Record Information
Version1.0
Creation Date2014-08-29 05:01:38 UTC
Update Date2026-03-26 23:03:41 UTC
Accession NumberCHEM003027
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).
Contaminant Sources
  • FooDB Chemicals
  • STOFF IDENT Compounds
  • T3DB toxins
Contaminant Type
  • Aldehyde
  • Ester
  • Food Toxin
  • Natural Compound
  • Organic Compound
  • Plant Toxin
Chemical Structure
Thumb
Synonyms
ValueSource
(3beta,5beta)-3-((6-Deoxy-alpha-L-mannopyranosyl)oxy)-5,14-dihydroxy-19-oxo-card-20(22)-enolideChEBI
(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-carbaldehydeChEBI
3beta-((6-Deoxy-alpha-L-mannopyranosyl)oxy)-5,14-dihydroxy-19-oxo-5beta-card-20(22)-enolideChEBI
5beta,14beta-Dihydroxy-19-oxo-3beta[(alpha-L-rhamnopyranosyl)oxy]card-20,22-enolideChEBI
ConvallatonChEBI
ConvallatoxosideChEBI
ConvallotoxinChEBI
CorglyconChEBI
CorglyconeChEBI
KorglykonChEBI
Strophanthidin 3-O-alpha-L-rhamnosideChEBI
Strophanthidin, 3-(6-deoxy-alpha-L-mannopyranoside)ChEBI
(3b,5b)-3-((6-Deoxy-a-L-mannopyranosyl)oxy)-5,14-dihydroxy-19-oxo-card-20(22)-enolideGenerator
(3Β,5β)-3-((6-deoxy-α-L-mannopyranosyl)oxy)-5,14-dihydroxy-19-oxo-card-20(22)-enolideGenerator
3b-((6-Deoxy-a-L-mannopyranosyl)oxy)-5,14-dihydroxy-19-oxo-5b-card-20(22)-enolideGenerator
3Β-((6-deoxy-α-L-mannopyranosyl)oxy)-5,14-dihydroxy-19-oxo-5β-card-20(22)-enolideGenerator
5b,14b-Dihydroxy-19-oxo-3b[(a-L-rhamnopyranosyl)oxy]card-20,22-enolideGenerator
5Β,14β-dihydroxy-19-oxo-3β[(α-L-rhamnopyranosyl)oxy]card-20,22-enolideGenerator
Strophanthidin 3-O-a-L-rhamnosideGenerator
Strophanthidin 3-O-α-L-rhamnosideGenerator
Strophanthidin, 3-(6-deoxy-a-L-mannopyranoside)Generator
Strophanthidin, 3-(6-deoxy-α-L-mannopyranoside)Generator
KorglyconMeSH
Strophanthidin-alpha-L-rhamnosideMeSH
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 KeyHULMNSIAKWANQO-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
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 FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00m0-0009580000-94284e83faa8b6bd753bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0109110000-87395201029cdf83f500Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-1239000000-53b6a52d347b09e3a7b7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000b-1004490000-9717fa8694719096cf5cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0f79-1109430000-c3c37aea6d0084944d23Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0ab9-2009200000-110f500b6b29a3d1baecSpectrum
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
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDNot Available
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDC00003612
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkConvallatoxin
Chemspider IDNot Available
ChEBI ID27663
PubChem Compound ID441852
Kegg Compound IDC08858
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=4232730
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=7450004