Back to Compounds

Showing Compound 15-Acetoxyscirpen-3,4-diol (FDB014626)

Record Information
Version1.0
Creation date2010-04-08 22:11:23 UTC
Update date2015-07-20 23:09:36 UTC
Primary IDFDB014626
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name15-Acetoxyscirpen-3,4-diol
DescriptionMonoacetoxyscirpenol 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 Monoacetoxyscirpenol.
CAS Number2623-22-5
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
15-Acetoxyscirpen-3,4-diolMeSH
15-AcetoxyscirpendiolHMDB
15-AcetoxyscirpenolHMDB
15-AcetylscirpenetriolHMDB
15-mono-O-AcetylscirpenolHMDB
15-O-AcetylscirpenetriolHMDB
4-DeacetylanguidinHMDB
ANGUIDINE, desacetyl(15-acetoxyscirpene-3,4-diol-BL5732)HMDB
DeacetylanguidinHMDB
DesacetylanguidineHMDB
{10',11'-dihydroxy-1',5'-dimethyl-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0²,⁷]dodecan]-5'-en-2'-yl}methyl acetic acidGenerator
MonoacetoxyscirpenolMeSH
(3a,4b)-15-Acetoxyscirpen-3,4-diolmanual
15-Mono-O-acetylscirpenolbiospider
ANGUIDINE, desacetyl(15-acetoxyscirpene-3,4-diol-bl5732)HMDB
Predicted Properties
PropertyValueSource
Water Solubility4.4 g/LALOGPS
logP0.57ALOGPS
logP-0.064ChemAxon
logS-1.9ALOGPS
pKa (Strongest Acidic)12.98ChemAxon
pKa (Strongest Basic)-3.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area88.52 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity79.95 m³·mol⁻¹ChemAxon
Polarizability33.22 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC17H24O6
IUPAC name10',11'-dihydroxy-1',5'-dimethyl-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0²,⁷]dodecan]-5'-en-2'-ylmethyl acetate
InChI IdentifierInChI=1S/C17H24O6/c1-9-4-5-16(7-21-10(2)18)11(6-9)23-14-12(19)13(20)15(16,3)17(14)8-22-17/h6,11-14,19-20H,4-5,7-8H2,1-3H3
InChI KeyIRXDUBNENLKYTC-UHFFFAOYSA-N
Isomeric SMILESCC(=O)OCC12CCC(C)=CC1OC1C(O)C(O)C2(C)C11CO1
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
  • 1,2-diol
  • Carboxylic acid ester
  • Secondary alcohol
  • Monocarboxylic acid or derivatives
  • Ether
  • Oxirane
  • Dialkyl ether
  • Carboxylic acid derivative
  • Oxacycle
  • Organoheterocyclic compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organooxygen compound
  • Organic oxygen compound
  • Alcohol
  • Carbonyl group
  • 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

Environmental 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 PointMp 172-173°DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]D -25 (CHCl3)DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-0a4l-7910000000-ee625a230f247ef2a1b92014-09-20View Spectrum
Predicted GC-MS15-Acetoxyscirpen-3,4-diol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0006-8983000000-2b3ece0fc071e0a02ae9Spectrum
Predicted GC-MS15-Acetoxyscirpen-3,4-diol, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0uml-9457500000-f0e1f929dc06f83e63b1Spectrum
Predicted GC-MS15-Acetoxyscirpen-3,4-diol, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS15-Acetoxyscirpen-3,4-diol, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00or-1069000000-8a4acc9ad6cac1bfcdab2015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-066r-1692000000-99bcb7b55345010c80a62015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014m-9750000000-f52ad6fdbbd8ca8364c12015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-3029000000-24597e127f3228e2aac52015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4l-9445000000-1e097d94c61293160cca2015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-1001-9800000000-44db093f8409c92cb2522015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0092000000-b8bd80fe17ca733ae85a2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-1091000000-e2b4db216b5792f8eeae2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0adl-3795000000-3e73cb01a148dd3b7cac2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0089-2094000000-79008c91e52055b40fa52021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-8090000000-2d13b1b0a398f7c82ecb2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9300000000-9cebaa91e008a17430942021-09-22View Spectrum
NMR
TypeDescriptionView
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
ChemSpider ID380266
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID429922
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB35848
CRC / DFC (Dictionary of Food Compounds) IDJPF97-A:JSZ59-H
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDC00012643
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