Acetyldigitoxin (CHEM022124)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 18:20:53 UTC
Update Date2016-11-09 01:17:25 UTC
Accession NumberCHEM022124
Identification
Common NameAcetyldigitoxin
ClassSmall Molecule
DescriptionCardioactive derivative of lanatoside A or of digitoxin used for fast digitalization in congestive heart failure.
Contaminant Sources
  • HMDB Contaminants - Urine
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
AcetildigitoxinaChEBI
Acetyl-digitoxin-alphaChEBI
AcetyldiginatinChEBI
AcetyldigitoxinumChEBI
AcetylgitaloxinChEBI
AcetylgitoxinChEBI
alpha-AcetyldigitoxinChEBI
alpha-AcetylgitaloxinChEBI
alpha-MonoacetyldigitoxinChEBI
Desglucolanatoside aChEBI
Digitoxin 3'''-acetateChEBI
AcylanidKegg
Acetyl-digitoxin-aGenerator
Acetyl-digitoxin-αGenerator
a-AcetyldigitoxinGenerator
Α-acetyldigitoxinGenerator
a-AcetylgitaloxinGenerator
Α-acetylgitaloxinGenerator
a-MonoacetyldigitoxinGenerator
Α-monoacetyldigitoxinGenerator
Digitoxin 3'''-acetic acidGenerator
3'''-O-acetyldigitoxinHMDB
AcedoxinHMDB
Digitoxin monoacetateHMDB
Desglucolanatosides aHMDB
AcetyldigitoxinsHMDB
Monoacetate, digitoxinHMDB
alpha AcetyldigitoxinHMDB
AdicinHMDB
AcetyldigitoxinChEBI
Chemical FormulaC43H66O14
Average Molecular Mass806.976 g/mol
Monoisotopic Mass806.445 g/mol
CAS Registry Number25395-32-8
IUPAC Name(2R,3R,4S,6S)-3-hydroxy-6-{[(2R,3S,4S,6S)-4-hydroxy-6-{[(2R,3S,4S,6R)-4-hydroxy-6-{[(1S,2S,5S,7R,10R,11S,14R,15R)-11-hydroxy-2,15-dimethyl-14-(5-oxo-2,5-dihydrofuran-3-yl)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-5-yl]oxy}-2-methyloxan-3-yl]oxy}-2-methyloxan-3-yl]oxy}-2-methyloxan-4-yl acetate
Traditional Nameacetyldigitoxin
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])CC[C@]12C)O[C@H]1C[C@H](O)[C@H](O[C@H]2C[C@H](O)[C@H](O[C@H]3C[C@H](OC(C)=O)[C@H](O)[C@@H](C)O3)[C@@H](C)O2)[C@@H](C)O1)C1=CC(=O)OC1
InChI IdentifierInChI=1S/C43H66O14/c1-21-38(48)33(54-24(4)44)19-37(51-21)57-40-23(3)53-36(18-32(40)46)56-39-22(2)52-35(17-31(39)45)55-27-9-12-41(5)26(16-27)7-8-30-29(41)10-13-42(6)28(11-14-43(30,42)49)25-15-34(47)50-20-25/h15,21-23,26-33,35-40,45-46,48-49H,7-14,16-20H2,1-6H3/t21-,22-,23-,26-,27+,28-,29+,30-,31+,32+,33+,35+,36+,37+,38-,39-,40-,41+,42-,43+/m1/s1
InChI KeyHPMZBILYSWLILX-UMDUKNJSSA-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
  • Oligosaccharide
  • 14-hydroxysteroid
  • Hydroxysteroid
  • Glycosyl compound
  • O-glycosyl compound
  • 2-furanone
  • Dicarboxylic acid or derivatives
  • Oxane
  • Cyclic alcohol
  • Dihydrofuran
  • Alpha,beta-unsaturated carboxylic ester
  • Enoate ester
  • Tertiary alcohol
  • Carboxylic acid ester
  • Lactone
  • Secondary alcohol
  • Organoheterocyclic compound
  • Oxacycle
  • Acetal
  • Carboxylic acid derivative
  • Alcohol
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Carbonyl group
  • Organooxygen compound
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.012 g/LALOGPS
logP2.87ALOGPS
logP4.04ChemAxon
logS-4.8ALOGPS
pKa (Strongest Acidic)7.18ChemAxon
pKa (Strongest Basic)0.24ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count12ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area188.9 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity200.87 m³·mol⁻¹ChemAxon
Polarizability87.95 ųChemAxon
Number of Rings8ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_4) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a71-0005222910-7b22ca7e5318bdf9f4b7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a70-0209223200-5e25596864f121172ca9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-057r-1429223100-404e3c261f236e1a490bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-3106112940-d5c44588f5d49791b469Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0abj-2309121200-9cbf616a6aded6e5a2c6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000t-4109200000-5025173723fe89d4d1b6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-7834593380-1280be32574b96c0c13dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-9501000230-fa0ac90f7e1fa2ab1c98Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-9500001010-3779d1ff36ff31fba6e9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0pbi-0427501890-72cf4b05d253d6d83300Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a5c-0953000130-18cb3f30ecf8c3dd0dacSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004m-0900000000-f1ba4a4812d78321f76cSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDB00511
HMDB IDHMDB0014652
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkAcetyldigitoxin
Chemspider ID4447572
ChEBI ID53773
PubChem Compound ID5284512
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9.
2. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10.
3. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20.
4. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621.
5. The lipid handbook with CD-ROM
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=10202961
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=13443540
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=13533294
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=13948234