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Record Information
Version2.0
Created at2022-09-09 11:03:52 UTC
Updated at2022-09-09 11:03:52 UTC
NP-MRD IDNP0283698
Secondary Accession NumbersNone
Natural Product Identification
Common Name(1's,2s,2'r,3's,7'r,9'r,10'r,11's)-11'-(acetyloxy)-3',10'-dihydroxy-1',5'-dimethyl-4'-oxo-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0²,⁷]dodecan]-5'-en-2'-ylmethyl acetate
DescriptionNivalenol diacetate, also known as 4,15-diacetylnivalenol or DNIV, 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,2s,2'r,3's,7'r,9'r,10'r,11's)-11'-(acetyloxy)-3',10'-dihydroxy-1',5'-dimethyl-4'-oxo-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0²,⁷]dodecan]-5'-en-2'-ylmethyl acetate is found in Fusarium culmorum. (1's,2s,2'r,3's,7'r,9'r,10'r,11's)-11'-(acetyloxy)-3',10'-dihydroxy-1',5'-dimethyl-4'-oxo-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0²,⁷]dodecan]-5'-en-2'-ylmethyl acetate was first documented in 1970 (PMID: 5453976). Based on a literature review very few articles have been published on Nivalenol diacetate.
Structure
Thumb
Synonyms
ValueSource
Nivalenol diacetic acidGenerator
4,15-DiacetylnivalenolMeSH
DNIVMeSH
Chemical FormulaC19H24O9
Average Mass396.3920 Da
Monoisotopic Mass396.14203 Da
IUPAC Name[(1'S,2S,2'R,3'S,7'R,9'R,10'R,11'S)-11'-(acetyloxy)-3',10'-dihydroxy-1',5'-dimethyl-4'-oxo-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0^{2,7}]dodecan]-5'-en-2'-yl]methyl acetate
Traditional Name(1'S,2S,2'R,3'S,7'R,9'R,10'R,11'S)-11'-(acetyloxy)-3',10'-dihydroxy-1',5'-dimethyl-4'-oxo-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(=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/C19H24O9/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/h5,11,13-16,23-24H,6-7H2,1-4H3/t11-,13-,14-,15-,16-,17-,18-,19+/m1/s1
InChI KeyPIHGROVBUUNPDW-OHQJEHTLSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Fusarium culmorumLOTUS 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
  • Cyclohexenone
  • Oxepane
  • Dicarboxylic acid or derivatives
  • Oxane
  • Cyclic alcohol
  • Carboxylic acid ester
  • Ketone
  • Secondary alcohol
  • Cyclic ketone
  • Ether
  • Oxirane
  • Dialkyl ether
  • Oxacycle
  • Organoheterocyclic compound
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organic oxide
  • Organic oxygen compound
  • Alcohol
  • Carbonyl group
  • 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-1ChemAxon
pKa (Strongest Acidic)12.58ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area131.89 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity91.13 m³·mol⁻¹ChemAxon
Polarizability38.13 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 IDC00012635
Chemspider ID19976657
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound21118291
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Tatsuno T, Morita Y, Tsunoda H, Umeda M: [Toxicologic studies of the metabolic substances of Fusarium nivale. VII. The 3rd metabolic substance of F. nivale, nivalenol diacetate]. Chem Pharm Bull (Tokyo). 1970 Jul;18(7):1485-7. [PubMed:5453976 ]
  2. LOTUS database [Link]