Neosolaniol
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Basic Info
| Common Name | Neosolaniol(F04955) |
| 2D Structure | |
| Description | Neosolaniol is a trichothecene. Trichothecenes are a very large family of chemically related mycotoxins produced by various species of Fusarium, Myrothecium, Trichoderma, Trichothecium, Cephalosporium, Verticimonosporium, and Stachybotrys. The most important structural features causing the biological activities of trichothecenes are: the 12,13-epoxy ring, the presence of hydroxyl or acetyl groups at appropriate positions on the trichothecene nucleus and the structure and position of the side-chain. They are produced on many different grains like wheat, oats or maize by various Fusarium species such as F. graminearum, F. sporotrichioides, F. poae and F. equiseti. Some molds that produce trichothecene mycotoxins, such as Stachybotrys chartarum, can grow in damp indoor environments and may contribute to health problems among building occupants. (L1948) |
| FRCD ID | F04955 |
| CAS Number | 36519-25-2 |
| PubChem CID | 426719 |
| Formula | C19H26O8 |
| IUPAC Name | None |
| InChI Key | TVZHDVCTOCZDNE-UHFFFAOYSA-N |
| InChI | InChI=1S/C19H26O8/c1-9-5-13-18(6-12(9)22,7-24-10(2)20)17(4)15(26-11(3)21)14(23)16(27-13)19(17)8-25-19/h5,12-16,22-23H,6-8H2,1-4H3 |
| Canonical SMILES | CC1=CC2C(CC1O)(C3(C(C(C(C34CO4)O2)O)OC(=O)C)C)COC(=O)C |
| Isomeric SMILES | CC1=CC2C(CC1O)(C3(C(C(C(C34CO4)O2)O)OC(=O)C)C)COC(=O)C |
| Synonyms |
Solaniol (sesquiterpene)
Trichothec-9-ene-3,4,8,15-tetrol, 12,13-epoxy-, 4,15-diacetate
Neosolaniol
Neozolaniol
Solaniol
NSC197212
NSC 197212
36519-25-2
AC1L8I3X
Neosolaniol from Fusaruim sp.
|
| Classifies |
Fungal Toxin
|
| Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
| Kingdom | Organic compounds |
| Superclass | Lipids and lipid-like molecules |
| Class | Prenol lipids |
| Subclass | Sesquiterpenoids |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Trichothecenes |
| Alternative Parents | |
| Molecular Framework | Aliphatic heteropolycyclic compounds |
| Substituents | Trichothecene skeleton - Oxepane - Dicarboxylic acid or derivatives - Oxane - Cyclic alcohol - Carboxylic acid ester - Secondary alcohol - Carboxylic acid derivative - Dialkyl ether - Oxirane - Ether - Oxacycle - Organoheterocyclic compound - Hydrocarbon derivative - Carbonyl group - Alcohol - Organooxygen compound - Organic oxygen compound - Organic oxide - Aliphatic heteropolycyclic compound |
| Description | This compound belongs to the class of organic compounds known as trichothecenes. These are sesquiterpene mycotoxins structurally characterized by the presence of an epoxide ring and a benzopyran derivative with a variant number of hydroxyl, acetyl, or other substituents. The most important structural features causing the biological activities of trichothecenes are the 12,13-epoxy ring, the presence of hydroxyl or acetyl groups at appropriate positions on the trichothecene nucleus and the structure and position of the side-chain. |
Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 382.409 |
| Hydrogen Bond Donor Count | 2 |
| Hydrogen Bond Acceptor Count | 8 |
| Rotatable Bond Count | 5 |
| Complexity | 719 |
| Monoisotopic Mass | 382.163 |
| Exact Mass | 382.163 |
| XLogP | -0.9 |
| Formal Charge | 0 |
| Heavy Atom Count | 27 |
| Defined Atom Stereocenter Count | 0 |
| Undefined Atom Stereocenter Count | 8 |
| 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+ | 0.6593 |
| Human Intestinal Absorption | HIA+ | 0.6371 |
| Caco-2 Permeability | Caco2- | 0.7516 |
| P-glycoprotein Substrate | Substrate | 0.8371 |
| P-glycoprotein Inhibitor | Inhibitor | 0.6200 |
| Non-inhibitor | 0.8556 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.8103 |
| Distribution | ||
