Asiaticoside (CHEM030317)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 01:48:59 UTC
Update Date2016-11-09 01:19:03 UTC
Accession NumberCHEM030317
Identification
Common NameAsiaticoside
ClassSmall Molecule
DescriptionAsiaticoside is found in green vegetables. Asiaticoside is a constituent of Centella asiatica (Asiatic pennywort)
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
AsiaticosidHMDB
BlastoestimulinaHMDB
BlastostimulinaHMDB
CentelaseHMDB, MeSH
DermatologicoHMDB
EmdecassolHMDB
FK 1080HMDB
MadecassolHMDB, MeSH
MarticassolHMDB
6-({[3,4-dihydroxy-6-(hydroxymethyl)-5-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-2-yl]oxy}methyl)-3,4,5-trihydroxyoxan-2-yl 10,11-dihydroxy-9-(hydroxymethyl)-1,2,6a,6b,9,12a-hexamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-4a-carboxylic acidGenerator
AsiaticosideMeSH
Chemical FormulaC48H78O19
Average Molecular Mass959.122 g/mol
Monoisotopic Mass958.514 g/mol
CAS Registry Number16830-15-2
IUPAC Name6-({[3,4-dihydroxy-6-(hydroxymethyl)-5-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-2-yl]oxy}methyl)-3,4,5-trihydroxyoxan-2-yl 10,11-dihydroxy-9-(hydroxymethyl)-1,2,6a,6b,9,12a-hexamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-4a-carboxylate
Traditional Name6-({[3,4-dihydroxy-6-(hydroxymethyl)-5-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-2-yl]oxy}methyl)-3,4,5-trihydroxyoxan-2-yl 10,11-dihydroxy-9-(hydroxymethyl)-1,2,6a,6b,9,12a-hexamethyl-2,3,4,5,6,7,8,8a,10,11,12,12b,13,14b-tetradecahydro-1H-picene-4a-carboxylate
SMILESCC1CCC2(CCC3(C)C(=CCC4C5(C)CC(O)C(O)C(C)(CO)C5CCC34C)C2C1C)C(=O)OC1OC(COC2OC(CO)C(OC3OC(C)C(O)C(O)C3O)C(O)C2O)C(O)C(O)C1O
InChI IdentifierInChI=1S/C48H78O19/c1-20-10-13-48(15-14-46(6)23(29(48)21(20)2)8-9-28-44(4)16-24(51)39(60)45(5,19-50)27(44)11-12-47(28,46)7)43(61)67-42-36(58)33(55)31(53)26(65-42)18-62-40-37(59)34(56)38(25(17-49)64-40)66-41-35(57)32(54)30(52)22(3)63-41/h8,20-22,24-42,49-60H,9-19H2,1-7H3
InChI KeyWYQVAPGDARQUBT-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 Parents
Substituents
  • Triterpene saponin
  • Triterpenoid
  • Oligosaccharide
  • 12-hydroxysteroid
  • Hydroxysteroid
  • Steroid
  • Glycosyl compound
  • O-glycosyl compound
  • Oxane
  • Cyclic alcohol
  • Secondary alcohol
  • Carboxylic acid ester
  • Polyol
  • Organoheterocyclic compound
  • Oxacycle
  • Monocarboxylic acid or derivatives
  • Acetal
  • Carboxylic acid derivative
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Carbonyl group
  • Alcohol
  • Primary alcohol
  • Aliphatic heteropolycyclic compound
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 Solubility0.8 g/LALOGPS
logP0.73ALOGPS
logP-0.54ChemAxon
logS-3.1ALOGPS
pKa (Strongest Acidic)11.75ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count18ChemAxon
Hydrogen Donor Count12ChemAxon
Polar Surface Area315.21 ŲChemAxon
Rotatable Bond Count10ChemAxon
Refractivity232.55 m³·mol⁻¹ChemAxon
Polarizability102.24 ųChemAxon
Number of Rings8ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
LC-MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-000i-1413900000-cc2ea0fd2de9ffa07833Spectrum
LC-MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-000i-1961400000-7cee33695712294ac774Spectrum
LC-MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-0udi-0111900000-16cabbfc20c02c08d555Spectrum
LC-MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-0a4i-0000001109-e01d354888a28a7a8820Spectrum
LC-MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-0a4i-0232903205-661ab8626faca25d96edSpectrum
LC-MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-0a4i-0123902206-f7e85ebeb0f76fde0b1fSpectrum
LC-MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-0f79-2972300000-d2d334efe06c3910aa60Spectrum
LC-MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-0a4i-0330210009-326f47f00c1f79b34572Spectrum
LC-MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-0f79-1920620000-e0e019038448d7a11cb8Spectrum
LC-MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-0a4i-0000001109-b593699a0f8b830d2090Spectrum
LC-MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-0a4i-0000101109-4bcdd1e6541bbf653d1dSpectrum
LC-MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-0309-0411900000-d4a6b092c20a0f6daec0Spectrum
LC-MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-0a4i-1000000009-8b4f1bc4a30c1b85d360Spectrum
LC-MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-0a4i-0123902206-551bcf6d8f6f437fabd8Spectrum
LC-MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-0udi-0111900000-6c6e685764dc08b8c228Spectrum
LC-MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-0a4i-0111800009-08bc2adcba0d5df1e750Spectrum
LC-MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-0udi-0112900000-ed4b9963225224752a07Spectrum
LC-MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-014i-0410900001-ed585d9a7ba45133268aSpectrum
LC-MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-0a4i-0123902206-6d35b1b96b3990ef1187Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00du-0001900204-b93638aa388a5548919eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0fka-0100902401-bef869354c1d59f6323eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-009e-1405900311-27485f711ceba6588208Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-05n0-1011901116-9a4644a85a2d38a4b924Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00kr-3513900314-58ccd8c851b2cb4f3be7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01p9-6841910110-e80f2530d3e5156799cfSpectrum
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
1D NMR13C 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 IDHMDB0036656
FooDB IDFDB015582
Phenol Explorer IDNot Available
KNApSAcK IDC00032742
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID97164
ChEBI IDNot Available
PubChem Compound ID108062
Kegg Compound IDC15428
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Kimura Y, Sumiyoshi M, Samukawa K, Satake N, Sakanaka M: Facilitating action of asiaticoside at low doses on burn wound repair and its mechanism. Eur J Pharmacol. 2008 Apr 28;584(2-3):415-23. doi: 10.1016/j.ejphar.2008.02.036. Epub 2008 Feb 21.
2. Liang X, Yan Ni Huang, Si Wei Chen, Wen Juan Wang, Xu N, Cui S, Liu XH, Zhang H, Yue Nan Liu, Liu S, Yang M, Dong Y: Antidepressant-like effect of asiaticoside in mice. Pharmacol Biochem Behav. 2008 May;89(3):444-9. doi: 10.1016/j.pbb.2008.01.020. Epub 2008 Feb 5.
3. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9.
4. 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.
5. 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.
6. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621.
7. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.
8. The lipid handbook with CD-ROM