Protoprimulagenin A 3-[rhamnosyl-(1->4)-rhamnosyl-(1->4)-[rhamnosyl-(1->2)]-glucosyl-(1->?)-glucuronide] (CHEM022663)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 18:45:52 UTC
Update Date2016-11-09 01:17:33 UTC
Accession NumberCHEM022663
Identification
Common NameProtoprimulagenin A 3-[rhamnosyl-(1->4)-rhamnosyl-(1->4)-[rhamnosyl-(1->2)]-glucosyl-(1->?)-glucuronide]
ClassSmall Molecule
DescriptionConstituent of roots of Siberian ginseng (Eleutherococcus (Acanthopanax) senticosus). Protoprimulagenin A 3-[rhamnosyl-(1->4)-rhamnosyl-(1->4)-[rhamnosyl-(1->2)]-glucosyl-(1->?)-glucuronide] is found in tea.
Contaminant Sources
  • FooDB Chemicals
  • HMDB Contaminants - Urine
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
5-{[5-({3,4-dihydroxy-6-methyl-5-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-2-yl}oxy)-4-hydroxy-6-(hydroxymethyl)-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-2-yl]oxy}-3,4-dihydroxy-6-({2-hydroxy-4,5,9,9,13,20,20-heptamethyl-24-oxahexacyclo[15.5.2.0¹,¹⁸.0⁴,¹⁷.0⁵,¹⁴.0⁸,¹³]tetracosan-10-yl}oxy)oxane-2-carboxylateGenerator
Chemical FormulaC60H98O26
Average Molecular Mass1235.405 g/mol
Monoisotopic Mass1234.635 g/mol
CAS Registry Number137682-21-4
IUPAC Name5-{[5-({3,4-dihydroxy-6-methyl-5-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-2-yl}oxy)-4-hydroxy-6-(hydroxymethyl)-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-2-yl]oxy}-3,4-dihydroxy-6-({2-hydroxy-4,5,9,9,13,20,20-heptamethyl-24-oxahexacyclo[15.5.2.0¹,¹⁸.0⁴,¹⁷.0⁵,¹⁴.0⁸,¹³]tetracosan-10-yl}oxy)oxane-2-carboxylic acid
Traditional Name5-{[5-({3,4-dihydroxy-6-methyl-5-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-2-yl}oxy)-4-hydroxy-6-(hydroxymethyl)-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-2-yl]oxy}-3,4-dihydroxy-6-({2-hydroxy-4,5,9,9,13,20,20-heptamethyl-24-oxahexacyclo[15.5.2.0¹,¹⁸.0⁴,¹⁷.0⁵,¹⁴.0⁸,¹³]tetracosan-10-yl}oxy)oxane-2-carboxylic acid
SMILESCC1OC(OC2C(C)OC(OC3C(O)C(OC4OC(C)C(O)C(O)C4O)C(OC4C(O)C(O)C(OC4OC4CCC5(C)C(CCC6(C)C5CCC57OCC8(CCC(C)(C)CC58)C(O)CC67C)C4(C)C)C(O)=O)OC3CO)C(O)C2O)C(O)C(O)C1O
InChI IdentifierInChI=1S/C60H98O26/c1-23-32(63)34(65)39(70)49(77-23)82-43-25(3)79-51(41(72)38(43)69)83-44-26(21-61)80-52(47(42(44)73)85-50-40(71)35(66)33(64)24(2)78-50)86-46-37(68)36(67)45(48(74)75)84-53(46)81-31-13-14-56(8)27(55(31,6)7)11-15-57(9)28(56)12-16-60-29-19-54(4,5)17-18-59(29,22-76-60)30(62)20-58(57,60)10/h23-47,49-53,61-73H,11-22H2,1-10H3,(H,74,75)
InChI KeyGVPGCVCHXXHJLC-UHFFFAOYSA-N
Chemical Taxonomy
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 ParentsNot Available
SubstituentsNot Available
Molecular FrameworkAliphatic heteropolycyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.43 g/LALOGPS
logP1.18ALOGPS
logP-0.016ChemAxon
logS-3.5ALOGPS
pKa (Strongest Acidic)3.36ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count26ChemAxon
Hydrogen Donor Count14ChemAxon
Polar Surface Area401.82 ŲChemAxon
Rotatable Bond Count12ChemAxon
Refractivity289.59 m³·mol⁻¹ChemAxon
Polarizability130.7 ųChemAxon
Number of Rings11ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-06du-7150906105-ff35cc736a492eb84844Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-052f-2100904204-f2db7e33d9a18dd0b814Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052g-2110903203-f6e2b10e6d2d87acc6b0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-6591715003-4ac716a2865103c31261Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-5451914002-e34a1d4b59baf5926afaSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-08fr-2601912001-09ce7f8e2c0a7d2316aeSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-2290400000-f25e85e624b7157e0459Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-7491301003-6ba1f71609f3868c3ee6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000l-8791300002-22b0c1dec43ddbd6e9deSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00lr-2390000000-257bd5a20d3bcc07528bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0592-8931001000-53db587486515b99656aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000f-9300202104-a8d6ebd2145c82f6ffbdSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0033158
FooDB IDFDB011164
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider IDNot Available
ChEBI IDNot Available
PubChem Compound ID131751384
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9.
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.
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.
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.
5. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.
6. The lipid handbook with CD-ROM