| Subcellular localization | Mitochondria | 0.6882 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.8308 |
| CYP450 2D6 Substrate | Non-substrate | 0.8750 |
| CYP450 3A4 Substrate | Substrate | 0.6637 |
| CYP450 1A2 Inhibitor | Non-inhibitor | 0.8874 |
| CYP450 2C9 Inhibitor | Non-inhibitor | 0.9062 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.9242 |
| CYP450 2C19 Inhibitor | Non-inhibitor | 0.8830 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.9359 |
| CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.8998 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.9878 |
| Non-inhibitor | 0.7847 | |
| AMES Toxicity | Non AMES toxic | 0.7391 |
| Carcinogens | Non-carcinogens | 0.9406 |
| Fish Toxicity | High FHMT | 0.9611 |
| Tetrahymena Pyriformis Toxicity | High TPT | 0.9934 |
| Honey Bee Toxicity | High HBT | 0.8475 |
| Biodegradation | Not ready biodegradable | 1.0000 |
| Acute Oral Toxicity | I | 0.8434 |
| Carcinogenicity (Three-class) | Non-required | 0.6675 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -3.5986 | LogS |
| Caco-2 Permeability | 0.4225 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 4.5443 | LD50, mol/kg |
| Fish Toxicity | 0.2852 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | 0.7344 | pIGC50, ug/L |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| First study on trichothecene and zearalenone exposure of the Romanian population through wheat-based products consumption. | Food Chem Toxicol | 2018 Nov | 30213551 |
| 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 |
| UDP-Glucosyltransferases from Rice, Brachypodium, and Barley: Substrate Specificities and Synthesis of Type A and B Trichothecene-3-O-β-d-glucosides. | Toxins (Basel) | 2018 Mar 6 | 29509722 |
| Evaluation of Mycotoxin Residues on Ready-to-Eat Food by Chromatographic Methods Coupled to Mass Spectrometry in Tandem. | Toxins (Basel) | 2018 Jun 15 | 29914055 |
| Anorectic responses to T-2 toxin, HT-2 toxin, diacetoxyscirpenol and neosolaniol correspond to plasma elevations of neurotransmitters 5-hydroxytryptamine and substance P. | Ecotoxicol Environ Saf | 2018 Jun 13 | 29909314 |
| Detection of NEO in muskmelon fruits inoculated with Fusarium sulphureum and its control by postharvest ozone treatment. | Food Chem | 2018 Jul 15 | 29548441 |
| Mycotoxin contamination of sorghum and its contribution to human dietary exposure in four sub-Saharan countries. | Food Addit Contam Part A Chem Anal Control Expo Risk Assess | 2018 Jul | 29912638 |
| Short communication: Analysis of mycotoxins in Spanish milk. | J Dairy Sci | 2018 Jan | 29055539 |
| Detection of new emerging type-A trichothecenes by untargeted mass spectrometry. | Talanta | 2018 Feb 1 | 29136836 |
| Development of an Analytical Method for Simultaneous Determination of the Modified Forms of 4,15-Diacetoxyscirpenol and their Occurrence in Japanese Retail Food. | Toxins (Basel) | 2018 Apr 26 | 29701674 |
| Role of Peptide YY3-36 and Glucose-Dependent Insulinotropic Polypeptide in Anorexia Induction by Trichothecences T-2 Toxin, HT-2 Toxin, Diacetoxyscirpenol, and Neosolaniol. | Toxicol Sci | 2017 Sep 1 | 28666375 |
| Gut satiety hormones cholecystokinin and glucagon-like Peptide-1<sub>7-36</sub> amide mediate anorexia induction by trichothecenes T-2 toxin, HT-2 toxin, diacetoxyscirpenol and neosolaniol. | Toxicol Appl Pharmacol | 2017 Nov 15 | 28964791 |
| In silico analysis sheds light on the structural basis underlying the ribotoxicity of trichothecenes-A tool for supporting the hazard identification process. | Toxicol Lett | 2017 Mar 15 | 28216416 |
| Iron (II, III) oxide/multi-walled carbon nanotube composite as solid-phase extraction sorbent followed by ultra-high performance liquid chromatography tandem mass spectrometry for simultaneous determination of zearalenone and type A trichothecenes in Salviae miltiorrhizae Radix et Rhizoma (Danshen). | J Chromatogr A | 2017 Jan 27 | 28017565 |
