Record Information
Version1.0
Creation date2010-04-08 22:11:59 UTC
Update date2019-11-26 03:12:01 UTC
Primary IDFDB015672
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameBilobalide A
DescriptionBilobalide A belongs to the class of organic compounds known as ginkgolides and bilobalides. These are diterpene lactones with a structure based either on the gingkolide or the bilobalide skeleton. The ginkgolide skeleton is a very rigid structure consisting of hexacyclic C20 trilactone. The cis-fused F/A/D/C ring junction forms an empty semi-ball hole, the D ring contains a cage form tetrahydrofuran ring which occupies the center of the empty hole, and the oxygen atoms of the D,C and F ring and 10-hydroxyl group consist of an analogous crown ether structure. Bilobalide A is an extremely weak basic (essentially neutral) compound (based on its pKa).
CAS Number33570-04-6
Structure
Thumb
Synonyms
SynonymSource
BilobalideHMDB
(-)-BilobalideMeSH
Predicted Properties
PropertyValueSource
Water Solubility10.3 g/LALOGPS
logP0.16ALOGPS
logP-0.52ChemAxon
logS-1.5ALOGPS
pKa (Strongest Acidic)11.97ChemAxon
pKa (Strongest Basic)-3.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area119.36 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity69.99 m³·mol⁻¹ChemAxon
Polarizability29.39 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC15H18O8
IUPAC name(1S,4R,7S,8S,9R,11S)-9-tert-butyl-7,9-dihydroxy-3,5,12-trioxatetracyclo[6.6.0.0¹,¹¹.0⁴,⁸]tetradecane-2,6,13-trione
InChI IdentifierInChI=1S/C15H18O8/c1-12(2,3)14(20)4-6-13(5-7(16)21-6)10(19)23-11-15(13,14)8(17)9(18)22-11/h6,8,11,17,20H,4-5H2,1-3H3/t6-,8+,11-,13-,14+,15+/m0/s1
InChI KeyMOLPUWBMSBJXER-NRSGSQFTSA-N
Isomeric SMILES[H][C@]12C[C@@](O)(C(C)(C)C)[C@]34[C@H](O)C(=O)O[C@@]3([H])OC(=O)[C@]14CC(=O)O2
Average Molecular Weight326.2986
Monoisotopic Molecular Weight326.100167552
Classification
Description Belongs to the class of organic compounds known as ginkgolides and bilobalides. These are diterpene lactones with a structure based either on the gingkolide or the bilobalide skeleton. The ginkgolide skeleton is a very rigid structure consisting of hexacyclic C20 trilactone. The cis-fused F/A/D/C ring junction forms an empty semi-ball hole, the D ring contains a cage form tetrahydrofuran ring which occupies the center of the empty hole, and the oxygen atoms of the D,C and F ring and 10-hydroxyl group consist of an analogous crown ether structure.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassTerpene lactones
Direct ParentGinkgolides and bilobalides
Alternative Parents
Substituents
  • Bilobalide
  • Diterpenoid
  • Tricarboxylic acid or derivatives
  • Furofuran
  • Acylal
  • Gamma butyrolactone
  • Cyclic alcohol
  • Tetrahydrofuran
  • Tertiary alcohol
  • Carboxylic acid ester
  • Lactone
  • Secondary alcohol
  • Organoheterocyclic compound
  • Oxacycle
  • Acetal
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Carbonyl group
  • Alcohol
  • Organooxygen compound
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 55.21%; H 5.56%; O 39.23%DFC
Melting PointMp 300°DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]20D -66.6DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSBilobalide A, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-056r-7090000000-409b29d29f5d92b036e1Spectrum
Predicted GC-MSBilobalide A, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-06dr-9025400000-db65ccd917ab30b1e85aSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a6r-0039000000-fd571dbea940514eb044Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a7i-1096000000-473f19a2a3e09916098bSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014r-3091000000-c7c1e8b2c82cbd9fa2dbSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0059-0089000000-7e83fcc43328f0da5170Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-057i-0097000000-41ff44d74a98fc8c733bSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000l-3190000000-cc31694b1766c38571faSpectrum
NMRNot Available
ChemSpider ID475104
ChEMBL IDNot Available
KEGG Compound IDC07605
Pubchem Compound ID545839
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB36735
CRC / DFC (Dictionary of Food Compounds) IDKFT43-S:KFT43-S
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDC00011512
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.