Cucurbitacin E (CHEM029722)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 01:22:01 UTC
Update Date2016-11-09 01:18:56 UTC
Accession NumberCHEM029722
Identification
Common NameCucurbitacin E
ClassSmall Molecule
DescriptionCucurbitacin e is a member of the class of compounds known as cucurbitacins. Cucurbitacins are polycyclic compounds containing the tetracyclic cucurbitane nucleus skeleton, 19-(10->9b)-abeo-10alanost-5-ene (also known as 9b-methyl-19-nor lanosta-5-ene), with a variety of oxygenation functionalities at different positions. Cucurbitacin e is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Cucurbitacin e is a bitter tasting compound found in cucumber, muskmelon, and watermelon, which makes cucurbitacin e a potential biomarker for the consumption of these food products.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
SynonymsNot Available
Chemical FormulaC32H44O8
Average Molecular Mass556.687 g/mol
Monoisotopic Mass556.304 g/mol
CAS Registry Number18444-66-1
IUPAC Name(3E)-6-{4,13-dihydroxy-1,6,6,11,15-pentamethyl-5,17-dioxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-3,7-dien-14-yl}-6-hydroxy-2-methyl-5-oxohept-3-en-2-yl acetate
Traditional Namecucurbitacin E
SMILESCC(=O)OC(C)(C)\C=C\C(=O)C(C)(O)C1C(O)CC2(C)C3CC=C4C(C=C(O)C(=O)C4(C)C)C3(C)C(=O)CC12C
InChI IdentifierInChI=1S/C32H44O8/c1-17(33)40-27(2,3)13-12-23(36)32(9,39)25-21(35)15-29(6)22-11-10-18-19(14-20(34)26(38)28(18,4)5)31(22,8)24(37)16-30(25,29)7/h10,12-14,19,21-22,25,34-35,39H,11,15-16H2,1-9H3/b13-12+
InChI KeyNDYMQXYDSVBNLL-OUKQBFOZSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as cucurbitacins. These are polycyclic compounds containing the tetracyclic cucurbitane nucleus skeleton, 19-(10->9b)-abeo-10alanost-5-ene (also known as 9b-methyl-19-nor lanosta-5-ene), with a variety of oxygenation functionalities at different positions.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassCucurbitacins
Direct ParentCucurbitacins
Alternative Parents
Substituents
  • Triterpenoid
  • Cucurbitacin skeleton
  • 22-oxosteroid
  • 21-oxosteroid
  • 20-hydroxysteroid
  • Steroid ester
  • 3-oxo-delta-1-steroid
  • 3-oxosteroid
  • 2-hydroxysteroid
  • 16-hydroxysteroid
  • Hydroxysteroid
  • Oxosteroid
  • 11-oxosteroid
  • Delta-1-steroid
  • Cyclohexenone
  • Acyloin
  • Cyclic alcohol
  • Alpha-hydroxy ketone
  • Tertiary alcohol
  • Alpha,beta-unsaturated ketone
  • Acryloyl-group
  • Enone
  • Cyclic ketone
  • Secondary alcohol
  • Carboxylic acid ester
  • Ketone
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Enol
  • Hydrocarbon derivative
  • Carbonyl group
  • Organic oxide
  • Alcohol
  • Organooxygen compound
  • Organic oxygen compound
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic 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 Solubility0.0034 g/LALOGPS
logP3.72ALOGPS
logP3.48ChemAxon
logS-5.2ALOGPS
pKa (Strongest Acidic)9.09ChemAxon
pKa (Strongest Basic)-2.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area138.2 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity152.61 m³·mol⁻¹ChemAxon
Polarizability60.61 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-052r-0002490000-a5e7e9b592435eef0ac6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-009j-1304920000-793e79191adae98d3d5cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0f7a-3359320000-f318c31d8a8c88c66927Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4j-3900380000-b3d176e28ee25f6c446fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4j-5903010000-cda6c5f37c8ec8d27f4cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9105300000-01af65138619a59e0c02Spectrum
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 IDNot Available
FooDB IDFDB014623
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkCucurbitacin E
Chemspider IDNot Available
ChEBI IDNot Available
PubChem Compound ID5353547
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General ReferencesNot Available