(3b,16a)-Dihydroxy-12-oleanen-28-oic acid 3-[glucosyl-(1->2)-arabinoside] 28-[rhamnosyl-(1->4)-glucosyl-(1->4)-glucosyl] ester (CHEM029392)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 01:08:24 UTC
Update Date2016-11-09 01:18:52 UTC
Accession NumberCHEM029392
Identification
Common Name(3b,16a)-Dihydroxy-12-oleanen-28-oic acid 3-[glucosyl-(1->2)-arabinoside] 28-[rhamnosyl-(1->4)-glucosyl-(1->4)-glucosyl] ester
ClassSmall Molecule
Description(3b,16a)-Dihydroxy-12-oleanen-28-oic acid 3-[glucosyl-(1->2)-arabinoside] 28-[rhamnosyl-(1->4)-glucosyl-(1->4)-glucosyl] ester is found in fruits. (3b,16a)-Dihydroxy-12-oleanen-28-oic acid 3-[glucosyl-(1->2)-arabinoside] 28-[rhamnosyl-(1->4)-glucosyl-(1->4)-glucosyl] ester is a constituent of Pithecellobium dulce (manila tamarind)
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(3b,16a)-Dihydroxy-12-oleanen-28-Oate 3-[glucosyl-(1->2)-arabinoside] 28-[rhamnosyl-(1->4)-glucosyl-(1->4)-glucosyl] esterGenerator
5-{[3,4-dihydroxy-6-(hydroxymethyl)-5-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-2-yl]oxy}-3,4-dihydroxy-6-(hydroxymethyl)oxan-2-yl 10-[(4,5-dihydroxy-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl)oxy]-5-hydroxy-2,2,6a,6b,9,9,12a-heptamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-4a-carboxylic acidGenerator
Chemical FormulaC59H96O27
Average Molecular Mass1237.377 g/mol
Monoisotopic Mass1236.614 g/mol
CAS Registry Number214219-70-2
IUPAC Name5-{[3,4-dihydroxy-6-(hydroxymethyl)-5-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-2-yl]oxy}-3,4-dihydroxy-6-(hydroxymethyl)oxan-2-yl 10-[(4,5-dihydroxy-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl)oxy]-5-hydroxy-2,2,6a,6b,9,9,12a-heptamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-4a-carboxylate
Traditional Name5-{[3,4-dihydroxy-6-(hydroxymethyl)-5-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-2-yl]oxy}-3,4-dihydroxy-6-(hydroxymethyl)oxan-2-yl 10-[(4,5-dihydroxy-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl)oxy]-5-hydroxy-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,7,8,8a,10,11,12,12b,13,14b-tetradecahydropicene-4a-carboxylate
SMILESCC1OC(OC2C(O)C(O)C(OC3C(O)C(O)C(OC(=O)C45CCC(C)(C)CC4C4=CCC6C7(C)CCC(OC8OCC(O)C(O)C8OC8OC(CO)C(O)C(O)C8O)C(C)(C)C7CCC6(C)C4(C)CC5O)OC3CO)OC2CO)C(O)C(O)C1O
InChI IdentifierInChI=1S/C59H96O27/c1-23-34(65)37(68)41(72)48(78-23)83-45-28(20-61)80-50(43(74)39(45)70)84-46-29(21-62)81-51(44(75)40(46)71)86-53(76)59-16-15-54(2,3)17-25(59)24-9-10-31-56(6)13-12-33(55(4,5)30(56)11-14-57(31,7)58(24,8)18-32(59)64)82-52-47(35(66)26(63)22-77-52)85-49-42(73)38(69)36(67)27(19-60)79-49/h9,23,25-52,60-75H,10-22H2,1-8H3
InChI KeyISIYNDLTTHPMEA-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
  • Glycosyl compound
  • O-glycosyl compound
  • Beta-hydroxy acid
  • Hydroxy acid
  • Oxane
  • Cyclic alcohol
  • Carboxylic acid ester
  • Secondary alcohol
  • Oxacycle
  • Carboxylic acid derivative
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Polyol
  • Acetal
  • Organic oxide
  • Organic oxygen compound
  • Primary alcohol
  • Hydrocarbon derivative
  • Carbonyl group
  • Alcohol
  • Organooxygen compound
  • 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 Solubility2.1 g/LALOGPS
logP0.34ALOGPS
logP-2.3ChemAxon
logS-2.8ALOGPS
pKa (Strongest Acidic)11.67ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count26ChemAxon
Hydrogen Donor Count16ChemAxon
Polar Surface Area433.05 ŲChemAxon
Rotatable Bond Count14ChemAxon
Refractivity289.72 m³·mol⁻¹ChemAxon
Polarizability130.15 ųChemAxon
Number of Rings10ChemAxon
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, Positivesplash10-02vj-7270202809-3155fa95023a22a86cf6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-016r-4120304809-7954ab968f363d26413eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014j-3530206906-b8dc840e6846956c6989Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-6590002404-b63de347db6ce6255773Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-5961100404-ba005d7eca1aaeaf35b2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-3900001202-bf058c05e08cfe5bc9e6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00kr-1590800400-658d05fbc6f769a1f647Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01w1-8920000101-b50b1a7e200adb8dd6ffSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0ar0-5800090603-dd2f3452dd61493d97eeSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-002u-5291001207-a9a6ebe6bd44023d948bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-3930000402-79902613c938810750afSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-02p4-9620100202-9fab4c680328d9797e4eSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
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 IDHMDB0035492
FooDB IDFDB014178
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 ID131751782
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