Diethylstilbestrol
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Basic Info
| Common Name | Diethylstilbestrol(F05494) |
| 2D Structure | |
| Description | A synthetic nonsteroidal estrogen used in the treatment of menopausal and postmenopausal disorders. It was also used formerly as a growth promoter in animals. According to the Fourth Annual Report on Carcinogens (NTP 85-002, 1985), diethylstilbestrol has been listed as a known carcinogen. |
| FRCD ID | F05494 |
| CAS Number | 56-53-1 |
| PubChem CID | 448537 |
| Formula | C18H20O2 |
| IUPAC Name | 4-[(E)-4-(4-hydroxyphenyl)hex-3-en-3-yl]phenol |
| InChI Key | RGLYKWWBQGJZGM-ISLYRVAYSA-N |
| InChI | InChI=1S/C18H20O2/c1-3-17(13-5-9-15(19)10-6-13)18(4-2)14-7-11-16(20)12-8-14/h5-12,19-20H,3-4H2,1-2H3/b18-17+ |
| Canonical SMILES | CCC(=C(CC)C1=CC=C(C=C1)O)C2=CC=C(C=C2)O |
| Isomeric SMILES | CC/C(=C(/CC)\C1=CC=C(C=C1)O)/C2=CC=C(C=C2)O |
| Wikipedia | Diethylstilbestrol |
| Synonyms |
Stilboestrol
diethylstilbestrol
56-53-1
Stilbestrol
Distilbene
Agostilben
Estrobene
Estromenin
Stilboestroform
Antigestil
|
| Classifies |
Illegal Additives
|
| Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
| Kingdom | Organic compounds |
| Superclass | Phenylpropanoids and polyketides |
| Class | Stilbenes |
| Subclass | Not available |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Stilbenes |
| Alternative Parents | |
| Molecular Framework | Aromatic homomonocyclic compounds |
| Substituents | Stilbene - Phenylpropane - 1-hydroxy-2-unsubstituted benzenoid - Phenol - Benzenoid - Monocyclic benzene moiety - Organic oxygen compound - Hydrocarbon derivative - Organooxygen compound - Aromatic homomonocyclic compound |
| Description | This compound belongs to the class of organic compounds known as stilbenes. These are organic compounds containing a 1,2-diphenylethylene moiety. Stilbenes (C6-C2-C6 ) are derived from the common phenylpropene (C6-C3) skeleton building block. The introduction of one or more hydroxyl groups to a phenyl ring lead to stilbenoids. |
Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 268.356 |
| Hydrogen Bond Donor Count | 2 |
| Hydrogen Bond Acceptor Count | 2 |
| Rotatable Bond Count | 4 |
| Complexity | 286 |
| Monoisotopic Mass | 268.146 |
| Exact Mass | 268.146 |
| XLogP | 5.1 |
| Formal Charge | 0 |
| Heavy Atom Count | 20 |
| Defined Atom Stereocenter Count | 0 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 1 |
| Undefined Bond Stereocenter Count | 0 |
| Isotope Atom Count | 0 |
| Covalently-Bonded Unit Count | 1 |
ADMET
| Model | Result | Probability |
|---|---|---|
| Absorption | ||
| Blood-Brain Barrier | BBB- | 0.5559 |
| Human Intestinal Absorption | HIA+ | 0.9973 |
| Caco-2 Permeability | Caco2+ | 0.8264 |
| P-glycoprotein Substrate | Substrate | 0.5737 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.6542 |
| Non-inhibitor | 0.8478 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.8465 |
| Distribution | ||
| Subcellular localization | Mitochondria | 0.8149 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.8149 |
| CYP450 2D6 Substrate | Non-substrate | 0.9116 |
| CYP450 3A4 Substrate | Non-substrate | 0.5107 |
| CYP450 1A2 Inhibitor | Inhibitor | 0.9106 |
| CYP450 2C9 Inhibitor | Inhibitor | 0.9064 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.7017 |
| CYP450 2C19 Inhibitor | Inhibitor | 0.9198 |
| CYP450 3A4 Inhibitor | Inhibitor | 0.8361 |
| CYP Inhibitory Promiscuity | High CYP Inhibitory Promiscuity | 0.9488 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.6894 |
| Non-inhibitor | 0.6408 | |
| AMES Toxicity | Non AMES toxic | 0.9579 |
| Carcinogens | Non-carcinogens | 0.6772 |
| Fish Toxicity | High FHMT | 0.9231 |
| Tetrahymena Pyriformis Toxicity | High TPT | 0.9955 |
| Honey Bee Toxicity | High HBT | 0.8211 |
| Biodegradation | Not ready biodegradable | 0.9111 |
| Acute Oral Toxicity | III | 0.8787 |
| Carcinogenicity (Three-class) | Danger | 0.7510 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -4.2877 | LogS |
| Caco-2 Permeability | 1.4588 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 1.9462 | LD50, mol/kg |
| Fish Toxicity | 0.5515 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | 1.8579 | pIGC50, ug/L |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| Multiresidue Determination of the Anabolic-Agent Residues Steroids, Stilbenes,and Resorcylic Acid Lactones in Bovine Urine by GC-MS/MS with Microwave-Assisted Derivatization. | J Agric Food Chem | 2018 Aug 15 | 30020779 |
| What is an endocrine disruptor? | C R Biol | 2017 Sep - Oct | 29126512 |
| 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 |
| Investigation of diethylstilbestrol residue level in human urine samples by aspecific monoclonal antibody. | Environ Sci Pollut Res Int | 2017 Mar | 28092005 |
| Thin metal organic frameworks coatings by cathodic electrodeposition forsolid-phase microextraction and analysis of trace exogenous estrogens in milk. | Anal Chim Acta | 2016 Sep 21 | 27590545 |
| Using Fenton Oxidation to Simultaneously Remove Different Estrogens from CowManure. | Int J Environ Res Public Health | 2016 Sep 15 | 27649223 |
