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Record Information
Version4.0
Creation Date2012-09-12 02:27:47 UTC
Update Date2017-09-27 08:33:09 UTC
HMDB IDHMDB0040859
Secondary Accession Numbers
  • HMDB40859
Metabolite Identification
Common Name28-Glucosyloleanolic acid 3-[rhamnosyl-(1->2)-galactosyl-(1->3)-glucuronide]
Description28-Glucosyloleanolic acid 3-[rhamnosyl-(1->2)-galactosyl-(1->3)-glucuronide] is found in fruits. 28-Glucosyloleanolic acid 3-[rhamnosyl-(1->2)-galactosyl-(1->3)-glucuronide] is a constituent of the famine food Ximenia americana (tallow nut).
Structure
Thumb
SynonymsNot Available
Chemical FormulaC54H84O24
Average Molecular Weight1117.2304
Monoisotopic Molecular Weight1116.535253616
IUPAC Name6-[(2-{[4,4,6a,6b,11,11,14b-heptamethyl-8a-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}carbonyl)-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,14a,14b-icosahydropicen-3-yl]oxy}-6-carboxy-3,5-dihydroxyoxan-4-yl)oxy]-3,4-dihydroxy-5-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxane-2-carboxylic acid
Traditional Name6-[(2-{[4,4,6a,6b,11,11,14b-heptamethyl-8a-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}carbonyl)-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy}-6-carboxy-3,5-dihydroxyoxan-4-yl)oxy]-3,4-dihydroxy-5-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxane-2-carboxylic acid
CAS Registry NumberNot Available
SMILES
CC1OC(OC2C(O)C(O)C(OC2OC2C(O)C(OC3CCC4(C)C(CCC5(C)C4CC=C4C6CC(C)(C)CCC6(CCC54C)C(=O)OC4OC(CO)C(O)C(O)C4O)C3(C)C)OC(C2O)C(O)=O)C(O)=O)C(O)C(O)C1O
InChI Identifier
InChI=1S/C54H84O24/c1-21-28(56)30(58)34(62)44(71-21)77-41-33(61)32(60)39(42(66)67)76-47(41)74-38-36(64)40(43(68)69)75-46(37(38)65)73-27-12-13-51(6)25(50(27,4)5)11-14-53(8)26(51)10-9-22-23-19-49(2,3)15-17-54(23,18-16-52(22,53)7)48(70)78-45-35(63)31(59)29(57)24(20-55)72-45/h9,21,23-41,44-47,55-65H,10-20H2,1-8H3,(H,66,67)(H,68,69)
InChI KeyIMPZGAYJJGGWNV-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
  • 1-o-glucuronide
  • O-glucuronide
  • Glucuronic acid or derivatives
  • Glycosyl compound
  • O-glycosyl compound
  • Tricarboxylic acid or derivatives
  • Beta-hydroxy acid
  • Pyran
  • Oxane
  • Hydroxy acid
  • Secondary alcohol
  • Carboxylic acid ester
  • Polyol
  • Carboxylic acid derivative
  • Carboxylic acid
  • Acetal
  • Oxacycle
  • Organoheterocyclic compound
  • Organooxygen compound
  • Organic oxygen compound
  • Organic oxide
  • Primary alcohol
  • Hydrocarbon derivative
  • Carbonyl group
  • Alcohol
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

  Organ and components:

Source:

  Biological:

    Animal:

Route of exposure:

  Enteral:

Role

Biological role:

Industrial application:

Process

Naturally occurring process:

  Biological 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 Solubility0.28 g/LALOGPS
logP1.72ALOGPS
logP0.7ChemAxon
logS-3.6ALOGPS
pKa (Strongest Acidic)2.82ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count23ChemAxon
Hydrogen Donor Count13ChemAxon
Polar Surface Area388.04 ŲChemAxon
Rotatable Bond Count12ChemAxon
Refractivity261.49 m³·mol⁻¹ChemAxon
Polarizability116.28 ųChemAxon
Number of Rings9ChemAxon
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, Positivesplash10-0f72-3400305419-dc4781eb543dbc7b94eeView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-1000-1300409514-0ea5e17e3dcbde521313View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-3500918422-26b81cb8a1f7b64f615fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0fr2-6700011229-06944065be24b3ea3320View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0292-7900014316-eab6f99ae03b406bbff9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03xr-5900104201-a70e2d7088c44978910aView in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Liver
PathwaysNot Available
NameSMPDB/PathwhizKEGG
No entries found
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 IDFDB020687
      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.