Record Information
Version1.0
Creation date2010-04-08 22:12:03 UTC
Update date2018-05-29 01:22:07 UTC
Primary IDFDB015787
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameCascarillin
DescriptionCascarillin belongs to the class of organic compounds known as colensane and clerodane diterpenoids. These are diterpenoids with a structure based on the clerodane or the colensane skeleton. Clerodanes arise from labdanes by two methyl migrations. Cascarillin is an extremely weak basic (essentially neutral) compound (based on its pKa).
CAS Number10118-56-6
Structure
Thumb
Synonyms
SynonymSource
4-Formyl-4-[2-(furan-3-yl)-2-hydroxyethyl]-7,8-dihydroxy-3,8,8a-trimethyl-decahydronaphthalen-2-yl acetic acidGenerator
Cascarillindb_source
Predicted Properties
PropertyValueSource
Water Solubility0.17 g/LALOGPS
logP1.31ALOGPS
logP0.91ChemAxon
logS-3.4ALOGPS
pKa (Strongest Acidic)13.37ChemAxon
pKa (Strongest Basic)-3.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area117.2 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity104.53 m³·mol⁻¹ChemAxon
Polarizability42.87 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC22H32O7
IUPAC name4-formyl-4-[2-(furan-3-yl)-2-hydroxyethyl]-7,8-dihydroxy-3,8,8a-trimethyl-decahydronaphthalen-2-yl acetate
InChI IdentifierInChI=1S/C22H32O7/c1-13-17(29-14(2)24)10-20(3)18(5-6-19(26)21(20,4)27)22(13,12-23)9-16(25)15-7-8-28-11-15/h7-8,11-13,16-19,25-27H,5-6,9-10H2,1-4H3
InChI KeyZOWKQQIGQBVKSV-UHFFFAOYSA-N
Isomeric SMILESCC1C(CC2(C)C(CCC(O)C2(C)O)C1(CC(O)C1=COC=C1)C=O)OC(C)=O
Average Molecular Weight408.4853
Monoisotopic Molecular Weight408.214803378
Classification
Description belongs to the class of organic compounds known as colensane and clerodane diterpenoids. These are diterpenoids with a structure based on the clerodane or the colensane skeleton. Clerodanes arise from labdanes by two methyl migrations.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassDiterpenoids
Direct ParentColensane and clerodane diterpenoids
Alternative Parents
Substituents
  • Clerodane diterpenoid
  • Cyclic alcohol
  • Furan
  • Tertiary alcohol
  • Heteroaromatic compound
  • Carboxylic acid ester
  • Secondary alcohol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Oxacycle
  • Organoheterocyclic compound
  • Aromatic alcohol
  • Hydrocarbon derivative
  • Aldehyde
  • Organooxygen compound
  • Organic oxide
  • Organic oxygen compound
  • Alcohol
  • Carbonyl group
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic 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 64.69%; H 7.90%; O 27.42%DFC
Melting PointMp 203.5°DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-1009000000-86634464ced29d7ac651JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-0cdi-5320198000-26e269a772d7d764854fJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-052g-0009200000-be2a1bd9ad5ea310e8bbJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-3019000000-7d538a6af9f4798fb3e3JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0002-9045000000-dae0120e98244640a0a9JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-2009600000-fe11de18189371daa65dJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-8019100000-72e5d67a776c02f33e64JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-066u-9026000000-dd273a6bb27cabeeffc3JSpectraViewer
ChemSpider ID4264331
ChEMBL IDNot Available
KEGG Compound IDC09071
Pubchem Compound ID5088211
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB36836
CRC / DFC (Dictionary of Food Compounds) IDKJB67-S:KJB69-U
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDC00003412
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