Protoprimulagenin A 3-[glucosyl-(1->3)-galactosyl-(1->4)-[rhamnosyl-(1->2)]-glucuronide] (CHEM022662)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 18:45:50 UTC
Update Date2016-11-09 01:17:33 UTC
Accession NumberCHEM022662
Identification
Common NameProtoprimulagenin A 3-[glucosyl-(1->3)-galactosyl-(1->4)-[rhamnosyl-(1->2)]-glucuronide]
ClassSmall Molecule
DescriptionConstituent of roots of Siberian ginseng (Eleutherococcus (Acanthopanax) senticosus). Protoprimulagenin A 3-[glucosyl-(1->3)-galactosyl-(1->4)-[rhamnosyl-(1->2)]-glucuronide] is found in tea.
Contaminant Sources
  • FooDB Chemicals
  • HMDB Contaminants - Urine
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
3-{[3,5-dihydroxy-6-(hydroxymethyl)-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-6-({4,5,9,9,13,20,20-heptamethyl-2-oxo-24-oxahexacyclo[15.5.2.0¹,¹⁸.0⁴,¹⁷.0⁵,¹⁴.0⁸,¹³]tetracosan-10-yl}oxy)-4-hydroxy-5-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxane-2-carboxylateGenerator
Chemical FormulaC54H86O23
Average Molecular Mass1103.247 g/mol
Monoisotopic Mass1102.556 g/mol
CAS Registry Number137682-20-3
IUPAC Name3-{[3,5-dihydroxy-6-(hydroxymethyl)-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-6-({4,5,9,9,13,20,20-heptamethyl-2-oxo-24-oxahexacyclo[15.5.2.0¹,¹⁸.0⁴,¹⁷.0⁵,¹⁴.0⁸,¹³]tetracosan-10-yl}oxy)-4-hydroxy-5-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxane-2-carboxylic acid
Traditional Name3-{[3,5-dihydroxy-6-(hydroxymethyl)-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-6-({4,5,9,9,13,20,20-heptamethyl-2-oxo-24-oxahexacyclo[15.5.2.0¹,¹⁸.0⁴,¹⁷.0⁵,¹⁴.0⁸,¹³]tetracosan-10-yl}oxy)-4-hydroxy-5-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxane-2-carboxylic acid
SMILESCC1OC(OC2C(O)C(OC3OC(CO)C(O)C(OC4OC(CO)C(O)C(O)C4O)C3O)C(OC2OC2CCC3(C)C(CCC4(C)C3CCC35OCC6(CCC(C)(C)CC36)C(=O)CC45C)C2(C)C)C(O)=O)C(O)C(O)C1O
InChI IdentifierInChI=1S/C54H86O23/c1-22-30(58)33(61)35(63)44(70-22)76-41-37(65)40(75-46-38(66)39(32(60)24(20-56)72-46)74-45-36(64)34(62)31(59)23(19-55)71-45)42(43(67)68)77-47(41)73-29-11-12-50(6)25(49(29,4)5)9-13-51(7)26(50)10-14-54-27-17-48(2,3)15-16-53(27,21-69-54)28(57)18-52(51,54)8/h22-27,29-42,44-47,55-56,58-66H,9-21H2,1-8H3,(H,67,68)
InChI KeyPDEIVZBSQXMHKN-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 Solubility0.47 g/LALOGPS
logP1.29ALOGPS
logP0.22ChemAxon
logS-3.4ALOGPS
pKa (Strongest Acidic)3.33ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count23ChemAxon
Hydrogen Donor Count12ChemAxon
Polar Surface Area359.97 ŲChemAxon
Rotatable Bond Count11ChemAxon
Refractivity259.44 m³·mol⁻¹ChemAxon
Polarizability116.97 ųChemAxon
Number of Rings10ChemAxon
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, Positivesplash10-052r-3300902608-7b766f8d7107dfa8825cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a5i-0200904604-b6780ffd56e54043204eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a7u-3401905702-2acec746a46395223be0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a5i-8901700225-17d3a95fb8861d56ae8bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0bu0-7901701313-7d5880add3995332dd52Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-06vi-4901601201-1915ff59c38325f88479Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0f9i-4600301904-4412a2c7afe09d3f451fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0pbm-0612212609-c1a358ca368a90574651Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0f76-9650602002-f69f07cdfb26cd3ff872Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-4900100003-2b299b6d54cf1a5e8a94Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0f9y-9200000004-30358677d0a9d50336ffSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a6r-9100004203-e8c71b0c41e20aa27e9eSpectrum
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 IDHMDB0033157
FooDB IDFDB011163
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 ID131751383
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