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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 22:17:58 UTC
Update Date2022-03-07 02:55:10 UTC
HMDB IDHMDB0037056
Secondary Accession Numbers
  • HMDB37056
Metabolite Identification
Common Name8-Oxodiacetoxyscirpenol
Description8-Oxodiacetoxyscirpenol 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. 8-Oxodiacetoxyscirpenol is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Data?1563862970
Synonyms
ValueSource
(3alpha,4beta)-4,15-Bis(acetyloxy)-12,13-epoxy-3-hydroxytrichothec-9-en-8-oneHMDB
4,15-Diacetyl-7-deoxynivalenolHMDB
[(2'r,7'r,9'r,10'r,11's)-11'-(Acetyloxy)-10'-hydroxy-1',5'-dimethyl-4'-oxo-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0²,⁷]dodecan]-5'-en-2'-yl]methyl acetic acidGenerator
Chemical FormulaC19H24O8
Average Molecular Weight380.3891
Monoisotopic Molecular Weight380.147117744
IUPAC Name(2'R,7'R,9'R,10'R,11'S)-11'-(acetyloxy)-10'-hydroxy-1',5'-dimethyl-4'-oxo-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0²,⁷]dodecan]-5'-en-2'-ylmethyl acetate
Traditional Name(2'R,7'R,9'R,10'R,11'S)-11'-(acetyloxy)-10'-hydroxy-1',5'-dimethyl-4'-oxo-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0²,⁷]dodecan]-5'-en-2'-ylmethyl acetate
CAS Registry Number77620-47-4
SMILES
[H][C@@]12O[C@]3([H])C=C(C)C(=O)C[C@]3(COC(C)=O)C(C)([C@H](OC(C)=O)[C@H]1O)C21CO1
InChI Identifier
InChI=1S/C19H24O8/c1-9-5-13-18(6-12(9)22,7-24-10(2)20)17(4)15(26-11(3)21)14(23)16(27-13)19(17)8-25-19/h5,13-16,23H,6-8H2,1-4H3/t13-,14-,15-,16-,17?,18-,19?/m1/s1
InChI KeyFAQMCKSIBZGZIB-WGTJCWDGSA-N
Chemical Taxonomy
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 ParentsNot Available
SubstituentsNot Available
Molecular FrameworkAliphatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
Process
Role
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility2.05 g/LALOGPS
logP0.16ALOGPS
logP-0.29ChemAxon
logS-2.3ALOGPS
pKa (Strongest Acidic)13.07ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area111.66 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity89.79 m³·mol⁻¹ChemAxon
Polarizability37.48 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+186.4931661259
DarkChem[M-H]-181.73631661259
DeepCCS[M-2H]-211.68730932474
DeepCCS[M+Na]+187.11130932474
AllCCS[M+H]+186.132859911
AllCCS[M+H-H2O]+183.632859911
AllCCS[M+NH4]+188.532859911
AllCCS[M+Na]+189.232859911
AllCCS[M-H]-191.532859911
AllCCS[M+Na-2H]-191.632859911
AllCCS[M+HCOO]-191.932859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
8-Oxodiacetoxyscirpenol[H][C@@]12O[C@]3([H])C=C(C)C(=O)C[C@]3(COC(C)=O)C(C)([C@H](OC(C)=O)[C@H]1O)C21CO14100.6Standard polar33892256
8-Oxodiacetoxyscirpenol[H][C@@]12O[C@]3([H])C=C(C)C(=O)C[C@]3(COC(C)=O)C(C)([C@H](OC(C)=O)[C@H]1O)C21CO12343.1Standard non polar33892256
8-Oxodiacetoxyscirpenol[H][C@@]12O[C@]3([H])C=C(C)C(=O)C[C@]3(COC(C)=O)C(C)([C@H](OC(C)=O)[C@H]1O)C21CO12616.9Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
8-Oxodiacetoxyscirpenol,1TMS,isomer #1CC(=O)OC[C@]12CC(=O)C(C)=C[C@H]1O[C@@H]1[C@H](O[Si](C)(C)C)[C@@H](OC(C)=O)C2(C)C12CO22586.7Semi standard non polar33892256
8-Oxodiacetoxyscirpenol,1TMS,isomer #2CC(=O)OC[C@]12C=C(O[Si](C)(C)C)C(C)=C[C@H]1O[C@@H]1[C@H](O)[C@@H](OC(C)=O)C2(C)C12CO22606.8Semi standard non polar33892256
8-Oxodiacetoxyscirpenol,2TMS,isomer #1CC(=O)OC[C@]12C=C(O[Si](C)(C)C)C(C)=C[C@H]1O[C@@H]1[C@H](O[Si](C)(C)C)[C@@H](OC(C)=O)C2(C)C12CO22633.4Semi standard non polar33892256
