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Record Information
Version2.0
Created at2022-04-28 04:24:49 UTC
Updated at2022-04-28 04:24:49 UTC
NP-MRD IDNP0059138
Secondary Accession NumbersNone
Natural Product Identification
Common Name(3alpha,4beta,7alpha,8alpha)-12,13-Epoxytrichothec-9-ene-3,4,7,8,15-pentol 4,15-diacetate
Description[(1'S,2R,2'S,3'R,4'S,7'R,9'R,10'R,11'S)-11'-(acetyloxy)-3',4',10'-trihydroxy-1',5'-dimethyl-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0²,⁷]Dodecan]-5'-en-2'-yl]methyl acetate 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. (3alpha,4beta,7alpha,8alpha)-12,13-Epoxytrichothec-9-ene-3,4,7,8,15-pentol 4,15-diacetate is found in Fusarium spp. Based on a literature review very few articles have been published on [(1'S,2R,2'S,3'R,4'S,7'R,9'R,10'R,11'S)-11'-(acetyloxy)-3',4',10'-trihydroxy-1',5'-dimethyl-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0²,⁷]Dodecan]-5'-en-2'-yl]methyl acetate.
Structure
Thumb
Synonyms
ValueSource
[(1's,2R,2's,3'r,4's,7'r,9'r,10'r,11's)-11'-(Acetyloxy)-3',4',10'-trihydroxy-1',5'-dimethyl-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0,]dodecan]-5'-en-2'-yl]methyl acetic acidGenerator
Chemical FormulaC19H26O9
Average Mass398.4080 Da
Monoisotopic Mass398.15768 Da
IUPAC Name[(1'S,2R,2'S,3'R,4'S,7'R,9'R,10'R,11'S)-11'-(acetyloxy)-3',4',10'-trihydroxy-1',5'-dimethyl-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0^{2,7}]dodecan]-5'-en-2'-yl]methyl acetate
Traditional Name(1'S,2R,2'S,3'R,4'S,7'R,9'R,10'R,11'S)-11'-(acetyloxy)-3',4',10'-trihydroxy-1',5'-dimethyl-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0^{2,7}]dodecan]-5'-en-2'-ylmethyl acetate
CAS Registry NumberNot Available
SMILES
CC(=O)OC[C@@]12[C@@H](O)[C@@H](O)C(C)=C[C@H]1O[C@@H]1[C@H](O)[C@@H](OC(C)=O)[C@@]2(C)[C@@]11CO1
InChI Identifier
InChI=1S/C19H26O9/c1-8-5-11-18(6-25-9(2)20,14(24)12(8)22)17(4)15(27-10(3)21)13(23)16(28-11)19(17)7-26-19/h5,11-16,22-24H,6-7H2,1-4H3/t11-,12+,13-,14+,15-,16-,17-,18+,19-/m1/s1
InChI KeyARKWUSFUCGIADI-SAVCMUSFSA-N
Experimental Spectra
Not Available
Predicted Spectra
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Fusarium spp.Fungi
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
  • Oxepane
  • Oxane
  • Dicarboxylic acid or derivatives
  • Cyclic alcohol
  • Secondary alcohol
  • Carboxylic acid ester
  • Oxacycle
  • Organoheterocyclic compound
  • Polyol
  • Ether
  • Oxirane
  • Dialkyl ether
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • 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
logP-0.12ALOGPS
logP-1.8ChemAxon
logS-1.7ALOGPS
pKa (Strongest Acidic)12.85ChemAxon
pKa (Strongest Basic)-3.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area135.05 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity91.82 m³·mol⁻¹ChemAxon
Polarizability39.11 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound162984919
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General ReferencesNot Available