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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 20:09:00 UTC
Update Date2022-03-07 02:54:24 UTC
HMDB IDHMDB0035201
Secondary Accession Numbers
  • HMDB35201
Metabolite Identification
Common Name4,8-Diacetyl-T2-tetrol
Description4,8-Diacetyl-T2-tetrol, also known as NT 1 or isoneosolaniol, 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. 4,8-Diacetyl-T2-tetrol is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Data?1563862682
Synonyms
ValueSource
IsoneosolaniolHMDB
NT 1HMDB
NT 1 ToxinHMDB
Toxin NT 1HMDB
Toxin NT-1HMDB
Toxin T 1HMDB
Toxin T1HMDB
4'-(Acetyloxy)-10'-hydroxy-2'-(hydroxymethyl)-1',5'-dimethyl-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0²,⁷]dodecan]-5'-en-11'-yl acetic acidGenerator
4 beta, 8 alpha-Diacetoxy-12,13-epoxytrichothec-9-ene-3 alpha,15-diolMeSH
Chemical FormulaC19H26O8
Average Molecular Weight382.4049
Monoisotopic Molecular Weight382.162767808
IUPAC Name4'-(acetyloxy)-10'-hydroxy-2'-(hydroxymethyl)-1',5'-dimethyl-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0²,⁷]dodecan]-5'-en-11'-yl acetate
Traditional Name4'-(acetyloxy)-10'-hydroxy-2'-(hydroxymethyl)-1',5'-dimethyl-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0²,⁷]dodecan]-5'-en-11'-yl acetate
CAS Registry Number65180-29-2
SMILES
CC(=O)OC1C(O)C2OC3C=C(C)C(CC3(CO)C1(C)C21CO1)OC(C)=O
InChI Identifier
InChI=1S/C19H26O8/c1-9-5-13-18(7-20,6-12(9)25-10(2)21)17(4)15(26-11(3)22)14(23)16(27-13)19(17)8-24-19/h5,12-16,20,23H,6-8H2,1-4H3
InChI KeyUROCTWOJYLMRHO-UHFFFAOYSA-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 Parents
Substituents
  • Trichothecene skeleton
  • Oxepane
  • Dicarboxylic acid or derivatives
  • Oxane
  • Cyclic alcohol
  • Secondary alcohol
  • Carboxylic acid ester
  • Oxacycle
  • Ether
  • Oxirane
  • Dialkyl ether
  • Carboxylic acid derivative
  • Organoheterocyclic compound
  • Primary alcohol
  • Hydrocarbon derivative
  • Organic oxide
  • Organooxygen compound
  • Organic oxygen compound
  • Alcohol
  • Carbonyl group
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
Process
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point172.5 - 173.5 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility2.54 g/LALOGPS
logP0.44ALOGPS
logP-0.85ChemAxon
logS-2.2ALOGPS
pKa (Strongest Acidic)13.07ChemAxon
pKa (Strongest Basic)-2.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area114.82 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity90.62 m³·mol⁻¹ChemAxon
Polarizability38.35 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+186.66831661259
DarkChem[M-H]-179.25331661259
DeepCCS[M-2H]-214.82630932474
DeepCCS[M+Na]+190.05330932474
AllCCS[M+H]+188.332859911
AllCCS[M+H-H2O]+185.832859911
AllCCS[M+NH4]+190.732859911
AllCCS[M+Na]+191.332859911
AllCCS[M-H]-191.932859911
AllCCS[M+Na-2H]-192.232859911
AllCCS[M+HCOO]-192.632859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
4,8-Diacetyl-T2-tetrolCC(=O)OC1C(O)C2OC3C=C(C)C(CC3(CO)C1(C)C21CO1)OC(C)=O3901.3Standard polar33892256
4,8-Diacetyl-T2-tetrolCC(=O)OC1C(O)C2OC3C=C(C)C(CC3(CO)C1(C)C21CO1)OC(C)=O2530.5Standard non polar33892256
4,8-Diacetyl-T2-tetrolCC(=O)OC1C(O)C2OC3C=C(C)C(CC3(CO)C1(C)C21CO1)OC(C)=O2685.5Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
