| Common Name |
Deslanoside
| Description |
Deslanoside is only found in individuals that have used or taken this drug. It is a cardiotonic glycoside from the leaves of Digitalis lanata. [PubChem]Deslanoside inhibits the Na-K-ATPase membrane pump, resliting in an increase in intracellliar sodium and calcium concentrations. Increased intracellliar 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.
| Structure |
| Synonyms |
| Value |
Source |
(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)-enolideChEBI
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)-enolideChEBI
Deacetyllanatoside CChEBI
Desacetyllanatoside CChEBI
DeslanosidoChEBI
DeslanosidumChEBI
GlucodigoxinChEBI
(3b,5b,12b)-3-{[b-D-glucopyranosyl-(1->4)-2,6-dideoxy-b-D-ribo-hexopyranosyl-(1->4)-2,6-dideoxy-b-D-ribo-hexopyranosyl-(1->4)-2,6-dideoxy-b-D-ribo-hexopyranosyl]oxy}-12,14-dihydroxycard-20(22)-enolideGenerator
(3β,5β,12β)-3-{[β-D-glucopyranosyl-(1->4)-2,6-dideoxy-β-D-ribo-hexopyranosyl-(1->4)-2,6-dideoxy-β-D-ribo-hexopyranosyl-(1->4)-2,6-dideoxy-β-D-ribo-hexopyranosyl]oxy}-12,14-dihydroxycard-20(22)-enolideGenerator
3-[(O-b-D-Glucopyranosyl-(1->4)-O-2,6-dideoxy-b-D-ribo-hexopyranosyl-(1->4)-O-2,6-dideoxy-b-D-ribo-hexopyranosyl-(1->4)-O-2,6-dideoxy-b-D-ribo-hexopyranosyl)oxy]-12,14-dihydroxy-3b,5b,12b-card-20(22)-enolideGenerator
3-[(O-β-D-glucopyranosyl-(1->4)-O-2,6-dideoxy-β-D-ribo-hexopyranosyl-(1->4)-O-2,6-dideoxy-β-D-ribo-hexopyranosyl-(1->4)-O-2,6-dideoxy-β-D-ribo-hexopyranosyl)oxy]-12,14-dihydroxy-3β,5β,12β-card-20(22)-enolideGenerator
Cedilanid-DMeSH
Desacetyl lanatosideMeSH
Desacetyldigilanide CMeSH
Deslanatoside CMeSH
C, DesacetyldigilanideMeSH
C, DesacetyllanatosideMeSH
C, DeslanatosideMeSH
Cedilanid DMeSH
CedilanidDMeSH
Lanatoside, desacetylMeSH
| Chemical Formlia |
C47H74O19
| Average Molecliar Weight |
943.0791
| Monoisotopic Molecliar Weight |
942.482430186
| 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
| Traditional Name |
deslanoside
| CAS Registry Number |
17598-65-1
| SMILES |
C[C@H]1O[C@H](C[C@H](O)[C@@H]1O[C@H]1C[C@H](O)[C@H](O[C@H]2C[C@H](O)[C@H](O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)[C@@H](C)O2)[C@@H](C)O1)O[C@H]1CC[C@@]2(C)[C@H](CC[C@@H]3[C@@H]2C[C@@H](O)[C@]2(C)[C@H](CC[C@]32O)C2=CC(=O)OC2)C1
| InChI Identifier |
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
| InChI Key |
OBATZBGFDSVCJD-LALPQLPRSA-N
| Chemical Taxonomy |
| Description |
This 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.
