beta-Zearalenol
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Basic Info
| Common Name | Beta-Zearalenol(F03248) |
| 2D Structure | |
| FRCD ID | F03248 |
| CAS Number | 71030-11-0 |
| PubChem CID | 6437352 |
| Formula | C18H24O5 |
| IUPAC Name | (2E,7S,11S)-7,15,17-trihydroxy-11-methyl-12-oxabicyclo[12.4.0]octadeca-1(18),2,14,16-tetraen-13-one |
| InChI Key | FPQFYIAXQDXNOR-PMRAARRBSA-N |
| InChI | InChI=1S/C18H24O5/c1-12-6-5-9-14(19)8-4-2-3-7-13-10-15(20)11-16(21)17(13)18(22)23-12/h3,7,10-12,14,19-21H,2,4-6,8-9H2,1H3/b7-3+/t12-,14-/m0/s1 |
| Canonical SMILES | CC1CCCC(CCCC=CC2=CC(=CC(=C2C(=O)O1)O)O)O |
| Isomeric SMILES | C[C@H]1CCC[C@H](CCC/C=C/C2=CC(=CC(=C2C(=O)O1)O)O)O |
| Synonyms |
beta-Zearalenol
71030-11-0
UNII-35E809PP7O
CHEMBL372840
35E809PP7O
beta zearalenol
.beta.-Zearalenol
beta-trans-Zearalenol
(-)-|A-Zearalenol
CHEBI:35072
|
| Classifies |
Predicted: Fungal Toxin
|
| Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
| Kingdom | Organic compounds |
| Superclass | Phenylpropanoids and polyketides |
| Class | Macrolides and analogues |
| Subclass | Not available |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Macrolides and analogues |
| Alternative Parents | |
| Molecular Framework | Aromatic heteropolycyclic compounds |
| Substituents | Macrolide - Dihydroxybenzoic acid - 1-hydroxy-4-unsubstituted benzenoid - 1-hydroxy-2-unsubstituted benzenoid - Benzenoid - Vinylogous acid - Carboxylic acid ester - Lactone - Secondary alcohol - Carboxylic acid derivative - Polyol - Monocarboxylic acid or derivatives - Oxacycle - Organoheterocyclic compound - Organooxygen compound - Organic oxide - Organic oxygen compound - Alcohol - Hydrocarbon derivative - Aromatic heteropolycyclic compound |
| Description | This compound belongs to the class of organic compounds known as macrolides and analogues. These are organic compounds containing a lactone ring of at least twelve members. |
Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 320.385 |
| Hydrogen Bond Donor Count | 3 |
| Hydrogen Bond Acceptor Count | 5 |
| Rotatable Bond Count | 0 |
| Complexity | 408 |
| Monoisotopic Mass | 320.162 |
| Exact Mass | 320.162 |
| XLogP | 4 |
| Formal Charge | 0 |
| Heavy Atom Count | 23 |
| Defined Atom Stereocenter Count | 2 |
| 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+ | 0.6232 |
| Human Intestinal Absorption | HIA+ | 0.9774 |
| Caco-2 Permeability | Caco2+ | 0.6384 |
| P-glycoprotein Substrate | Substrate | 0.7665 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.9861 |
| Non-inhibitor | 0.9729 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.9107 |
| Distribution | ||
| Subcellular localization | Mitochondria | 0.6120 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.7044 |
| CYP450 2D6 Substrate | Non-substrate | 0.8247 |
| CYP450 3A4 Substrate | Substrate | 0.5154 |
| CYP450 1A2 Inhibitor | Inhibitor | 0.7660 |
| CYP450 2C9 Inhibitor | Non-inhibitor | 0.8937 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.9007 |
| CYP450 2C19 Inhibitor | Non-inhibitor | 0.7246 |
| CYP450 3A4 Inhibitor | Inhibitor | 0.7682 |
| CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.8975 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.9040 |
| Non-inhibitor | 0.8444 | |
| AMES Toxicity | Non AMES toxic | 0.8792 |
| Carcinogens | Non-carcinogens | 0.9616 |
| Fish Toxicity | High FHMT | 0.9724 |
| Tetrahymena Pyriformis Toxicity | High TPT | 0.9973 |
| Honey Bee Toxicity | High HBT | 0.7104 |
| Biodegradation | Ready biodegradable | 0.5709 |
| Acute Oral Toxicity | III | 0.3986 |
| Carcinogenicity (Three-class) | Non-required | 0.6604 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -3.1683 | LogS |
| Caco-2 Permeability | 0.7022 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 2.1384 | LD50, mol/kg |
| Fish Toxicity | 1.0197 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | 1.0235 | pIGC50, ug/L |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| Reduced graphene oxide and gold nanoparticle composite-based solid-phase extraction coupled with ultra-high-performance liquid chromatography-tandem mass spectrometry for the determination of 9 mycotoxins in milk. | Food Chem | 2018 Oct 30 | 29853368 |
| Mycotoxins induce developmental toxicity and behavioural aberrations in zebrafish larvae. | Environ Pollut | 2018 Nov | 30005262 |
| Stability of fumonisin B<sub>1</sub>, deoxynivalenol, zearalenone, and T-2 toxin during processing of traditional Nigerian beer and spices. | Mycotoxin Res | 2018 Nov | 29725912 |
