Convallatoxin (T3D4067)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesGene RegulationXML
Record Information
Version2.0
Creation Date2014-08-29 05:01:38 UTC
Update Date2014-12-24 20:26:37 UTC
Accession NumberT3D4067
Identification
Common NameConvallatoxin
ClassSmall Molecule
DescriptionConvallatoxin is a glycoside extracted from Convallaria majalis. Convallatoxin is also isolated from the trunk bark of Antiaris toxicaria (1).
Compound Type
  • Aldehyde
  • Ester
  • Food Toxin
  • Natural Compound
  • Organic Compound
  • Plant Toxin
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
Synonym
(3beta,5beta)-3-((6-Deoxy-alpha-L-mannopyranosyl)oxy)-5,14-dihydroxy-19-oxo-card-20(22)-enolide
(3S,5S,8R,9S,10S,13R,14S,17R)-5,14-Dihydroxy-13-methyl-17-(5-oxo-2,5-dihydrofuran-3-yl)-3-((2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyltetrahydro-2H-pyran-2-yloxy)hexadecahydro-1H-cyclopenta[a]phenanthrene-10-carbaldehyde
3beta-((6-Deoxy-alpha-L-mannopyranosyl)oxy)-5,14-dihydroxy-19-oxo-5beta-card-20(22)-enolide
5beta,14beta-Dihydroxy-19-oxo-3beta[(alpha-L-rhamnopyranosyl)oxy]card-20,22-enolide
Convallaton
Convallatoxoside
Convallotoxin
Corglycon
Corglycone
Korglykon
Strophanthidin 3-O-alpha-L-rhamnoside
Strophanthidin, 3-(6-deoxy-alpha-L-mannopyranoside)
Chemical FormulaC29H42O10
Average Molecular Mass550.638 g/mol
Monoisotopic Mass550.278 g/mol
CAS Registry Number508-75-8
IUPAC Name(1S,2S,5S,7S,10R,11S,14R,15R)-7,11-dihydroxy-15-methyl-14-(5-oxo-2,5-dihydrofuran-3-yl)-5-{[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecane-2-carbaldehyde
Traditional Nameconvallatoxin
SMILES[H][C@@]1(CC[C@]2(O)[C@]3([H])CC[C@]4(O)C[C@]([H])(CC[C@]4(C=O)[C@@]3([H])CC[C@]12C)O[C@]1([H])O[C@@]([H])(C)[C@]([H])(O)[C@@]([H])(O)[C@@]1([H])O)C1=CC(=O)OC1
InChI IdentifierInChI=1S/C29H42O10/c1-15-22(32)23(33)24(34)25(38-15)39-17-3-8-27(14-30)19-4-7-26(2)18(16-11-21(31)37-13-16)6-10-29(26,36)20(19)5-9-28(27,35)12-17/h11,14-15,17-20,22-25,32-36H,3-10,12-13H2,1-2H3/t15-,17-,18+,19-,20+,22-,23+,24+,25-,26+,27-,28-,29-/m0/s1
InChI KeyInChIKey=HULMNSIAKWANQO-JQKSAQOKSA-N
Chemical Taxonomy
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-oxosteroid
  • 14-hydroxysteroid
  • Oxosteroid
  • 5-hydroxysteroid
  • Hydroxysteroid
  • Hexose monosaccharide
  • Glycosyl compound
  • O-glycosyl compound
  • 2-furanone
  • Oxane
  • Monosaccharide
  • Cyclic alcohol
  • Dihydrofuran
  • Alpha,beta-unsaturated carboxylic ester
  • Enoate ester
  • Tertiary alcohol
  • Carboxylic acid ester
  • Secondary alcohol
  • Lactone
  • Polyol
  • Acetal
  • Organoheterocyclic compound
  • Oxacycle
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Alcohol
  • Organic oxygen compound
  • Organic oxide
  • Carbonyl group
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aldehyde
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Cell surface
  • Cytoplasm
  • Extracellular
  • Plasma Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
Applications
Biological Roles
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
LogPNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.52 g/LALOGPS
logP0.14ALOGPS
logP0.14ChemAxon
logS-3ALOGPS
pKa (Strongest Acidic)7.18ChemAxon
pKa (Strongest Basic)0.27ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area162.98 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity136.79 m³·mol⁻¹ChemAxon
Polarizability58.08 ųChemAxon
Number of Rings6ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00m0-0009580000-94284e83faa8b6bd753b2016-08-02View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0109110000-87395201029cdf83f5002016-08-02View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-1239000000-53b6a52d347b09e3a7b72016-08-02View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000b-1004490000-9717fa8694719096cf5c2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0f79-1109430000-c3c37aea6d0084944d232016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0ab9-2009200000-110f500b6b29a3d1baec2016-08-03View Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityConvallatoxin (CNT) is classified as a cardiac glycoside. Cardiac glycosides are well known Na+/K+-ATPase inhibitors, and some of them are used to treat congestive heart failure and atrial arrhythmias. Recent studies have reported that cardiac glycosides have potential as anticancer agents. CNT exerts cytotoxic effects on a number of cancer and normal cell lines and induces apoptosis by increasing caspase-3 and poly ADP ribose polymerase (PARP) cleavage. Moreover, dose- and time-dependent autophagic activity was detected in CNT-treated cells, and mammalian target of rapamycin (mTOR)/p70S6K signal pathway inhibition was observed. Notably, CNT inhibits human umbilical vein endothelial cell (HUVEC) growth and exerts anti-angiogenic activity in vitro and in vivo. (1)
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesConvallatoxin is a glycoside extracted from Convallaria majalis. Convallatoxin is also isolated from the trunk bark of Antiaris toxicaria (1).
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
DrugBank IDNot Available
HMDB IDNot Available
PubChem Compound ID441852
ChEMBL IDCHEMBL399336
ChemSpider ID390428
KEGG IDC08858
UniProt IDNot Available
OMIM ID
ChEBI IDCHEBI:27663
BioCyc IDNot Available
CTD IDNot Available
Stitch IDNot Available
PDB IDNot Available
ACToR IDNot Available
Wikipedia LinkConvallatoxin
References
Synthesis ReferenceNot Available
MSDST3D4067.pdf
General References
  1. Yang SY, Kim NH, Cho YS, Lee H, Kwon HJ: Convallatoxin, a dual inducer of autophagy and apoptosis, inhibits angiogenesis in vitro and in vivo. PLoS One. 2014 Mar 24;9(3):e91094. doi: 10.1371/journal.pone.0091094. eCollection 2014. [24663328 ]
Gene Regulation
Up-Regulated GenesNot Available
Down-Regulated GenesNot Available