Quillaic acid 3-[galactosyl-(1->2)-[xylosyl-(1->3)]-glucuronide] 28-[6-acetyl-glucosyl-(1->3)-[xylosyl-(1->4)-rhamnosyl-(1->2)]-4-acetyl-fucosyl] ester (CHEM022684)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 18:47:10 UTC
Update Date2016-11-09 01:17:33 UTC
Accession NumberCHEM022684
Identification
Common NameQuillaic acid 3-[galactosyl-(1->2)-[xylosyl-(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)-[xylosyl-(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)-[xylosyl-(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-trihydroxyoxan-2-yl)oxy]oxane-2-carboxylateHMDB
Chemical FormulaC74H114O39
Average Molecular Mass1627.674 g/mol
Monoisotopic Mass1626.694 g/mol
CAS Registry Number299184-68-2
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-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-({3,4-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-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(O)C1OC1OCC(O)C(O)C1O
InChI IdentifierInChI=1S/C74H114O39/c1-26-53(107-61-47(89)40(82)32(79)22-99-61)46(88)51(93)63(101-26)112-59-57(110-65-50(92)45(87)43(85)35(105-65)24-98-28(3)77)54(103-29(4)78)27(2)102-66(59)113-68(97)74-18-17-69(5,6)19-31(74)30-11-12-37-70(7)15-14-39(71(8,25-76)36(70)13-16-72(37,9)73(30,10)20-38(74)81)106-67-58(111-64-49(91)44(86)42(84)34(21-75)104-64)55(52(94)56(109-67)60(95)96)108-62-48(90)41(83)33(80)23-100-62/h11,25-27,31-59,61-67,75,79-94H,12-24H2,1-10H3,(H,95,96)
InChI KeyHQXVDKYGUHXBNZ-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 Solubility3.2 g/LALOGPS
logP0.24ALOGPS
logP-3.9ChemAxon
logS-2.7ALOGPS
pKa (Strongest Acidic)3.28ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count36ChemAxon
Hydrogen Donor Count18ChemAxon
Polar Surface Area597.17 ŲChemAxon
Rotatable Bond Count23ChemAxon
Refractivity366 m³·mol⁻¹ChemAxon
Polarizability164.73 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, Positivesplash10-0a4i-0202916013-40d92956d6a3af87a0c6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a70-1456904134-e3a4c7491737181027b4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a7r-3967704233-261f42b08227a4bd7714Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a70-4954788005-b49f3e0c77b44aa9ed25Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a6s-5935525001-640f846020bf179745fbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-054k-5941000000-34eb8e5991cb1d17e72eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-05di-0232948000-0519d291a4529b2b1bb3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004r-2111619212-13216dd90ecf79f62ad1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004r-3300339011-e8660d450c0ba0b8fcd3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0000369000-8f93682abbd56e2b137fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0kdl-3400695012-2c004ab02fa5988eceb6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-022i-1081011922-81ac0fe9dc1439906372Spectrum
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 IDHMDB0036948
FooDB IDFDB015918
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 ID131752105
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