Bakkenolide D (CHEM028944)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 00:49:02 UTC
Update Date2016-11-09 01:18:47 UTC
Accession NumberCHEM028944
Identification
Common NameBakkenolide D
ClassSmall Molecule
DescriptionBakkenolide D is found in giant butterbur. Bakkenolide D is a constituent of Petasites japonicus (sweet coltsfoot)
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
S-FukinolideHMDB
3-(Acetyloxy)-7,7a-dimethyl-4'-methylidene-2'-oxo-octahydrospiro[indene-2,3'-oxolane]-4-yl (2E)-3-(methylsulfanyl)prop-2-enoic acidGenerator
3-(Acetyloxy)-7,7a-dimethyl-4'-methylidene-2'-oxo-octahydrospiro[indene-2,3'-oxolane]-4-yl (2E)-3-(methylsulphanyl)prop-2-enoateGenerator
3-(Acetyloxy)-7,7a-dimethyl-4'-methylidene-2'-oxo-octahydrospiro[indene-2,3'-oxolane]-4-yl (2E)-3-(methylsulphanyl)prop-2-enoic acidGenerator
Chemical FormulaC21H28O6S
Average Molecular Mass408.508 g/mol
Monoisotopic Mass408.161 g/mol
CAS Registry Number18456-03-6
IUPAC Name3-(acetyloxy)-7,7a-dimethyl-4'-methylidene-2'-oxo-octahydrospiro[indene-2,3'-oxolane]-4-yl (2E)-3-(methylsulfanyl)prop-2-enoate
Traditional Name3-(acetyloxy)-7,7a-dimethyl-4'-methylidene-2'-oxo-hexahydro-1H-spiro[indene-2,3'-oxolane]-4-yl (2E)-3-(methylsulfanyl)prop-2-enoate
SMILESCS\C=C\C(=O)OC1CCC(C)C2(C)CC3(C(OC(C)=O)C12)C(=C)COC3=O
InChI IdentifierInChI=1S/C21H28O6S/c1-12-6-7-15(27-16(23)8-9-28-5)17-18(26-14(3)22)21(11-20(12,17)4)13(2)10-25-19(21)24/h8-9,12,15,17-18H,2,6-7,10-11H2,1,3-5H3/b9-8+
InChI KeyLWHLMCCRIWZBQO-CMDGGOBGSA-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
  • Sesquiterpenoid
  • Tricarboxylic acid or derivatives
  • Gamma butyrolactone
  • Vinylogous thioester
  • Acrylic acid or derivatives
  • Tetrahydrofuran
  • Alpha,beta-unsaturated carboxylic ester
  • Enoate ester
  • Carboxylic acid ester
  • Lactone
  • Thioenolether
  • Oxacycle
  • Carboxylic acid derivative
  • Organoheterocyclic compound
  • Sulfenyl compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organosulfur compound
  • Organooxygen compound
  • Carbonyl group
  • Organic oxygen compound
  • 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 Solubility0.0024 g/LALOGPS
logP3.15ALOGPS
logP2.96ChemAxon
logS-5.2ALOGPS
pKa (Strongest Basic)-6.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area78.9 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity105.29 m³·mol⁻¹ChemAxon
Polarizability42.38 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0007-2096000000-127a97a26a37fa000630Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0pbc-1339400000-0aca307ad51758c001f0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udm-3987000000-be55624df7db07ed1f47Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-9550000000-0622b67bb3bf0d2e4b47Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4j-8019500000-0cee82757e3ff155dfc7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-9013000000-dc3736b2cbfaed31a02eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0002-9041000000-5c074c776272a17d1d52Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-9000400000-75a5d8f8bd30a0b93a5eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-9000100000-f3dd72dbe8d14845d991Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052g-9000000000-34082956b045ac84e6beSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0026900000-3b1f7c7b9f39147cd7aeSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-052p-0092100000-71b2e7543ee2af54d94aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03fs-6891000000-114aad8126c9fb1345c5Spectrum
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 IDHMDB0034998
FooDB IDFDB013602
Phenol Explorer IDNot Available
KNApSAcK IDC00021355
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID35013813
ChEBI ID168811
PubChem Compound ID12299953
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