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Cucurbitacin I (FDB013226)

Record Information
Version1.0
Creation date2010-04-08 22:10:36 UTC
Update date2019-11-26 03:08:09 UTC
Primary IDFDB013226
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameCucurbitacin I
DescriptionCucurbitacin i 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 i is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Cucurbitacin i can be found in cucumber, which makes cucurbitacin i a potential biomarker for the consumption of this food product.
CAS Number2222-07-3
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
Not AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.013 g/LALOGPS
logP3.33ALOGPS
logP3.04ChemAxon
logS-4.6ALOGPS
pKa (Strongest Acidic)9.09ChemAxon
pKa (Strongest Basic)-2.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area132.13 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity143.46 m³·mol⁻¹ChemAxon
Polarizability56.73 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC30H42O7
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]heptadeca-3,7-diene-5,17-dione
InChI IdentifierInChI=1S/C30H42O7/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/h9,11-13,17,19-20,23,31-32,36-37H,10,14-15H2,1-8H3/b12-11+
InChI KeyNISPVUDLMHQFRQ-VAWYXSNFSA-N
Isomeric SMILESCC(C)(O)\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
Average Molecular Weight514.6503
Monoisotopic Molecular Weight514.293053698
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
  • 25-hydroxysteroid
  • 22-oxosteroid
  • 21-oxosteroid
  • 20-hydroxysteroid
  • 3-oxo-delta-1-steroid
  • 3-oxosteroid
  • 2-hydroxysteroid
  • Hydroxysteroid
  • 11-oxosteroid
  • Oxosteroid
  • 16-hydroxysteroid
  • Delta-1-steroid
  • Cyclohexenone
  • Acyloin
  • Alpha-hydroxy ketone
  • Acryloyl-group
  • Enone
  • Tertiary alcohol
  • Cyclic alcohol
  • Alpha,beta-unsaturated ketone
  • Ketone
  • Cyclic ketone
  • Secondary alcohol
  • Enol
  • Organooxygen compound
  • Hydrocarbon derivative
  • Carbonyl group
  • Organic oxygen compound
  • Alcohol
  • Organic oxide
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External DescriptorsNot Available
Ontology
OntologyNo ontology term
Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 70.01%; H 8.23%; O 21.76%DFC
Melting PointMp 148-149° dec.DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]20D -58.5 (MeOH)DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MSNot Available
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-002b-0001910000-86ad0009eca6ce5bf81e2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004s-2305900000-9b33e0b7f85fb0c0d2c62016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0gec-4259500000-7cccf843f7f261460f3f2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-08fr-2901580000-bc8ef536ad8be9c3de6c2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0bti-2903100000-147500bed0168fa48c3f2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4r-3109200000-4010e05c1498fb8ba8fa2016-08-03View Spectrum
NMRNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDC01901
Pubchem Compound IDNot Available
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDJPP60-I:HPT09-X
EAFUS IDNot Available
Dr. Duke IDCUCURBITACIN-I
BIGG IDNot Available
KNApSAcK IDC00003689
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 carcinomic35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
anti gibberellin35222 A substance that diminishes the rate of a chemical reaction.DUKE
anti leukemic35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
antitumor35610 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
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
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).