Medicagenic acid 28-O-[b-D-xylosyl-(1->4)-a-L-rhamnosyl-(1->2)-a-L-arabinosyl] ester (CHEM032626)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 03:34:53 UTC
Update Date2016-11-09 01:20:45 UTC
Accession NumberCHEM032626
Identification
Common NameMedicagenic acid 28-O-[b-D-xylosyl-(1->4)-a-L-rhamnosyl-(1->2)-a-L-arabinosyl] ester
ClassSmall Molecule
DescriptionMedicagenic acid 28-O-[b-D-xylosyl-(1->4)-a-L-rhamnosyl-(1->2)-a-L-arabinosyl] ester is found in cereals and cereal products. Medicagenic acid 28-O-[b-D-xylosyl-(1->4)-a-L-rhamnosyl-(1->2)-a-L-arabinosyl] ester is isolated from the roots of Medicago sativa (alfalfa).
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
Medicagenate 28-O-[b-D-xylosyl-(1->4)-a-L-rhamnosyl-(1->2)-a-L-arabinosyl] esterGenerator
8a-({[3-({3,4-dihydroxy-6-methyl-5-[(3,4,5-trihydroxyoxan-2-yl)oxy]oxan-2-yl}oxy)-4,5-dihydroxyoxan-2-yl]oxy}carbonyl)-2,3-dihydroxy-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-carboxylateGenerator
Chemical FormulaC46H72O18
Average Molecular Mass913.053 g/mol
Monoisotopic Mass912.472 g/mol
CAS Registry Number129570-95-2
IUPAC Name8a-({[3-({3,4-dihydroxy-6-methyl-5-[(3,4,5-trihydroxyoxan-2-yl)oxy]oxan-2-yl}oxy)-4,5-dihydroxyoxan-2-yl]oxy}carbonyl)-2,3-dihydroxy-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-carboxylic acid
Traditional Name8a-({[3-({3,4-dihydroxy-6-methyl-5-[(3,4,5-trihydroxyoxan-2-yl)oxy]oxan-2-yl}oxy)-4,5-dihydroxyoxan-2-yl]oxy}carbonyl)-2,3-dihydroxy-4,6a,6b,11,11,14b-hexamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicene-4-carboxylic acid
SMILESCC1OC(OC2C(O)C(O)COC2OC(=O)C23CCC(C)(C)CC2C2=CCC4C5(C)CC(O)C(O)C(C)(C5CCC4(C)C2(C)CC3)C(O)=O)C(O)C(O)C1OC1OCC(O)C(O)C1O
InChI IdentifierInChI=1S/C46H72O18/c1-20-33(62-36-31(53)28(50)24(48)18-59-36)30(52)32(54)37(61-20)63-34-29(51)25(49)19-60-38(34)64-40(58)46-14-12-41(2,3)16-22(46)21-8-9-26-42(4)17-23(47)35(55)45(7,39(56)57)27(42)10-11-44(26,6)43(21,5)13-15-46/h8,20,22-38,47-55H,9-19H2,1-7H3,(H,56,57)
InChI KeyNVYDZIYMAONXJL-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassTriterpenoids
Direct ParentTriterpenoids
Alternative Parents
Substituents
  • Triterpenoid
  • Oligosaccharide
  • 12-hydroxysteroid
  • 15-hydroxysteroid
  • Hydroxysteroid
  • Steroid
  • O-glycosyl compound
  • Glycosyl compound
  • Beta-hydroxy acid
  • Oxane
  • Dicarboxylic acid or derivatives
  • Hydroxy acid
  • Cyclic alcohol
  • Secondary alcohol
  • Carboxylic acid ester
  • Organoheterocyclic compound
  • Acetal
  • Carboxylic acid derivative
  • Polyol
  • Carboxylic acid
  • Oxacycle
  • Alcohol
  • Carbonyl group
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • 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 Solubility0.38 g/LALOGPS
logP1.45ALOGPS
logP1.21ChemAxon
logS-3.4ALOGPS
pKa (Strongest Acidic)4.47ChemAxon
pKa (Strongest Basic)-3.5ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count17ChemAxon
Hydrogen Donor Count10ChemAxon
Polar Surface Area291.82 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity220.49 m³·mol⁻¹ChemAxon
Polarizability95.25 ųChemAxon
Number of Rings8ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0gw0-0110955431-6cdea135564f94b4d86fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00kr-0210947400-362740bf6766ac64c99fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-1721945210-726f683f262534f95d25Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0gx3-2250956383-3946462e5be83b079d19Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0f89-0980777430-d2c4c0a5645f442e29e4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01qc-5910133000-66891b1a14fe2b1f928eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0f6t-0000941122-569d3d3e3071b90a43f6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-06wi-5900152241-d4610c87a22ad714cd0fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0pc1-1500930000-b908987f95faa4ddafabSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-02ti-0000119124-0083e1214f1a6cea9bcdSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014r-2101649001-0ad69a557175481e0057Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-114r-1922431002-56bb593e274fbe41e142Spectrum
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 IDHMDB0039295
FooDB IDFDB018841
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 ID131752601
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