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Showing Compound Bioside (FDB004142)

Record Information
Version1.0
Creation date2010-04-08 22:06:06 UTC
Update date2019-11-26 02:59:50 UTC
Primary IDFDB004142
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameBioside
DescriptionBioside is a member of the class of compounds known as steroidal saponins. Steroidal saponins are saponins in which the aglycone moiety is a steroid. The steroidal aglycone is usually a spirostane, furostane, spirosolane, solanidane, or curcubitacin derivative. Bioside is slightly soluble (in water) and a very weakly acidic compound (based on its pKa). Bioside can be found in horseradish, which makes bioside a potential biomarker for the consumption of this food product. The joining of simple sugars into a double sugar happens by a condensation reaction, which involves the elimination of a water molecule from the functional groups only. Breaking apart a double sugar into its two simple sugars is accomplished by hydrolysis with the help of a type of enzyme called a disaccharidase. As building the larger sugar ejects a water molecule, breaking it down consumes a water molecule. These reactions are vital in metabolism. Each disaccharide is broken down with the help of a corresponding disaccharidase (sucrase, lactase, and maltase) .
CAS Number92622-05-4
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
Predicted Properties
PropertyValueSource
Water Solubility1 g/LALOGPS
logP-0.51ALOGPS
logP-0.88ChemAxon
logS-2.9ALOGPS
pKa (Strongest Acidic)11.94ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count15ChemAxon
Hydrogen Donor Count9ChemAxon
Polar Surface Area237.45 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity182.65 m³·mol⁻¹ChemAxon
Polarizability81.11 ųChemAxon
Number of Rings8ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC38H62O15
IUPAC name(2S,3R,4S,5S,6R)-2-{[(2R,3R,4R,5R,6R)-4,5-dihydroxy-2-(hydroxymethyl)-6-[(2R,7'S,9'S,10'S,13'S,15'R,16'R)-7',9',13'-trimethyl-5'-oxaspiro[oxane-2,6'-pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosane]-10',15'-dioloxy]oxan-3-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol
InChI IdentifierInChI=1S/C38H62O15/c1-16-27-23(53-38(16)8-4-5-9-48-38)11-20-18-7-6-17-10-22(21(41)13-36(17,2)19(18)12-26(42)37(20,27)3)49-34-32(47)30(45)33(25(15-40)51-34)52-35-31(46)29(44)28(43)24(14-39)50-35/h16-35,39-47H,4-15H2,1-3H3/t16-,17?,18?,19?,20?,21+,22+,23?,24+,25+,26-,27?,28+,29-,30+,31+,32+,33-,34+,35-,36-,37+,38+/m0/s1
InChI KeyMTZLHTRAIKFJLJ-PYUCPRTRSA-N
Isomeric SMILESC[C@H]1C2C(CC3C4CCC5C[C@@H](O[C@@H]6O[C@H](CO)[C@H](O[C@@H]7O[C@H](CO)[C@@H](O)[C@H](O)[C@H]7O)[C@H](O)[C@H]6O)[C@H](O)C[C@]5(C)C4C[C@H](O)[C@]23C)O[C@]11CCCCO1
Average Molecular Weight758.8899
Monoisotopic Molecular Weight758.408871314
Classification
Description Belongs to the class of organic compounds known as steroidal saponins. These are saponins in which the aglycone moiety is a steroid. The steroidal aglycone is usually a spirostane, furostane, spirosolane, solanidane, or curcubitacin derivative.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassSteroidal glycosides
Direct ParentSteroidal saponins
Alternative Parents
Substituents
  • Steroidal saponin
  • 12-hydroxysteroid
  • 2-hydroxysteroid
  • Hydroxysteroid
  • Disaccharide
  • Glycosyl compound
  • O-glycosyl compound
  • Ketal
  • Oxane
  • Tetrahydrofuran
  • Cyclic alcohol
  • Secondary alcohol
  • Polyol
  • Acetal
  • Organoheterocyclic compound
  • Oxacycle
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Alcohol
  • Primary alcohol
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
OntologyNo ontology term
Physico-Chemical Properties
Physico-Chemical Properties - Experimental
Spectra
Spectra
EI-MS/GC-MSNot Available
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00my-4001871900-8fc4e1a1f0d147d94ce02016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00n0-2102940100-ca351ab54508fe3f6e7b2016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052r-6204920100-26e0a4943f4fa55da2992016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-5311542900-88e8958b3296807ab7692016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-003r-2402940300-f8cd339ec966649801142016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-6602910000-f8d3e682fe909ab13adb2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-052b-0501330900-22e941333a593820faf12021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-4903451600-b1f23e2e43a48d257fb12021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0005-9520112000-33eb55029ca5cb9ffa872021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0000030900-f120be1cb698bb186e442021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-6301333900-39913bac403a5c8c4a462021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a59-9310731000-dfddfb81ece9dce932b52021-10-21View Spectrum
NMRNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDC08932
Pubchem Compound ID3084119
Pubchem Substance IDNot Available
ChEBI ID2999
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDBIOSIDE
BIGG IDNot Available
KNApSAcK IDNot Available
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
Processing...
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— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).