Record Information
Version1.0
Creation date2010-04-08 22:14:36 UTC
Update date2019-11-26 03:17:53 UTC
Primary IDFDB019813
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameMadecassoside
DescriptionMadecassoside 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. Based on a literature review a small amount of articles have been published on Madecassoside.
CAS Number34540-22-2
Structure
Thumb
Synonyms
SynonymSource
Asiaticoside aHMDB, MeSH
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 8,10,11-trihydroxy-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
MadecassosideMeSH
Asiaticoside Adb_source
Predicted Properties
PropertyValueSource
Water Solubility1.71 g/LALOGPS
logP-0.03ALOGPS
logP-1.8ChemAxon
logS-2.8ALOGPS
pKa (Strongest Acidic)11.75ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count19ChemAxon
Hydrogen Donor Count13ChemAxon
Polar Surface Area335.44 ŲChemAxon
Rotatable Bond Count10ChemAxon
Refractivity234.14 m³·mol⁻¹ChemAxon
Polarizability102.02 ųChemAxon
Number of Rings8ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC48H78O20
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 8,10,11-trihydroxy-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
InChI IdentifierInChI=1S/C48H78O20/c1-19-10-11-48(13-12-46(6)22(28(48)20(19)2)8-9-27-44(4)14-24(52)39(61)45(5,18-50)38(44)23(51)15-47(27,46)7)43(62)68-42-35(59)32(56)30(54)26(66-42)17-63-40-36(60)33(57)37(25(16-49)65-40)67-41-34(58)31(55)29(53)21(3)64-41/h8,19-21,23-42,49-61H,9-18H2,1-7H3
InChI KeyBNMGUJRJUUDLHW-UHFFFAOYSA-N
Isomeric SMILESCC1CCC2(CCC3(C)C(=CCC4C5(C)CC(O)C(O)C(C)(CO)C5C(O)CC34C)C2C1C)C(=O)OC1OC(COC2OC(CO)C(OC3OC(C)C(O)C(O)C3O)C(O)C2O)C(O)C(O)C1O
Average Molecular Weight975.1209
Monoisotopic Molecular Weight974.508644936
Classification
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
  • 7-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
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 59.12%; H 8.06%; O 32.81%DFC
Melting PointMp 220-223°DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]D -19 (c, 2 in H2O)DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MSNot Available
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-00di-1000000009-1514f9a005de8d37fa382021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-0udi-0710090000-36ac87f2d49ea70dec9a2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-0fa9-0221911012-383879a6d8fe31462b2e2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-00di-0112020009-c8aae0b49ab9bbda40b42021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-01b9-0201910000-46ab97f6d3e1dd039b1f2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-00di-0100710009-319fcd649102fc946bff2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-0gb9-0422950000-16ca9209482d4e7d10d62021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 6V, Negativesplash10-00xr-0000830009-ec55540eb2fe1b2df2572021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-0fa9-0221911012-a543e04e1df1b2c664b52021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-0fk9-0000070009-e58f572a5ea9becc52ce2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-014i-0704960003-b58f6f62803f694bfe512021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-0udi-2811090000-1c2b7491c32c741a5c132021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-00di-0000000009-057565a69873a88304c22021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-0udi-0200090010-60198b412c614e6bc10b2021-09-20View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-052r-0001920047-98e1b7e96c967e98973b2015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-07br-0201923071-d7048d8205ba3ebae8cc2015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0bvr-2616940062-ba4c29fe57c5a95aac9d2015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4r-1111731039-bec186e7638d7fb24b442015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-4725940168-b7b3b2d773136d0695532015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0udi-7951280110-81a0114e6e022e676aa22015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0000210019-a59e55bbfb3c04b68fe92021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-05bg-2200100209-2e30dd401fe5791905f82021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00dr-2100900110-4ee1d65bdbc977fe24e22021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0500300029-aab3659ddb8d6c15997d2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03fs-1601211093-304aa039d20b7fb2ff062021-09-22View Spectrum
NMRNot Available
ChemSpider ID142124
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID161823
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB40122
CRC / DFC (Dictionary of Food Compounds) IDKDS60-C:MCT07-L
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDC00033137
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference