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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 20:44:19 UTC
Update Date2022-03-07 02:54:36 UTC
HMDB IDHMDB0035724
Secondary Accession Numbers
  • HMDB35724
Metabolite Identification
Common Name15-Deacetylcalonectrin
DescriptionCrotocin 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. Crotocin is an extremely weak basic (essentially neutral) compound (based on its pKa). Crotocin is a potentially toxic compound.
Structure
Data?1563862761
Synonyms
ValueSource
15-DecalonectrinHMDB
15-DesacetylcalonectrinHMDB
15-O-DeacetylcalonectrinHMDB
2'-(Hydroxymethyl)-1',5'-dimethyl-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0²,⁷]dodecan]-5'-en-10'-yl acetic acidGenerator
Chemical FormulaC17H24O5
Average Molecular Weight308.3695
Monoisotopic Molecular Weight308.162373878
IUPAC Name2'-(hydroxymethyl)-1',5'-dimethyl-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0²,⁷]dodecan]-5'-en-10'-yl acetate
Traditional Name2'-(hydroxymethyl)-1',5'-dimethyl-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0²,⁷]dodecan]-5'-en-10'-yl acetate
CAS Registry Number38818-66-5
SMILES
CC(=O)OC1CC2(C)C3(CO3)C1OC1C=C(C)CCC21CO
InChI Identifier
InChI=1S/C17H24O5/c1-10-4-5-16(8-18)13(6-10)22-14-12(21-11(2)19)7-15(16,3)17(14)9-20-17/h6,12-14,18H,4-5,7-9H2,1-3H3
InChI KeyDFPPNUOWRKIOKO-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
  • Fatty acid ester
  • Oxepane
  • Oxane
  • Fatty acyl
  • Alpha,beta-unsaturated carboxylic ester
  • Enoate ester
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Dialkyl ether
  • Oxirane
  • Ether
  • Monocarboxylic acid or derivatives
  • Oxacycle
  • Organoheterocyclic compound
  • Organic oxide
  • Carbonyl group
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effect
Disposition
Process
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point184 - 186 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.67 g/LALOGPS
logP1.05ALOGPS
logP0.85ChemAxon
logS-2.7ALOGPS
pKa (Strongest Acidic)15ChemAxon
pKa (Strongest Basic)-2.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area68.29 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity78.74 m³·mol⁻¹ChemAxon
Polarizability32.66 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]+171.24431661259
DarkChem[M-H]-166.66931661259
DeepCCS[M-2H]-200.85130932474
DeepCCS[M+Na]+176.41130932474
AllCCS[M+H]+173.732859911
AllCCS[M+H-H2O]+170.632859911
AllCCS[M+NH4]+176.632859911
AllCCS[M+Na]+177.432859911
AllCCS[M-H]-178.532859911
AllCCS[M+Na-2H]-178.532859911
AllCCS[M+HCOO]-178.632859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
15-DeacetylcalonectrinCC(=O)OC1CC2(C)C3(CO3)C1OC1C=C(C)CCC21CO3361.0Standard polar33892256
15-DeacetylcalonectrinCC(=O)OC1CC2(C)C3(CO3)C1OC1C=C(C)CCC21CO2135.2Standard non polar33892256
15-DeacetylcalonectrinCC(=O)OC1CC2(C)C3(CO3)C1OC1C=C(C)CCC21CO2280.6Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
15-Deacetylcalonectrin,1TMS,isomer #1CC(=O)OC1CC2(C)C3(CO[Si](C)(C)C)CCC(C)=CC3OC1C21CO12293.6Semi standard non polar33892256
15-Deacetylcalonectrin,1TBDMS,isomer #1CC(=O)OC1CC2(C)C3(CO[Si](C)(C)C(C)(C)C)CCC(C)=CC3OC1C21CO12542.0Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 15-Deacetylcalonectrin GC-MS (Non-derivatized) - 70eV, Positivesplash10-00di-2790000000-58d5fe44c3d8451e20062017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 15-Deacetylcalonectrin GC-MS (1 TMS) - 70eV, Positivesplash10-000w-7974000000-b9f5a14f4ecaa9aa53532017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 15-Deacetylcalonectrin 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 - 15-Deacetylcalonectrin 10V, Positive-QTOFsplash10-0a4m-0093000000-1a76e07ae046fa9a9b0f2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 15-Deacetylcalonectrin 20V, Positive-QTOFsplash10-0007-1490000000-17c4d54e369c052c1cd92016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 15-Deacetylcalonectrin 40V, Positive-QTOFsplash10-0g02-9560000000-35060a99d577814692622016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 15-Deacetylcalonectrin 10V, Negative-QTOFsplash10-0a4i-3198000000-3fcf809901b942d3b4542016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 15-Deacetylcalonectrin 20V, Negative-QTOFsplash10-0ap1-2291000000-25170e54a6b6bfb982d32016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 15-Deacetylcalonectrin 40V, Negative-QTOFsplash10-0a4l-4900000000-a44bc6833c08dedf141f2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 15-Deacetylcalonectrin 10V, Negative-QTOFsplash10-0aor-0079000000-60809020eca26b8c9a622021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 15-Deacetylcalonectrin 20V, Negative-QTOFsplash10-0a4i-9072000000-a130cf130eca5de8ca882021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 15-Deacetylcalonectrin 40V, Negative-QTOFsplash10-0a4i-9151000000-849c4f3bf5f58763e7332021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 15-Deacetylcalonectrin 10V, Positive-QTOFsplash10-0a4i-0049000000-051e4a84519c33b4e7dc2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 15-Deacetylcalonectrin 20V, Positive-QTOFsplash10-052g-0091000000-c1387d5eff85992eb9432021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 15-Deacetylcalonectrin 40V, Positive-QTOFsplash10-05mo-9140000000-6caa09c91f3ee2ceaaf72021-09-22Wishart 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 IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound286691
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.