3b,8b-Dihydroxy-6b-(3-chloro-2-hydroxy-2-methylbutanoyloxy)-7(11)-eremophilen-12,8-olide (CHEM030213)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 01:44:24 UTC
Update Date2016-11-09 01:19:02 UTC
Accession NumberCHEM030213
Identification
Common Name3b,8b-Dihydroxy-6b-(3-chloro-2-hydroxy-2-methylbutanoyloxy)-7(11)-eremophilen-12,8-olide
ClassSmall Molecule
Description3b,8b-Dihydroxy-6b-(3-chloro-2-hydroxy-2-methylbutanoyloxy)-7(11)-eremophilen-12,8-olide is a constituent of Petasites japonicus (sweet coltsfoot).
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
6,9a-Dihydroxy-3,4a,5-trimethyl-2-oxo-2H,4H,4ah,5H,6H,7H,8H,8ah,9H,9ah-naphtho[2,3-b]furan-4-yl 3-chloro-2-hydroxy-2-methylbutanoic acidHMDB
Chemical FormulaC20H29ClO7
Average Molecular Mass416.893 g/mol
Monoisotopic Mass416.160 g/mol
CAS Registry Number264607-21-8
IUPAC Name6,9a-dihydroxy-3,4a,5-trimethyl-2-oxo-2H,4H,4aH,5H,6H,7H,8H,8aH,9H,9aH-naphtho[2,3-b]furan-4-yl 3-chloro-2-hydroxy-2-methylbutanoate
Traditional Name6,9a-dihydroxy-3,4a,5-trimethyl-2-oxo-4H,5H,6H,7H,8H,8aH,9H-naphtho[2,3-b]furan-4-yl 3-chloro-2-hydroxy-2-methylbutanoate
SMILESCC(Cl)C(C)(O)C(=O)OC1C2=C(C)C(=O)OC2(O)CC2CCC(O)C(C)C12C
InChI IdentifierInChI=1S/C20H29ClO7/c1-9-14-15(27-17(24)19(5,25)11(3)21)18(4)10(2)13(22)7-6-12(18)8-20(14,26)28-16(9)23/h10-13,15,22,25-26H,6-8H2,1-5H3
InChI KeyIYBZGGXFPLMHRX-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as terpene lactones. These are prenol lipids containing a lactone ring.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassTerpene lactones
Direct ParentTerpene lactones
Alternative Parents
Substituents
  • Terpene lactone
  • Eremophilanolide or secoeremophilanolide
  • Sesquiterpenoid
  • Naphthofuran
  • Fatty acid ester
  • 2-furanone
  • Dicarboxylic acid or derivatives
  • Fatty acyl
  • Cyclic alcohol
  • Dihydrofuran
  • Alpha,beta-unsaturated carboxylic ester
  • Enoate ester
  • Tertiary alcohol
  • Carboxylic acid ester
  • Chlorohydrin
  • Secondary alcohol
  • Halohydrin
  • Hemiacetal
  • Lactone
  • Organoheterocyclic compound
  • Oxacycle
  • Carboxylic acid derivative
  • Alkyl chloride
  • Hydrocarbon derivative
  • Organic oxide
  • Alcohol
  • Alkyl halide
  • Organic oxygen compound
  • Carbonyl group
  • Organooxygen compound
  • Organohalogen compound
  • Organochloride
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.38 g/LALOGPS
logP1.37ALOGPS
logP2.23ChemAxon
logS-3ALOGPS
pKa (Strongest Acidic)11.06ChemAxon
pKa (Strongest Basic)-2.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area113.29 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity100.75 m³·mol⁻¹ChemAxon
Polarizability41.61 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-05fr-4529000000-23fd3dceaf4cf759952dSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-00b9-5920152000-c4844badf8e80b7c642cSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014j-0139300000-166ae6f892fd166b1da0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00kk-5898100000-48f5f0631cb117c0ca50Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014r-2920000000-f6fd2e15c1600e577caeSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-1257900000-2335a4c444a659f1bb83Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0aor-3749100000-b3ee2426370f82a0f50aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a70-2290000000-e1fade7a461d56fe04b2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-015a-0009500000-a8d91049b9dd77ce78c9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00kb-2198200000-9ea3e5bdd393d1117f28Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0cds-3690000000-7ab23b0a147f1fe3daa6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014r-5410900000-f4dbdf892de0dc2ab932Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-9300100000-70ab0ff3bcd12781f757Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-9000000000-aff380d12baac4fdebf1Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0036524
FooDB IDFDB015424
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID35014160
ChEBI IDNot Available
PubChem Compound ID131752004
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9.
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.
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.
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.
5. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.
6. The lipid handbook with CD-ROM