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Showing Compound Nivalenol (FDB023361)

Record Information
Version1.0
Creation date2011-09-21 00:28:43 UTC
Update date2015-07-21 06:57:39 UTC
Primary IDFDB023361
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameNivalenol
DescriptionNivalenol is a trichothecene produced by Fusaria, Stachybotrys, Trichoderma and other fungi, and some higher plants. They may contaminate food or feed grains, induce emesis and hemorrhage in lungs and brain, and damage bone marrow due to protein and DNA synthesis inhibition.(PubChem) It has been reported in the urine of patients suffering chronic idiopathic spastic paraparesis. These patients are usually found in hot and humid regions, most of which have heavy rains, and these conditions allow foods to be polluted by fungi some of which become toxigenic (PubMed ID 8855894 ) [HMDB]
CAS Number23282-20-4
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
Predicted Properties
PropertyValueSource
Water Solubility64.6 g/LALOGPS
logP-0.79ALOGPS
logP-1.9ChemAxon
logS-0.68ALOGPS
pKa (Strongest Acidic)12.23ChemAxon
pKa (Strongest Basic)-2.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area119.75 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity72.83 m³·mol⁻¹ChemAxon
Polarizability30.14 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC15H20O7
IUPAC name(1'S,2R,2'R,3'S,7'R,9'R,10'R,11'S)-3',10',11'-trihydroxy-2'-(hydroxymethyl)-1',5'-dimethyl-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0²,⁷]dodecan]-5'-en-4'-one
InChI IdentifierInChI=1S/C15H20O7/c1-6-3-7-14(4-16,11(20)8(6)17)13(2)10(19)9(18)12(22-7)15(13)5-21-15/h3,7,9-12,16,18-20H,4-5H2,1-2H3/t7-,9-,10-,11-,12-,13-,14-,15-/m1/s1
InChI KeyUKOTXHQERFPCBU-YQPARWETSA-N
Isomeric SMILES[H][C@@]12O[C@]3([H])C=C(C)C(=O)[C@@H](O)[C@]3(CO)[C@@](C)([C@H](O)[C@H]1O)[C@@]21CO1
Average Molecular Weight312.3151
Monoisotopic Molecular Weight312.120902994
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
  • Cyclohexenone
  • Oxepane
  • Oxane
  • Cyclic alcohol
  • Ketone
  • Secondary alcohol
  • Cyclic ketone
  • Dialkyl ether
  • Oxirane
  • Ether
  • Oxacycle
  • Polyol
  • Organoheterocyclic compound
  • Organic oxide
  • Carbonyl group
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Alcohol
  • Primary alcohol
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Biological role:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSNivalenol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0kai-6290000000-2911fd296ba057ae09a6Spectrum
Predicted GC-MSNivalenol, 4 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-000i-1022190000-2a675063c4f13c2c2f00Spectrum
Predicted GC-MSNivalenol, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSNivalenol, TBDMS_2_4, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSNivalenol, TBDMS_3_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSNivalenol, TBDMS_3_5, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSNivalenol, TBDMS_3_6, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSNivalenol, TBDMS_4_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSNivalenol, TBDMS_4_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSNivalenol, TBDMS_4_4, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSNivalenol, "Nivalenol,2TBDMS,#4" TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01ot-0095000000-1a5c96aabc3407c96a582017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-054t-0691000000-27d03079b4a3017e4ae62017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004i-4690000000-0e33ef132bad477872252017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0059000000-ff9e3108776ac7ec47e02017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03ec-0291000000-e9bacc0055cfdbc1ce732017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0v0a-7900000000-3fed75622c3dfbbf2ace2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0009000000-8c08f5008f04459cecc52021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-0069000000-31d25081330244050f032021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001l-4970000000-17c950a72b871800b3912021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0009000000-77331bab21c19de7c6e52021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03e9-0097000000-b75a12b7a67f62d1c60b2021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0w30-3292000000-d226ebdf00fdf68ba3742021-09-25View Spectrum
NMRNot Available
ChemSpider ID389738
ChEMBL IDNot Available
KEGG Compound IDC06080
Pubchem Compound ID440908
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB04304
CRC / DFC (Dictionary of Food Compounds) IDNot Available
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
Processing...
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference