Record Information
Version1.0
Creation date2010-04-08 22:05:55 UTC
Update date2018-05-28 23:12:57 UTC
Primary IDFDB003695
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameSaponins
DescriptionSaponins, also known as aescin or opino, is a member of the class of compounds known as triterpene saponins. Triterpene saponins 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. Saponins is practically insoluble (in water) and a weakly acidic compound (based on its pKa). Saponins can be found in a number of food items such as dandelion, soy bean, fenugreek, and carob, which makes saponins a potential biomarker for the consumption of these food products. Saponins are a class of chemical compounds found in particular abundance in various plant species. More specifically, they are amphipathic glycosides grouped phenomenologically by the soap-like foaming they produce when shaken in aqueous solutions, and structurally by having one or more hydrophilic glycoside moieties combined with a lipophilic triterpene derivative .
CAS Number8047-15-2
Structure
Thumb
Synonyms
SynonymSource
AescinMeSH
FeparilMeSH
FlebostasinMeSH
EscinMeSH
OpinoMeSH
beta EscinMeSH
EscinaMeSH
sankyo Brand OF escinMeSH
opino BiomoMeSH
beta AescinMeSH
beta-EscinMeSH
ReparilMeSH
beta-AescinMeSH
biomo Brand OF escinMeSH
OpinobiomoMeSH
AescusanMeSH
EskuzanMeSH
FepalitanMeSH
opino-BiomoMeSH
Madaus brand OF escinMeSH
Beta-aescinbiospider
Beta-aescinubiospider
Beta-aescusanbiospider
Beta-escinbiospider
Beta-escin, beta-reparil, beta-aescinubiospider
Beta-reparilbiospider
Saponinumbiospider
Predicted Properties
PropertyValueSource
Water Solubility0.77 g/LALOGPS
logP1.17ALOGPS
logP-0.88ChemAxon
logS-3.2ALOGPS
pKa (Strongest Acidic)3.35ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count22ChemAxon
Hydrogen Donor Count13ChemAxon
Polar Surface Area388.04 ŲChemAxon
Rotatable Bond Count16ChemAxon
Refractivity269.78 m³·mol⁻¹ChemAxon
Polarizability118.36 ųChemAxon
Number of Rings8ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC55H86O24
IUPAC name(2S,3S,4S,5R,6R)-6-{[(3S,4S,6aR,6bS,8R,8aR,9R,10R,14bR)-9-(acetyloxy)-8-hydroxy-4,8a-bis(hydroxymethyl)-4,6a,6b,11,11,14b-hexamethyl-10-{[(2Z)-2-methylbut-2-enoyl]oxy}-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,14a,14b-icosahydropicen-3-yl]oxy}-4-hydroxy-3,5-bis({[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})oxane-2-carboxylic acid
InChI IdentifierInChI=1S/C55H86O24/c1-10-23(2)46(71)79-43-44(72-24(3)60)55(22-59)26(17-50(43,4)5)25-11-12-30-51(6)15-14-32(52(7,21-58)29(51)13-16-53(30,8)54(25,9)18-31(55)61)75-49-41(77-48-38(67)36(65)34(63)28(20-57)74-48)39(68)40(42(78-49)45(69)70)76-47-37(66)35(64)33(62)27(19-56)73-47/h10-11,26-44,47-49,56-59,61-68H,12-22H2,1-9H3,(H,69,70)/b23-10-/t26?,27-,28-,29?,30?,31-,32+,33-,34-,35+,36+,37-,38-,39+,40+,41-,42+,43+,44+,47+,48+,49-,51+,52-,53-,54-,55+/m1/s1
InChI KeyAXNVHPCVMSNXNP-ZELRDNAQSA-N
Isomeric SMILES[H]\C(C)=C(/C)C(=O)O[C@@]1([H])[C@]([H])(OC(C)=O)[C@]2(CO)[C@]([H])(O)C[C@]3(C)C(=CCC4([H])[C@@]5(C)CC[C@]([H])(O[C@]6([H])O[C@]([H])(C(O)=O)[C@@]([H])(O[C@]7([H])O[C@]([H])(CO)[C@@]([H])(O)[C@]([H])(O)[C@@]7([H])O)[C@]([H])(O)[C@@]6([H])O[C@]6([H])O[C@]([H])(CO)[C@@]([H])(O)[C@]([H])(O)[C@@]6([H])O)[C@](C)(CO)C5([H])CC[C@@]34C)C2([H])CC1(C)C
Average Molecular Weight1131.269
Monoisotopic Molecular Weight1130.550903649
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
  • Hydroxysteroid
  • 16-oxosteroid
  • Oxosteroid
  • 7-alpha-hydroxysteroid
  • 7-hydroxysteroid
  • Steroid
  • Fatty acyl glycoside
  • 1-o-glucuronide
  • O-glucuronide
  • Glucuronic acid or derivatives
  • Glycosyl compound
  • O-glycosyl compound
  • Tricarboxylic acid or derivatives
  • Fatty acid ester
  • Fatty acyl
  • Pyran
  • Oxane
  • Alpha,beta-unsaturated carboxylic ester
  • Enoate ester
  • Cyclic alcohol
  • Secondary alcohol
  • Carboxylic acid ester
  • Polyol
  • Acetal
  • Organoheterocyclic compound
  • Carboxylic acid
  • Carboxylic acid derivative
  • Oxacycle
  • Primary alcohol
  • Organic oxide
  • Hydrocarbon derivative
  • Carbonyl group
  • Organic oxygen compound
  • Organooxygen compound
  • Alcohol
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
OntologyShould have ontology for this compound
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0il0-4400014009-f06d64ace21402db4ebeView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0w30-2100017029-6a00c22031db97c4eab6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0kar-9201036157-ea73022dd09b841311edView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03fs-9700003006-e3cfade1c29d2ef78217View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03fs-7800014009-40da76f396b4e80d9977View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9700024033-17f2d40add1d22734505View in MoNA
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID6441501
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDSAPONINS|SAPONIN
BIGG IDNot Available
KNApSAcK IDNot Available
HET 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 / Bioactivities
DescriptorIDDefinitionReference
anti hepatomic35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
anti mutagenicDUKE
antitumor35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
immunomodulator50846 Biologically active substance whose activity affects or plays a role in the functioning of the immune system.DUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).