Record Information
Version1.0
Creation date2010-04-08 22:11:57 UTC
Update date2019-11-26 03:11:58 UTC
Primary IDFDB015629
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameCrispolide
DescriptionCrispolide belongs to the class of organic compounds known as germacranolides and derivatives. These are sesquiterpene lactones with a structure based on the germacranolide skeleton, characterized by a gamma lactone fused to a 1,7-dimethylcyclodec-1-ene moiety. Crispolide is an extremely weak basic (essentially neutral) compound (based on its pKa).
CAS Number83217-86-1
Structure
Thumb
Synonyms
SynonymSource
1b-Hydroperoxy-5b-hydroxy-4,14-cyclo-9,11-germacradien-12,6a-olidedb_source
Predicted Properties
PropertyValueSource
Water Solubility4.14 g/LALOGPS
logP1.21ALOGPS
logP1.76ChemAxon
logS-1.8ALOGPS
pKa (Strongest Acidic)11.71ChemAxon
pKa (Strongest Basic)-3.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area75.99 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity71.4 m³·mol⁻¹ChemAxon
Polarizability28.83 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC15H20O5
IUPAC name(2R,3S,7S,11R)-11-hydroperoxy-2-hydroxy-1-methyl-6-methylidene-4-oxatricyclo[8.3.1.0^{3,7}]tetradec-9-en-5-one
InChI IdentifierInChI=1S/C15H20O5/c1-8-10-4-3-9-7-15(2,6-5-11(9)20-18)13(16)12(10)19-14(8)17/h3,10-13,16,18H,1,4-7H2,2H3/b9-3+/t10-,11+,12-,13-,15?/m0/s1
InChI KeyJXXWNBNYEWOORY-BASWEGAOSA-N
Isomeric SMILESCC12CC[C@@H](OO)C(C1)=CC[C@@H]1[C@H](OC(=O)C1=C)[C@@H]2O
Average Molecular Weight280.3163
Monoisotopic Molecular Weight280.13107375
Classification
Description belongs to the class of organic compounds known as germacranolides and derivatives. These are sesquiterpene lactones with a structure based on the germacranolide skeleton, characterized by a gamma lactone fused to a 1,7-dimethylcyclodec-1-ene moiety.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassTerpene lactones
Direct ParentGermacranolides and derivatives
Alternative Parents
Substituents
  • Germacranolide
  • Sesquiterpenoid
  • Gamma butyrolactone
  • Alpha,beta-unsaturated carboxylic ester
  • Enoate ester
  • Tetrahydrofuran
  • Secondary alcohol
  • Hydroperoxide
  • Lactone
  • Carboxylic acid ester
  • Alkyl hydroperoxide
  • Oxacycle
  • Organoheterocyclic compound
  • Peroxol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • 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 CompositionC 64.27%; H 7.19%; O 28.54%DFC
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]24D -20 (c, 0.90 in Py)DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0090000000-698e664e0a207be77339JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0bu0-0290000000-4475ca098a61865215d2JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-4920000000-a3bfe65ba5c30be661c1JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0090000000-76fe62351e2f8f8c07d1JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01ti-0090000000-61845d890a5c86cfd654JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0udj-9050000000-3e960cb66850fd32d4cfJSpectraViewer
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 IDHMDB36695
CRC / DFC (Dictionary of Food Compounds) IDKFF31-V:KFF31-V
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDC00012420
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
Flavours
FlavorCitations
bitter
  1. Ayana Wiener, Marina Shudler, Anat Levit, Masha Y. Niv. BitterDB: a database of bitter compounds. Nucleic Acids Res 2012, 40(Database issue):D413-419. DOI:10.1093/nar/gkr755
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference