Record Information
Version1.0
Creation date2010-04-08 22:12:08 UTC
Update date2018-05-29 01:23:25 UTC
Primary IDFDB015923
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameQuillaic acid 3-[galactosyl-(1->2)-[rhamnosyl-(1->3)]-glucuronide] 28-[6-acetyl-glucosyl-(1->3)-[glucosyl-(1->3)-[xylosyl-(1->4)]-rhamnosyl-(1->2)]-4-acetyl-fucosyl] ester
DescriptionQuillaic acid 3-[galactosyl-(1->2)-[rhamnosyl-(1->3)]-glucuronide] 28-[6-acetyl-glucosyl-(1->3)-[glucosyl-(1->3)-[xylosyl-(1->4)]-rhamnosyl-(1->2)]-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)-[rhamnosyl-(1->3)]-glucuronide] 28-[6-acetyl-glucosyl-(1->3)-[glucosyl-(1->3)-[xylosyl-(1->4)]-rhamnosyl-(1->2)]-4-acetyl-fucosyl] ester is an extremely weak basic (essentially neutral) compound (based on its pKa).
CAS Number299184-62-6
Structure
Thumb
Synonyms
SynonymSource
Quillaate 3-[galactosyl-(1->2)-[rhamnosyl-(1->3)]-glucuronide] 28-[6-acetyl-glucosyl-(1->3)-[glucosyl-(1->3)-[xylosyl-(1->4)]-rhamnosyl-(1->2)]-4-acetyl-fucosyl] esterGenerator
6-{[8a-({[5-(acetyloxy)-4-({6-[(acetyloxy)methyl]-3,4,5-trihydroxyoxan-2-yl}oxy)-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-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-carboxylateGenerator
Quillaic acid 3-[galactosyl-(1->2)-[rhamnosyl-(1->3)]-glucuronide] 28-[6-acetyl-glucosyl-(1->3)-[glucosyl-(1->3)-[xylosyl-(1->4)]-rhamnosyl-(1->2)]-4-acetyl-fucosyl] estermanual
Predicted Properties
PropertyValueSource
Water Solubility6.91 g/LALOGPS
logP0.23ALOGPS
logP-5.3ChemAxon
logS-2.4ALOGPS
pKa (Strongest Acidic)3.32ChemAxon
pKa (Strongest Basic)-3.9ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count41ChemAxon
Hydrogen Donor Count21ChemAxon
Polar Surface Area676.32 ŲChemAxon
Rotatable Bond Count26ChemAxon
Refractivity402.83 m³·mol⁻¹ChemAxon
Polarizability180.61 ųChemAxon
Number of Rings13ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC81H126O44
IUPAC name6-{[8a-({[5-(acetyloxy)-4-({6-[(acetyloxy)methyl]-3,4,5-trihydroxyoxan-2-yl}oxy)-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-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
InChI IdentifierInChI=1S/C81H126O44/c1-27-42(89)47(94)52(99)68(110-27)119-60-56(103)62(66(105)106)121-74(64(60)123-70-54(101)49(96)45(92)36(23-83)115-70)117-41-15-16-77(8)38(78(41,9)26-84)14-17-79(10)39(77)13-12-32-33-20-76(6,7)18-19-81(33,40(88)21-80(32,79)11)75(107)125-73-65(63(59(29(3)112-73)113-31(5)86)122-71-55(102)50(97)46(93)37(116-71)25-108-30(4)85)124-72-57(104)61(120-69-53(100)48(95)44(91)35(22-82)114-69)58(28(2)111-72)118-67-51(98)43(90)34(87)24-109-67/h12,26-29,33-65,67-74,82-83,87-104H,13-25H2,1-11H3,(H,105,106)
InChI KeyVKCJVAKTFKLQPX-UHFFFAOYSA-N
Isomeric SMILESCC1OC(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(COC(C)=O)C(O)C(O)C5O)C4OC4OC(C)C(OC5OCC(O)C(O)C5O)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
Average Molecular Weight1803.8407
Monoisotopic Molecular Weight1802.7621974
Classification
Description 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
  • Tetracarboxylic acid or derivatives
  • Glycosyl compound
  • O-glycosyl compound
  • Beta-hydroxy acid
  • Fatty acyl
  • Pyran
  • Oxane
  • Hydroxy acid
  • Cyclic alcohol
  • Secondary alcohol
  • Carboxylic acid ester
  • Organoheterocyclic compound
  • Carboxylic acid derivative
  • Polyol
  • Carboxylic acid
  • Acetal
  • Oxacycle
  • Aldehyde
  • Alcohol
  • Organooxygen compound
  • Organic oxygen compound
  • Primary alcohol
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxide
  • 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:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 53.93%; H 7.04%; O 39.03%DFC
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0f79-0003227913-dea52eb0f3e9a3fe0638JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0f79-0514956522-12fac28eccc7be92c112JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-0911844531-fbe67ee0bc21e9218621JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a59-1112234902-c6395e7a559c86505c37JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0560-3723675900-543c5571ccd88a71a9deJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a6r-5913312000-7042a7f4b48230e2f8ffJSpectraViewer
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound IDNot Available
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB36953
CRC / DFC (Dictionary of Food Compounds) IDHNV40-W:KKO55-H
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference