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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 20:02:52 UTC
Update Date2022-03-07 02:54:22 UTC
HMDB IDHMDB0035104
Secondary Accession Numbers
  • HMDB35104
Metabolite Identification
Common NameDiacetoxyscirpenol
DescriptionAnguidine, also known as ANG 66 or NSC 141537, 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 small amount of articles have been published on Anguidine.
Structure
Data?1563862666
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
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
[11'-(Acetyloxy)-10'-hydroxy-1',5'-dimethyl-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0²,⁷]dodecan]-5'-en-2'-yl]methyl acetic acidHMDB
Trichothec-9-ene-3alpha, 4beta, 15-triol, 12,13-epoxy-, 4,15-diacetateHMDB
DiacetoxyscirpenolHMDB
AnguidineHMDB, MeSH
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
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
  • 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 effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point161 - 162 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
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]+186.96931661259
DarkChem[M-H]-177.81731661259
DeepCCS[M-2H]-209.930932474
DeepCCS[M+Na]+185.37930932474
AllCCS[M+H]+185.432859911
AllCCS[M+H-H2O]+182.732859911
AllCCS[M+NH4]+187.832859911
AllCCS[M+Na]+188.532859911
AllCCS[M-H]-189.732859911
AllCCS[M+Na-2H]-189.932859911
AllCCS[M+HCOO]-190.232859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
DiacetoxyscirpenolCC(=O)OCC12CCC(C)=CC1OC1C(O)C(OC(C)=O)C2(C)C11CO13710.8Standard polar33892256
DiacetoxyscirpenolCC(=O)OCC12CCC(C)=CC1OC1C(O)C(OC(C)=O)C2(C)C11CO12284.8Standard non polar33892256
DiacetoxyscirpenolCC(=O)OCC12CCC(C)=CC1OC1C(O)C(OC(C)=O)C2(C)C11CO12513.8Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Diacetoxyscirpenol,1TMS,isomer #1CC(=O)OCC12CCC(C)=CC1OC1C(O[Si](C)(C)C)C(OC(C)=O)C2(C)C12CO22462.5Semi standard non polar33892256
Diacetoxyscirpenol,1TBDMS,isomer #1CC(=O)OCC12CCC(C)=CC1OC1C(O[Si](C)(C)C(C)(C)C)C(OC(C)=O)C2(C)C12CO22695.2Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Diacetoxyscirpenol GC-MS (Non-derivatized) - 70eV, Positivesplash10-03dl-2592000000-16f4741dd58f1f85bc7e2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Diacetoxyscirpenol GC-MS (1 TMS) - 70eV, Positivesplash10-03di-7394100000-ab75df657e170290fbeb2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Diacetoxyscirpenol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Diacetoxyscirpenol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Diacetoxyscirpenol GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-11-03Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Diacetoxyscirpenol 10V, Positive-QTOFsplash10-0ar0-0019000000-9bebdb0b538385dbe8ed2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Diacetoxyscirpenol 20V, Positive-QTOFsplash10-0aor-1559000000-edcde62355aabd0612c42015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Diacetoxyscirpenol 40V, Positive-QTOFsplash10-02ta-6392000000-dad5b393198b429ebf392015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Diacetoxyscirpenol 10V, Negative-QTOFsplash10-01b9-2009000000-f394e8aa968e190568f92015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Diacetoxyscirpenol 20V, Negative-QTOFsplash10-0a4i-7419000000-8da1fcc85358f3e682292015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Diacetoxyscirpenol 40V, Negative-QTOFsplash10-0a4i-6900000000-c84c06511eac299b64022015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Diacetoxyscirpenol 10V, Positive-QTOFsplash10-0690-0009000000-930a1f13798f354350ac2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Diacetoxyscirpenol 20V, Positive-QTOFsplash10-0002-2094000000-bf8d2f1d7d17ced7c4412021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Diacetoxyscirpenol 40V, Positive-QTOFsplash10-00kg-2396000000-b01a3a1b96f6d77de1f72021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Diacetoxyscirpenol 10V, Negative-QTOFsplash10-0600-3039000000-57746e7e306faca6b02a2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Diacetoxyscirpenol 20V, Negative-QTOFsplash10-0a4i-9000000000-c90d1a35659a45bfc1bd2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Diacetoxyscirpenol 40V, Negative-QTOFsplash10-0a4l-9100000000-0233b0fddd2d620f6c902021-09-24Wishart 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 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
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.