Medicagenic acid 3-O-[a-D-glucosyl-(1->4)-b-D-glucoside] (CHEM032622)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 03:34:36 UTC
Update Date2016-11-09 01:20:45 UTC
Accession NumberCHEM032622
Identification
Common NameMedicagenic acid 3-O-[a-D-glucosyl-(1->4)-b-D-glucoside]
ClassSmall Molecule
DescriptionMedicagenic acid beta-maltoside is found in cereals and cereal products. Medicagenic acid beta-maltoside is a constituent of the roots of Medicago sativa (alfalfa).
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
Medicagenate b-maltosideGenerator
Medicagenate beta-maltosideGenerator
Medicagenate β-maltosideGenerator
Medicagenic acid b-maltosideGenerator
Medicagenic acid β-maltosideGenerator
3-{[3,4-dihydroxy-6-(hydroxymethyl)-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-2-hydroxy-4,6a,6b,11,11,14b-hexamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,14a,14b-icosahydropicene-4,8a-dicarboxylateGenerator
Medicagenate 3-O-[a-D-glucosyl-(1->4)-b-D-glucoside]Generator
Chemical FormulaC42H66O16
Average Molecular Mass826.964 g/mol
Monoisotopic Mass826.435 g/mol
CAS Registry Number49792-25-8
IUPAC Name3-{[3,4-dihydroxy-6-(hydroxymethyl)-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-2-hydroxy-4,6a,6b,11,11,14b-hexamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,14a,14b-icosahydropicene-4,8a-dicarboxylic acid
Traditional Name3-{[3,4-dihydroxy-6-(hydroxymethyl)-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-2-hydroxy-4,6a,6b,11,11,14b-hexamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicene-4,8a-dicarboxylic acid
SMILESCC1(C)CCC2(CCC3(C)C(=CCC4C5(C)CC(O)C(OC6OC(CO)C(OC7OC(CO)C(O)C(O)C7O)C(O)C6O)C(C)(C5CCC34C)C(O)=O)C2C1)C(O)=O
InChI IdentifierInChI=1S/C42H66O16/c1-37(2)11-13-42(36(53)54)14-12-39(4)19(20(42)15-37)7-8-24-38(3)16-21(45)32(41(6,35(51)52)25(38)9-10-40(24,39)5)58-34-30(50)28(48)31(23(18-44)56-34)57-33-29(49)27(47)26(46)22(17-43)55-33/h7,20-34,43-50H,8-18H2,1-6H3,(H,51,52)(H,53,54)
InChI KeyAFLNGLSTOJPKJJ-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
  • 12-hydroxysteroid
  • 15-hydroxysteroid
  • Hydroxysteroid
  • Steroid
  • Fatty acyl glycoside
  • Fatty acyl glycoside of mono- or disaccharide
  • Disaccharide
  • Glycosyl compound
  • O-glycosyl compound
  • Oxane
  • Dicarboxylic acid or derivatives
  • Fatty acyl
  • Cyclic alcohol
  • Secondary alcohol
  • Organoheterocyclic compound
  • Polyol
  • Carboxylic acid derivative
  • Carboxylic acid
  • Acetal
  • Oxacycle
  • Organooxygen compound
  • Primary alcohol
  • Organic oxygen compound
  • Organic oxide
  • Alcohol
  • Hydrocarbon derivative
  • Carbonyl group
  • 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 Solubility0.43 g/LALOGPS
logP1.53ALOGPS
logP1.17ChemAxon
logS-3.3ALOGPS
pKa (Strongest Acidic)4.07ChemAxon
pKa (Strongest Basic)-3.2ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count16ChemAxon
Hydrogen Donor Count10ChemAxon
Polar Surface Area273.36 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity201.53 m³·mol⁻¹ChemAxon
Polarizability88.04 ųChemAxon
Number of Rings7ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_4) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_5) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_6) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_7) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_8) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_9) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_10) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - 6V, Negativesplash10-004i-0200000090-162ba3e84a4e658e7cbaSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0pbj-0000739370-eb311f82aceab975c501Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0frj-0100948000-54ef762c9ddc5790a845Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-114r-1601966010-452b156885a25b0fa30aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0pbj-0000739370-eb311f82aceab975c501Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0frj-0100948000-54ef762c9ddc5790a845Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-114r-1601966010-452b156885a25b0fa30aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0m30-0311246690-8a304b1035b80243eccdSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-114i-2501798430-151f422ed75d031462e2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0zfr-4600891000-02038025beca4fbb3479Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0m30-0311246690-8a304b1035b80243eccdSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-114i-2501798430-151f422ed75d031462e2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0zfr-4600891000-02038025beca4fbb3479Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0000003090-2fbc11b6f9bdca0d878fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-08i0-3902203740-2e1d3766382d9907d087Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0aor-9200815100-8de6a7a11b57ab3a39dbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01ta-0600204490-a93643953406dc9055e0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004s-4933136250-5f6baa76688c67bdfab1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0002-4900004110-3b12368c886e56867becSpectrum
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 IDHMDB0039290
FooDB IDFDB018835
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 ID14447545
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