Cucurbitacin A (CHEM025829)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 22:37:44 UTC
Update Date2016-11-09 01:18:09 UTC
Accession NumberCHEM025829
Identification
Common NameCucurbitacin A
ClassSmall Molecule
DescriptionCucurbitacin a 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 a is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Cucurbitacin a can be found in cucumber, which makes cucurbitacin a a potential biomarker for the consumption of this food product.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
SynonymsNot Available
Chemical FormulaC32H46O9
Average Molecular Mass574.702 g/mol
Monoisotopic Mass574.314 g/mol
CAS Registry NumberNot Available
IUPAC Name(3E)-6-[4,13-dihydroxy-1-(hydroxymethyl)-6,6,11,15-tetramethyl-5,17-dioxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-14-yl]-6-hydroxy-2-methyl-5-oxohept-3-en-2-yl acetate
Traditional Name(3E)-6-[4,13-dihydroxy-1-(hydroxymethyl)-6,6,11,15-tetramethyl-5,17-dioxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-14-yl]-6-hydroxy-2-methyl-5-oxohept-3-en-2-yl acetate
SMILESCC(=O)OC(C)(C)\C=C\C(=O)C(C)(O)C1C(O)CC2(C)C3CC=C4C(CC(O)C(=O)C4(C)C)C3(CO)C(=O)CC12C
InChI IdentifierInChI=1S/C32H46O9/c1-17(34)41-27(2,3)12-11-23(37)31(8,40)25-21(36)14-29(6)22-10-9-18-19(13-20(35)26(39)28(18,4)5)32(22,16-33)24(38)15-30(25,29)7/h9,11-12,19-22,25,33,35-36,40H,10,13-16H2,1-8H3/b12-11+
InChI KeyIHTCCHVMPGDDSL-VAWYXSNFSA-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
  • Cucurbitacin skeleton
  • Triterpenoid
  • 22-oxosteroid
  • 21-oxosteroid
  • 20-hydroxysteroid
  • Steroid ester
  • 3-oxo-delta-5-steroid
  • 2-hydroxysteroid
  • Hydroxysteroid
  • 11-oxosteroid
  • 3-oxosteroid
  • Oxosteroid
  • 16-hydroxysteroid
  • Delta-5-steroid
  • Acyloin
  • Acryloyl-group
  • Cyclic alcohol
  • Alpha,beta-unsaturated ketone
  • Alpha-hydroxy ketone
  • Tertiary alcohol
  • Enone
  • Cyclic ketone
  • Secondary alcohol
  • Carboxylic acid ester
  • Ketone
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Hydrocarbon derivative
  • Carbonyl group
  • Organic oxide
  • Alcohol
  • Primary 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 Solubility0.018 g/LALOGPS
logP2.81ALOGPS
logP1.85ChemAxon
logS-4.5ALOGPS
pKa (Strongest Acidic)12.8ChemAxon
pKa (Strongest Basic)-2.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area158.43 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity152.82 m³·mol⁻¹ChemAxon
Polarizability62.05 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, Positivesplash10-0a4i-0001190000-7b7be3b68804a4727497Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ap1-1304980000-3b9afd0e27bb922bfcf1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ktr-3119760000-1bc95e418f4085b380d4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0aba-3600190000-8a7eefab3b631d68113cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-5903040000-39fa24ac541a1f96343aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9105220000-48181e0121538c0d89aaSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014j-1300980000-1d99e9338fedf3784a07Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01p5-9600530000-13479b8c6bdd9b92f892Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014r-9401100000-d8dfb0f8970e6ab674a0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0000390000-d3ccb30a60f7df91a751Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-9000110000-7f9b5f8b92a15f73a7c4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-5001940000-e5fa13bf4a5205397142Spectrum
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 IDFDB005284
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkCucurbitacin
Chemspider IDNot Available
ChEBI IDNot Available
PubChem Compound ID5903498
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General ReferencesNot Available