| Liquid chromatography - high resolution mass spectrometry method for monitoring of 17 mycotoxins in human plasma for exposure studies. | J Chromatogr A | 2018 May 4 | 29576275 |
| Ultra-High-Performance Supercritical Fluid Chromatography as a Separation Tool for <i>Fusarium</i> Mycotoxins and Their Modified Forms. | J AOAC Int | 2018 May 1 | 28964272 |
| Preparation of a broad-spectrum anti-zearalenone and its primary analogues antibody and its application in an indirect competitive enzyme-linked immunosorbent assay. | Food Chem | 2018 May 1 | 29277231 |
| Estrogenic activity of zearalenone, α-zearalenol and β-zearalenol assessed using the E-screen assay in MCF-7 cells. | Toxicol Mech Methods | 2018 May | 29057713 |
| [Simultaneous determination of six zeranols in milk samples by immunoaffinity solid phase extraction coupled with ultra-performance convergence chromatography-tandem mass spectrometry]. | Se Pu | 2018 Jun 8 | 30136479 |
| Evaluation of Mycotoxin Residues on Ready-to-Eat Food by Chromatographic Methods Coupled to Mass Spectrometry in Tandem. | Toxins (Basel) | 2018 Jun 15 | 29914055 |
| On the distribution and metabolism of Fusarium-toxins along the gastrointestinal tract of endotoxaemic pigs. | Arch Anim Nutr | 2018 Jun | 29741131 |
| Multi-Mycotoxin Occurrence in Dairy Cattle Feeds from the Gauteng Province of South Africa: A Pilot Study Using UHPLC-QTOF-MS/MS. | Toxins (Basel) | 2018 Jul 16 | 30013005 |
| [Occurrences of mycotoxins in human breast milk in 15 provinces in China in2011]. | Wei Sheng Yan Jiu | 2018 Jan | 29903226 |
| Tolerance and Excretion of the Mycotoxins Aflatoxin B₁, Zearalenone,Deoxynivalenol, and Ochratoxin A by Alphitobius diaperinus and Hermetia illucens from Contaminated Substrates. | Toxins (Basel) | 2018 Feb 24 | 29495278 |
| Measurement of urinary concentrations of the mycotoxins zearalenone and sterigmatocystin as biomarkers of exposure in mares. | Reprod Domest Anim | 2018 Feb | 28921680 |
| Determination of aflatoxin and zearalenone analogs in edible and medicinal herbs using a group-specific immunoaffinity column coupled to ultra-high-performance liquid chromatography with tandem mass spectrometry. | J Chromatogr B Analyt Technol Biomed Life Sci | 2018 Aug 15 | 29909149 |
| High-throughput and sensitive determination of urinary zearalenone and metabolites by UPLC-MS/MS and its application to a human exposure study. | Anal Bioanal Chem | 2018 Aug | 29951770 |
| Modified <i>Fusarium</i> Mycotoxins in Cereals and Their Products-Metabolism, Occurrence, and Toxicity: An Updated Review. | Molecules | 2018 Apr 20 | 29677133 |
| Toxicological effects of regulated mycotoxins and persistent organochloride pesticides: In vitro cytotoxic assessment of single and defined mixtures on MA-10 murine Leydig cell line. | Toxicol In Vitro | 2018 Apr | 29307701 |
| Role of mycotoxins in herds with and without problems with tail necrosis in neonatal pigs. | Vet Rec | 2017 Nov 18 | 28982783 |
| 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 |
Targets
- General Function:
- Tumor necrosis factor receptor binding
- Specific Function:
- Signal transducer and transcription activator that mediates cellular responses to interferons (IFNs), cytokine KITLG/SCF and other cytokines and other growth factors. Following type I IFN (IFN-alpha and IFN-beta) binding to cell surface receptors, signaling via protein kinases leads to activation of Jak kinases (TYK2 and JAK1) and to tyrosine phosphorylation of STAT1 and STAT2. The phosphorylated STATs dimerize and associate with ISGF3G/IRF-9 to form a complex termed ISGF3 transcription factor, that enters the nucleus. ISGF3 binds to the IFN stimulated response element (ISRE) to activate the transcription of IFN-stimulated genes (ISG), which drive the cell in an antiviral state. In response to type II IFN (IFN-gamma), STAT1 is tyrosine- and serine-phosphorylated. It then forms a homodimer termed IFN-gamma-activated factor (GAF), migrates into the nucleus and binds to the IFN gamma activated sequence (GAS) to drive the expression of the target genes, inducing a cellular antiviral state. Becomes activated in response to KITLG/SCF and KIT signaling. May mediate cellular responses to activated FGFR1, FGFR2, FGFR3 and FGFR4.
- Gene Name:
- STAT1
- Uniprot ID:
- P42224
- Molecular Weight:
- 87334.175 Da
References
- Liu T, Lin Y, Wen X, Jorissen RN, Gilson MK: BindingDB: a web-accessible database of experimentally determined protein-ligand binding affinities. Nucleic Acids Res. 2007 Jan;35(Database issue):D198-201. Epub 2006 Dec 1. [17145705 ]