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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 20:09:21 UTC
Update Date2022-03-07 02:54:24 UTC
HMDB IDHMDB0035206
Secondary Accession Numbers
  • HMDB35206
Metabolite Identification
Common NameBakkenolide B
DescriptionBakkenolide B, also known as fukinolide or petasilide, belongs to the class of organic compounds known as terpene lactones. These are prenol lipids containing a lactone ring. Based on a literature review a small amount of articles have been published on Bakkenolide B.
Structure
Data?1563862682
Synonyms
ValueSource
FukinolideHMDB
PetasilideHMDB
(2R,3R,3AR,4S,7S,7ar)-3-(acetyloxy)-7,7a-dimethyl-4'-methylidene-2'-oxo-octahydrospiro[indene-2,3'-oxolane]-4-yl (2E)-2-methylbut-2-enoic acidHMDB
Bakkenolide-bHMDB
Chemical FormulaC22H30O6
Average Molecular Weight390.47
Monoisotopic Molecular Weight390.204238692
IUPAC Name(1R,2R,3aR,4S,7S,7aR)-1-(acetyloxy)-3a,4-dimethyl-4'-methylidene-2'-oxo-octahydrospiro[indene-2,3'-oxolane]-7-yl (2E)-2-methylbut-2-enoate
Traditional Name(2R,3R,3aR,4S,7S,7aR)-3-(acetyloxy)-7,7a-dimethyl-4'-methylidene-2'-oxo-hexahydro-1H-spiro[indene-2,3'-oxolane]-4-yl (2E)-2-methylbut-2-enoate
CAS Registry Number18455-98-6
SMILES
[H][C@@]12[C@@H](OC(C)=O)[C@@]3(C[C@]1(C)[C@@H](C)CC[C@@H]2OC(=O)C(\C)=C\C)C(=C)COC3=O
InChI Identifier
InChI=1S/C22H30O6/c1-7-12(2)19(24)28-16-9-8-13(3)21(6)11-22(14(4)10-26-20(22)25)18(17(16)21)27-15(5)23/h7,13,16-18H,4,8-11H2,1-3,5-6H3/b12-7+/t13-,16-,17+,18+,21+,22+/m0/s1
InChI KeyAVAGQVZSHJYDED-NWAIQIOLSA-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
  • Fatty acid ester
  • Gamma butyrolactone
  • Fatty acyl
  • Alpha,beta-unsaturated carboxylic ester
  • Enoate ester
  • Tetrahydrofuran
  • Lactone
  • Carboxylic acid ester
  • Oxacycle
  • Carboxylic acid derivative
  • Organoheterocyclic compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organooxygen compound
  • Organic oxygen compound
  • Carbonyl group
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point101 - 102 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.71 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.0056 g/LALOGPS
logP3.59ALOGPS
logP3.51ChemAxon
logS-4.8ALOGPS
pKa (Strongest Basic)-6.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area78.9 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity102.47 m³·mol⁻¹ChemAxon
Polarizability41.25 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]+194.88331661259
DarkChem[M-H]-184.42931661259
DeepCCS[M-2H]-229.96730932474
DeepCCS[M+Na]+204.58930932474
AllCCS[M+H]+192.232859911
AllCCS[M+H-H2O]+189.832859911
AllCCS[M+NH4]+194.432859911
AllCCS[M+Na]+195.132859911
AllCCS[M-H]-196.132859911
AllCCS[M+Na-2H]-196.732859911
AllCCS[M+HCOO]-197.532859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Bakkenolide B[H][C@@]12[C@@H](OC(C)=O)[C@@]3(C[C@]1(C)[C@@H](C)CC[C@@H]2OC(=O)C(\C)=C\C)C(=C)COC3=O3683.4Standard polar33892256
Bakkenolide B[H][C@@]12[C@@H](OC(C)=O)[C@@]3(C[C@]1(C)[C@@H](C)CC[C@@H]2OC(=O)C(\C)=C\C)C(=C)COC3=O2494.5Standard non polar33892256
Bakkenolide B[H][C@@]12[C@@H](OC(C)=O)[C@@]3(C[C@]1(C)[C@@H](C)CC[C@@H]2OC(=O)C(\C)=C\C)C(=C)COC3=O2515.2Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Bakkenolide B GC-MS (Non-derivatized) - 70eV, Positivesplash10-057i-8095000000-771595dfb645a7bc49bb2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Bakkenolide B GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Bakkenolide B 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 - Bakkenolide B 10V, Positive-QTOFsplash10-000x-2029000000-b946949ebaa41fcb44302016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bakkenolide B 20V, Positive-QTOFsplash10-001l-9054000000-e54f23ffb0dd52d519852016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bakkenolide B 40V, Positive-QTOFsplash10-001i-9010000000-0a0736f26fda60c1efae2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bakkenolide B 10V, Negative-QTOFsplash10-000j-1009000000-1096244ad87ddf1b063e2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bakkenolide B 20V, Negative-QTOFsplash10-052b-6029000000-b518066daffc7894734d2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bakkenolide B 40V, Negative-QTOFsplash10-052e-9074000000-faf9b679f7fd4608bb8d2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bakkenolide B 10V, Positive-QTOFsplash10-0006-0039000000-65cceab66715a09603d22021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bakkenolide B 20V, Positive-QTOFsplash10-00rx-0291000000-0b32115941b61fa362ad2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bakkenolide B 40V, Positive-QTOFsplash10-0a4i-9220000000-ce528b7a4bc4ec8b75c92021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bakkenolide B 10V, Negative-QTOFsplash10-0a4r-9004000000-df21f6d41468395815062021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bakkenolide B 20V, Negative-QTOFsplash10-0a4i-9052000000-d0695c967ff9ee9474a72021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bakkenolide B 40V, Negative-QTOFsplash10-0a4i-9000000000-e8ed178dee360c30d8062021-09-22Wishart 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 IDFDB015490
KNApSAcK IDC00021354
Chemspider ID30777078
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound101289733
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1848401
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.