(2R,3R,4S,6S)-6-{[(2R,3S,4S,6S)-6-{[(2R,3S,4S,6R)-6-{[(1S,2S,5S,7R,10R,11S,14R,15S,16R)-11,16-dihydroxy-2,15-dimethyl-14-(5-oxo-2,5-dihydrofuran-3-yl)tetracyclo[8.7.0.02,7.011,15]heptadecan-5-yl]oxy}-4-hydroxy-2-methyloxan-3-yl]oxy}-4-hydroxy-2-methyloxan-3-yl]oxy}-3-hydroxy-2-methyloxan-4-yl acetate

• ChemBase ID: 159231
• Molecular Formular: C43H66O15
• Molecular Mass: 822.97514
• Monoisotopic Mass: 822.44017141
• SMILES: C1C[C@@H](C[C@@H]2[C@]1([C@@H]1[C@@H](CC2)[C@]2(O)[C@]([C@@H](C1)O)([C@H](CC2)C1=CC(=O)OC1)C)C)O[C@@H]1O[C@H]([C@H]([C@H](C1)O)O[C@@H]1O[C@H]([C@H]([C@H](C1)O)O[C@@H]1O[C@H]([C@H]([C@H](C1)OC(=O)C)O)C)C)C
• Canonical SMILES: CC(=O)O[C@H]1C[C@H](O[C@H]2[C@@H](O)C[C@@H](O[C@H]2C)O[C@H]2[C@@H](O)C[C@@H](O[C@H]2C)O[C@H]2CC[C@]3([C@@H](C2)CC[C@@H]2[C@@H]3C[C@@H](O)[C@]3([C@]2(O)CC[C@@H]3C2=CC(=O)OC2)C)C)O[C@H]([C@H]1O)C
• InChI: InChI=1S/C43H66O15/c1-20-38(49)32(55-23(4)44)18-37(52-20)58-40-22(3)54-36(17-31(40)46)57-39-21(2)53-35(16-30(39)45)56-26-9-11-41(5)25(14-26)7-8-28-29(41)15-33(47)42(6)27(10-12-43(28,42)50)24-13-34(48)51-19-24/h13,20-22,25-33,35-40,45-47,49-50H,7-12,14-19H2,1-6H3/t20-,21-,22-,25-,26+,27-,28-,29+,30+,31+,32+,33-,35+,36+,37+,38-,39-,40-,41+,42+,43+/m1/s1
• InChIKey: HWKJSYYYURVNQU-DXJNJSHLSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3R,4S,6S)-6-{[(2R,3S,4S,6S)-6-{[(2R,3S,4S,6R)-6-{[(1S,2S,5S,7R,10R,11S,14R,15S,16R)-11,16-dihydroxy-2,15-dimethyl-14-(5-oxo-2,5-dihydrofuran-3-yl)tetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadecan-5-yl]oxy}-4-hydroxy-2-methyloxan-3-yl]oxy}-4-hydroxy-2-methyloxan-3-yl]oxy}-3-hydroxy-2-methyloxan-4-yl acetate
• IUPAC Traditional name: acetyldigoxin; (2R,3R,4S,6S)-6-{[(2R,3S,4S,6S)-6-{[(2R,3S,4S,6R)-6-{[(1S,2S,5S,7R,10R,11S,14R,15S,16R)-11,16-dihydroxy-2,15-dimethyl-14-(5-oxo-2,5-dihydrofuran-3-yl)tetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadecan-5-yl]oxy}-4-hydroxy-2-methyloxan-3-yl]oxy}-4-hydroxy-2-methyloxan-3-yl]oxy}-3-hydroxy-2-methyloxan-4-yl acetate
• Synonyms: (3β,5β,12β)-3-[(O-3-O-Acetyl-2,6-dideoxy-β-D-ribo-hexopyranosyl-(14)-O-2,6-dideoxy-β-D-ribo-hexopyranosyl-(14)-2,6-dideoxy-β-D-ribo-hexopyranosyl)oxy]-12,14-dihydroxycard-20(22)-enolide; 3'''-Acetyldigoxin; Desglucolanatoside C; Lanatilin; α-Acetyl Digoxin; Decardil; Dioxanin; Sandolanid; Digoride B; Alpha-Acetyldigoxin

Database IDs

• CAS Number: 5511-98-8
• PubChem SID: 162253366
• PubChem CID: 11765960

CALCULATED PROPERTIES

• Acid pKa: 7.151116
• H Acceptors: 13
• H Donor: 5
• LogD (pH = 5.5): 2.798226
• LogD (pH = 7.4): 2.3656268
• Log P: 2.807806
• Molar Refractivity: 202.3843 cm^3
• Polarizability: 82.86105 Å^3
• Polar Surface Area: 209.13 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: Off-White to Pale Yellow Solid
• Melting Point: >187°C (dec.)

Safety Information

• Storage Condition: -20°C Freezer

Pharmacology Properties

• Mechanism of Action: Increases intracellular calcium ion concentration.; Inotropic-POS; NA-K-Atpase inhibitor

Product Information

• Application(s): Cardiant; Cardioglycoside

DETAILS

Toronto Research Chemicals - A173660

Digoxin derivative, a cardiotonic glycosides steroid.

REFERENCES

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