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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 22:48:37 UTC
Update Date2022-03-07 02:55:23 UTC
HMDB IDHMDB0037559
Secondary Accession Numbers
  • HMDB37559
Metabolite Identification
Common NameCadabicilone
DescriptionCadabicilone belongs to the class of organic compounds known as eudesmanolides, secoeudesmanolides, and derivatives. These are terpenoids with a structure based on the eudesmanolide (a 3,5a,9-trimethyl-naphtho[1,2-b]furan-2-one derivative) or secoeudesmanolide (a 3,6-dimethyl-5-(pentan-2-yl)-1-benzofuran-2-one derivative) skeleton. Based on a literature review a small amount of articles have been published on Cadabicilone.
Structure
Data?1563863051
SynonymsNot Available
Chemical FormulaC15H22O3
Average Molecular Weight250.3334
Monoisotopic Molecular Weight250.15689457
IUPAC Name3,5a,9-trimethyl-dodecahydronaphtho[1,2-b]furan-2,8-dione
Traditional Name3,5a,9-trimethyl-octahydro-3H-naphtho[1,2-b]furan-2,8-dione
CAS Registry Number14804-47-8
SMILES
CC1C2CCC3(C)CCC(=O)C(C)C3C2OC1=O
InChI Identifier
InChI=1S/C15H22O3/c1-8-10-4-6-15(3)7-5-11(16)9(2)12(15)13(10)18-14(8)17/h8-10,12-13H,4-7H2,1-3H3
InChI KeyBXRGGUXPWTWACZ-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as eudesmanolides, secoeudesmanolides, and derivatives. These are terpenoids with a structure based on the eudesmanolide (a 3,5a,9-trimethyl-naphtho[1,2-b]furan-2-one derivative) or secoeudesmanolide (a 3,6-dimethyl-5-(pentan-2-yl)-1-benzofuran-2-one derivative) skeleton.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassTerpene lactones
Direct ParentEudesmanolides, secoeudesmanolides, and derivatives
Alternative Parents
Substituents
  • Eudesmanolide
  • Sesquiterpenoid
  • Naphthofuran
  • Gamma butyrolactone
  • Tetrahydrofuran
  • Cyclic ketone
  • Lactone
  • Ketone
  • Carboxylic acid ester
  • Oxacycle
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Organic oxide
  • Organooxygen compound
  • Organic oxygen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • 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 Point118 - 120 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility902.3 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.26 g/LALOGPS
logP1.95ALOGPS
logP2.72ChemAxon
logS-3ALOGPS
pKa (Strongest Acidic)19.37ChemAxon
pKa (Strongest Basic)-6.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area43.37 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity67.21 m³·mol⁻¹ChemAxon
Polarizability27.93 ųChemAxon
Number of Rings3ChemAxon
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]+158.51631661259
DarkChem[M-H]-156.43231661259
DeepCCS[M+H]+159.07730932474
DeepCCS[M-H]-156.71930932474
DeepCCS[M-2H]-190.030932474
DeepCCS[M+Na]+165.1730932474
AllCCS[M+H]+158.932859911
AllCCS[M+H-H2O]+155.332859911
AllCCS[M+NH4]+162.332859911
AllCCS[M+Na]+163.332859911
AllCCS[M-H]-166.132859911
AllCCS[M+Na-2H]-166.232859911
AllCCS[M+HCOO]-166.432859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
CadabiciloneCC1C2CCC3(C)CCC(=O)C(C)C3C2OC1=O2710.0Standard polar33892256
CadabiciloneCC1C2CCC3(C)CCC(=O)C(C)C3C2OC1=O2043.1Standard non polar33892256
CadabiciloneCC1C2CCC3(C)CCC(=O)C(C)C3C2OC1=O2128.8Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Cadabicilone,1TMS,isomer #1CC1=C(O[Si](C)(C)C)CCC2(C)CCC3C(C)C(=O)OC3C122170.5Semi standard non polar33892256
Cadabicilone,1TMS,isomer #1CC1=C(O[Si](C)(C)C)CCC2(C)CCC3C(C)C(=O)OC3C122066.2Standard non polar33892256
Cadabicilone,1TMS,isomer #2CC1C(=O)OC2C1CCC1(C)CC=C(O[Si](C)(C)C)C(C)C212162.9Semi standard non polar33892256
Cadabicilone,1TMS,isomer #2CC1C(=O)OC2C1CCC1(C)CC=C(O[Si](C)(C)C)C(C)C212022.5Standard non polar33892256
Cadabicilone,1TBDMS,isomer #1CC1=C(O[Si](C)(C)C(C)(C)C)CCC2(C)CCC3C(C)C(=O)OC3C122385.5Semi standard non polar33892256
Cadabicilone,1TBDMS,isomer #1CC1=C(O[Si](C)(C)C(C)(C)C)CCC2(C)CCC3C(C)C(=O)OC3C122327.3Standard non polar33892256
Cadabicilone,1TBDMS,isomer #2CC1C(=O)OC2C1CCC1(C)CC=C(O[Si](C)(C)C(C)(C)C)C(C)C212392.0Semi standard non polar33892256
Cadabicilone,1TBDMS,isomer #2CC1C(=O)OC2C1CCC1(C)CC=C(O[Si](C)(C)C(C)(C)C)C(C)C212236.9Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Cadabicilone GC-MS (Non-derivatized) - 70eV, Positivesplash10-009f-2960000000-0f725431c374e162b1822017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Cadabicilone GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Cadabicilone 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 - Cadabicilone 10V, Positive-QTOFsplash10-0udi-0390000000-ef79242d3d8ed92df4322016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cadabicilone 20V, Positive-QTOFsplash10-0udi-0960000000-0e31a2abe3fc23ef704a2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cadabicilone 40V, Positive-QTOFsplash10-014l-9300000000-18f7baac75a5bf82d8282016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cadabicilone 10V, Negative-QTOFsplash10-0002-0090000000-9b15449c1771ca1ca3572016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cadabicilone 20V, Negative-QTOFsplash10-052b-0190000000-db53a1d787fa4bc456302016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cadabicilone 40V, Negative-QTOFsplash10-0udi-7930000000-365fbba38169a90c69142016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cadabicilone 10V, Positive-QTOFsplash10-001i-0290000000-754dd18a87ade78d631c2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cadabicilone 20V, Positive-QTOFsplash10-0ka9-0970000000-7c888b536a8ea7e866ac2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cadabicilone 40V, Positive-QTOFsplash10-056r-1900000000-0548aa46854407ab988f2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cadabicilone 10V, Negative-QTOFsplash10-0002-0090000000-09b8c5776dceef2c388e2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cadabicilone 20V, Negative-QTOFsplash10-0002-0190000000-181a6ad7f7eb4f01b2762021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cadabicilone 40V, Negative-QTOFsplash10-000b-1930000000-511b9486ec0e22ae8c732021-09-24Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • 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 IDFDB016641
KNApSAcK IDC00054320
Chemspider ID288033
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound325292
PDB IDNot Available
ChEBI ID174307
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1862041
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.