Equol
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Basic Info
| Common Name | Equol(F05163) |
| 2D Structure | |
| Description | Equol is a metabolite of daidzein, a phytoestrogen common in the human diet and abundant in soy. Intestinal bacteria in humans can reduce daidzein to equol, and can be found in normal human urine. 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. (A3188, A3189). |
| FRCD ID | F05163 |
| CAS Number | 531-95-3 |
| PubChem CID | 91469 |
| Formula | C15H14O3 |
| IUPAC Name | (3S)-3-(4-hydroxyphenyl)-3,4-dihydro-2H-chromen-7-ol |
| InChI Key | ADFCQWZHKCXPAJ-GFCCVEGCSA-N |
| InChI | InChI=1S/C15H14O3/c16-13-4-1-10(2-5-13)12-7-11-3-6-14(17)8-15(11)18-9-12/h1-6,8,12,16-17H,7,9H2/t12-/m1/s1 |
| Canonical SMILES | C1C(COC2=C1C=CC(=C2)O)C3=CC=C(C=C3)O |
| Isomeric SMILES | C1[C@H](COC2=C1C=CC(=C2)O)C3=CC=C(C=C3)O |
| Wikipedia | Equol |
| Synonyms |
(-)-(S)-Equol
Equol
531-95-3
(S)-3-(4-Hydroxyphenyl)chroman-7-ol
(S)-Equol
S-Equol
(-)-Equol
UNII-2T6D2HPX7Q
4',7-Isoflavandiol
CCRIS 9222
|
| Classifies |
Animal Toxin
|
| Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
| Kingdom | Organic compounds |
| Superclass | Phenylpropanoids and polyketides |
| Class | Isoflavonoids |
| Subclass | Isoflavans |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Isoflavanols |
| Alternative Parents | |
| Molecular Framework | Aromatic heteropolycyclic compounds |
| Substituents | Hydroxyisoflavonoid - Isoflavanol - Chromane - Benzopyran - 1-benzopyran - Alkyl aryl ether - 1-hydroxy-2-unsubstituted benzenoid - Phenol - Monocyclic benzene moiety - Benzenoid - Ether - Oxacycle - Organoheterocyclic compound - Organooxygen compound - Hydrocarbon derivative - Organic oxygen compound - Aromatic heteropolycyclic compound |
| Description | This compound belongs to the class of organic compounds known as isoflavanols. These are polycyclic compounds containing a hydroxylated isoflavan skeleton. |
Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 242.274 |
| Hydrogen Bond Donor Count | 2 |
| Hydrogen Bond Acceptor Count | 3 |
| Rotatable Bond Count | 1 |
| Complexity | 273 |
| Monoisotopic Mass | 242.094 |
| Exact Mass | 242.094 |
| XLogP | 3 |
| Formal Charge | 0 |
| Heavy Atom Count | 18 |
| Defined Atom Stereocenter Count | 1 |
| 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+ | 0.7260 |
| Human Intestinal Absorption | HIA+ | 1.0000 |
| Caco-2 Permeability | Caco2+ | 0.7095 |
| P-glycoprotein Substrate | Non-substrate | 0.5657 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.9365 |
| Non-inhibitor | 0.7232 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.8165 |
| Distribution | ||
| Subcellular localization | Mitochondria | 0.8405 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.8212 |
| CYP450 2D6 Substrate | Non-substrate | 0.8861 |
| CYP450 3A4 Substrate | Non-substrate | 0.7076 |
| CYP450 1A2 Inhibitor | Inhibitor | 0.7895 |
| CYP450 2C9 Inhibitor | Inhibitor | 0.6922 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.8598 |
| CYP450 2C19 Inhibitor | Inhibitor | 0.8789 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.8928 |
| CYP Inhibitory Promiscuity | High CYP Inhibitory Promiscuity | 0.7223 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.9333 |
| Non-inhibitor | 0.8439 | |
| AMES Toxicity | Non AMES toxic | 0.7050 |
| Carcinogens | Non-carcinogens | 0.9092 |
| Fish Toxicity | High FHMT | 0.7624 |
| Tetrahymena Pyriformis Toxicity | High TPT | 0.9520 |
| Honey Bee Toxicity | High HBT | 0.6953 |
| Biodegradation | Not ready biodegradable | 0.8677 |
