Quillaic acid 3-[rhamnosyl-(1->3)-[galactosyl-(1->2)]-glucuronide], 28-[apiosyl-(1->3)-xylosyl-(1->4)-[glucosyl-(1->3)]-rhamnosyl-(1->2)-4-[5-[[5-(arabinosyloxy)-3-hydroxy-6-methyl-1-oxooctyl]oxy]-3-hydroxy-6-methyl-1-oxooctyl]-fucosyl] ester (CHEM022674)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 18:46:33 UTC
Update Date2016-11-09 01:17:33 UTC
Accession NumberCHEM022674
Identification
Common NameQuillaic acid 3-[rhamnosyl-(1->3)-[galactosyl-(1->2)]-glucuronide], 28-[apiosyl-(1->3)-xylosyl-(1->4)-[glucosyl-(1->3)]-rhamnosyl-(1->2)-4-[5-[[5-(arabinosyloxy)-3-hydroxy-6-methyl-1-oxooctyl]oxy]-3-hydroxy-6-methyl-1-oxooctyl]-fucosyl] ester
ClassSmall Molecule
DescriptionQuillaic acid 3-[rhamnosyl-(1->3)-[galactosyl-(1->2)]-glucuronide], 28-[apiosyl-(1->3)-xylosyl-(1->4)-[glucosyl-(1->3)]-rhamnosyl-(1->2)-4-[5-[[5-(arabinosyloxy)-3-hydroxy-6-methyl-1-oxooctyl]oxy]-3-hydroxy-6-methyl-1-oxooctyl]-fucosyl] ester is a constituent of Quillaja saponaria (soap-bark tree)
Contaminant Sources
  • FooDB Chemicals
  • HMDB Contaminants - Urine
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
Quillaate 3-[rhamnosyl-(1->3)-[galactosyl-(1->2)]-glucuronide], 28-[apiosyl-(1->3)-xylosyl-(1->4)-[glucosyl-(1->3)]-rhamnosyl-(1->2)-4-[5-[[5-(arabinosyloxy)-3-hydroxy-6-methyl-1-oxooctyl]oxy]-3-hydroxy-6-methyl-1-oxooctyl]-fucosyl] esterGenerator
6-{[8a-({[3-({5-[(4-{[3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-3,5-dihydroxyoxan-2-yl)oxy]-3-hydroxy-6-methyl-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl}oxy)-5-({5-[(5-{[3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}-3-hydroxy-6-methyloctanoyl)oxy]-3-hydroxy-6-methyloctanoyl}oxy)-4-hydroxy-6-methyloxan-2-yl]oxy}carbonyl)-4-formyl-8-hydroxy-4,6a,6b,11,11,14b-hexamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,14a,14b-icosahydropicen-3-yl]oxy}-3-hydroxy-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxane-2-carboxylateHMDB
Chemical FormulaC99H160O51
Average Molecular Mass2166.299 g/mol
Monoisotopic Mass2164.993 g/mol
CAS Registry Number263259-78-5
IUPAC Name6-{[8a-({[3-({5-[(4-{[3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-3,5-dihydroxyoxan-2-yl)oxy]-3-hydroxy-6-methyl-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl}oxy)-5-({5-[(5-{[3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}-3-hydroxy-6-methyloctanoyl)oxy]-3-hydroxy-6-methyloctanoyl}oxy)-4-hydroxy-6-methyloxan-2-yl]oxy}carbonyl)-4-formyl-8-hydroxy-4,6a,6b,11,11,14b-hexamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,14a,14b-icosahydropicen-3-yl]oxy}-3-hydroxy-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxane-2-carboxylic acid
Traditional Name6-{[8a-({[3-({5-[(4-{[3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-3,5-dihydroxyoxan-2-yl)oxy]-3-hydroxy-6-methyl-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl}oxy)-5-({5-[(5-{[3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}-3-hydroxy-6-methyloctanoyl)oxy]-3-hydroxy-6-methyloctanoyl}oxy)-4-hydroxy-6-methyloxan-2-yl]oxy}carbonyl)-4-formyl-8-hydroxy-4,6a,6b,11,11,14b-hexamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy}-3-hydroxy-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxane-2-carboxylic acid
