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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 19:50:36 UTC
Update Date2022-03-07 02:54:16 UTC
HMDB IDHMDB0034915
Secondary Accession Numbers
  • HMDB34915
Metabolite Identification
Common NameCalonectrin
DescriptionCalonectrin 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. Calonectrin is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Data?1563862634
Synonyms
ValueSource
(+)-CalonectrinHMDB
(3-alpha)-12,13-Epoxytrichothec-9-ene-3,15-diol diacetateHMDB
[10'-(Acetyloxy)-1',5'-dimethyl-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0²,⁷]dodecan]-5'-en-2'-yl]methyl acetic acidGenerator
Chemical FormulaC19H26O6
Average Molecular Weight350.4061
Monoisotopic Molecular Weight350.172938564
IUPAC Name10'-(acetyloxy)-1',5'-dimethyl-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0²,⁷]dodecan]-5'-en-2'-ylmethyl acetate
Traditional Name10'-(acetyloxy)-1',5'-dimethyl-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0²,⁷]dodecan]-5'-en-2'-ylmethyl acetate
CAS Registry NumberNot Available
SMILES
CC(=O)OCC12CCC(C)=CC1OC1C(CC2(C)C11CO1)OC(C)=O
InChI Identifier
InChI=1S/C19H26O6/c1-11-5-6-18(9-22-12(2)20)15(7-11)25-16-14(24-13(3)21)8-17(18,4)19(16)10-23-19/h7,14-16H,5-6,8-10H2,1-4H3
InChI KeyIGDIDZAQDRAJRB-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
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Dialkyl ether
  • Oxirane
  • Ether
  • Oxacycle
  • Organoheterocyclic compound
  • Organic oxygen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Carbonyl group
  • Organic oxide
  • 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 Point83 - 85 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.063 g/LALOGPS
logP1.6ALOGPS
logP1.3ChemAxon
logS-3.7ALOGPS
pKa (Strongest Basic)-3.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area74.36 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity87.89 m³·mol⁻¹ChemAxon
Polarizability36.57 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]+183.46531661259
DarkChem[M-H]-177.13431661259
DeepCCS[M-2H]-208.35130932474
DeepCCS[M+Na]+183.57830932474
AllCCS[M+H]+183.132859911
AllCCS[M+H-H2O]+180.432859911
AllCCS[M+NH4]+185.632859911
AllCCS[M+Na]+186.332859911
AllCCS[M-H]-187.532859911
AllCCS[M+Na-2H]-187.732859911
AllCCS[M+HCOO]-188.032859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
CalonectrinCC(=O)OCC12CCC(C)=CC1OC1C(CC2(C)C11CO1)OC(C)=O3598.0Standard polar33892256
CalonectrinCC(=O)OCC12CCC(C)=CC1OC1C(CC2(C)C11CO1)OC(C)=O2221.6Standard non polar33892256
CalonectrinCC(=O)OCC12CCC(C)=CC1OC1C(CC2(C)C11CO1)OC(C)=O2392.1Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Calonectrin GC-MS (Non-derivatized) - 70eV, Positivesplash10-00no-5982000000-afa7bb31148659b03f392017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Calonectrin 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 - Calonectrin 10V, Positive-QTOFsplash10-0k96-1079000000-a854005a4ce642e7af7f2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Calonectrin 20V, Positive-QTOFsplash10-0006-1593000000-26cc5fd68f78e4b0df662016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Calonectrin 40V, Positive-QTOFsplash10-0005-6491000000-0d6f8f4554ed3cbb98d62016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Calonectrin 10V, Negative-QTOFsplash10-052b-2019000000-d4eac27ff76c4bace7e62016-08-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Calonectrin 20V, Negative-QTOFsplash10-0a4i-9447000000-eb55ba2988e9f5da6c862016-08-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Calonectrin 40V, Negative-QTOFsplash10-052f-5900000000-f204688001cd628fa71e2016-08-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Calonectrin 10V, Negative-QTOFsplash10-052b-1039000000-07759321ead4c2e7e99c2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Calonectrin 20V, Negative-QTOFsplash10-0a4i-9031000000-24f6b3d0dcfc50a41eeb2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Calonectrin 40V, Negative-QTOFsplash10-0a4i-9234000000-eefbcfe8f80e34bb4e852021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Calonectrin 10V, Positive-QTOFsplash10-0006-0092000000-504de686a60a99b207142021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Calonectrin 20V, Positive-QTOFsplash10-000f-1091000000-65cda9f72013c23ae7dd2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Calonectrin 40V, Positive-QTOFsplash10-002f-9272000000-83d0f62e0515f2eaf7fe2021-09-24Wishart 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 IDFDB013498
KNApSAcK IDC00012631
Chemspider ID468927
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound538469
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.