| Kingdom |
Organic compounds
| Super Class |
Lipids and lipid-like moleclies
| Class |
Steroids and steroid derivatives
| Sub Class |
Steroid lactones
| Direct Parent |
Cardenolide glycosides and derivatives
| Alternative Parents |
Steroidal glycosides
Oligosaccharides
12-hydroxysteroids
14-hydroxysteroids
O-glycosyl compounds
Butenolides
Oxanes
Tertiary alcohols
Enoate esters
Secondary alcohols
Cyclic alcohols and derivatives
Lactones
Oxacyclic compounds
Polyols
Acetals
Monocarboxylic acids and derivatives
Hydrocarbon derivatives
Primary alcohols
Carbonyl compounds
Organic oxides
| Substituents |
Cardanolide-glycoside
Steroidal glycoside
Oligosaccharide
12-hydroxysteroid
14-hydroxysteroid
Hydroxysteroid
Glycosyl compound
O-glycosyl compound
2-furanone
Oxane
Cyclic alcohol
Dihydrofuran
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tertiary alcohol
Secondary alcohol
Carboxylic acid ester
Lactone
Polyol
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Acetal
Oxacycle
Organoheterocyclic compound
Organic oxide
Organic oxygen compound
Organooxygen compound
Alcohol
Hydrocarbon derivative
Carbonyl group
Primary alcohol
Aliphatic heteropolycyclic compound
| Molecliar Framework |
Aliphatic heteropolycyclic compounds
| External Descriptors |
tetrasaccharide derivative (CHEBI:31468 )
14beta-hydroxy steroid (CHEBI:31468 )
cardenolide glycoside (CHEBI:31468 )
12beta-hydroxy steroid (CHEBI:31468 )
| Ontology |
| Status |
Expected but not Quantified
| Origin |
Drug
| Biofunction |
Anti-Arrhythmia Agents
Cardiotonic Agents
Cell signaling
Enzyme Inhibitors
Fuel and energy storage
Fuel or energy source
Membrane integrity/stability
| Application |
Nutrients
Pharmaceutical
Stabilizers
Surfactants and Emlisifiers
| Cellliar locations |
Extracellliar
Membrane
| Physical Properties |
| State |
Solid
| Experimental Properties |
| Property |
Value |
Reference |
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility4.68e-01 g/LNot Available
LogP0.2Not Available
| Predicted Properties |
| Property |
Value |
Source |
Water Solubility0.47 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
Rlie of FiveYesChemAxon
Ghose FilterYesChemAxon
Vebers RlieYesChemAxon
MDDR-like RlieYesChemAxon
| Spectra |
| Spectra |
| Spectrum Type |
Description |
Splash Key |
|
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 10V, PositiveNot Available
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 20V, PositiveNot Available
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 40V, PositiveNot Available
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 10V, NegativeNot Available
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 20V, NegativeNot Available
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 40V, NegativeNot Available
| Biological Properties |
| Cellliar Locations |
Extracellliar
Membrane
| Biofluid Locations |
Blood
Urine
| Tissue Location |
Not Available
| Pathways |
Not Available
| Normal Concentrations |
| Biofluid |
Status |
Age |
Condition |
Reference |
Details |
BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB01078
21059682
details
UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB01078
21059682
details
|
| Abnormal Concentrations |
|
Not Available
| Associated Disorders and Diseases |
| Disease References |
None
| Associated OMIM IDs |
None
| External Links |
| DrugBank ID |
DB01078
| DrugBank Metabolite ID |
Not Available
| Phenol Explorer Compound ID |
Not Available
| Phenol Explorer Metabolite ID |
Not Available
| FoodDB ID |
Not Available
| KNApSAcK ID |
Not Available
| Chemspider ID |
26618
| KEGG Compound ID |
Not Available
| BioCyc ID |
Not Available
| BiGG ID |
Not Available
| Wikipedia Link |
Deslanoside
| NuGOwiki Link |
HMDB15211
| Metagene Link |
HMDB15211
| METLIN ID |
Not Available
| PubChem Compound |
28620
| PDB ID |
Not Available
| ChEBI ID |
31468
Product: Triapine
References |
| Synthesis Reference |
Not Available |
| Material Safety Data Sheet (MSDS) |
Not Available |
| General References |
Not Available |
Enzymes
- General function:
- Involved in ATP 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
References
- 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 ]
- Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
PMID: 3184125
