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
Version3.6
Creation Date2012-09-11 21:21:06 UTC
Update Date2017-08-18 01:22:07 UTC
HMDB IDHMDB0036269
Secondary Accession Numbers
  • HMDB36269
Metabolite Identification
Common NameQuillaic acid 3-[rhamnosyl-(1->3)-[galactosyl-(1->2)]-glucuronide], 28-[apiosyl-(1->3)-xylosyl-(1->4)-[glucosyl-(1->3)]-rhamnosyl-(1->2)-4-[5-[[5-(arabinosyloxy)-3-hydroxy-6-methyl-1-oxooctyl]oxy]-3-hydroxy-6-methyl-1-oxooctyl]-fucosyl] ester
DescriptionQuillaic acid 3-[rhamnosyl-(1->3)-[galactosyl-(1->2)]-glucuronide], 28-[apiosyl-(1->3)-xylosyl-(1->4)-[glucosyl-(1->3)]-rhamnosyl-(1->2)-4-[5-[[5-(arabinosyloxy)-3-hydroxy-6-methyl-1-oxooctyl]oxy]-3-hydroxy-6-methyl-1-oxooctyl]-fucosyl] ester is a constituent of Quillaja saponaria (soap-bark tree). Quillaic acid 3-[rhamnosyl-(1->3)-[galactosyl-(1->2)]-glucuronide], 28-[apiosyl-(1->3)-xylosyl-(1->4)-[glucosyl-(1->3)]-rhamnosyl-(1->2)-4-[5-[[5-(arabinosyloxy)-3-hydroxy-6-methyl-1-oxooctyl]oxy]-3-hydroxy-6-methyl-1-oxooctyl]-fucosyl] ester belongs to the family of Mixed Pentose/Hexoses Oligosaccharides. These are oligosaccharides made up of pentose and hexose saccharide units.
Structure
Thumb
SynonymsNot Available
Chemical FormulaC99H160O51
Average Molecular Weight2166.2991
Monoisotopic Molecular Weight2164.992650842
IUPAC Name6-{[8a-({[3-({5-[(4-{[3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-3,5-dihydroxyoxan-2-yl)oxy]-3-hydroxy-6-methyl-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl}oxy)-5-({5-[(5-{[3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}-3-hydroxy-6-methyloctanoyl)oxy]-3-hydroxy-6-methyloctanoyl}oxy)-4-hydroxy-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-trihydroxy-6-methyloxan-2-yl)oxy]oxane-2-carboxylic acid
Traditional Name6-{[8a-({[3-({5-[(4-{[3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-3,5-dihydroxyoxan-2-yl)oxy]-3-hydroxy-6-methyl-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl}oxy)-5-({5-[(5-{[3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}-3-hydroxy-6-methyloctanoyl)oxy]-3-hydroxy-6-methyloctanoyl}oxy)-4-hydroxy-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-trihydroxy-6-methyloxan-2-yl)oxy]oxane-2-carboxylic acid
CAS Registry Number263259-78-5
SMILES
CCC(C)C(CC(O)CC(=O)OC(CC(O)CC(=O)OC1C(C)OC(OC(=O)C23CCC(C)(C)CC2C2=CCC4C5(C)CCC(OC6OC(C(O)C(OC7OC(C)C(O)C(O)C7O)C6OC6OC(CO)C(O)C(O)C6O)C(O)=O)C(C)(C=O)C5CCC4(C)C2(C)CC3O)C(OC2OC(C)C(OC3OCC(O)C(OC4OCC(O)(CO)C4O)C3O)C(OC3OC(CO)C(O)C(O)C3O)C2O)C1O)C(C)CC)OC1OC(CO)C(O)C1O
InChI Identifier
InChI=1S/C99H160O51/c1-14-37(3)47(136-56(109)26-43(106)25-48(38(4)15-2)137-85-65(118)61(114)51(32-102)138-85)24-42(105)27-57(110)142-73-40(6)135-89(79(69(73)122)148-88-72(125)77(146-86-67(120)63(116)59(112)49(30-100)139-86)74(41(7)134-88)143-83-71(124)75(46(107)33-131-83)144-91-81(126)98(130,35-104)36-132-91)150-92(129)99-23-22-93(8,9)28-45(99)44-16-17-53-94(10)20-19-55(95(11,34-103)52(94)18-21-96(53,12)97(44,13)29-54(99)108)141-90-80(149-87-68(121)64(117)60(113)50(31-101)140-87)76(70(123)78(147-90)82(127)128)145-84-66(119)62(115)58(111)39(5)133-84/h16,34,37-43,45-55,58-81,83-91,100-102,104-108,111-126,130H,14-15,17-33,35-36H2,1-13H3,(H,127,128)
InChI KeyMWZYPLKAQQZARZ-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
  • O-glucuronide
  • 1-o-glucuronide
  • Tetracarboxylic acid or derivatives
  • Glucuronic acid or derivatives
  • Alkyl glycoside
  • Glycosyl compound
  • O-glycosyl compound
  • Fatty alcohol
  • Fatty acid ester
  • 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
  • Aldehyde
  • Organooxygen compound
  • Carbonyl group
  • Primary alcohol
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Organic oxide
  • Alcohol
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
StatusExpected but not Quantified
Origin
  • Food
Biofunction
  • Nutrient
  • Waste products
Application
  • Nutrient
Cellular locations
  • Cytoplasm
  • Extracellular
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 Solubility4.24 mg/mLALOGPS
logP0.71ALOGPS
logP-4.7ChemAxon
logS-2.7ALOGPS
pKa (Strongest Acidic)3.32ChemAxon
pKa (Strongest Basic)-3.9ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count48ChemAxon
Hydrogen Donor Count26ChemAxon
Polar Surface Area795.93 Å2ChemAxon
Rotatable Bond Count41ChemAxon
Refractivity494.03 m3·mol-1ChemAxon
Polarizability221.1 Å3ChemAxon
Number of Rings14ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Liver
PathwaysNot Available
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 IDFDB015134
      KNApSAcK IDNot Available
      Chemspider IDNot Available
      KEGG Compound IDNot Available
      BioCyc IDNot Available
      BiGG IDNot Available
      Wikipedia LinkNot Available
      NuGOwiki LinkHMDB0036269
      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. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .