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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 20:52:10 UTC
Update Date2022-03-07 02:54:39 UTC
HMDB IDHMDB0035846
Secondary Accession Numbers
  • HMDB35846
Metabolite Identification
Common NameAnguidol
DescriptionAnguidol, also known as scirpenetriol, 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. Anguidol is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Data?1563862781
Synonyms
ValueSource
12,13-Epoxy-trichothec-9-ene-3alpha,4beta,15-triolHMDB
Anguidine deriv scirpentriolHMDB
Scirpene-3,4,15-triolHMDB
ScirpenetriolHMDB
ScirpenolHMDB
ScirpentriolHMDB
T-2 TriolMeSH
3,4,15-Trihydroxy-8-(3-methylbutyryloxy)-1,2,3-epoxytrichothec--9-eneMeSH
Chemical FormulaC15H22O5
Average Molecular Weight282.3322
Monoisotopic Molecular Weight282.146723814
IUPAC Name2'-(hydroxymethyl)-1',5'-dimethyl-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0²,⁷]dodecan]-5'-ene-10',11'-diol
Traditional Name2'-(hydroxymethyl)-1',5'-dimethyl-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0²,⁷]dodecan]-5'-ene-10',11'-diol
CAS Registry Number2270-41-9
SMILES
CC1=CC2OC3C(O)C(O)C(C)(C33CO3)C2(CO)CC1
InChI Identifier
InChI=1S/C15H22O5/c1-8-3-4-14(6-16)9(5-8)20-12-10(17)11(18)13(14,2)15(12)7-19-15/h5,9-12,16-18H,3-4,6-7H2,1-2H3
InChI KeyPXEBOIUZEXXBGH-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 ParentsNot Available
SubstituentsNot Available
Molecular FrameworkAliphatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
Process
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point189 - 191 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility42.3 g/LALOGPS
logP-0.32ALOGPS
logP-0.51ChemAxon
logS-0.82ALOGPS
pKa (Strongest Acidic)12.97ChemAxon
pKa (Strongest Basic)-2.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area82.45 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity70.8 m³·mol⁻¹ChemAxon
Polarizability29.23 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]+165.04731661259
DarkChem[M-H]-157.36231661259
DeepCCS[M-2H]-199.23230932474
DeepCCS[M+Na]+174.79730932474
AllCCS[M+H]+167.032859911
AllCCS[M+H-H2O]+163.632859911
AllCCS[M+NH4]+170.132859911
AllCCS[M+Na]+171.032859911
AllCCS[M-H]-171.032859911
AllCCS[M+Na-2H]-170.732859911
AllCCS[M+HCOO]-170.632859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
AnguidolCC1=CC2OC3C(O)C(O)C(C)(C33CO3)C2(CO)CC13421.9Standard polar33892256
AnguidolCC1=CC2OC3C(O)C(O)C(C)(C33CO3)C2(CO)CC12220.9Standard non polar33892256
AnguidolCC1=CC2OC3C(O)C(O)C(C)(C33CO3)C2(CO)CC12327.0Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Anguidol,1TMS,isomer #1CC1=CC2OC3C(O[Si](C)(C)C)C(O)C(C)(C2(CO)CC1)C31CO12359.9Semi standard non polar33892256
Anguidol,1TMS,isomer #2CC1=CC2OC3C(O)C(O[Si](C)(C)C)C(C)(C2(CO)CC1)C31CO12371.3Semi standard non polar33892256
Anguidol,1TMS,isomer #3CC1=CC2OC3C(O)C(O)C(C)(C2(CO[Si](C)(C)C)CC1)C31CO12323.6Semi standard non polar33892256
Anguidol,2TMS,isomer #1CC1=CC2OC3C(O[Si](C)(C)C)C(O[Si](C)(C)C)C(C)(C2(CO)CC1)C31CO12365.7Semi standard non polar33892256
Anguidol,2TMS,isomer #2CC1=CC2OC3C(O[Si](C)(C)C)C(O)C(C)(C2(CO[Si](C)(C)C)CC1)C31CO12329.3Semi standard non polar33892256
Anguidol,2TMS,isomer #3CC1=CC2OC3C(O)C(O[Si](C)(C)C)C(C)(C2(CO[Si](C)(C)C)CC1)C31CO12331.4Semi standard non polar33892256
Anguidol,3TMS,isomer #1CC1=CC2OC3C(O[Si](C)(C)C)C(O[Si](C)(C)C)C(C)(C2(CO[Si](C)(C)C)CC1)C31CO12356.5Semi standard non polar33892256
Anguidol,1TBDMS,isomer #1CC1=CC2OC3C(O[Si](C)(C)C(C)(C)C)C(O)C(C)(C2(CO)CC1)C31CO12612.8Semi standard non polar33892256
