Quillaic acid 3-[galactosyl-(1->2)-[rhamnosyl-(1->3)]-glucuronide] 28-[6-acetyl-glucosyl-(1->3)-[xylosyl-(1->4)-rhamnosyl-(1->2)]-4-acetyl-fucosyl] ester (CHEM022685)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 18:47:13 UTC
Update Date2016-11-09 01:17:33 UTC
Accession NumberCHEM022685
Identification
Common NameQuillaic acid 3-[galactosyl-(1->2)-[rhamnosyl-(1->3)]-glucuronide] 28-[6-acetyl-glucosyl-(1->3)-[xylosyl-(1->4)-rhamnosyl-(1->2)]-4-acetyl-fucosyl] ester
ClassSmall Molecule
DescriptionQuillaic acid 3-[galactosyl-(1->2)-[rhamnosyl-(1->3)]-glucuronide] 28-[6-acetyl-glucosyl-(1->3)-[xylosyl-(1->4)-rhamnosyl-(1->2)]-4-acetyl-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-[galactosyl-(1->2)-[rhamnosyl-(1->3)]-glucuronide] 28-[6-acetyl-glucosyl-(1->3)-[xylosyl-(1->4)-rhamnosyl-(1->2)]-4-acetyl-fucosyl] esterGenerator
6-{[8a-({[5-(acetyloxy)-4-({6-[(acetyloxy)methyl]-3,4,5-trihydroxyoxan-2-yl}oxy)-3-({3,4-dihydroxy-6-methyl-5-[(3,4,5-trihydroxyoxan-2-yl)oxy]oxan-2-yl}oxy)-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 FormulaC75H116O39
Average Molecular Mass1641.700 g/mol
Monoisotopic Mass1640.709 g/mol
CAS Registry Number299184-61-5
IUPAC Name6-{[8a-({[5-(acetyloxy)-4-({6-[(acetyloxy)methyl]-3,4,5-trihydroxyoxan-2-yl}oxy)-3-({3,4-dihydroxy-6-methyl-5-[(3,4,5-trihydroxyoxan-2-yl)oxy]oxan-2-yl}oxy)-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-({[5-(acetyloxy)-4-({6-[(acetyloxy)methyl]-3,4,5-trihydroxyoxan-2-yl}oxy)-3-({3,4-dihydroxy-6-methyl-5-[(3,4,5-trihydroxyoxan-2-yl)oxy]oxan-2-yl}oxy)-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
SMILESCC1OC(OC2C(O)C(OC(OC3CCC4(C)C(CCC5(C)C4CC=C4C6CC(C)(C)CCC6(C(O)CC54C)C(=O)OC4OC(C)C(OC(C)=O)C(OC5OC(COC(C)=O)C(O)C(O)C5O)C4OC4OC(C)C(OC5OCC(O)C(O)C5O)C(O)C4O)C3(C)C=O)C2OC2OC(CO)C(O)C(O)C2O)C(O)=O)C(O)C(O)C1O
InChI IdentifierInChI=1S/C75H116O39/c1-26-40(82)44(86)49(91)63(101-26)109-56-53(95)57(61(96)97)110-68(59(56)112-65-50(92)45(87)42(84)34(22-76)105-65)107-39-15-16-71(8)36(72(39,9)25-77)14-17-73(10)37(71)13-12-31-32-20-70(6,7)18-19-75(32,38(81)21-74(31,73)11)69(98)114-67-60(113-64-52(94)47(89)54(27(2)102-64)108-62-48(90)41(83)33(80)23-100-62)58(55(28(3)103-67)104-30(5)79)111-66-51(93)46(88)43(85)35(106-66)24-99-29(4)78/h12,25-28,32-60,62-68,76,80-95H,13-24H2,1-11H3,(H,96,97)
InChI KeyYZXHDUJUOVKVIS-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
  • 1-o-glucuronide
  • O-glucuronide
  • Glucuronic acid or derivatives
  • Tetracarboxylic acid or derivatives
  • Glycosyl compound
  • O-glycosyl compound
  • Beta-hydroxy acid
  • Fatty acyl
  • Pyran
  • Oxane
  • Hydroxy acid
  • Cyclic alcohol
  • Secondary alcohol
  • Carboxylic acid ester
  • Organoheterocyclic compound
  • Carboxylic acid derivative
  • Polyol
  • Carboxylic acid
  • Acetal
  • Oxacycle
  • Aldehyde
  • Alcohol
  • Organooxygen compound
  • Organic oxygen compound
  • Primary alcohol
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxide
  • 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 Solubility2.86 g/LALOGPS
logP0.47ALOGPS
logP-3.5ChemAxon
logS-2.8ALOGPS
pKa (Strongest Acidic)3.32ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count36ChemAxon
Hydrogen Donor Count18ChemAxon
Polar Surface Area597.17 ŲChemAxon
Rotatable Bond Count23ChemAxon
Refractivity370.42 m³·mol⁻¹ChemAxon
Polarizability167.3 ųChemAxon
Number of Rings12ChemAxon
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, Positivesplash10-00di-0302916013-3bbf3e40f27cd28a6d92Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0fft-1637903043-ade7b63cadb9391ed727Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fmj-2936603032-418195c0f8fd054bffb9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-05i1-4932687005-3bbdbfe42600fe9dd2caSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-076s-5933325002-ea7d0fdff2254ca14bbdSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-06tb-5931000000-66c7ffbc1b4a6c84515bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-009y-0523859000-c422b466f40935180a28Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03ed-0918402000-0a870e0942468560aa94Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-7702479452-62812d88d3ae815671d8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-002r-0100139001-b395b895d6f8fddcd9e1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0cg0-5200293000-677303556e56670b7e93Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052r-7142972000-f9037713f694755c9225Spectrum
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
1D NMR1H 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 IDHMDB0036949
FooDB IDFDB015919
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 ID131752106
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