soyasapogenol B (PAMDB110358)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 11:54:54 AM
Metabolite IDPAMDB110358
Identification
Name: soyasapogenol B
Description:A pentacyclic triterpenoid that is oleanane containing a double bond between positions 12 and 13 and substituted by hydroxy groups at the 3β, 22β and 24-positions.
Structure
Thumb
🔍MOLSDFPDBSMILESInChIView Structure
Synonyms:
  • 24-hydroxysophoradiol
Chemical Formula: C30H50O3
Average Molecular Weight: 458.72
Monoisotopic Molecular Weight: 458.3759954713
InChI Key: YOQAQNKGFOLRGT-FNBSVUNXSA-N
InChI: InChI=1S/C30H50O3/c1-25(2)16-20-19-8-9-22-27(4)12-11-23(32)28(5,18-31)21(27)10-13-30(22,7)29(19,6)15-14-26(20,3)24(33)17-25/h8,20-24,31-33H,9-18H2,1-7H3/t20?,21?,22?,23-,24+,26+,27-,28+,29+,30+/m0/s1
CAS number: 595-15-3
IUPAC Name:(3β,22β)-olean-12-ene-3,22,24-triol
Traditional IUPAC Name: 4-(hydroxymethyl)-4,6a,6b,8a,11,11,14b-heptamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicene-3,9-diol
SMILES:CC3(CC4(C2(=CCC5(C1(CCC(C(C1CCC(C2(CCC(C(C3)O)4C)C)5C)(CO)C)O)C))))C
Chemical Taxonomy
Taxonomy DescriptionThis compound belongs to the class of organic compounds known as oleanane triterpenoids. These are triterpenoids with a structure based on the oleanane skeleton, an 4,4,6a,8a,11,14b-heptamethyl-hexadecahydropicene derivative.
Kingdom Organic compounds
Super ClassLipids and lipid-like molecules
Class Prenol lipids
Sub ClassTriterpenoids
Direct Parent Oleanane triterpenoids
Alternative Parents
Substituents
  • Oleanane triterpenoid
  • Steroid
  • Cyclic alcohol
  • Secondary alcohol
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular Framework Aliphatic homopolycyclic compounds
External Descriptors
Physical Properties
State: Not Available
Charge:0
Melting point: 258 - 259 °C
Experimental Properties:
PropertyValueReference
Melting Point258 - 259 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.004 mg/mLALOGPS
logP5.82ALOGPS
logP4.89ChemAxon
logS-5ALOGPS
pKa (Strongest Acidic)14.49ChemAxon
pKa (Strongest Basic)-0.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area60.69 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity135.2 m3·mol-1ChemAxon
Polarizability55.98 Å3ChemAxon
Number of Rings5ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Not Available
Reactions:
Pathways:
    Spectra
    Spectra:
    Spectrum TypeDescriptionSplash Key
    Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
    Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
    Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
    Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
    Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
    Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
    References
    References:
    • Kurosawa Y, Takahara H, Shiraiwa M (2002)UDP-glucuronic acid:soyasapogenol glucuronosyltransferase involved in saponin biosynthesis in germinating soybean seeds. Planta 215, Pubmed: 12172845
    • Shibuya M, Hoshino M, Katsube Y, Hayashi H, Kushiro T, Ebizuka Y (2006)Identification of beta-amyrin and sophoradiol 24-hydroxylase by expressed sequence tag mining and functional expression assay. The FEBS journal 273, Pubmed: 16478469
    • Evidente A, Cimmino A, Fernández-Aparicio M, Rubiales D, Andolfi A, Melck D (2011)Soyasapogenol B and trans-22-dehydrocam- pesterol from common vetch (Vicia sativa L.) root exudates stimulate broomrape seed germination. Pest management science 67, Pubmed: 21480462
    Synthesis Reference: Not Available
    Material Safety Data Sheet (MSDS) Not Available
    External Links:
    ResourceLink
    ChEBI9209
    HMDBHMDB34648
    KEGGC08980
    PubChem13632844