| Multi-Mycotoxin Analysis in Durum Wheat Pasta by Liquid Chromatography Coupled to Quadrupole Orbitrap Mass Spectrometry. | Toxins (Basel) | 2017 Feb 9 | 28208797 |
| Metabolism of T-2 Toxin in Farm Animals and Human In Vitro and in Chickens In Vivo Using Ultra High-Performance Liquid Chromatography- Quadrupole/Time-of-Flight Hybrid Mass Spectrometry Along with Online Hydrogen/Deuterium Exchange Technique. | J Agric Food Chem | 2017 Aug 23 | 28737905 |
| Determination of type A trichothecenes in coix seed by magnetic solid-phase extraction based on magnetic multi-walled carbon nanotubes coupled with ultra-high performance liquid chromatography-tandem mass spectrometry. | Anal Bioanal Chem | 2016 Sep | 27475443 |
| Determination of T-2 toxin, HT-2 toxin, and three other type A trichothecenes in layer feed by high-performance liquid chromatography-tandem mass spectrometry (LC-MS/MS)--comparison of two sample preparation methods. | Mycotoxin Res | 2016 May | 26940912 |
| Draft genome sequence and chemical profiling of Fusarium langsethiae, an emerging producer of type A trichothecenes. | Int J Food Microbiol | 2016 Mar 16 | 26803271 |
| Analysis of trichothecenes in laboratory rat feed by gas chromatography-tandem mass spectrometry. | Food Addit Contam Part A Chem Anal Control Expo Risk Assess | 2016 | 26616914 |
Targets
- General Function:
- Structural constituent of ribosome
- Gene Name:
- MRPS5
- Uniprot ID:
- P82675
- Molecular Weight:
- 48006.135 Da
- Mechanism of Action:
- Trichothecenes move freely across the plasma membrane and bind specifically to ribosomes with high-affinity. Specifically, they interfere with the active site of peptidyl transferase at the 3'-end of large 28S ribosomal RNA and inhibit the initiation, elongation or termination step of protein synthesis, as well as cause polyribosomal disaggregation. Trichothecenes are cytotoxic because protein synthesis is an essential function in all tissues. Additionally, binding to ribosomes is thought to activate proteins in downstream signalling events related to immune response and apoptosis, such as mitogen-activated protein kinases. This is known as ribotoxic stress response.
References
- Pestka JJ: Mechanisms of deoxynivalenol-induced gene expression and apoptosis. Food Addit Contam Part A Chem Anal Control Expo Risk Assess. 2008 Sep;25(9):1128-40. [19238623 ]
- General Function:
- Temperature-gated cation channel activity
- Specific Function:
- Receptor-activated non-selective cation channel involved in detection of pain and possibly also in cold perception and inner ear function (PubMed:25389312, PubMed:25855297). Has a central role in the pain response to endogenous inflammatory mediators and to a diverse array of volatile irritants, such as mustard oil, cinnamaldehyde, garlic and acrolein, an irritant from tears gas and vehicule exhaust fumes (PubMed:25389312, PubMed:20547126). Is also activated by menthol (in vitro)(PubMed:25389312). Acts also as a ionotropic cannabinoid receptor by being activated by delta(9)-tetrahydrocannabinol (THC), the psychoactive component of marijuana (PubMed:25389312). May be a component for the mechanosensitive transduction channel of hair cells in inner ear, thereby participating in the perception of sounds. Probably operated by a phosphatidylinositol second messenger system (By similarity).
- Gene Name:
- TRPA1
- Uniprot ID:
- O75762
- Molecular Weight:
- 127499.88 Da
References
- Nilius B, Prenen J, Owsianik G: Irritating channels: the case of TRPA1. J Physiol. 2011 Apr 1;589(Pt 7):1543-9. doi: 10.1113/jphysiol.2010.200717. Epub 2010 Nov 15. [21078588 ]