4,8-Diacetyl-T2-tetrol,1TMS,isomer #1CC(=O)OC1CC2(CO)C(C=C1C)OC1C(O[Si](C)(C)C)C(OC(C)=O)C2(C)C12CO22571.5Semi standard non polar33892256
4,8-Diacetyl-T2-tetrol,1TMS,isomer #2CC(=O)OC1CC2(CO[Si](C)(C)C)C(C=C1C)OC1C(O)C(OC(C)=O)C2(C)C12CO22546.4Semi standard non polar33892256
4,8-Diacetyl-T2-tetrol,2TMS,isomer #1CC(=O)OC1CC2(CO[Si](C)(C)C)C(C=C1C)OC1C(O[Si](C)(C)C)C(OC(C)=O)C2(C)C12CO22562.8Semi standard non polar33892256
4,8-Diacetyl-T2-tetrol,1TBDMS,isomer #1CC(=O)OC1CC2(CO)C(C=C1C)OC1C(O[Si](C)(C)C(C)(C)C)C(OC(C)=O)C2(C)C12CO22810.4Semi standard non polar33892256
4,8-Diacetyl-T2-tetrol,1TBDMS,isomer #2CC(=O)OC1CC2(CO[Si](C)(C)C(C)(C)C)C(C=C1C)OC1C(O)C(OC(C)=O)C2(C)C12CO22787.4Semi standard non polar33892256
4,8-Diacetyl-T2-tetrol,2TBDMS,isomer #1CC(=O)OC1CC2(CO[Si](C)(C)C(C)(C)C)C(C=C1C)OC1C(O[Si](C)(C)C(C)(C)C)C(OC(C)=O)C2(C)C12CO23043.2Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 4,8-Diacetyl-T2-tetrol GC-MS (Non-derivatized) - 70eV, Positivesplash10-0ac4-2697000000-7c9c4165f00398def9ba2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4,8-Diacetyl-T2-tetrol GC-MS (2 TMS) - 70eV, Positivesplash10-0udl-3069510000-bcd3bfeead9609e6fa262017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4,8-Diacetyl-T2-tetrol 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 - 4,8-Diacetyl-T2-tetrol 10V, Positive-QTOFsplash10-00yl-0009000000-4a8811890c925b09e4e02015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4,8-Diacetyl-T2-tetrol 20V, Positive-QTOFsplash10-00di-0219000000-dedf3280ed246d0bee0d2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4,8-Diacetyl-T2-tetrol 40V, Positive-QTOFsplash10-008a-3296000000-be9fbb6d9713ee622b3e2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4,8-Diacetyl-T2-tetrol 10V, Negative-QTOFsplash10-008i-1009000000-ce0713ed8bebd6258d092015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4,8-Diacetyl-T2-tetrol 20V, Negative-QTOFsplash10-0abi-2119000000-e27a05b759195273b0922015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4,8-Diacetyl-T2-tetrol 40V, Negative-QTOFsplash10-0a4i-6900000000-d5115259f05431013b9b2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4,8-Diacetyl-T2-tetrol 10V, Negative-QTOFsplash10-0a59-7009000000-e40f70e205c39a6d7bcd2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4,8-Diacetyl-T2-tetrol 20V, Negative-QTOFsplash10-0a4i-9000000000-16136d19660877190b492021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4,8-Diacetyl-T2-tetrol 40V, Negative-QTOFsplash10-052r-9023000000-ea83f892b6c75195ddc02021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4,8-Diacetyl-T2-tetrol 10V, Positive-QTOFsplash10-00di-0009000000-ff1d6a000948010607f42021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4,8-Diacetyl-T2-tetrol 20V, Positive-QTOFsplash10-05uu-1029000000-5ff9a18963d4560078d92021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4,8-Diacetyl-T2-tetrol 40V, Positive-QTOFsplash10-014i-9612000000-92d17d5c2f6eeaac9be72021-09-22Wishart 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 IDFDB013847
KNApSAcK IDC00012639
Chemspider ID8198344
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound10022771
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.