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 21:21:51 UTC
Update Date2016-02-11 02:44:19 UTC
HMDB IDHMDB36271
Secondary Accession NumbersNone
Metabolite Identification
Common NameQuillaic acid 3-[galactosyl-(1->2)-[xylosyl-(1->3)]-glucuronide] 28-[glucosyl-(1->3)-[xylosyl-(1->4)]-rhamnosyl-(1->2)-3-[5-[[5-(arabinosyloxy)-3-hydroxy-6-methyl-1-oxooctyl]oxy]-3-hydroxy-6-methyl-1-oxooctyl]-fucosyl] ester
DescriptionQuillaic acid 3-[galactosyl-(1->2)-[xylosyl-(1->3)]-glucuronide] 28-[glucosyl-(1->3)-[xylosyl-(1->4)]-rhamnosyl-(1->2)-3-[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-[galactosyl-(1->2)-[xylosyl-(1->3)]-glucuronide] 28-[glucosyl-(1->3)-[xylosyl-(1->4)]-rhamnosyl-(1->2)-3-[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 FormulaC93H150O47
Average Molecular Weight2020.1579
Monoisotopic Molecular Weight2018.934742034
IUPAC Name6-{[8a-({[4-({5-[(5-{[3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}-3-hydroxy-6-methyloctanoyl)oxy]-3-hydroxy-6-methyloctanoyl}oxy)-5-hydroxy-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-trihydroxyoxan-2-yl)oxy]oxane-2-carboxylic acid
Traditional Name6-{[8a-({[4-({5-[(5-{[3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}-3-hydroxy-6-methyloctanoyl)oxy]-3-hydroxy-6-methyloctanoyl}oxy)-5-hydroxy-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-1,2,3,4a,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 Number263259-80-9
SMILES
CCC(C)C(CC(O)CC(=O)OC(CC(O)CC(=O)OC1C(O)C(C)OC(OC(=O)C23CCC(C)(C)CC2C2=CCC4C5(C)CCC(OC6OC(C(O)C(OC7OCC(O)C(O)C7O)C6OC6OC(CO)C(O)C(O)C6O)C(O)=O)C(C)(C=O)C5CCC4(C)C2(C)CC3O)C1OC1OC(C)C(OC2OCC(O)C(O)C2O)C(OC2OC(CO)C(O)C(O)C2O)C1O)C(C)CC)OC1OC(CO)C(O)C1O
InChI Identifier
InChI=1/C93H150O47/c1-13-35(3)45(127-54(103)25-40(99)24-46(36(4)14-2)128-81-66(115)61(110)49(31-96)129-81)23-39(98)26-55(104)133-72-56(105)37(5)125-85(76(72)139-84-70(119)74(136-82-67(116)62(111)59(108)47(29-94)130-82)71(38(6)126-84)134-79-64(113)57(106)43(100)32-123-79)140-87(122)93-22-21-88(7,8)27-42(93)41-15-16-51-89(9)19-18-53(90(10,34-97)50(89)17-20-91(51,11)92(41,12)28-52(93)102)132-86-77(138-83-68(117)63(112)60(109)48(30-95)131-83)73(69(118)75(137-86)78(120)121)135-80-65(114)58(107)44(101)33-124-80/h15,34-40,42-53,56-77,79-86,94-96,98-102,105-119H,13-14,16-33H2,1-12H3,(H,120,121)
InChI KeyInChIKey=XRWQSYOIYKDFDG-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
  • Tetracarboxylic acid or derivatives
  • Glucuronic acid or derivatives
  • Alkyl glycoside
  • O-glycosyl compound
  • Glycosyl compound
  • Pyran carboxylic acid
  • Pyran carboxylic acid or derivatives
  • Fatty alcohol
  • Fatty acid ester
  • Beta-hydroxy acid
  • Fatty acyl
  • Pyran
  • Oxane
  • Hydroxy acid
  • Saccharide
  • Oxolane
  • 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
  • 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 Solubility3.45 mg/mLALOGPS
logP0.65ALOGPS
logP-3.9ChemAxon
logS-2.8ALOGPS
pKa (Strongest Acidic)3.28ChemAxon
pKa (Strongest Basic)-3.9ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count44ChemAxon
Hydrogen Donor Count24ChemAxon
Polar Surface Area737.01 Å2ChemAxon
Rotatable Bond Count38ChemAxon
Refractivity462.94 m3·mol-1ChemAxon
Polarizability206.32 Å3ChemAxon
Number of Rings13ChemAxon
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 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 IDFDB015136
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB36271
Metagene LinkHMDB36271
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.