Record Information
Version1.0
Creation date2010-04-08 22:05:06 UTC
Update date2019-11-26 02:56:40 UTC
Primary IDFDB001782
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name3beta-Chlorodehydrocostuslactone
Description3beta-chlorodehydrocostuslactone belongs to guaianolides and derivatives class of compounds. Those are diterpene lactones with a structure characterized by the presence of a gamma-lactone fused to a guaiane, forming 3,6,9-trimethyl-azuleno[4,5-b]furan-2-one or a derivative. 3beta-chlorodehydrocostuslactone is practically insoluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). 3beta-chlorodehydrocostuslactone can be found in sweet bay, which makes 3beta-chlorodehydrocostuslactone a potential biomarker for the consumption of this food product.
CAS Number272780-97-9
Structure
Thumb
Synonyms
SynonymSource
(3Abeta,6abeta,9abeta,9balpha)-3,6,9-trismethylene-8a-chlorododecahydroazuleno[4,5-b]furan-2-oneGenerator
(3Abeta,6abeta,9abeta,9balpha)-3,6,9-trismethylene-8α-chlorododecahydroazuleno[4,5-b]furan-2-oneGenerator
3b-ChlorodehydrocostuslactoneGenerator
3Β-chlorodehydrocostuslactoneGenerator
Predicted Properties
PropertyValueSource
Water Solubility0.092 g/LALOGPS
logP3.14ALOGPS
logP3.2ChemAxon
logS-3.5ALOGPS
pKa (Strongest Basic)-6.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.3 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity70.54 m³·mol⁻¹ChemAxon
Polarizability27.67 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC15H17ClO2
IUPAC name(3aS,6aR,8S,9aR,9bS)-8-chloro-3,6,9-trimethylidene-dodecahydroazuleno[4,5-b]furan-2-one
InChI IdentifierInChI=1S/C15H17ClO2/c1-7-4-5-10-8(2)15(17)18-14(10)13-9(3)12(16)6-11(7)13/h10-14H,1-6H2/t10-,11-,12-,13-,14-/m0/s1
InChI KeyXVGIEOUYQLZGPH-PEDHHIEDSA-N
Isomeric SMILES[H][C@@]12CCC(=C)[C@]3([H])C[C@H](Cl)C(=C)[C@]3([H])[C@@]1([H])OC(=O)C2=C
Average Molecular Weight264.747
Monoisotopic Molecular Weight264.091707495
Classification
Description Belongs to the class of organic compounds known as guaianolides and derivatives. These are diterpene lactones with a structure characterized by the presence of a gamma-lactone fused to a guaiane, forming 3,6,9-trimethyl-azuleno[4,5-b]furan-2-one or a derivative.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassTerpene lactones
Direct ParentGuaianolides and derivatives
Alternative Parents
Substituents
  • Guaianolide-skeleton
  • Guaiane sesquiterpenoid
  • Sesquiterpenoid
  • Gamma butyrolactone
  • Tetrahydrofuran
  • Alpha,beta-unsaturated carboxylic ester
  • Enoate ester
  • Carboxylic acid ester
  • Lactone
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Oxacycle
  • Organoheterocyclic compound
  • Organooxygen compound
  • Organochloride
  • Organohalogen compound
  • Alkyl chloride
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Carbonyl group
  • Alkyl halide
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
OntologyNo ontology term
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MSNot Available
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0290000000-cd2fb1592ef834402660Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-0980000000-a1d0ea5a34c07b1b1702Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0zi0-8900000000-a1d4baa6de888e798e4eSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0090000000-f0d9e36db776470bf4b2Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0400-0090000000-e020137d64a33c1490c4Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0uxu-9540000000-166e2bfbf536aadaef36Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0090000000-3bb50308f6a8d5bad4abSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-0190000000-025f06c17207dd089c65Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4l-0920000000-c997eeb10e0dc4122d01Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0090000000-2d167fa136b10896c25fSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01q9-8090000000-f9e421effefab2572c32Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03di-2190000000-52b8a268b5106d0551e8Spectrum
NMRNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound IDNot Available
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDC00029488
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.