Quillaic acid 3-[galactosyl-(1->2)-[xylosyl-(1->3)]-glucuronide] 28-[6-acetyl-glucosyl-(1->3)-[glucosyl-(1->3)-[xylosyl-(1->4)]-rhamnosyl-(1->2)]-4-acetyl-fucosyl] ester (CHEM022688)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 18:47:22 UTC
Update Date2016-11-09 01:17:33 UTC
Accession NumberCHEM022688
Identification
Common NameQuillaic acid 3-[galactosyl-(1->2)-[xylosyl-(1->3)]-glucuronide] 28-[6-acetyl-glucosyl-(1->3)-[glucosyl-(1->3)-[xylosyl-(1->4)]-rhamnosyl-(1->2)]-4-acetyl-fucosyl] ester
ClassSmall Molecule
DescriptionQuillaic acid 3-[galactosyl-(1->2)-[xylosyl-(1->3)]-glucuronide] 28-[6-acetyl-glucosyl-(1->3)-[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)-[xylosyl-(1->3)]-glucuronide] 28-[6-acetyl-glucosyl-(1->3)-[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-hydroxy-6-methyl-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-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-trihydroxyoxan-2-yl)oxy]oxane-2-carboxylateHMDB
Chemical FormulaC80H124O44
Average Molecular Mass1789.814 g/mol
Monoisotopic Mass1788.747 g/mol
CAS Registry Number299184-69-3
IUPAC Name6-{[8a-({[5-(acetyloxy)-4-({6-[(acetyloxy)methyl]-3,4,5-trihydroxyoxan-2-yl}oxy)-3-[(3-hydroxy-6-methyl-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-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-trihydroxyoxan-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-hydroxy-6-methyl-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-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-trihydroxyoxan-2-yl)oxy]oxane-2-carboxylic acid
SMILESCC1OC(OC2C(OC(=O)C34CCC(C)(C)CC3C3=CCC5C6(C)CCC(OC7OC(C(O)C(OC8OCC(O)C(O)C8O)C7OC7OC(CO)C(O)C(O)C7O)C(O)=O)C(C)(C=O)C6CCC5(C)C3(C)CC4O)OC(C)C(OC(C)=O)C2OC2OC(COC(C)=O)C(O)C(O)C2O)C(O)C(OC2OC(CO)C(O)C(O)C2O)C1OC1OCC(O)C(O)C1O
InChI IdentifierInChI=1S/C80H124O44/c1-27-57(117-66-50(97)42(89)33(86)23-108-66)60(119-68-52(99)47(94)44(91)35(21-81)113-68)56(103)71(110-27)123-64-62(121-70-54(101)49(96)46(93)37(115-70)25-107-29(3)84)58(112-30(4)85)28(2)111-72(64)124-74(106)80-18-17-75(5,6)19-32(80)31-11-12-39-76(7)15-14-41(77(8,26-83)38(76)13-16-78(39,9)79(31,10)20-40(80)88)116-73-63(122-69-53(100)48(95)45(92)36(22-82)114-69)59(55(102)61(120-73)65(104)105)118-67-51(98)43(90)34(87)24-109-67/h11,26-28,32-64,66-73,81-82,86-103H,12-25H2,1-10H3,(H,104,105)
InChI KeyIPTFGTAXXVOSDM-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 Solubility7.44 g/LALOGPS
logP0.09ALOGPS
logP-5.7ChemAxon
logS-2.4ALOGPS
pKa (Strongest Acidic)3.28ChemAxon
pKa (Strongest Basic)-3.9ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count41ChemAxon
Hydrogen Donor Count21ChemAxon
Polar Surface Area676.32 ŲChemAxon
Rotatable Bond Count26ChemAxon
Refractivity398.41 m³·mol⁻¹ChemAxon
Polarizability178.25 ųChemAxon
Number of Rings13ChemAxon
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, Positivesplash10-05g0-0003216912-afd10c6755c825860b4eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00du-0303924511-46b702b2ba91872bd166Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00dl-0600914511-6b100aa06a6383c58169Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0691-1201323902-e9fd69099f5f6385c5a2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0699-3823593800-d7ee58d9469a7c77b6faSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a6r-5913312100-020af6e24662f419d9a6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0000013900-567a0693d2ccb732241cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-2200003911-3efcd027f851336f4b7bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03ds-1000611913-48872e9995174555d25aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0000253900-05916bb4d9ab8977063dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-1310216901-cd273a82e2a4eb7d532cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-4400008900-ef01891adbde1df21eb5Spectrum
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 IDHMDB0036952
FooDB IDFDB015922
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 ID131752109
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