through the induction of NR0B2 or FGF19 expression, via two distinct mechanisms. Activates the intestinal bile acid-binding protein (IBABP). Activates the transcription of bile salt export pump ABCB11 by directly recruiting histone methyltransferase CARM1 to this locus.
- Gene Name:
- NR1H4
- Uniprot ID:
- Q96RI1
- Molecular Weight:
- 55913.915 Da
References
- Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]
- General Function:
- Zinc ion binding
- Specific Function:
- Nuclear hormone receptor. The steroid hormones and their receptors are involved in the regulation of eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues. Ligand-dependent nuclear transactivation involves either direct homodimer binding to a palindromic estrogen response element (ERE) sequence or association with other DNA-binding transcription factors, such as AP-1/c-Jun, c-Fos, ATF-2, Sp1 and Sp3, to mediate ERE-independent signaling. Ligand binding induces a conformational change allowing subsequent or combinatorial association with multiprotein coactivator complexes through LXXLL motifs of their respective components. Mutual transrepression occurs between the estrogen receptor (ER) and NF-kappa-B in a cell-type specific manner. Decreases NF-kappa-B DNA-binding activity and inhibits NF-kappa-B-mediated transcription from the IL6 promoter and displace RELA/p65 and associated coregulators from the promoter. Recruited to the NF-kappa-B response element of the CCL2 and IL8 promoters and can displace CREBBP. Present with NF-kappa-B components RELA/p65 and NFKB1/p50 on ERE sequences. Can also act synergistically with NF-kappa-B to activate transcription involving respective recruitment adjacent response elements; the function involves CREBBP. Can activate the transcriptional activity of TFF1. Also mediates membrane-initiated estrogen signaling involving various kinase cascades. Isoform 3 is involved in activation of NOS3 and endothelial nitric oxide production. Isoforms lacking one or several functional domains are thought to modulate transcriptional activity by competitive ligand or DNA binding and/or heterodimerization with the full length receptor. Essential for MTA1-mediated transcriptional regulation of BRCA1 and BCAS3. Isoform 3 can bind to ERE and inhibit isoform 1.
- Gene Name:
- ESR1
- Uniprot ID:
- P03372
- Molecular Weight:
- 66215.45 Da
References
- Matsuda H, Shimoda H, Morikawa T, Yoshikawa M: Phytoestrogens from the roots of Polygonum cuspidatum (Polygonaceae): structure-requirement of hydroxyanthraquinones for estrogenic activity. Bioorg Med Chem Lett. 2001 Jul 23;11(14):1839-42. [11459643 ]
- General Function:
- Transcription regulatory region dna binding
- Specific Function:
- Ligand-activated transcriptional activator. Binds to the XRE promoter region of genes it activates. Activates the expression of multiple phase I and II xenobiotic chemical metabolizing enzyme genes (such as the CYP1A1 gene). Mediates biochemical and toxic effects of halogenated aromatic hydrocarbons. Involved in cell-cycle regulation. Likely to play an important role in the development and maturation of many tissues. Regulates the circadian clock by inhibiting the basal and circadian expression of the core circadian component PER1. Inhibits PER1 by repressing the CLOCK-ARNTL/BMAL1 heterodimer mediated transcriptional activation of PER1.
- Gene Name:
- AHR
- Uniprot ID:
- P35869
- Molecular Weight:
- 96146.705 Da
References
- Wang H, Li J, Gao Y, Xu Y, Pan Y, Tsuji I, Sun ZJ, Li XM: Xeno-oestrogens and phyto-oestrogens are alternative ligands for the androgen receptor. Asian J Androl. 2010 Jul;12(4):535-47. doi: 10.1038/aja.2010.14. Epub 2010 May 3. [20436506 ]