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Cucurbitacin B (FDB013515)

Record Information
Version1.0
Creation date2010-04-08 22:10:45 UTC
Update date2019-11-26 03:08:31 UTC
Primary IDFDB013515
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameCucurbitacin B
DescriptionCucurbitacin B 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. Based on a literature review a small amount of articles have been published on Cucurbitacin B.
CAS Number6199-67-3
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
Not AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0056 g/LALOGPS
logP3.7ALOGPS
logP3.13ChemAxon
logS-5ALOGPS
pKa (Strongest Acidic)12.8ChemAxon
pKa (Strongest Basic)-2.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area138.2 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity151.04 m³·mol⁻¹ChemAxon
Polarizability60.69 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC32H46O8
IUPAC name(3E)-6-{4,13-dihydroxy-1,6,6,11,15-pentamethyl-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
InChI IdentifierInChI=1S/C32H46O8/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/h10,12-13,19-22,25,34-35,39H,11,14-16H2,1-9H3/b13-12+
InChI KeyIXQKXEUSCPEQRD-OUKQBFOZSA-N
Isomeric 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(C)C(=O)CC12C
Average Molecular Weight558.7028
Monoisotopic Molecular Weight558.319268448
Classification
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
  • 3-oxosteroid
  • 11-oxosteroid
  • Oxosteroid
  • 16-hydroxysteroid
  • Delta-5-steroid
  • Acyloin
  • Acryloyl-group
  • Alpha,beta-unsaturated ketone
  • Cyclic alcohol
  • Alpha-hydroxy ketone
  • Tertiary alcohol
  • Enone
  • Cyclic ketone
  • Secondary alcohol
  • Carboxylic acid ester
  • Ketone
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Carbonyl group
  • Organic oxide
  • Alcohol
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organic oxygen compound
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 68.79%; H 8.30%; O 22.91%DFC
Melting PointMp 180-182°DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]25D +87.5 (96% EtOH)DFC
Spectroscopic UV Data[neutral] lmax 229 (e 13300) (EtOH) (Berdy)DFC
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSCucurbitacin B, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0gvn-2204590000-999244d691afface476fSpectrum
Predicted GC-MSCucurbitacin B, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-01b9-3102195000-67590cd44207aca4c298Spectrum
Predicted GC-MSCucurbitacin B, "Cucurbitacin B,1TMS,#1" TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCucurbitacin B, TMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCucurbitacin B, TMS_1_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCucurbitacin B, TMS_1_4, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCucurbitacin B, TMS_1_5, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCucurbitacin B, TMS_2_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCucurbitacin B, TMS_2_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCucurbitacin B, TMS_2_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCucurbitacin B, TMS_2_4, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCucurbitacin B, TMS_2_5, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCucurbitacin B, TMS_2_6, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCucurbitacin B, TMS_2_7, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCucurbitacin B, TMS_2_8, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCucurbitacin B, TMS_2_9, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCucurbitacin B, TMS_2_10, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCucurbitacin B, TMS_3_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCucurbitacin B, TMS_3_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCucurbitacin B, TMS_3_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCucurbitacin B, TMS_3_4, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCucurbitacin B, TMS_3_5, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCucurbitacin B, TMS_3_6, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCucurbitacin B, TMS_3_7, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCucurbitacin B, TMS_3_8, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-052f-0002490000-340cd111be87d04d21092016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000w-1304920000-962e19bce41b3a8d95b92016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000l-2129410000-7ddb916021a8e5112d5a2016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4j-3900380000-17ed96fef5434e9fdd142016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4j-5903120000-0a58b6b4a29153fefb702016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9105300000-aed0a8da08a2f614aacc2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0000910000-2fb757c84672eba50afa2021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-9000000000-adc51a9625e7766250c52021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4v-4001900000-b913bef2cb75f8c0debc2021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000t-0100910000-d57bb7e6e5b6c72590242021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000e-9501410000-a5aebb06a3552f6953f02021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014l-9612300000-18db14fe4f5cfcf5b1fa2021-09-25View Spectrum
NMRNot Available
ChemSpider ID4510124
ChEMBL IDCHEMBL1728549
KEGG Compound IDC08794
Pubchem Compound ID5353545
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB34927
CRC / DFC (Dictionary of Food Compounds) IDJDV65-L:JDV66-M
EAFUS IDNot Available
Dr. Duke IDCUCURBITACIN-B
BIGG IDNot Available
KNApSAcK IDC00003683
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 / Bioactivities
DescriptorIDDefinitionReference
anti gibberellin35222 A substance that diminishes the rate of a chemical reaction.DUKE
anti hepatotoxic62868 Any compound that is able to prevent damage to the liver.DUKE
anti inflammatory35472 A substance that reduces or suppresses inflammation.DUKE
antitumor35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
cancer preventive35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
cytotoxic52209 A role played by the molecular entity or part thereof which causes the development of a pathological process.DUKE
insectifuge24852 Strictly, a substance intended to kill members of the class Insecta. In common usage, any substance used for preventing, destroying, repelling or controlling insects.DUKE
Insectiphile24852 Strictly, a substance intended to kill members of the class Insecta. In common usage, any substance used for preventing, destroying, repelling or controlling insects.DUKE
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— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.