Anguidol,1TBDMS,isomer #2CC1=CC2OC3C(O)C(O[Si](C)(C)C(C)(C)C)C(C)(C2(CO)CC1)C31CO12624.6Semi standard non polar33892256
Anguidol,1TBDMS,isomer #3CC1=CC2OC3C(O)C(O)C(C)(C2(CO[Si](C)(C)C(C)(C)C)CC1)C31CO12578.5Semi standard non polar33892256
Anguidol,2TBDMS,isomer #1CC1=CC2OC3C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C(C)(C2(CO)CC1)C31CO12849.1Semi standard non polar33892256
Anguidol,2TBDMS,isomer #2CC1=CC2OC3C(O[Si](C)(C)C(C)(C)C)C(O)C(C)(C2(CO[Si](C)(C)C(C)(C)C)CC1)C31CO12809.3Semi standard non polar33892256
Anguidol,2TBDMS,isomer #3CC1=CC2OC3C(O)C(O[Si](C)(C)C(C)(C)C)C(C)(C2(CO[Si](C)(C)C(C)(C)C)CC1)C31CO12813.1Semi standard non polar33892256
Anguidol,3TBDMS,isomer #1CC1=CC2OC3C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C(C)(C2(CO[Si](C)(C)C(C)(C)C)CC1)C31CO13031.8Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Anguidol GC-MS (Non-derivatized) - 70eV, Positivesplash10-0fk9-3980000000-70e0c82b919ac960d4542017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Anguidol GC-MS (3 TMS) - 70eV, Positivesplash10-000t-7964800000-3fe4b14d05f42aabb7772017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Anguidol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Anguidol 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 - Anguidol 10V, Positive-QTOFsplash10-0159-0090000000-464ef52cd83df1b85f0b2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Anguidol 20V, Positive-QTOFsplash10-066s-1590000000-80f55d84841d3b2450482016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Anguidol 40V, Positive-QTOFsplash10-0gba-9640000000-31027155a4571b4c96c12016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Anguidol 10V, Negative-QTOFsplash10-001i-0090000000-dafc5573bf4d9a60e7dd2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Anguidol 20V, Negative-QTOFsplash10-0gx0-0390000000-441c56c96bb039aec8cf2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Anguidol 40V, Negative-QTOFsplash10-0a4j-6900000000-783e38eac8480236c0612016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Anguidol 10V, Negative-QTOFsplash10-001i-0090000000-4206ab54dd729eeefe272021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Anguidol 20V, Negative-QTOFsplash10-001i-0190000000-a703d689dc48fee957832021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Anguidol 40V, Negative-QTOFsplash10-0uec-1390000000-eef9ee988a3cf07e65282021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Anguidol 10V, Positive-QTOFsplash10-001i-0090000000-0d73455ff384d5026de72021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Anguidol 20V, Positive-QTOFsplash10-00lr-0190000000-7cb1ce92533c3aa5266c2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Anguidol 40V, Positive-QTOFsplash10-0zgi-4090000000-4789e9a33c6444e84c052021-09-24Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 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, 1000 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, 200 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, 300 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, 400 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, 500 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, 600 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, 700 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, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C 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 IDFDB014624
KNApSAcK IDC00012642
Chemspider ID2807424
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound3570295
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.