| Record Information |
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| Version | 2.0 |
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| Created at | 2022-09-12 04:10:44 UTC |
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| Updated at | 2022-09-12 04:10:44 UTC |
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| NP-MRD ID | NP0324230 |
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| Secondary Accession Numbers | None |
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| Natural Product Identification |
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| Common Name | (1's,2r,2'r,4's,7'r,9'r,10'r,11's)-2'-[(acetyloxy)methyl]-10',11'-dihydroxy-1',5'-dimethyl-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0²,⁷]dodecan]-5'-en-4'-yl 3-methylbutanoate |
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| Description | HT-2 Toxin, also known as toxin HT 2, 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. (1's,2r,2'r,4's,7'r,9'r,10'r,11's)-2'-[(acetyloxy)methyl]-10',11'-dihydroxy-1',5'-dimethyl-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0²,⁷]dodecan]-5'-en-4'-yl 3-methylbutanoate is found in Fusarium heterosporum and Fusarium sporotrichioides. (1's,2r,2'r,4's,7'r,9'r,10'r,11's)-2'-[(acetyloxy)methyl]-10',11'-dihydroxy-1',5'-dimethyl-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0²,⁷]dodecan]-5'-en-4'-yl 3-methylbutanoate was first documented in 2022 (PMID: 35990316). Based on a literature review a small amount of articles have been published on HT-2 Toxin (PMID: 36075166) (PMID: 35940788) (PMID: 35853424). |
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| Structure | CC(C)CC(=O)O[C@H]1C[C@@]2(COC(C)=O)[C@H](O[C@@H]3[C@H](O)[C@@H](O)[C@@]2(C)[C@@]32CO2)C=C1C InChI=1S/C22H32O8/c1-11(2)6-16(24)29-14-8-21(9-27-13(4)23)15(7-12(14)3)30-19-17(25)18(26)20(21,5)22(19)10-28-22/h7,11,14-15,17-19,25-26H,6,8-10H2,1-5H3/t14-,15+,17+,18+,19+,20+,21+,22+/m0/s1 |
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| Synonyms | | Value | Source |
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| 3,4-Dihydroxy-15-acetoxy-8-(3-methylbutyryloxy)-12,13-epoxy-delta9-trichothecene | MeSH | | Toxin HT 2 | MeSH |
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| Chemical Formula | C22H32O8 |
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| Average Mass | 424.4900 Da |
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| Monoisotopic Mass | 424.20972 Da |
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| IUPAC Name | (1'S,2R,2'R,4'S,7'R,9'R,10'R,11'S)-2'-[(acetyloxy)methyl]-10',11'-dihydroxy-1',5'-dimethyl-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0^{2,7}]dodecan]-5'-en-4'-yl 3-methylbutanoate |
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| Traditional Name | (1'S,2R,2'R,4'S,7'R,9'R,10'R,11'S)-2'-[(acetyloxy)methyl]-10',11'-dihydroxy-1',5'-dimethyl-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0^{2,7}]dodecan]-5'-en-4'-yl 3-methylbutanoate |
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| CAS Registry Number | Not Available |
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| SMILES | CC(C)CC(=O)O[C@H]1C[C@@]2(COC(C)=O)[C@H](O[C@@H]3[C@H](O)[C@@H](O)[C@@]2(C)[C@@]32CO2)C=C1C |
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| InChI Identifier | InChI=1S/C22H32O8/c1-11(2)6-16(24)29-14-8-21(9-27-13(4)23)15(7-12(14)3)30-19-17(25)18(26)20(21,5)22(19)10-28-22/h7,11,14-15,17-19,25-26H,6,8-10H2,1-5H3/t14-,15+,17+,18+,19+,20+,21+,22+/m0/s1 |
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| InChI Key | PNKLMTPXERFKEN-ZIOSACBISA-N |
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| Experimental Spectra |
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| Not Available | | Predicted Spectra |
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| Not Available | | Chemical Shift Submissions |
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| Not Available | | Species |
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| Species of Origin | |
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| Chemical Taxonomy |
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| Description | 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. |
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| Kingdom | Organic compounds |
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| Super Class | Lipids and lipid-like molecules |
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| Class | Prenol lipids |
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| Sub Class | Sesquiterpenoids |
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| Direct Parent | Trichothecenes |
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| Alternative Parents | |
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| Substituents | - Trichothecene skeleton
- Fatty acid ester
- Oxepane
- Fatty acyl
- Dicarboxylic acid or derivatives
- Oxane
- Cyclic alcohol
- Carboxylic acid ester
- 1,2-diol
- Secondary alcohol
- Ether
- Oxirane
- Organoheterocyclic compound
- Dialkyl ether
- Oxacycle
- Carboxylic acid derivative
- Organooxygen compound
- Hydrocarbon derivative
- Organic oxide
- Carbonyl group
- Organic oxygen compound
- Alcohol
- Aliphatic heteropolycyclic compound
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| Molecular Framework | Aliphatic heteropolycyclic compounds |
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| External Descriptors | Not Available |
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| Physical Properties |
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| State | Not Available |
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| Experimental Properties | | Property | Value | Reference |
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| Melting Point | Not Available | Not Available | | Boiling Point | Not Available | Not Available | | Water Solubility | Not Available | Not Available | | LogP | Not Available | Not Available |
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| Predicted Properties | |
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| General References | - Jia Y, Shi S, Cheng B, Cheng S, Liu L, Meng P, Yang X, Chu X, Wen Y, Zhang F, Guo X: Fluorine impairs carboxylesterase 1-mediated hydrolysis of T-2 toxin and increases its chondrocyte toxicity. Front Nutr. 2022 Aug 3;9:935112. doi: 10.3389/fnut.2022.935112. eCollection 2022. [PubMed:35990316 ]
- Keskin E, Eyupoglu OE: Determination of mycotoxins by HPLC, LC-MS/MS and health risk assessment of the mycotoxins in bee products of Turkey. Food Chem. 2023 Jan 30;400:134086. doi: 10.1016/j.foodchem.2022.134086. Epub 2022 Sep 5. [PubMed:36075166 ]
- Wang X, Liu C, van der Fels-Klerx HJ: Regional prediction of multi-mycotoxin contamination of wheat in Europe using machine learning. Food Res Int. 2022 Sep;159:111588. doi: 10.1016/j.foodres.2022.111588. Epub 2022 Jun 27. [PubMed:35940788 ]
- Sarkar R, Shinde R, Dhanshetty M, Banerjee K: Multi-mycotoxin analysis method using liquid chromatography with tandem mass spectrometry and fluorescence detection in Indian medicinal herbs: Development and validation. J Chromatogr A. 2022 Aug 16;1677:463310. doi: 10.1016/j.chroma.2022.463310. Epub 2022 Jul 8. [PubMed:35853424 ]
- LOTUS database [Link]
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