Record Information
Version1.0
Creation date2010-04-08 22:06:42 UTC
Update date2019-11-26 03:00:35 UTC
Primary IDFDB005482
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameGlycosides
DescriptionGlycosides, also known as ouabain or acocantherin, belongs to the class of organic compounds known as cardenolide glycosides and derivatives. Cardenolide glycosides and derivatives are compounds containing a carbohydrate glycosidically bound to the cardenolide moiety. Glycosides is an extremely weak basic (essentially neutral) compound (based on its pKa).
CAS Number630-60-4
Structure
Thumb
Synonyms
SynonymSource
AcocantherinHMDB
Acolongifloriside KHMDB
AstrobainHMDB
g-StrophanthinHMDB
g-StrophicorHMDB
GratibainHMDB
Gratus strophanthinHMDB
KombetinHMDB
Ouabagenin L-rhamnosideHMDB
OuabainHMDB
OuabaineHMDB
PurostrophanHMDB
RectobainaHMDB
SolufantinaHMDB
StrodivalHMDB
StrophalenHMDB
Strophanthin gHMDB
StrophopermHMDB
StrophosanHMDB
UabainaHMDB
GlycosidesMeSH
Acolongifloroside KMeSH
g StrophanthinMeSH
Acolongifloriside kbiospider
G-strophanthinbiospider
G-strophicorbiospider
Ouabagenin l-rhamnosidebiospider
Predicted Properties
PropertyValueSource
Water Solubility4.61 g/LALOGPS
logP-1ALOGPS
logP-2.8ChemAxon
logS-2.1ALOGPS
pKa (Strongest Acidic)7.18ChemAxon
pKa (Strongest Basic)-2.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count11ChemAxon
Hydrogen Donor Count8ChemAxon
Polar Surface Area206.6 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity140.83 m³·mol⁻¹ChemAxon
Polarizability60.53 ųChemAxon
Number of Rings6ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC29H44O12
IUPAC name4-[(1S,2R,3S,5S,7R,10R,11R,14S,15R,17R)-3,7,11,17-tetrahydroxy-2-(hydroxymethyl)-15-methyl-5-{[(2R,3R,4R,5S,6R)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]-2,5-dihydrofuran-2-one
InChI IdentifierInChI=1S/C29H44O12/c1-13-22(34)23(35)24(36)25(40-13)41-15-8-19(32)28(12-30)21-17(3-5-27(28,37)9-15)29(38)6-4-16(14-7-20(33)39-11-14)26(29,2)10-18(21)31/h7,13,15-19,21-25,30-32,34-38H,3-6,8-12H2,1-2H3/t13-,15+,16+,17-,18-,19+,21-,22-,23-,24-,25+,26-,27-,28-,29-/m1/s1
InChI KeyLPMXVESGRSUGHW-NZMIQZKWSA-N
Isomeric SMILESC[C@H]1O[C@@H](O[C@H]2C[C@H](O)[C@]3(CO)[C@H]4[C@H](O)C[C@]5(C)[C@@H](CC[C@@]5(O)[C@@H]4CC[C@@]3(O)C2)C2=CC(=O)OC2)[C@H](O)[C@H](O)[C@@H]1O
Average Molecular Weight584.6525
Monoisotopic Molecular Weight584.283276872
Classification
Description belongs to the class of organic compounds known as cardenolide glycosides and derivatives. Cardenolide glycosides and derivatives are compounds containing a carbohydrate glycosidically bound to the cardenolide moiety.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassSteroid lactones
Direct ParentCardenolide glycosides and derivatives
Alternative Parents
Substituents
  • Cardanolide-glycoside
  • Steroidal glycoside
  • 19-hydroxysteroid
  • 1-hydroxysteroid
  • 14-hydroxysteroid
  • 5-hydroxysteroid
  • Hydroxysteroid
  • 11-hydroxysteroid
  • 11-alpha-hydroxysteroid
  • Hexose monosaccharide
  • Glycosyl compound
  • O-glycosyl compound
  • 2-furanone
  • Monosaccharide
  • Oxane
  • Tertiary alcohol
  • Cyclic alcohol
  • Dihydrofuran
  • Enoate ester
  • Alpha,beta-unsaturated carboxylic ester
  • Secondary alcohol
  • Carboxylic acid ester
  • Lactone
  • Polyol
  • Acetal
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Oxacycle
  • Organoheterocyclic compound
  • Organic oxygen compound
  • Organooxygen compound
  • Alcohol
  • Primary alcohol
  • Organic oxide
  • Hydrocarbon derivative
  • Carbonyl group
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Process

Naturally occurring process:

Role

Biological role:

Industrial application:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionNot Available
Melting Point200 oC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logP-2.00SANGSTER (1994)
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0aou-0209050000-ff5d29b9a71cc0dd04e9JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-004u-2506409000-f6e6b4b9ec8f6ae25647JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00r2-0000490000-ba806aa277f179583eecJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-0101930000-7f40284ce7a78f730699JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00di-1112910000-f68efe23826a53a2145eJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-015i-0000590000-b6bd31b640d6b6350b74JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014r-1101940000-a2d91864bf2df81659a2JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4u-2005900000-252c65c11aeae5b683b8JSpectraViewer
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDC01443
Pubchem Compound ID637579
Pubchem Substance IDNot Available
ChEBI ID24400
Phenol-Explorer IDNot Available
DrugBank IDDB01092
HMDB IDHMDB31448
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDGLYCOSIDES
BIGG IDNot Available
KNApSAcK IDC00003633
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— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).