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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 21:22:28 UTC
Update Date2018-05-20 20:35:40 UTC
HMDB IDHMDB0036273
Secondary Accession Numbers
  • HMDB36273
Metabolite Identification
Common NameQuillaic acid 3-[galactosyl-(1->2)-glucuronide] 28-[xylosyl-(1->4)-rhamnosyl-(1->2)-[rhamnosyl-(1->3)]-4-acetyl-fucosyl] ester
DescriptionQuillaic acid 3-[galactosyl-(1->2)-glucuronide] 28-[xylosyl-(1->4)-rhamnosyl-(1->2)-[rhamnosyl-(1->3)]-4-acetyl-fucosyl] ester 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. Quillaic acid 3-[galactosyl-(1->2)-glucuronide] 28-[xylosyl-(1->4)-rhamnosyl-(1->2)-[rhamnosyl-(1->3)]-4-acetyl-fucosyl] ester is slightly soluble (in water) and a weakly acidic compound (based on its pKa). Quillaic acid 3-[galactosyl-(1->2)-glucuronide] 28-[xylosyl-(1->4)-rhamnosyl-(1->2)-[rhamnosyl-(1->3)]-4-acetyl-fucosyl] ester has been found in human liver and kidney tissues, and has also been detected in multiple biofluids, such as urine and blood. Within the cell, quillaic acid 3-[galactosyl-(1->2)-glucuronide] 28-[xylosyl-(1->4)-rhamnosyl-(1->2)-[rhamnosyl-(1->3)]-4-acetyl-fucosyl] ester is primarily located in the cytoplasm.
Structure
Thumb
SynonymsNot Available
Chemical FormulaC67H104O33
Average Molecular Weight1437.5229
Monoisotopic Molecular Weight1436.645985854
IUPAC Name6-{[8a-({[5-(acetyloxy)-3-({3,4-dihydroxy-6-methyl-5-[(3,4,5-trihydroxyoxan-2-yl)oxy]oxan-2-yl}oxy)-6-methyl-4-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-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}-3,4-dihydroxy-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxane-2-carboxylic acid
Traditional Name6-{[8a-({[5-(acetyloxy)-3-({3,4-dihydroxy-6-methyl-5-[(3,4,5-trihydroxyoxan-2-yl)oxy]oxan-2-yl}oxy)-6-methyl-4-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-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}-3,4-dihydroxy-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxane-2-carboxylic acid
CAS Registry Number287386-81-6
SMILES
CC1OC(OC2C(OC(C)=O)C(C)OC(OC(=O)C34CCC(C)(C)CC3C3=CCC5C6(C)CCC(OC7OC(C(O)C(O)C7OC7OC(CO)C(O)C(O)C7O)C(O)=O)C(C)(C=O)C6CCC5(C)C3(C)CC4O)C2OC2OC(C)C(OC3OCC(O)C(O)C3O)C(O)C2O)C(O)C(O)C1O
InChI Identifier
InChI=1S/C67H104O33/c1-24-36(73)39(76)45(82)56(89-24)98-52-49(92-27(4)70)26(3)91-60(53(52)99-57-47(84)43(80)48(25(2)90-57)95-55-44(81)37(74)30(71)22-88-55)100-61(87)67-18-17-62(5,6)19-29(67)28-11-12-33-63(7)15-14-35(64(8,23-69)32(63)13-16-65(33,9)66(28,10)20-34(67)72)94-59-51(42(79)41(78)50(96-59)54(85)86)97-58-46(83)40(77)38(75)31(21-68)93-58/h11,23-26,29-53,55-60,68,71-84H,12-22H2,1-10H3,(H,85,86)
InChI KeyNCECUVMWTCHHHY-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound 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
  • Glycosyl compound
  • O-glycosyl compound
  • Tricarboxylic acid or derivatives
  • Beta-hydroxy acid
  • Pyran
  • Oxane
  • Fatty acyl
  • Hydroxy acid
  • Cyclic alcohol
  • Secondary alcohol
  • Carboxylic acid ester
  • Polyol
  • Acetal
  • Organoheterocyclic compound
  • Oxacycle
  • Carboxylic acid derivative
  • Carboxylic acid
  • Primary alcohol
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Carbonyl group
  • Organooxygen compound
  • Aldehyde
  • Alcohol
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility1.75 g/LALOGPS
logP0.51ALOGPS
logP-2.2ChemAxon
logS-2.9ALOGPS
pKa (Strongest Acidic)3.31ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count31ChemAxon
Hydrogen Donor Count16ChemAxon
Polar Surface Area511.95 ŲChemAxon
Rotatable Bond Count18ChemAxon
Refractivity328.85 m³·mol⁻¹ChemAxon
Polarizability147.33 ųChemAxon
Number of Rings11ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-066r-2461902051-7fdb3ec193f9a366c0deView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-066r-4930401056-1ef94aa19233815336acView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014j-1911301023-09fe5d87e05a2d6e0513View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0ar0-7594600030-2af37fd2659e65fc0d4eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01dj-4952300010-299a9d904c4fba478973View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-06te-5920000000-e66f512692a6fa8bf031View in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Liver
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableNormal
    details
    UrineExpected but not Quantified Not AvailableNot AvailableNormal
      details
      Abnormal Concentrations
      Not Available
      Associated Disorders and Diseases
      Disease ReferencesNone
      Associated OMIM IDsNone
      DrugBank IDNot Available
      Phenol Explorer Compound IDNot Available
      FoodDB IDFDB015138
      KNApSAcK IDNot Available
      Chemspider IDNot Available
      KEGG Compound IDNot Available
      BioCyc IDNot Available
      BiGG IDNot Available
      Wikipedia LinkNot Available
      METLIN IDNot Available
      PubChem CompoundNot Available
      PDB IDNot Available
      ChEBI IDNot Available
      References
      Synthesis ReferenceNot Available
      Material Safety Data Sheet (MSDS)Not Available
      General References
      1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
      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. [PubMed:16902246 ]
      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. [PubMed:17374880 ]
      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. [PubMed:20044567 ]
      5. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
      6. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.