Record Information
Version1.0
Creation date2010-04-08 22:11:35 UTC
Update date2019-11-26 03:11:04 UTC
Primary IDFDB014986
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameAcetyldeoxynivalenol
DescriptionAcetyldeoxynivalenol, also known as 3-acetyl DON, 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. Acetyldeoxynivalenol is an extremely weak basic (essentially neutral) compound (based on its pKa). Acetyldeoxynivalenol is a potentially toxic compound.
CAS Number50722-38-8
Structure
Thumb
Synonyms
SynonymSource
3-Acetyl DONHMDB
3-AcetyldeoxynivalenolHMDB
Dehydronivalenol monoacetateHMDB
Deoxynivalenol monoacetateHMDB
AcetylDONHMDB
3'-Hydroxy-2'-(hydroxymethyl)-1',5'-dimethyl-4'-oxo-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0²,⁷]dodecan]-5'-en-10'-yl acetic acidGenerator
3-Acetyl donbiospider
3-acetyldeoxynivalenolbiospider
Acetyldeoxynivalenoldb_source
Predicted Properties
PropertyValueSource
Water Solubility5.99 g/LALOGPS
logP-0.61ALOGPS
logP-0.53ChemAxon
logS-1.8ALOGPS
pKa (Strongest Acidic)12.75ChemAxon
pKa (Strongest Basic)-2.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area105.59 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity80.77 m³·mol⁻¹ChemAxon
Polarizability33.55 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC17H22O7
IUPAC name3'-hydroxy-2'-(hydroxymethyl)-1',5'-dimethyl-4'-oxo-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0²,⁷]dodecan]-5'-en-10'-yl acetate
InChI IdentifierInChI=1S/C17H22O7/c1-8-4-11-16(6-18,13(21)12(8)20)15(3)5-10(23-9(2)19)14(24-11)17(15)7-22-17/h4,10-11,13-14,18,21H,5-7H2,1-3H3
InChI KeyADFIQZBYNGPCGY-UHFFFAOYSA-N
Isomeric SMILESCC(=O)OC1CC2(C)C3(CO3)C1OC1C=C(C)C(=O)C(O)C21CO
Average Molecular Weight338.3524
Monoisotopic Molecular Weight338.136553058
Classification
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
  • Cyclohexenone
  • Oxane
  • Carboxylic acid ester
  • Ketone
  • Secondary alcohol
  • Cyclic ketone
  • Monocarboxylic acid or derivatives
  • Ether
  • Oxirane
  • Dialkyl ether
  • Carboxylic acid derivative
  • Organoheterocyclic compound
  • Oxacycle
  • Carbonyl group
  • Primary alcohol
  • Organic oxide
  • Organic oxygen compound
  • Organooxygen compound
  • Alcohol
  • Hydrocarbon derivative
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Biological location:

Source:

Process

Naturally occurring process:

Role

Biological role:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 60.35%; H 6.55%; O 33.10%DFC
Melting PointMp 185.5-186°DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]D +43 (c, 0.2 in MeOH)DFC
Spectroscopic UV Data[neutral] lmax 220 (e 7100) (MeOH)DFC
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSAcetyldeoxynivalenol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0fc0-9685000000-a41157b6d23e342e41c2Spectrum
Predicted GC-MSAcetyldeoxynivalenol, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00sl-7319500000-dfc010c08fe50763dc33Spectrum
Predicted GC-MSAcetyldeoxynivalenol, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSAcetyldeoxynivalenol, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSAcetyldeoxynivalenol, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSAcetyldeoxynivalenol, TBDMS_2_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSAcetyldeoxynivalenol, TBDMS_2_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSAcetyldeoxynivalenol, "Acetyldeoxynivalenol,2TMS,#1" TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSAcetyldeoxynivalenol, TMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSAcetyldeoxynivalenol, TMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSAcetyldeoxynivalenol, TMS_1_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSAcetyldeoxynivalenol, TMS_2_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSAcetyldeoxynivalenol, TMS_2_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSAcetyldeoxynivalenol, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSAcetyldeoxynivalenol, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSAcetyldeoxynivalenol, TBDMS_1_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSAcetyldeoxynivalenol, TBDMS_2_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00g0-0059000000-0575ba57e28e5e6faf89Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00bi-1978000000-05e4adf19bf150ba20afSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fb9-2690000000-00a566c2b765095d32d7Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00g0-0059000000-0575ba57e28e5e6faf89Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00bi-1978000000-05e4adf19bf150ba20afSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fb9-2690000000-00a566c2b765095d32d7Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-2049000000-7fa8366f42fafeaf11dfSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0aos-3396000000-2a6bc6a3d399b2084c87Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052o-5900000000-1712b7cd5cd0ab353c0fSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-2049000000-7fa8366f42fafeaf11dfSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0aos-3396000000-2a6bc6a3d399b2084c87Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052o-5900000000-1712b7cd5cd0ab353c0fSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0009000000-de819ae41779936fff4dSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05n4-0094000000-a3dd225710e5c4f81ee8Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0f6x-9182000000-26fabb5a5d0a59d67397Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000j-0079000000-640229692c86b9dd9c85Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-9083000000-57219594fa23ea18c830Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9252000000-660921396a2be2357e87Spectrum
NMRNot Available
ChemSpider ID94569
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID104759
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB36137
CRC / DFC (Dictionary of Food Compounds) IDJXX18-T:JXS02-L
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference