28-Glucosyloleanolic acid 3-[rhamnosyl-(1->2)-galactosyl-(1->3)-glucuronide] (CHEM034001)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 04:35:31 UTC
Update Date2016-11-09 01:21:03 UTC
Accession NumberCHEM034001
Identification
Common Name28-Glucosyloleanolic acid 3-[rhamnosyl-(1->2)-galactosyl-(1->3)-glucuronide]
ClassSmall Molecule
Description28-Glucosyloleanolic acid 3-[rhamnosyl-(1->2)-galactosyl-(1->3)-glucuronide] is found in fruits. 28-Glucosyloleanolic acid 3-[rhamnosyl-(1->2)-galactosyl-(1->3)-glucuronide] is a constituent of the famine food Ximenia americana (tallow nut).
Contaminant Sources
  • FooDB Chemicals
  • HMDB Contaminants - Urine
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
28-Glucosyloleanolate 3-[rhamnosyl-(1->2)-galactosyl-(1->3)-glucuronide]Generator
6-[(2-{[4,4,6a,6b,11,11,14b-heptamethyl-8a-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}carbonyl)-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,14a,14b-icosahydropicen-3-yl]oxy}-6-carboxy-3,5-dihydroxyoxan-4-yl)oxy]-3,4-dihydroxy-5-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxane-2-carboxylateGenerator
Chemical FormulaC54H84O24
Average Molecular Mass1117.230 g/mol
Monoisotopic Mass1116.535 g/mol
CAS Registry NumberNot Available
IUPAC Name6-[(2-{[4,4,6a,6b,11,11,14b-heptamethyl-8a-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}carbonyl)-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,14a,14b-icosahydropicen-3-yl]oxy}-6-carboxy-3,5-dihydroxyoxan-4-yl)oxy]-3,4-dihydroxy-5-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxane-2-carboxylic acid
Traditional Name6-[(2-{[4,4,6a,6b,11,11,14b-heptamethyl-8a-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}carbonyl)-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy}-6-carboxy-3,5-dihydroxyoxan-4-yl)oxy]-3,4-dihydroxy-5-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxane-2-carboxylic acid
SMILESCC1OC(OC2C(O)C(O)C(OC2OC2C(O)C(OC3CCC4(C)C(CCC5(C)C4CC=C4C6CC(C)(C)CCC6(CCC54C)C(=O)OC4OC(CO)C(O)C(O)C4O)C3(C)C)OC(C2O)C(O)=O)C(O)=O)C(O)C(O)C1O
InChI IdentifierInChI=1S/C54H84O24/c1-21-28(56)30(58)34(62)44(71-21)77-41-33(61)32(60)39(42(66)67)76-47(41)74-38-36(64)40(43(68)69)75-46(37(38)65)73-27-12-13-51(6)25(50(27,4)5)11-14-53(8)26(51)10-9-22-23-19-49(2,3)15-17-54(23,18-16-52(22,53)7)48(70)78-45-35(63)31(59)29(57)24(20-55)72-45/h9,21,23-41,44-47,55-65H,10-20H2,1-8H3,(H,66,67)(H,68,69)
InChI KeyIMPZGAYJJGGWNV-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as triterpene saponins. These are glycosylated derivatives of triterpene sapogenins. The sapogenin moiety backbone is usually based on the oleanane, ursane, taraxastane, bauerane, lanostane, lupeol, lupane, dammarane, cycloartane, friedelane, hopane, 9b,19-cyclo-lanostane, cycloartane, or cycloartanol skeleton.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassTerpene glycosides
Direct ParentTriterpene saponins
Alternative Parents
Substituents
  • Triterpene saponin
  • Triterpenoid
  • Oligosaccharide
  • 1-o-glucuronide
  • O-glucuronide
  • Glucuronic acid or derivatives
  • Glycosyl compound
  • O-glycosyl compound
  • Tricarboxylic acid or derivatives
  • Beta-hydroxy acid
  • Pyran
  • Oxane
  • Hydroxy acid
  • Secondary alcohol
  • Carboxylic acid ester
  • Polyol
  • Carboxylic acid derivative
  • Carboxylic acid
  • Acetal
  • Oxacycle
  • Organoheterocyclic compound
  • Organooxygen compound
  • Organic oxygen compound
  • Organic oxide
  • Primary alcohol
  • Hydrocarbon derivative
  • Carbonyl group
  • Alcohol
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic 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 Solubility0.28 g/LALOGPS
logP1.72ALOGPS
logP0.7ChemAxon
logS-3.6ALOGPS
pKa (Strongest Acidic)2.82ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count23ChemAxon
Hydrogen Donor Count13ChemAxon
Polar Surface Area388.04 ŲChemAxon
Rotatable Bond Count12ChemAxon
Refractivity261.49 m³·mol⁻¹ChemAxon
Polarizability116.28 ųChemAxon
Number of Rings9ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0f72-3400305419-dc4781eb543dbc7b94eeSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-1000-1300409514-0ea5e17e3dcbde521313Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-3500918422-26b81cb8a1f7b64f615fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0fr2-6700011229-06944065be24b3ea3320Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0292-7900014316-eab6f99ae03b406bbff9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03xr-5900104201-a70e2d7088c44978910aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014j-9700001104-3263ef45595d0bfb2ee6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0pdi-9100000002-28ef861cfe5a18d0551fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a6s-9200001316-abff8a86f7e751169ea3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0q2a-3300000019-82e81593b0b6f304f686Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0zmi-0500202249-5af42ff7477422921c38Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ktr-9613602402-d76d95ba93be964cb9dfSpectrum
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 IDHMDB0040859
FooDB IDFDB020687
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider IDNot Available
ChEBI IDNot Available
PubChem Compound ID131752956
Kegg Compound IDNot Available
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