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Showing Compound Obacunone 17-O-beta-D-glucoside (FDB005061)

Record Information
Version1.0
Creation date2010-04-08 22:06:31 UTC
Update date2019-11-26 03:00:21 UTC
Primary IDFDB005061
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameObacunone 17-O-beta-D-glucoside
DescriptionObacunone 17-o-beta-d-glucoside is a member of the class of compounds known as limonoids. Limonoids are highly oxygenated, modified terpenoids with a prototypical structure either containing or derived from a precursor with a 4,4,8-trimethyl-17-furanylsteroid skeleton. All naturally occurring citrus limonoids contain a furan ring attached to the D-ring, at C-17, as well as oxygen containing functional groups at C-3, C-4, C-7, C-16 and C-17. Obacunone 17-o-beta-d-glucoside is practically insoluble (in water) and a weakly acidic compound (based on its pKa). Obacunone 17-o-beta-d-glucoside can be found in lemon, mandarin orange (clementine, tangerine), and sweet orange, which makes obacunone 17-o-beta-d-glucoside a potential biomarker for the consumption of these food products.
CAS NumberNot Available
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
Predicted Properties
PropertyValueSource
Water Solubility0.24 g/LALOGPS
logP1.62ALOGPS
logP1.45ChemAxon
logS-3.4ALOGPS
pKa (Strongest Acidic)4.04ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count11ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area205.72 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity152.09 m³·mol⁻¹ChemAxon
Polarizability63.57 ųChemAxon
Number of Rings6ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC32H42O13
IUPAC name9-[furan-3-yl({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})methyl]-5,5,7a,9,11b-pentamethyl-3,7-dioxo-5,5a,6,7,7a,9,10,11,11a,11b-decahydro-3H-spiro[naphtho[2,1-c]oxepine-8,2'-oxirane]-3'-carboxylic acid
InChI IdentifierInChI=1S/C32H42O13/c1-28(2)18-12-19(34)31(5)17(29(18,3)9-7-20(35)44-28)6-10-30(4,32(31)25(45-32)26(39)40)24(15-8-11-41-14-15)43-27-23(38)22(37)21(36)16(13-33)42-27/h7-9,11,14,16-18,21-25,27,33,36-38H,6,10,12-13H2,1-5H3,(H,39,40)
InChI KeyMXZVBPOYCKIXHN-UHFFFAOYSA-N
Isomeric SMILESCC1(CCC2C3(C)C=CC(=O)OC(C)(C)C3CC(=O)C2(C)C11OC1C(O)=O)C(OC1OC(CO)C(O)C(O)C1O)C1=COC=C1
Average Molecular Weight634.6681
Monoisotopic Molecular Weight634.26254143
Classification
Description Belongs to the class of organic compounds known as limonoids. These are highly oxygenated, modified terpenoids with a prototypical structure either containing or derived from a precursor with a 4,4,8-trimethyl-17-furanylsteroid skeleton. All naturally occurring citrus limonoids contain a furan ring attached to the D-ring, at C-17, as well as oxygen containing functional groups at C-3, C-4, C-7, C-16 and C-17.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassTriterpenoids
Direct ParentLimonoids
Alternative Parents
Substituents
  • Limonoid skeleton
  • Hexose monosaccharide
  • Glycosyl compound
  • O-glycosyl compound
  • Dicarboxylic acid or derivatives
  • Monosaccharide
  • Oxane
  • Oxirane carboxylic acid
  • Oxirane carboxylic acid or derivatives
  • Alpha,beta-unsaturated carboxylic ester
  • Enoate ester
  • Furan
  • Heteroaromatic compound
  • Secondary alcohol
  • Carboxylic acid ester
  • Ketone
  • Lactone
  • Oxacycle
  • Organoheterocyclic compound
  • Polyol
  • Carboxylic acid derivative
  • Carboxylic acid
  • Dialkyl ether
  • Acetal
  • Oxirane
  • Ether
  • Carbonyl group
  • Primary alcohol
  • Organic oxygen compound
  • Organic oxide
  • Organooxygen compound
  • Alcohol
  • Hydrocarbon derivative
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
OntologyNo ontology term
Physico-Chemical Properties
Physico-Chemical Properties - Experimental
Spectra
Spectra
EI-MS/GC-MSNot Available
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0avr-0000936000-c341f0e1647121212ac12016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ab9-0200900000-35187d7d4af20d4e090a2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0571-3622900000-1d227fb4f1a2b04ba1152016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001r-1202798000-68b23b7a04a158897d4e2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0100-3100912000-d787e66de5c66d6905002016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-5002900000-15d83e8cd557cbfe68682016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00ri-0000509000-e45c19160ceb49b236c02021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03y0-0100196000-a670653c8fffe258c2fb2021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03el-4700981000-5e4fece3e8af40a37a472021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0540-0000049000-85cc40c8266b9c0259832021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-053r-4000097000-6ab360c8e41936d83f012021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-054n-9001500000-d4f995bac2c22dc9dfbe2021-10-21View Spectrum
NMRNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
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) IDJWX03-E:MOM97-J
EAFUS IDNot Available
Dr. Duke IDOBACUNONE-17-O-BETA-D-GLUCOSIDE|OBACUNONE-17-O-BETA-D-GLUCOPYRANOSIDE|OBACUNONE-GLUCOSIDE
BIGG IDNot Available
KNApSAcK IDNot Available
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
Processing...
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
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).