Rhodexin A (CHEM003075)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2014-08-29 05:17:53 UTC
Update Date2026-05-21 00:37:49 UTC
Accession NumberCHEM003075
Identification
Common NameRhodexin A
ClassSmall Molecule
DescriptionRhodexin A is a toxic glycoside that is the rhamnoside of sarmentogenin. Found in the leaves and roots of the Japanese evergreen Rhodea japonica, it has also been found in several other plant species. Besides being the only compound in its family to display a digitalis-like action in the cat heart, rhodexin A is also active against human leukemia K562 cells. Indeed, it is one of a series of cardiac glycosides that have potent antiproliferative activity, which has been attributed to their ability to inhibit synthesis of hypoxia inducible factor 1 (HIF-1-alpha) (1, 2).
Contaminant Sources
  • T3DB toxins
Contaminant Type
  • Ester
  • Natural Compound
  • Organic Compound
  • PFAS
  • Phytotoxin
  • Plant Toxin
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
Sarmentogenin 3-O-alpha-L-rhamnosideKegg
Sarmentogenin 3-O-a-L-rhamnosideGenerator
Sarmentogenin 3-O-α-L-rhamnosideGenerator
Chemical FormulaC29H44O9
Average Molecular Mass536.654 g/mol
Monoisotopic Mass536.299 g/mol
CAS Registry Number545-49-3
IUPAC NameNot Available
Traditional Namerhodexin A
SMILES[H][C@@]1(CC[C@]2(O)[C@]3([H])CC[C@]4([H])C[C@]([H])(CC[C@]4(C)[C@@]3([H])[C@]([H])(O)C[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/C29H44O9/c1-14-23(32)24(33)25(34)26(37-14)38-17-6-8-27(2)16(11-17)4-5-19-22(27)20(30)12-28(3)18(7-9-29(19,28)35)15-10-21(31)36-13-15/h10,14,16-20,22-26,30,32-35H,4-9,11-13H2,1-3H3/t14-,16+,17-,18+,19+,20+,22+,23-,24+,25+,26-,27-,28+,29-/m0/s1
InChI KeyHFMLTKBZNAPPNY-CEKKCSHUSA-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
  • 14-hydroxysteroid
  • Hydroxysteroid
  • 11-hydroxysteroid
  • 11-alpha-hydroxysteroid
  • Hexose monosaccharide
  • Glycosyl compound
  • O-glycosyl compound
  • 2-furanone
  • Monosaccharide
  • Oxane
  • Tertiary alcohol
  • Enoate ester
  • Alpha,beta-unsaturated carboxylic ester
  • Cyclic alcohol
  • Dihydrofuran
  • Secondary alcohol
  • Carboxylic acid ester
  • Lactone
  • Polyol
  • Acetal
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Organoheterocyclic compound
  • Oxacycle
  • Alcohol
  • Organic oxygen compound
  • Carbonyl group
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Cytoplasm
  • Extracellular
Biofluid LocationsNot Available
Tissue LocationsNot Available
Pathways
NameSMPDB LinkKEGG Link
ApoptosisNot Availablemap04210
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.34 g/LALOGPS
logP0.62ALOGPS
logP1.03ChemAxon
logS-3.2ALOGPS
pKa (Strongest Acidic)7.18ChemAxon
pKa (Strongest Basic)-2.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area145.91 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity136.1 m³·mol⁻¹ChemAxon
Polarizability58.16 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, Positivesplash10-0603-0009260000-bb170ac005046f3ad713Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-0109010000-d80977118a3b64dfd416Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00di-0419000000-990a989497149887cd59Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-1108490000-43e72c73fe7ddf13183eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00dr-1109110000-028762707b22d6cf702aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4v-1009000000-381aa79d64f14d554af9Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesFound in the leaves and roots of the Japanese evergreen Rhodea japonica, it has also been found in several other plant species.
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 IDC00003634
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider IDNot Available
ChEBI IDNot Available
PubChem Compound ID441868
Kegg Compound IDC08877
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General ReferencesNot Available