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Showing Compound 3-Acetoxyscirpene-4,15-diol (FDB013089)

Record Information
Version1.0
Creation date2010-04-08 22:10:31 UTC
Update date2018-05-29 01:02:57 UTC
Primary IDFDB013089
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name3-Acetoxyscirpene-4,15-diol
Description3-Acetoxyscirpene-4,15-diol 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. Based on a literature review a significant number of articles have been published on 3-Acetoxyscirpene-4,15-diol.
CAS Number70402-13-0
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
(3-alpha,4-beta-)-3-Acetoxyscirpene-4,15-diolHMDB
11'-Hydroxy-2'-(hydroxymethyl)-1',5'-dimethyl-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0²,⁷]dodecan]-5'-en-10'-yl acetic acidGenerator
(3a,4b)-3-Acetoxyscirpene-4,15-diolmanual
3-Acetoxyscirpene-4,15-diolbiospider
Predicted Properties
PropertyValueSource
Water Solubility4.41 g/LALOGPS
logP0.53ALOGPS
logP-0.064ChemAxon
logS-1.9ALOGPS
pKa (Strongest Acidic)13.51ChemAxon
pKa (Strongest Basic)-2.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area88.52 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity79.95 m³·mol⁻¹ChemAxon
Polarizability33.44 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC17H24O6
IUPAC name11'-hydroxy-2'-(hydroxymethyl)-1',5'-dimethyl-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0²,⁷]dodecan]-5'-en-10'-yl acetate
InChI IdentifierInChI=1S/C17H24O6/c1-9-4-5-16(7-18)11(6-9)23-14-12(22-10(2)19)13(20)15(16,3)17(14)8-21-17/h6,11-14,18,20H,4-5,7-8H2,1-3H3
InChI KeyNFFRTZSZVQIMDJ-UHFFFAOYSA-N
Isomeric SMILESCC(=O)OC1C(O)C2(C)C3(CO3)C1OC1C=C(C)CCC21CO
Average Molecular Weight324.3689
Monoisotopic Molecular Weight324.1572885
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
  • Oxane
  • Cyclic alcohol
  • Carboxylic acid ester
  • Secondary alcohol
  • Oxacycle
  • Carboxylic acid derivative
  • Organoheterocyclic compound
  • Dialkyl ether
  • Oxirane
  • Ether
  • Monocarboxylic acid or derivatives
  • Carbonyl group
  • Alcohol
  • Organooxygen compound
  • Organic oxygen compound
  • Organic oxide
  • Primary 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
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 62.95%; H 7.46%; O 29.59%DFC
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]D -11.7 (CHCl3)DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MS3-Acetoxyscirpene-4,15-diol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00du-3981000000-4b3d0372bb25dd3c6674Spectrum
Predicted GC-MS3-Acetoxyscirpene-4,15-diol, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-002g-4291200000-377d1cbcbb354bfbdd99Spectrum
Predicted GC-MS3-Acetoxyscirpene-4,15-diol, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-056r-0069000000-4cb5715dfafc9651186f2016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0aor-1494000000-a7912aa2bd1e4b1b706c2016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014i-9470000000-1bc983cfa72e54e484602016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-2069000000-a3625f03328c7f4a26c32016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-5393000000-af4aba9897b36e553eb92016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9700000000-052d99ea358f2383c4652016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0029000000-ef8f490d2b19b4246c792021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-056r-0098000000-7e9c9a2fe6b2ce0284502021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0k97-8691000000-ccae418670c4f63445f92021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0009000000-fdc1f5bf2fb6e471fcb92021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03k9-0095000000-0fab9f43e4548f091c8a2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0gx0-1090000000-592db9b2f315c39b85cc2021-09-22View Spectrum
NMRNot Available
ChemSpider ID381884
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID431810
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB34576
CRC / DFC (Dictionary of Food Compounds) IDJPF97-A:HOL07-A
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