You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version4.0
Creation Date2012-09-11 21:23:02 UTC
Update Date2017-09-27 08:31:16 UTC
HMDB IDHMDB0036276
Secondary Accession Numbers
  • HMDB36276
Metabolite Identification
Common NameQuillaic acid 3-[galactosyl-(1->2)-[rhamnosyl-(1->3)]-glucuronide] 28-[apiosyl-(1->3)-xylosyl-(1->4)-rhamnosyl-(1->2)-[rhamnosyl-(1->3)]-4-acetyl-fucosyl] ester
DescriptionQuillaic acid 3-[galactosyl-(1->2)-[rhamnosyl-(1->3)]-glucuronide] 28-[apiosyl-(1->3)-xylosyl-(1->4)-rhamnosyl-(1->2)-[rhamnosyl-(1->3)]-4-acetyl-fucosyl] ester is a constituent of Quillaja saponaria (soap-bark tree)
Structure
Thumb
SynonymsNot Available
Chemical FormulaC78H122O41
Average Molecular Weight1715.7787
Monoisotopic Molecular Weight1714.746153406
IUPAC Name6-{[8a-({[5-(acetyloxy)-3-({5-[(4-{[3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-3,5-dihydroxyoxan-2-yl)oxy]-3,4-dihydroxy-6-methyloxan-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-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)-3-({5-[(4-{[3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-3,5-dihydroxyoxan-2-yl)oxy]-3,4-dihydroxy-6-methyloxan-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-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
CAS Registry Number287386-84-9
SMILES
CC1OC(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(C)C(O)C(O)C5O)C4OC4OC(C)C(OC5OCC(O)C(OC6OCC(O)(CO)C6O)C5O)C(O)C4O)C3(C)C=O)C2OC2OC(CO)C(O)C(O)C2O)C(O)=O)C(O)C(O)C1O
InChI Identifier
InChI=1S/C78H122O41/c1-27-40(85)43(88)47(92)64(105-27)114-56-51(96)57(62(99)100)115-69(59(56)117-67-49(94)45(90)42(87)35(22-79)110-67)111-39-15-16-73(8)36(74(39,9)24-80)14-17-75(10)37(73)13-12-32-33-20-72(6,7)18-19-78(33,38(84)21-76(32,75)11)71(101)119-68-60(58(54(30(4)108-68)109-31(5)82)116-65-48(93)44(89)41(86)28(2)106-65)118-66-50(95)46(91)53(29(3)107-66)112-63-52(97)55(34(83)23-103-63)113-70-61(98)77(102,25-81)26-104-70/h12,24,27-30,33-61,63-70,79,81,83-98,102H,13-23,25-26H2,1-11H3,(H,99,100)
InChI KeyKOTNBFRPUJOEMU-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities 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.
KingdomChemical entities
Super ClassOrganic compounds
ClassLipids and lipid-like molecules
Sub ClassPrenol lipids
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
  • 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
  • Primary alcohol
  • Aldehyde
  • Organooxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

  Organ and components:

Source:

  Biological:

    Animal:

Route of exposure:

  Enteral:

Role

Biological role:

Process

Naturally occurring process:

  Biological process:

    Biochemical pathway:

    Chemical reaction:

    Biochemical process:

Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility4.26 g/LALOGPS
logP0.34ALOGPS
logP-4.2ChemAxon
logS-2.6ALOGPS
pKa (Strongest Acidic)3.32ChemAxon
pKa (Strongest Basic)-3.9ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count39ChemAxon
Hydrogen Donor Count20ChemAxon
Polar Surface Area629.79 ŲChemAxon
Rotatable Bond Count23ChemAxon
Refractivity386.39 m³·mol⁻¹ChemAxon
Polarizability172.99 ųChemAxon
Number of Rings13ChemAxon
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, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Liver
PathwaysNot Available
NameSMPDB/PathwhizKEGG
No entries found
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
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
      DrugBank Metabolite IDNot Available
      Phenol Explorer Compound IDNot Available
      Phenol Explorer Metabolite IDNot Available
      FoodDB IDFDB015141
      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.. .