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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 22:16:52 UTC
Update Date2022-03-07 02:55:10 UTC
HMDB IDHMDB0037038
Secondary Accession Numbers
  • HMDB37038
Metabolite Identification
Common NameCyclodehydroisolubimin
DescriptionCyclodehydroisolubimin belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other. Based on a literature review a significant number of articles have been published on Cyclodehydroisolubimin.
Structure
Data?1563862967
Synonyms
ValueSource
4,10-Epoxy-11-spirovetiven-2-oneHMDB
Sulfonium, dodecyldimethyl- iodideHMDB
Chemical FormulaC15H22O2
Average Molecular Weight234.334
Monoisotopic Molecular Weight234.161979948
IUPAC Name5-methyl-4'-(prop-1-en-2-yl)-6-oxaspiro[bicyclo[3.2.1]octane-8,1'-cyclopentane]-3-one
Traditional Name5-methyl-4'-(prop-1-en-2-yl)-6-oxaspiro[bicyclo[3.2.1]octane-8,1'-cyclopentane]-3-one
CAS Registry Number72055-93-7
SMILES
CC(=C)C1CCC2(C1)C1COC2(C)CC(=O)C1
InChI Identifier
InChI=1S/C15H22O2/c1-10(2)11-4-5-15(7-11)12-6-13(16)8-14(15,3)17-9-12/h11-12H,1,4-9H2,2-3H3
InChI KeyYHIWYGHFGRMQMO-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassMonoterpenoids
Direct ParentBicyclic monoterpenoids
Alternative Parents
Substituents
  • Bicyclic monoterpenoid
  • Oxepane
  • Tetrahydrofuran
  • Cyclic ketone
  • Ketone
  • Oxacycle
  • Organoheterocyclic compound
  • Ether
  • Dialkyl ether
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
Process
Role
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.067 g/LALOGPS
logP2.59ALOGPS
logP2.47ChemAxon
logS-3.5ALOGPS
pKa (Strongest Acidic)18.25ChemAxon
pKa (Strongest Basic)-4.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.3 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity67.04 m³·mol⁻¹ChemAxon
Polarizability26.75 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+155.98931661259
DarkChem[M-H]-152.68531661259
DeepCCS[M+H]+155.79330932474
DeepCCS[M-H]-153.43530932474
DeepCCS[M-2H]-186.5430932474
DeepCCS[M+Na]+161.88730932474
AllCCS[M+H]+155.532859911
AllCCS[M+H-H2O]+151.732859911
AllCCS[M+NH4]+158.932859911
AllCCS[M+Na]+159.932859911
AllCCS[M-H]-163.332859911
AllCCS[M+Na-2H]-163.432859911
AllCCS[M+HCOO]-163.732859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
CyclodehydroisolubiminCC(=C)C1CCC2(C1)C1COC2(C)CC(=O)C12541.3Standard polar33892256
CyclodehydroisolubiminCC(=C)C1CCC2(C1)C1COC2(C)CC(=O)C11747.7Standard non polar33892256
CyclodehydroisolubiminCC(=C)C1CCC2(C1)C1COC2(C)CC(=O)C11874.0Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Cyclodehydroisolubimin,1TMS,isomer #1C=C(C)C1CCC2(C1)C1C=C(O[Si](C)(C)C)CC2(C)OC11845.1Semi standard non polar33892256
Cyclodehydroisolubimin,1TMS,isomer #1C=C(C)C1CCC2(C1)C1C=C(O[Si](C)(C)C)CC2(C)OC11759.3Standard non polar33892256
Cyclodehydroisolubimin,1TMS,isomer #2C=C(C)C1CCC2(C1)C1COC2(C)C=C(O[Si](C)(C)C)C11850.0Semi standard non polar33892256
Cyclodehydroisolubimin,1TMS,isomer #2C=C(C)C1CCC2(C1)C1COC2(C)C=C(O[Si](C)(C)C)C11765.1Standard non polar33892256
Cyclodehydroisolubimin,1TBDMS,isomer #1C=C(C)C1CCC2(C1)C1C=C(O[Si](C)(C)C(C)(C)C)CC2(C)OC12083.5Semi standard non polar33892256
Cyclodehydroisolubimin,1TBDMS,isomer #1C=C(C)C1CCC2(C1)C1C=C(O[Si](C)(C)C(C)(C)C)CC2(C)OC11962.2Standard non polar33892256
Cyclodehydroisolubimin,1TBDMS,isomer #2C=C(C)C1CCC2(C1)C1COC2(C)C=C(O[Si](C)(C)C(C)(C)C)C12082.3Semi standard non polar33892256
Cyclodehydroisolubimin,1TBDMS,isomer #2C=C(C)C1CCC2(C1)C1COC2(C)C=C(O[Si](C)(C)C(C)(C)C)C11959.3Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Cyclodehydroisolubimin GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9440000000-0ed03726272da8f88c912017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Cyclodehydroisolubimin 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 - Cyclodehydroisolubimin 10V, Positive-QTOFsplash10-000i-0190000000-a6b5746e34222663523a2016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cyclodehydroisolubimin 20V, Positive-QTOFsplash10-00kr-4790000000-63ef827ae210e3b13e2a2016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cyclodehydroisolubimin 40V, Positive-QTOFsplash10-014m-9310000000-ce9ff9380146428224012016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cyclodehydroisolubimin 10V, Negative-QTOFsplash10-001i-0090000000-d38cd97eac084545e5632016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cyclodehydroisolubimin 20V, Negative-QTOFsplash10-001i-0090000000-4c5832e665dfd95f5da42016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cyclodehydroisolubimin 40V, Negative-QTOFsplash10-0pvi-2940000000-91a5c066609e1c584a592016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cyclodehydroisolubimin 10V, Positive-QTOFsplash10-000i-0390000000-cd7fca1e3e1027ed0ca02021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cyclodehydroisolubimin 20V, Positive-QTOFsplash10-00kr-1960000000-e23513ff9fcec61a43382021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cyclodehydroisolubimin 40V, Positive-QTOFsplash10-0fsc-6490000000-792c5d642efcba5375c82021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cyclodehydroisolubimin 10V, Negative-QTOFsplash10-001i-0090000000-9087f47ed0ae51229a172021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cyclodehydroisolubimin 20V, Negative-QTOFsplash10-001i-0090000000-9087f47ed0ae51229a172021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cyclodehydroisolubimin 40V, Negative-QTOFsplash10-001i-1290000000-0ccac9941aa10f30d4f42021-09-25Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
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 IDFDB016020
KNApSAcK IDC00021575
Chemspider ID35014354
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound14258974
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.