SMILESCCC(C)C(CC(O)CC(=O)OC(CC(O)CC(=O)OC1C(C)OC(OC(=O)C23CCC(C)(C)CC2C2=CCC4C5(C)CCC(OC6OC(C(O)C(OC7OC(C)C(O)C(O)C7O)C6OC6OC(CO)C(O)C(O)C6O)C(O)=O)C(C)(C=O)C5CCC4(C)C2(C)CC3O)C(OC2OC(C)C(OC3OCC(O)C(OC4OCC(O)(CO)C4O)C3O)C(OC3OC(CO)C(O)C(O)C3O)C2O)C1O)C(C)CC)OC1OC(CO)C(O)C1O
InChI IdentifierInChI=1S/C99H160O51/c1-14-37(3)47(136-56(109)26-43(106)25-48(38(4)15-2)137-85-65(118)61(114)51(32-102)138-85)24-42(105)27-57(110)142-73-40(6)135-89(79(69(73)122)148-88-72(125)77(146-86-67(120)63(116)59(112)49(30-100)139-86)74(41(7)134-88)143-83-71(124)75(46(107)33-131-83)144-91-81(126)98(130,35-104)36-132-91)150-92(129)99-23-22-93(8,9)28-45(99)44-16-17-53-94(10)20-19-55(95(11,34-103)52(94)18-21-96(53,12)97(44,13)29-54(99)108)141-90-80(149-87-68(121)64(117)60(113)50(31-101)140-87)76(70(123)78(147-90)82(127)128)145-84-66(119)62(115)58(111)39(5)133-84/h16,34,37-43,45-55,58-81,83-91,100-102,104-108,111-126,130H,14-15,17-33,35-36H2,1-13H3,(H,127,128)
InChI KeyMWZYPLKAQQZARZ-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
  • Steroid
  • Fatty acyl glycoside
  • O-glucuronide
  • 1-o-glucuronide
  • Tetracarboxylic acid or derivatives
  • Glucuronic acid or derivatives
  • Alkyl glycoside
  • Glycosyl compound
  • O-glycosyl compound
  • Fatty alcohol
  • Fatty acid ester
  • Beta-hydroxy acid
  • Fatty acyl
  • Hydroxy acid
  • Pyran
  • Oxane
  • Cyclic alcohol
  • Tetrahydrofuran
  • Tertiary alcohol
  • Secondary alcohol
  • Carboxylic acid ester
  • Polyol
  • Carboxylic acid derivative
  • Carboxylic acid
  • Acetal
  • Oxacycle
  • Organoheterocyclic compound
  • Aldehyde
  • Organooxygen compound
  • Carbonyl group
  • Primary alcohol
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Organic oxide
  • 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 Solubility4.24 g/LALOGPS
logP0.71ALOGPS
logP-4.7ChemAxon
logS-2.7ALOGPS
pKa (Strongest Acidic)3.32ChemAxon
pKa (Strongest Basic)-3.9ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count48ChemAxon
Hydrogen Donor Count26ChemAxon
Polar Surface Area795.93 ŲChemAxon
Rotatable Bond Count41ChemAxon
Refractivity494.03 m³·mol⁻¹ChemAxon
Polarizability221.1 ųChemAxon
Number of Rings14ChemAxon
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, Positivesplash10-0002-6900033057-0a32eff0e1af11abcce4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0gbj-4500243195-e1dfb397dbe32925bfeaSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05n1-3510330291-d7537f2c079c8b2d0b58Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-3900021025-ffdd64e06b96165b7a10Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-1901033122-796c88d61e70e51be2cfSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004r-1900050011-301e2d6d2faab251b821Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-6900000031-69ef9280d5539d10622dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-1900000041-46b3589fa65d0bc6ace9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0aw9-6900001034-52a6bf8b1d2a6eca71daSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-8921100002-bcf074bd22feb2b49795Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-08gi-9500000010-4c84ce577774da9946dbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03di-8900000817-50623b6ca31f8e3df237Spectrum
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 IDHMDB0036269
FooDB IDFDB015134
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 ID131751928
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