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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 20:02:52 UTC
Update Date2019-01-11 19:49:34 UTC
HMDB IDHMDB0035104
Secondary Accession Numbers
  • HMDB35104
Metabolite Identification
Common NameDiacetoxyscirpenol
DescriptionDiacetoxyscirpenol is a constituent of Fusarium species Mycotoxin
Structure
Data?1547236174
Synonyms
ValueSource
4, 15-Diacetoxyscirpen-3-olHMDB
4,15-Di-O-acetylscirpenolHMDB
4,15-Diacetoxyscirp-9-en-3-olHMDB
4,15-Diacetoxyscirpen-3-olHMDB
4,15-DiacetoxyscirpenolHMDB
4alpha-Hydroxy-12,13-epoxytrichothec-9-eneHMDB
ANG 66HMDB
AnguidinHMDB
AnguidineHMDB
Anguidine analog diacetoxyscirpenolHMDB
DiazetoxyskirpenolHMDB
NSC 141537HMDB
Scirp-9-ene-3alpha,4beta,15-triol, 4,15-diacetateHMDB
Scirpenetriol 4,15-diacetateHMDB
Trichothec-9-ene-3,4,15-triol, 12,13-epoxy-, 4,15-diacetateHMDB
Chemical FormulaC19H26O7
Average Molecular Weight366.4055
Monoisotopic Molecular Weight366.167853186
IUPAC Name11'-(acetyloxy)-10'-hydroxy-1',5'-dimethyl-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0²,⁷]dodecan]-5'-en-2'-ylmethyl acetate
Traditional Namediacetoxyscirpenol
CAS Registry Number2270-40-8
SMILES
CC(=O)OCC12CCC(C)=CC1OC1C(O)C(OC(C)=O)C2(C)C11CO1
InChI Identifier
InChI=1S/C19H26O7/c1-10-5-6-18(8-23-11(2)20)13(7-10)26-16-14(22)15(25-12(3)21)17(18,4)19(16)9-24-19/h7,13-16,22H,5-6,8-9H2,1-4H3
InChI KeyAUGQEEXBDZWUJY-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound 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
  • Dicarboxylic acid or derivatives
  • Oxane
  • Cyclic alcohol
  • Carboxylic acid ester
  • Secondary alcohol
  • Carboxylic acid derivative
  • Dialkyl ether
  • Oxirane
  • Ether
  • Oxacycle
  • Organoheterocyclic compound
  • Hydrocarbon derivative
  • Carbonyl group
  • Alcohol
  • Organooxygen compound
  • Organic oxygen compound
  • Organic oxide
  • 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:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point161 - 162 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility1.03 g/LALOGPS
logP1.03ALOGPS
logP0.38ChemAxon
logS-2.6ALOGPS
pKa (Strongest Acidic)13.07ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area94.59 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity89.1 m³·mol⁻¹ChemAxon
Polarizability37.39 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-03dl-2592000000-16f4741dd58f1f85bc7eView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-03di-7394100000-ab75df657e170290fbebView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0ar0-0019000000-9bebdb0b538385dbe8edView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0aor-1559000000-edcde62355aabd0612c4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-02ta-6392000000-dad5b393198b429ebf39View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-01b9-2009000000-f394e8aa968e190568f9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-7419000000-8da1fcc85358f3e68229View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-6900000000-c84c06511eac299b6402View in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB013733
KNApSAcK IDC00003129
Chemspider ID373646
KEGG Compound IDC09662
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkDiacetoxyscirpenol
METLIN IDNot Available
PubChem Compound422111
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  2. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  3. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  4. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  5. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
  6. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.