Record Information
Version1.0
Creation date2010-04-08 22:14:01 UTC
Update date2019-11-27 17:36:27 UTC
Primary IDFDB018908
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameAzukisaponin III
DescriptionAzukisaponin III 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. Azukisaponin III is an extremely weak basic (essentially neutral) compound (based on its pKa).
CAS Number82801-38-5
Structure
Thumb
Synonyms
SynonymSource
6-{[11-carboxy-4-(hydroxymethyl)-4,6a,6b,8a,11,14b-hexamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,14a,14b-icosahydropicen-3-yl]oxy}-3,4-dihydroxy-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxane-2-carboxylateGenerator
Azukisaponin IIIdb_source
Predicted Properties
PropertyValueSource
Water Solubility0.092 g/LALOGPS
logP2.24ALOGPS
logP2.09ChemAxon
logS-4ALOGPS
pKa (Strongest Acidic)3.34ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count15ChemAxon
Hydrogen Donor Count9ChemAxon
Polar Surface Area253.13 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity200.09 m³·mol⁻¹ChemAxon
Polarizability86.66 ųChemAxon
Number of Rings7ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC42H66O15
IUPAC name6-{[11-carboxy-4-(hydroxymethyl)-4,6a,6b,8a,11,14b-hexamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,14a,14b-icosahydropicen-3-yl]oxy}-3,4-dihydroxy-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxane-2-carboxylic acid
InChI IdentifierInChI=1S/C42H66O15/c1-37-13-14-38(2,36(52)53)17-21(37)20-7-8-24-39(3)11-10-25(40(4,19-44)23(39)9-12-42(24,6)41(20,5)16-15-37)55-35-32(29(48)28(47)31(56-35)33(50)51)57-34-30(49)27(46)26(45)22(18-43)54-34/h7,21-32,34-35,43-49H,8-19H2,1-6H3,(H,50,51)(H,52,53)
InChI KeyFXYSHYMHTAACSV-UHFFFAOYSA-N
Isomeric SMILESCC12CCC(C)(CC1C1=CCC3C4(C)CCC(OC5OC(C(O)C(O)C5OC5OC(CO)C(O)C(O)C5O)C(O)=O)C(C)(CO)C4CCC3(C)C1(C)CC2)C(O)=O
Average Molecular Weight810.975
Monoisotopic Molecular Weight810.440171425
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 ParentsNot Available
SubstituentsNot Available
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 62.20%; H 8.20%; O 29.59%DFC
Melting PointMp 218-221°DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]28D +2.5 (c, 1.1 in MeOH)DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-059x-0100907710-646c30bedf4a56c909e6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ac0-0100905100-2d7b72859fa25d8b2bfcView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05i0-1401903100-40a21f8ef5cad98ec6b2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0kkc-1500709840-32bb48d73a639be69d9cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00b9-2500904300-111755c6c77d303dff27View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00fu-5600901000-7a957698a0fd51249935View in MoNA
ChemSpider ID3681115
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID4483254
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB39352
CRC / DFC (Dictionary of Food Compounds) IDJJZ27-L:LND99-A
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDC00003504
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— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.