| Acute Oral Toxicity | III | 0.5178 |
| Carcinogenicity (Three-class) | Non-required | 0.5735 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -2.7334 | LogS |
| Caco-2 Permeability | 1.2376 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 2.7268 | LD50, mol/kg |
| Fish Toxicity | 1.0535 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | 0.8954 | pIGC50, ug/L |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| Main Isoflavones Found in Dietary Sources as Natural Anti-inflammatory Agents. | Curr Drug Targets | 2018 | 29141545 |
| Association between Dietary Share of Ultra-Processed Foods and UrinaryConcentrations of Phytoestrogens in the US. | Nutrients | 2017 Feb 28 | 28264475 |
| 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 |
| Bovine and soybean milk bioactive compounds: Effects on inflammatory response of human intestinal Caco-2 cells. | Food Chem | 2016 Nov 1 | 27211648 |
| 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 |
| Probiotics: a proactive approach to health. A symposium report. | Br J Nutr | 2015 Dec | 26548336 |
| Cooperative effects of soy isoflavones and carotenoids on osteoclast formation. | J Clin Biochem Nutr | 2014 Mar | 24688220 |
| Gastrointestinal metabolism of phytoestrogens in lactating dairy cows fed silageswith different botanical composition. | J Dairy Sci | 2014 Dec | 25306275 |
| Assessment of ABCG2-mediated transport of xenobiotics across the blood-milk barrier of dairy animals using a new MDCKII in vitro model. | Arch Toxicol | 2013 Sep | 23652544 |
| Determination of functional ABCG2 activity and assessment of drug-ABCG2interactions in dairy animals using a novel MDCKII in vitro model. | J Pharm Sci | 2013 Feb | 23192864 |
| Xylitol affects the intestinal microbiota and metabolism of daidzein in adultmale mice. | Int J Mol Sci | 2013 Dec 10 | 24336061 |
| Dietary factors influence production of the soy isoflavone metabolite s-(-)equol in healthy adults. | J Nutr | 2013 Dec | 24089421 |
| Synergistic and Selective Cancer Cell Killing Mediated by the Oncolytic Adenoviral Mutant AdΔΔ and Dietary Phytochemicals in Prostate Cancer Models. | Hum Gene Ther | 2012 Sep | 22788991 |
| Urinary isoflavonoids and risk of coronary heart disease. | Int J Epidemiol | 2012 Oct | 22927214 |
| Equol production changes over time in postmenopausal women. | J Nutr Biochem | 2012 Jun | 21775122 |
| Long-term treatment of ovariectomized mice with estradiol or phytoestrogens as a new model to study the role of estrogenic substances in the heart. | Planta Med | 2012 Jan | 21928168 |
| Synthesis of isoflavone aglycones and equol in soy milks fermented by food-related lactic acid bacteria and their effect on human intestinal Caco-2 cells. | J Agric Food Chem | 2010 Oct 13 | 20822177 |
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
- Mueller SO, Simon S, Chae K, Metzler M, Korach KS: Phytoestrogens and their human metabolites show distinct agonistic and antagonistic properties on estrogen receptor alpha (ERalpha) and ERbeta in human cells. Toxicol Sci. 2004 Jul;80(1):14-25. Epub 2004 Apr 14. [15084758 ]
- 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
- Witters H, Freyberger A, Smits K, Vangenechten C, Lofink W, Weimer M, Bremer S, Ahr PH, Berckmans P: The assessment of estrogenic or anti-estrogenic activity of chemicals by the human stably transfected estrogen sensitive MELN cell line: results of test performance and transferability. Reprod Toxicol. 2010 Aug;30(1):60-72. doi: 10.1016/j.reprotox.2010.02.008. Epub 2010 Mar 31. [20362049 ]