15-Deacetylcalonectrin
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Basic Info
| Common Name | 15-Deacetylcalonectrin(F04950) |
| 2D Structure | |
| Description | 15-Deacetylcalonectrin is a metabolite of Calonectria nivalis 15-Deacetylcalonectrin belongs to the family of Trichothecenes. These are sesquiterpene mycotoxins structurally characterized by the presence of an epoxide ring and a benzoyran derivative with a variant number of hydroxyl, acetly, or other substituents [1]. (Reference: [1] http://www.inchem.org/documents/ehc/ehc/ehc105.htm). |
| FRCD ID | F04950 |
| CAS Number | 38818-66-5 |
| PubChem CID | 587712 |
| Formula | C17H24O5 |
| IUPAC Name | None |
| InChI Key | DFPPNUOWRKIOKO-UHFFFAOYSA-N |
| InChI | InChI=1S/C17H24O5/c1-10-4-5-16(8-18)13(6-10)22-14-12(21-11(2)19)7-15(16,3)17(14)9-20-17/h6,12-14,18H,4-5,7-9H2,1-3H3 |
| Canonical SMILES | CC1=CC2C(CC1)(C3(CC(C(C34CO4)O2)OC(=O)C)C)CO |
| Isomeric SMILES | CC1=CC2C(CC1)(C3(CC(C(C34CO4)O2)OC(=O)C)C)CO |
| Synonyms |
15-Desacetylcalonectrin
15-Deacetylcalonectrin
15-decalonectrin
15-O-deacetylcalonectrin
15-Deacetycalonectrin
AC1LBRFN
DFPPNUOWRKIOKO-UHFFFAOYSA-N
Trichothec-9-ene-3,15-diol, 12,13-epoxy-, 3-acetate, (3.alpha.)-
Spiro[2,5-methano-1-benzoxepin-10,2'-oxirane], trichothec-9-ene-3,15-diol deriv.
|
| 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 - Oxane - Carboxylic acid ester - Organoheterocyclic compound - Monocarboxylic acid or derivatives - Ether - Oxirane - Dialkyl ether - Carboxylic acid derivative - Oxacycle - Hydrocarbon derivative - Primary alcohol - Organic oxide - Organic oxygen compound - Organooxygen compound - Alcohol - Carbonyl group - 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 | 308.374 |
| Hydrogen Bond Donor Count | 1 |
| Hydrogen Bond Acceptor Count | 5 |
| Rotatable Bond Count | 3 |
| Complexity | 557 |
| Monoisotopic Mass | 308.162 |
| Exact Mass | 308.162 |
| XLogP | 0.6 |
| Formal Charge | 0 |
| Heavy Atom Count | 22 |
| Defined Atom Stereocenter Count | 0 |
| Undefined Atom Stereocenter Count | 6 |
| 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+ | 0.9295 |
| Human Intestinal Absorption | HIA+ | 0.9079 |
| Caco-2 Permeability | Caco2- | 0.7821 |
| P-glycoprotein Substrate | Substrate | 0.8065 |
| P-glycoprotein Inhibitor | Inhibitor | 0.8244 |
| Non-inhibitor | 0.6305 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.6984 |
| Distribution | ||
| Subcellular localization | Mitochondria | 0.7586 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.8237 |
| CYP450 2D6 Substrate | Non-substrate | 0.8564 |
| CYP450 3A4 Substrate | Substrate | 0.7271 |
| CYP450 1A2 Inhibitor | Non-inhibitor | 0.8088 |
| CYP450 2C9 Inhibitor | Non-inhibitor | 0.7934 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.9448 |
| CYP450 2C19 Inhibitor | Non-inhibitor | 0.8403 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.9200 |
| CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.9062 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.9651 |
| Non-inhibitor | 0.5375 | |
| AMES Toxicity | Non AMES toxic | 0.8620 |
| Carcinogens | Non-carcinogens | 0.9528 |
| Fish Toxicity | High FHMT | 0.9343 |
| Tetrahymena Pyriformis Toxicity | High TPT | 0.9968 |
| Honey Bee Toxicity | High HBT | 0.8550 |
| Biodegradation | Not ready biodegradable | 0.9915 |
| Acute Oral Toxicity | I | 0.6402 |
| Carcinogenicity (Three-class) | Non-required | 0.6595 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -4.5268 | LogS |
| Caco-2 Permeability | 0.5131 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 3.9140 | LD50, mol/kg |
| Fish Toxicity | 0.6689 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | 1.0108 | pIGC50, ug/L |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| Development of a simultaneous liquid chromatography/tandem mass spectrometric method for the determination of type B trichothecenes, their derivatives, and precursors in wheat. | Rapid Commun Mass Spectrom | 2011 Dec 15 | 22095495 |
| Murine lymphocyte proliferation impaired by substituted neosolaniols and calonectrins--Fusarium metabolites associated with trichothecene biosynthesis. | Toxicon | 1991 | 1796475 |
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 ]