| Human UDP-Glucuronosyltransferases 1A1, 1A3, 1A9, 2B4 and 2B7 are Inhibited by Diethylstilbestrol. | Basic Clin Pharmacol Toxicol | 2016 Nov | 27176228 |
| [Rapid detection of diethylstilbestrol using a quartz crystal microbalance withgold nanoparticals amplification]. | Zhonghua Yu Fang Yi Xue Za Zhi | 2016 Mar | 26957248 |
| Multiplug filtration cleanup method with multi-walled carbon nanotubes for theanalysis of malachite green, diethylstilbestrol residues, and their metabolitesin aquatic products by liquid chromatography-tandem mass spectrometry. | Anal Bioanal Chem | 2016 Aug | 27311954 |
| Development and characterization of a nanodendritic silver-based solid-phaseextraction sorbent for selective enrichment of endocrine-disrupting chemicals in water and milk samples. | Anal Chim Acta | 2015 Nov 5 | 26572841 |
| Deep eutectic liquid organic salt as a new solvent for liquid-phasemicroextraction and its application in ligandless extraction and preconcentraion of lead and cadmium in edible oils. | Talanta | 2015 Nov 1 | 26452873 |
| Diethylstilbestrol can effectively accelerate estradiol-17-O-glucuronidation, while potently inhibiting estradiol-3-O-glucuronidation. | Toxicol Appl Pharmacol | 2015 Mar 1 | 25596428 |
| Novel molecularly imprinted stir bar sorptive extraction based on an 8-electrode array for preconcentration of trace exogenous estrogens in meat. | Anal Chim Acta | 2015 Jan 1 | 25467478 |
| Transferability and inter-laboratory variability assessment of the in vitro bovine oocyte fertilization test. | Reprod Toxicol | 2015 Jan | 25625651 |
| Pubertal timing after neonatal diethylstilbestrol exposure in female rats:neuroendocrine vs peripheral effects and additive role of prenatal foodrestriction. | Reprod Toxicol | 2014 Apr | 24316331 |
| Are benefits from diabetes self-management education sustained? | Am J Manag Care | 2013 Feb | 23448107 |
| Liquid chromatography-mass spectrometry method for the quantitative determinationof residues of selected veterinary hormones in powdered ingredients derived from bovine milk. | J Agric Food Chem | 2013 Dec 4 | 24215545 |
| Postweaning exposure to dietary zearalenone, a mycotoxin, promotes premature onset of puberty and disrupts early pregnancy events in female mice. | Toxicol Sci | 2013 Apr | 23291560 |
| Synthesis of molecularly imprinted polymer using attapulgite as matrix byultrasonic irradiation for simultaneous on-line solid phase extraction and highperformance liquid chromatography determination of four estrogens. | J Chromatogr A | 2012 Mar 16 | 22318004 |
| Endocrine disrupters: a review of some sources, effects, and mechanisms ofactions on behaviour and neuroendocrine systems. | J Neuroendocrinol | 2012 Jan | 21951193 |
Targets
- Uniprot ID:
- P05184
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:
- 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
- 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:
- Orphan receptor that acts as transcription activator in the absence of bound ligand. Binds specifically to an estrogen response element and activates reporter genes controlled by estrogen response elements (By similarity). Induces the expression of PERM1 in the skeletal muscle.
- Gene Name:
- ESRRG
- Uniprot ID:
- P62508
- Molecular Weight:
- 51305.485 Da
References
- Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [10592235 ]
- 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
- 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 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
- 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:
- Purine nucleoside binding
- Specific Function:
- Receptor for adenosine. The activity of this receptor is mediated by G proteins which inhibit adenylyl cyclase.
- Gene Name:
- ADORA1
- Uniprot ID:
- P30542
- Molecular Weight:
- 36511.325 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:
- Steroid hormone receptors are ligand-activated transcription factors that regulate eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues. Transcription factor activity is modulated by bound coactivator and corepressor proteins. Transcription activation is down-regulated by NR0B2. Activated, but not phosphorylated, by HIPK3 and ZIPK/DAPK3.
- Gene Name:
- AR
- Uniprot ID:
- P10275
- Molecular Weight:
- 98987.9 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
- 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:
- Receptor for glucocorticoids (GC). Has a dual mode of action: as a transcription factor that binds to glucocorticoid response elements (GRE), both for nuclear and mitochondrial DNA, and as a modulator of other transcription factors. Affects inflammatory responses, cellular proliferation and differentiation in target tissues. Could act as a coactivator for STAT5-dependent transcription upon growth hormone (GH) stimulation and could reveal an essential role of hepatic GR in the control of body growth. Involved in chromatin remodeling. May play a negative role in adipogenesis through the regulation of lipolytic and antilipogenic genes expression.
- Gene Name:
- NR3C1
- Uniprot ID:
- P04150
- Molecular Weight:
- 85658.57 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 ]