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Showing Compound Lupeyl acetate (FDB014104)

Record Information
Version1.0
Creation date2010-04-08 22:11:05 UTC
Update date2019-11-26 03:09:31 UTC
Primary IDFDB014104
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameLupeyl acetate
DescriptionLupeyl acetate, also known as lupeyl acetic acid, is a member of the class of compounds known as triterpenoids. Triterpenoids are terpene molecules containing six isoprene units. Lupeyl acetate is practically insoluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). Lupeyl acetate can be found in burdock, date, and fig, which makes lupeyl acetate a potential biomarker for the consumption of these food products.
CAS Number1617-68-1
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
Lupeyl acetic acidGenerator
3-Acetyllupeolbiospider
3-O-Acetyllupeolbiospider
Lup-20(29)-en-3-ol, acetate, (3beta)-biospider
Lup-20(29)-en-3-yl acetatebiospider
Lup-20(29)-en-3beta-ol, acetate (8CI)biospider
Lupenyl acetatebiospider
Lupeol (20[29]-lupenol) acetatebiospider
Lupeol acetatebiospider
Lupeyl acetatebiospider
Predicted Properties
PropertyValueSource
Water Solubility7.0e-05 g/LALOGPS
logP6.49ALOGPS
logP7.89ChemAxon
logS-6.8ALOGPS
pKa (Strongest Basic)-7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.3 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity140.06 m³·mol⁻¹ChemAxon
Polarizability58.24 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC32H52O2
IUPAC name1,2,5,14,18,18-hexamethyl-8-(prop-1-en-2-yl)pentacyclo[11.8.0.0²,¹⁰.0⁵,⁹.0¹⁴,¹⁹]henicosan-17-yl acetate
InChI IdentifierInChI=1S/C32H52O2/c1-20(2)22-12-15-29(6)18-19-31(8)23(27(22)29)10-11-25-30(7)16-14-26(34-21(3)33)28(4,5)24(30)13-17-32(25,31)9/h22-27H,1,10-19H2,2-9H3
InChI KeyODSSDTBFHAYYMD-UHFFFAOYSA-N
Isomeric SMILESCC(=O)OC1CCC2(C)C(CCC3(C)C2CCC2C4C(CCC4(C)CCC32C)C(C)=C)C1(C)C
Average Molecular Weight468.7541
Monoisotopic Molecular Weight468.396730908
Classification
Description Belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassTriterpenoids
Direct ParentTriterpenoids
Alternative Parents
Substituents
  • Triterpenoid
  • Steroid
  • Carboxylic acid ester
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External DescriptorsNot Available
Ontology
OntologyNo ontology term
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 81.99%; H 11.18%; O 6.83%DFC
Melting PointMp 215-216°DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]30D +46.2 (c, 1.5 in CHCl3)DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSLupeyl acetate, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0udl-2105900000-75f33fe37eab4d2e5e0fSpectrum
Predicted GC-MSLupeyl acetate, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0000900000-2894efc65b136e1f9a022016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05r0-0244900000-6c94648035da463d87652016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0gc0-1249100000-78ff4f983a03a67611432016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-016r-0000900000-5855265e201e31e5b3c02016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00or-2000900000-d6f7373aa6bc45ccfaac2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-6002900000-bf568d154b49dcf388192016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0002900000-fc0a0a5ba28870a182d62021-10-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-07m3-6790700000-1151d34a4cef6097ddf72021-10-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a59-9352000000-f7191766a232bb920bde2021-10-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0000900000-4aa37882d5aaa0c855a02021-10-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-1000900000-29a96d30025138f107802021-10-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-3000900000-05ee0e9016cd3583cb662021-10-12View Spectrum
NMRNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDC08630
Pubchem Compound ID92157
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDJFT17-C:JNX92-T
EAFUS IDNot Available
Dr. Duke IDLUPEOL-ACETATE
BIGG IDNot Available
KNApSAcK IDC00003750
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 hyperglycemicDUKE
anti ulcer49201 One of various classes of drugs with different action mechanisms used to treat or ameliorate peptic ulcer or irritation of the gastrointestinal tract.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).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.