(2R,3R,4S,6S)-3-hydroxy-6-{[(2R,4S,6S)-4-hydroxy-6-{[(2R,3S,4S,6R)-4-hydroxy-6-{[(1S,2S,7R,10R,11S,14R,15R)-11-hydroxy-2,15-dimethyl-14-(5-oxo-2,5-dihydrofuran-3-yl)tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-5-yl]oxy}-2-methyloxan-3-yl]oxy}-2-methyloxan-3-yl]oxy}-2-methyloxan-4-yl acetate

• ChemBase ID: 393
• Molecular Formular: C43H66O14
• Molecular Mass: 806.97574
• Monoisotopic Mass: 806.44525679
• SMILES: O[C@@]12[C@H]3[C@@H]([C@@]4([C@H](CC3)CC(O[C@@H]3O[C@@H]([C@@H](O[C@@H]5O[C@@H](C(O[C@@H]6O[C@@H]([C@@H](O)[C@@H](OC(=O)C)C6)C)[C@@H](O)C5)C)[C@@H](O)C3)C)CC4)C)CC[C@@]1([C@H](CC2)C1=CC(=O)OC1)C
• Canonical SMILES: CC(=O)O[C@H]1C[C@H](OC2[C@@H](O)C[C@@H](O[C@@H]2C)O[C@H]2[C@@H](O)C[C@@H](O[C@@H]2C)OC2CC[C@]3([C@@H](C2)CC[C@@H]2[C@@H]3CC[C@]3([C@]2(O)CC[C@@H]3C2=CC(=O)OC2)C)C)O[C@@H]([C@H]1O)C
• InChI: InChI=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
• InChIKey: HPMZBILYSWLILX-NUZCUNEWSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3R,4S,6S)-3-hydroxy-6-{[(2R,4S,6S)-4-hydroxy-6-{[(2R,3S,4S,6R)-4-hydroxy-6-{[(1S,2S,7R,10R,11S,14R,15R)-11-hydroxy-2,15-dimethyl-14-(5-oxo-2,5-dihydrofuran-3-yl)tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-5-yl]oxy}-2-methyloxan-3-yl]oxy}-2-methyloxan-3-yl]oxy}-2-methyloxan-4-yl acetate
• IUPAC Traditional name: digitoxin, monoacetate
• Brand Name: Acylanid; Crystodigin; Acigoxin
• Synonyms: Acetyldigitoxin

Database IDs

• CAS Number: 25395-32-8
• PubChem SID: 160963856
• PubChem CID: 68949

CALCULATED PROPERTIES

JChem

• Acid pKa: 7.182636
• H Acceptors: 12
• H Donor: 4
• LogD (pH = 5.5): 4.029699
• LogD (pH = 7.4): 3.6162667
• Log P: 4.038617
• Molar Refractivity: 200.8688 cm^3
• Polarizability: 82.196144 Å^3
• Polar Surface Area: 188.9 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: 2.87
• LOG S: -4.82
• Solubility (Water): 1.23e-02 g/l

PROPERTIES

Physical Property

• Solubility: 0.0274 mg/L at 25 oC [MEYLAN,WM et al. (1996)]
• Hydrophobicity(logP): 3.7

DETAILS

DrugBank - DB00511

• Drug Groups: approved
• Description: Cardioactive derivative of lanatoside A or of digitoxin used for fast digitalization in congestive heart failure.
• Indication: Used for fast digitalization in congestive heart failure.
• Pharmacology: The main pharmacological effects of acetyldigitoxin are on the heart. Extracardiac effects are responsible for many of the adverse effects. Its main cardiac effects are 1) a decrease of conduction of electrical impulses through the AV node, making it a commonly used drug in controlling the heart rate during atrial fibrillation or atrial flutter, and 2) an increase of force of contraction via inhibition of the Na^+/K^+ ATPase pump.
• Toxicity: Toxicity includes ventricular tachycardia or ventricular fibrillation, or progressive bradyarrhythmias, or heart block. LD50 = 7.8 mg/kg (orally in mice).
• Affected Organisms: Humans and other mammals
• Absorption: Bioavailability is 60 to 80% following oral administration.
• External Links: Wikipedia