Cucurbitacin D (CHEM028718)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 00:38:47 UTC
Update Date2016-11-09 01:18:44 UTC
Accession NumberCHEM028718
Identification
Common NameCucurbitacin D
ClassSmall Molecule
DescriptionIsolated from plants of the Cucurbitaceae. Cucurbitacin D is found in cucumber, calabash, and green vegetables.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
Cucurbitacine (D)HMDB
Elatericin aHMDB
Elatericine aHMDB
23,24-Dihydro-cucurbitacin DMeSH
Cucurbitacin DMeSH
Chemical FormulaC30H44O7
Average Molecular Mass516.666 g/mol
Monoisotopic Mass516.309 g/mol
CAS Registry Number3877-86-9
IUPAC Name14-[(4E)-2,6-dihydroxy-6-methyl-3-oxohept-4-en-2-yl]-4,13-dihydroxy-1,6,6,11,15-pentamethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-ene-5,17-dione
Traditional Name14-[(4E)-2,6-dihydroxy-6-methyl-3-oxohept-4-en-2-yl]-4,13-dihydroxy-1,6,6,11,15-pentamethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-ene-5,17-dione
SMILESCC(C)(O)\C=C\C(=O)C(C)(O)C1C(O)CC2(C)C3CC=C4C(CC(O)C(=O)C4(C)C)C3(C)C(=O)CC12C
InChI IdentifierInChI=1S/C30H44O7/c1-25(2,36)12-11-21(33)30(8,37)23-19(32)14-27(5)20-10-9-16-17(13-18(31)24(35)26(16,3)4)29(20,7)22(34)15-28(23,27)6/h9,11-12,17-20,23,31-32,36-37H,10,13-15H2,1-8H3/b12-11+
InChI KeySRPHMISUTWFFKJ-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
  • 25-hydroxysteroid
  • 22-oxosteroid
  • 21-oxosteroid
  • 20-hydroxysteroid
  • 3-oxo-delta-5-steroid
  • 2-hydroxysteroid
  • 3-oxosteroid
  • Hydroxysteroid
  • 11-oxosteroid
  • Oxosteroid
  • 16-hydroxysteroid
  • Delta-5-steroid
  • Acyloin
  • Acryloyl-group
  • Alpha,beta-unsaturated ketone
  • Enone
  • Alpha-hydroxy ketone
  • Tertiary alcohol
  • Cyclic alcohol
  • Cyclic ketone
  • Secondary alcohol
  • Ketone
  • Organic oxide
  • Alcohol
  • Organic oxygen compound
  • Carbonyl group
  • Organooxygen compound
  • Hydrocarbon derivative
  • 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 Solubility0.024 g/LALOGPS
logP3.11ALOGPS
logP2.69ChemAxon
logS-4.3ALOGPS
pKa (Strongest Acidic)12.8ChemAxon
pKa (Strongest Basic)-2.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area132.13 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity141.89 m³·mol⁻¹ChemAxon
Polarizability57.64 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0udi-2203920000-313542718d1a47804651Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0002-1102019000-fd1275dbc427cd0de224Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000t-0001910000-a64a24f594c3d1241987Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-1204900000-7126fe9f002d2651f753Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-3139700000-7e34ad54867747ba290dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-066r-2901580000-9c731b728e47c61e945dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-2903100000-2eeffae45ef3a0281d3fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-3109200000-794f4dd1592bf02054f3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0000090000-2baf3d361706523f7619Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-066r-2505590000-33738230505cef2e30caSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000l-2002900000-fc65466bcba50ae737c9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000t-0002910000-058b07d31397432c267cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-052k-9002300000-1e1f05ab63a984fb3523Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014j-9413100000-426980d4dc43fb5d4715Spectrum
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 IDHMDB0034695
FooDB IDFDB013225
Phenol Explorer IDNot Available
KNApSAcK IDC00003685
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkCucurbitacin D
Chemspider ID4510125
ChEBI IDNot Available
PubChem Compound ID5353546
Kegg Compound IDC08796
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9.
2. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10.
3. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20.
4. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621.
5. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.
6. The lipid handbook with CD-ROM