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Record Information
Version3.6
Creation Date2012-09-11 22:10:37 UTC
Update Date2016-02-11 02:44:36 UTC
HMDB IDHMDB36955
Secondary Accession NumbersNone
Metabolite Identification
Common NameQuillaic acid 3-[galactosyl-(1->2)-[rhamnosyl-(1->3)]-glucuronide] 28-[glucosyl-(1->3)-[glucosyl-(1->3)-rhamnosyl-(1->2)]-4-acetyl-fucosyl] ester
DescriptionQuillaic acid 3-[galactosyl-(1->2)-[rhamnosyl-(1->3)]-glucuronide] 28-[glucosyl-(1->3)-[glucosyl-(1->3)-rhamnosyl-(1->2)]-4-acetyl-fucosyl] ester is a constituent of Quillaja saponaria (soap-bark tree).
Structure
Thumb
SynonymsNot Available
Chemical FormulaC74H116O39
Average Molecular Weight1629.6894
Monoisotopic Molecular Weight1628.70937397
IUPAC Name6-{[8a-({[5-(acetyloxy)-3-[(3,5-dihydroxy-6-methyl-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-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-trihydroxy-6-methyloxan-2-yl)oxy]oxane-2-carboxylic acid
Traditional Name6-{[8a-({[5-(acetyloxy)-3-[(3,5-dihydroxy-6-methyl-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-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-trihydroxy-6-methyloxan-2-yl)oxy]oxane-2-carboxylic acid
CAS Registry Number299184-58-0
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(CO)C(O)C(O)C5O)C4OC4OC(C)C(O)C(OC5OC(CO)C(O)C(O)C5O)C4O)C3(C)C=O)C2OC2OC(CO)C(O)C(O)C2O)C(O)=O)C(O)C(O)C1O
InChI Identifier
InChI=1/C74H116O39/c1-25-38(81)43(86)47(90)61(99-25)108-55-51(94)56(60(96)97)109-67(58(55)111-64-50(93)46(89)42(85)33(23-77)105-64)106-37-14-15-70(7)34(71(37,8)24-78)13-16-72(9)35(70)12-11-29-30-19-69(5,6)17-18-74(30,36(80)20-73(29,72)10)68(98)113-66-59(57(53(27(3)101-66)102-28(4)79)110-63-49(92)45(88)41(84)32(22-76)104-63)112-65-52(95)54(39(82)26(2)100-65)107-62-48(91)44(87)40(83)31(21-75)103-62/h11,24-27,30-59,61-67,75-77,80-95H,12-23H2,1-10H3,(H,96,97)
InChI KeyInChIKey=KPVWVXXXAFTINI-UHFFFAOYNA-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
  • Polycyclic triterpenoid
  • Triterpenoid
  • Oleanane triterpenoid
  • Oligosaccharide
  • Steroid
  • Fatty acyl glycoside
  • O-glucuronide
  • 1-o-glucuronide
  • Glucuronic acid or derivatives
  • O-glycosyl compound
  • Glycosyl compound
  • Pyran carboxylic acid
  • Pyran carboxylic acid or derivatives
  • Beta-hydroxy acid
  • Fatty acyl
  • Pyran
  • Oxane
  • Hydroxy acid
  • Dicarboxylic acid or derivatives
  • Acetate salt
  • Cyclic alcohol
  • Secondary alcohol
  • Polyol
  • Carboxylic acid ester
  • 1,2-diol
  • Oxacycle
  • Organoheterocyclic compound
  • Carboxylic acid
  • Carboxylic acid derivative
  • Acetal
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Carbonyl group
  • Aldehyde
  • Alcohol
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
  • Food
Biofunction
  • Cell signaling
  • Fuel and energy storage
  • Fuel or energy source
  • Membrane integrity/stability
  • Nutrient
  • Waste products
Application
  • Nutrient
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Cytoplasm
  • Extracellular
  • Membrane
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 Solubility5.52 mg/mLALOGPS
logP0.12ALOGPS
logP-4.6ChemAxon
logS-2.5ALOGPS
pKa (Strongest Acidic)3.32ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count37ChemAxon
Hydrogen Donor Count20ChemAxon
Polar Surface Area611.33 Å2ChemAxon
Rotatable Bond Count22ChemAxon
Refractivity367.23 m3·mol-1ChemAxon
Polarizability163.8 Å3ChemAxon
Number of Rings12ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Liver
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableNormal
  • Not Applicable
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableNormal
  • Not Applicable
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 IDFDB015925
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB36955
Metagene LinkHMDB36955
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.