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Identification
NameDeslanoside
Accession NumberDB01078  (APRD00909)
TypeSmall Molecule
GroupsApproved
Description

Deacetyllanatoside C. A cardiotonic glycoside from the leaves of Digitalis lanata. [PubChem]

Structure
Thumb
Synonyms
(3beta,5beta,12beta)-3-{[beta-D-glucopyranosyl-(1->4)-2,6-dideoxy-beta-D-ribo-hexopyranosyl-(1->4)-2,6-dideoxy-beta-D-ribo-hexopyranosyl-(1->4)-2,6-dideoxy-beta-D-ribo-hexopyranosyl]oxy}-12,14-dihydroxycard-20(22)-enolide
3-[(O-beta-D-Glucopyranosyl-(1->4)-O-2,6-dideoxy-beta-D-ribo-hexopyranosyl-(1->4)-O-2,6-dideoxy-beta-D-ribo-hexopyranosyl-(1->4)-O-2,6-dideoxy-beta-D-ribo-hexopyranosyl)oxy]-12,14-dihydroxy-3beta,5beta,12beta-card-20(22)-enolide
Deacetyllanatoside C
Desacetyllanatoside C
Deslanosido
Deslanosidum
Glucodigoxin
External Identifiers Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
Cedilanid-dNot Available
Brand mixturesNot Available
SaltsNot Available
Categories
UNIIYGY317RK75
CAS number17598-65-1
WeightAverage: 943.0791
Monoisotopic: 942.482430186
Chemical FormulaC47H74O19
InChI KeyInChIKey=OBATZBGFDSVCJD-LALPQLPRSA-N
InChI
InChI=1S/C47H74O19/c1-20-41(64-36-16-30(50)42(21(2)60-36)65-37-17-31(51)43(22(3)61-37)66-44-40(56)39(55)38(54)32(18-48)63-44)29(49)15-35(59-20)62-25-8-10-45(4)24(13-25)6-7-27-28(45)14-33(52)46(5)26(9-11-47(27,46)57)23-12-34(53)58-19-23/h12,20-22,24-33,35-44,48-52,54-57H,6-11,13-19H2,1-5H3/t20-,21-,22-,24-,25+,26-,27-,28+,29+,30+,31+,32-,33-,35+,36+,37+,38-,39+,40-,41-,42-,43-,44+,45+,46+,47+/m1/s1
IUPAC Name
4-[(1S,2S,5S,7R,10R,11S,14R,15S,16R)-11,16-dihydroxy-5-{[(2R,4S,5S,6R)-4-hydroxy-5-{[(2S,4S,5S,6R)-4-hydroxy-5-{[(2S,4S,5S,6R)-4-hydroxy-6-methyl-5-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-6-methyloxan-2-yl]oxy}-6-methyloxan-2-yl]oxy}-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]-2,5-dihydrofuran-2-one
SMILES
C[[email protected]]1O[[email protected]](C[[email protected]](O)[C@@H]1O[[email protected]]1C[[email protected]](O)[[email protected]](O[[email protected]]2C[[email protected]](O)[[email protected]](O[C@@H]3O[[email protected]](CO)[C@@H](O)[[email protected]](O)[[email protected]]3O)[C@@H](C)O2)[C@@H](C)O1)O[[email protected]]1CC[C@@]2(C)[[email protected]](CC[C@@H]3[C@@H]2C[C@@H](O)[C@]2(C)[[email protected]](CC[C@]32O)C2=CC(=O)OC2)C1
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as cardenolide glycosides and derivatives. These 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
  • Hydroxysteroid
  • 12-hydroxysteroid
  • O-glycosyl compound
  • Glycosyl compound
  • Oxane
  • Saccharide
  • 2-furanone
  • Alpha,beta-unsaturated carboxylic ester
  • Enoate ester
  • Tertiary alcohol
  • Dihydrofuran
  • Cyclic alcohol
  • Secondary alcohol
  • Polyol
  • Lactone
  • Carboxylic acid ester
  • 1,2-diol
  • Oxacycle
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Acetal
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External Descriptors
Pharmacology
IndicationFor the treatment and management of Congestive cardiac insufficiency, arrhythmias and heart failure.
PharmacodynamicsDeslanoside is a cardiac glycoside used to treat congestive heart failure and supraventricular arrhythmias due to reentry mechanisms, and to control ventricular rate in the treatment of chronic atrial fibrillation.
Mechanism of actionDeslanoside inhibits the Na-K-ATPase membrane pump, resulting in an increase in intracellular sodium and calcium concentrations. Increased intracellular concentrations of calcium may promote activation of contractile proteins (e.g., actin, myosin). Deslanoside also acts on the electrical activity of the heart, increasing the slope of phase 4 depolarization, shortening the action potential duration, and decreasing the maximal diastolic potential.
Related Articles
AbsorptionLittle absorption from the gastrointestinal tract (40%).
Volume of distributionNot Available
Protein binding20%
MetabolismNot Available
Route of eliminationNot Available
Half life36 hours
ClearanceNot Available
ToxicitySymptoms of overdose include ventricular tachycardia, ventricular fibrillation, progressive bradyarrhythmias, or heart block.
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.8985
Blood Brain Barrier-0.5781
Caco-2 permeable-0.924
P-glycoprotein substrateSubstrate0.8738
P-glycoprotein inhibitor IInhibitor0.5533
P-glycoprotein inhibitor IIInhibitor0.6189
Renal organic cation transporterNon-inhibitor0.8371
CYP450 2C9 substrateNon-substrate0.8483
CYP450 2D6 substrateNon-substrate0.8905
CYP450 3A4 substrateSubstrate0.7052
CYP450 1A2 substrateNon-inhibitor0.9197
CYP450 2C9 inhibitorNon-inhibitor0.9182
CYP450 2D6 inhibitorNon-inhibitor0.938
CYP450 2C19 inhibitorNon-inhibitor0.9284
CYP450 3A4 inhibitorNon-inhibitor0.9194
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9237
Ames testNon AMES toxic0.9309
CarcinogenicityNon-carcinogens0.9583
BiodegradationNot ready biodegradable0.9845
Rat acute toxicity4.9815 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9515
hERG inhibition (predictor II)Inhibitor0.8395
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
logP0.2Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.468 mg/mLALOGPS
logP-0.49ALOGPS
logP0.6ChemAxon
logS-3.3ALOGPS
pKa (Strongest Acidic)7.15ChemAxon
pKa (Strongest Basic)-3.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count18ChemAxon
Hydrogen Donor Count9ChemAxon
Polar Surface Area282.21 Å2ChemAxon
Rotatable Bond Count10ChemAxon
Refractivity225.65 m3·mol-1ChemAxon
Polarizability100.65 Å3ChemAxon
Number of Rings9ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
References
Synthesis ReferenceNot Available
General ReferencesNot Available
External Links
ATC CodesC01AA07
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

Targets

Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
inhibitor
General Function:
Steroid hormone binding
Specific Function:
This is the catalytic component of the active enzyme, which catalyzes the hydrolysis of ATP coupled with the exchange of sodium and potassium ions across the plasma membrane. This action creates the electrochemical gradient of sodium and potassium ions, providing the energy for active transport of various nutrients.
Gene Name:
ATP1A1
Uniprot ID:
P05023
Molecular Weight:
112895.01 Da
References
  1. Zhao YN, Pan Y, Tao JL, Xing DM, Du LJ: Study on cardioactive effects of brazilein. Pharmacology. 2006;76(2):76-83. Epub 2005 Nov 24. [PubMed:16319518 ]
  2. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
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Drug created on June 13, 2005 07:24 / Updated on September 16, 2013 17:13