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Record Information
Version2.0
Created at2022-09-12 04:10:44 UTC
Updated at2022-09-12 04:10:44 UTC
NP-MRD IDNP0324230
Secondary Accession NumbersNone
Natural Product Identification
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
DescriptionHT-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).
Structure
Thumb
Synonyms
ValueSource
3,4-Dihydroxy-15-acetoxy-8-(3-methylbutyryloxy)-12,13-epoxy-delta9-trichotheceneMeSH
Toxin HT 2MeSH
Chemical FormulaC22H32O8
Average Mass424.4900 Da
Monoisotopic Mass424.20972 Da
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
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
CAS Registry NumberNot Available
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
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
InChI KeyPNKLMTPXERFKEN-ZIOSACBISA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Fusarium heterosporumLOTUS Database
Fusarium sporotrichioidesLOTUS Database
Chemical Taxonomy
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.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassSesquiterpenoids
Direct ParentTrichothecenes
Alternative Parents
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
Molecular FrameworkAliphatic heteropolycyclic compounds
External DescriptorsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP0.58ChemAxon
pKa (Strongest Acidic)12.98ChemAxon
pKa (Strongest Basic)-3.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area114.82 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity104.39 m³·mol⁻¹ChemAxon
Polarizability44.28 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDC00012651
Chemspider ID285297
KEGG Compound IDC19952
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound322238
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. 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 ]
  2. 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 ]
  3. 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 ]
  4. 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 ]
  5. LOTUS database [Link]