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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 22:09:16 UTC
Update Date2017-12-07 03:49:29 UTC
HMDB IDHMDB0036950
Secondary Accession Numbers
  • HMDB36950
Metabolite Identification
Common NameQuillaic acid 3-[galactosyl-(1->2)-[xylosyl-(1->3)]-glucuronide] 28-[glucosyl-(1->3)-[glucosyl-(1->3)-[xylosyl-(1->4)]-rhamnosyl-(1->2)]-4-acetyl-fucosyl] ester
DescriptionQuillaic acid 3-[galactosyl-(1->2)-[xylosyl-(1->3)]-glucuronide] 28-[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).
Structure
Thumb
SynonymsNot Available
Chemical FormulaC78H122O43
Average Molecular Weight1747.7775
Monoisotopic Molecular Weight1746.73598265
IUPAC Name6-{[8a-({[5-(acetyloxy)-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-methyl-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-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-trihydroxyoxan-2-yl)oxy]oxane-2-carboxylic acid
Traditional Name6-{[8a-({[5-(acetyloxy)-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-methyl-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-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-trihydroxyoxan-2-yl)oxy]oxane-2-carboxylic acid
CAS Registry Number299184-67-1
SMILES
CC1OC(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(CO)C(O)C(O)C2O)C(O)C(OC2OC(CO)C(O)C(O)C2O)C1OC1OCC(O)C(O)C1O
InChI Identifier
InChI=1S/C78H122O43/c1-26-55(114-64-48(95)40(87)31(84)23-105-64)58(116-66-50(97)45(92)42(89)33(20-79)110-66)54(101)69(107-26)120-62-60(118-67-51(98)46(93)43(90)34(21-80)111-67)56(109-28(3)83)27(2)108-70(62)121-72(104)78-17-16-73(4,5)18-30(78)29-10-11-37-74(6)14-13-39(75(7,25-82)36(74)12-15-76(37,8)77(29,9)19-38(78)86)113-71-61(119-68-52(99)47(94)44(91)35(22-81)112-68)57(53(100)59(117-71)63(102)103)115-65-49(96)41(88)32(85)24-106-65/h10,25-27,30-62,64-71,79-81,84-101H,11-24H2,1-9H3,(H,102,103)
InChI KeyFJIPBFYLXJVQNV-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
  • 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

Biological Location:

  Subcellular:

  Biofluid and excreta:

  Organ and components:

  Cell and elements:

Source:

  Biological:

    Animal:

Route of exposure:

  Enteral:

Role

Biological role:

Industrial application:

Process

Naturally occurring process:

  Biological process:

    Cellular 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 Solubility12.5 g/LALOGPS
logP0.1ALOGPS
logP-6.2ChemAxon
logS-2.1ALOGPS
pKa (Strongest Acidic)3.28ChemAxon
pKa (Strongest Basic)-3.9ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count41ChemAxon
Hydrogen Donor Count22ChemAxon
Polar Surface Area670.25 ŲChemAxon
Rotatable Bond Count24ChemAxon
Refractivity389.26 m³·mol⁻¹ChemAxon
Polarizability174.5 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, Positivesplash10-00p0-0120381902-bfd48f342a7ba49e2f40View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0v00-0520950411-13097aceb0a953d452a6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0uml-0700941410-68dfd060722fa0d7e639View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-056r-1330763904-4263f2887bd13d71354eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-2803961701-f011fb3c50a0bded94f0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a6r-3911311000-31d8af310841c5f6e10fView in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Liver
PathwaysNot Available
NameSMPDB/PathwhizKEGG
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 IDFDB015920
      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.