8-Oxodiacetoxyscirpenol,2TMS,isomer #1CC(=O)OC[C@]12C=C(O[Si](C)(C)C)C(C)=C[C@H]1O[C@@H]1[C@H](O[Si](C)(C)C)[C@@H](OC(C)=O)C2(C)C12CO22629.8Standard non polar33892256
8-Oxodiacetoxyscirpenol,1TBDMS,isomer #1CC(=O)OC[C@]12CC(=O)C(C)=C[C@H]1O[C@@H]1[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](OC(C)=O)C2(C)C12CO22804.4Semi standard non polar33892256
8-Oxodiacetoxyscirpenol,1TBDMS,isomer #2CC(=O)OC[C@]12C=C(O[Si](C)(C)C(C)(C)C)C(C)=C[C@H]1O[C@@H]1[C@H](O)[C@@H](OC(C)=O)C2(C)C12CO22847.8Semi standard non polar33892256
8-Oxodiacetoxyscirpenol,2TBDMS,isomer #1CC(=O)OC[C@]12C=C(O[Si](C)(C)C(C)(C)C)C(C)=C[C@H]1O[C@@H]1[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](OC(C)=O)C2(C)C12CO23096.6Semi standard non polar33892256
8-Oxodiacetoxyscirpenol,2TBDMS,isomer #1CC(=O)OC[C@]12C=C(O[Si](C)(C)C(C)(C)C)C(C)=C[C@H]1O[C@@H]1[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](OC(C)=O)C2(C)C12CO23013.1Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 8-Oxodiacetoxyscirpenol GC-MS (Non-derivatized) - 70eV, Positivesplash10-004l-9276000000-d6ed3dc847737cb7b64b2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 8-Oxodiacetoxyscirpenol GC-MS (1 TMS) - 70eV, Positivesplash10-004i-8093100000-88cb63e6391e0374e78a2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 8-Oxodiacetoxyscirpenol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 8-Oxodiacetoxyscirpenol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8-Oxodiacetoxyscirpenol 10V, Positive-QTOFsplash10-008i-0009000000-272edc2f63f59664fb372016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8-Oxodiacetoxyscirpenol 20V, Positive-QTOFsplash10-0fk9-0239000000-1e6dda4f5041f38018a52016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8-Oxodiacetoxyscirpenol 40V, Positive-QTOFsplash10-004i-3294000000-8bfb63f511ceb0d0914b2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8-Oxodiacetoxyscirpenol 10V, Negative-QTOFsplash10-004r-2009000000-469c982ceb03adee2d6f2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8-Oxodiacetoxyscirpenol 20V, Negative-QTOFsplash10-0a70-7319000000-5f3134de0154c54dc2c02016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8-Oxodiacetoxyscirpenol 40V, Negative-QTOFsplash10-0a4i-6900000000-23269370b8999519ad342016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8-Oxodiacetoxyscirpenol 10V, Positive-QTOFsplash10-00e9-0009000000-e9f0dd021c25733bc2382021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8-Oxodiacetoxyscirpenol 20V, Positive-QTOFsplash10-074i-0079000000-31e9de625d1ee15da62c2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8-Oxodiacetoxyscirpenol 40V, Positive-QTOFsplash10-002o-5957000000-fd7d9677be16abd0d0552021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8-Oxodiacetoxyscirpenol 10V, Negative-QTOFsplash10-056r-3019000000-cd7c79c764c69c7abd062021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8-Oxodiacetoxyscirpenol 20V, Negative-QTOFsplash10-0a4i-9005000000-7b45340cf6d9899a02212021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8-Oxodiacetoxyscirpenol 40V, Negative-QTOFsplash10-054n-8139000000-e325f105c5e6f2f8bfbc2021-09-22Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
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
FooDB IDFDB016039
KNApSAcK IDC00012641
Chemspider ID292181
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound131752136
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents 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.