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-5-methoxy-6-methyloxan-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

• ChemBase ID: 173557
• Molecular Formular: C42H66O14
• Molecular Mass: 794.96504
• Monoisotopic Mass: 794.44525679
• 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)O)OC)C)C)C
• Canonical SMILES: CO[C@H]1[C@@H](O)C[C@@H](O[C@H]1C)O[C@H]1[C@@H](O)C[C@@H](O[C@H]1C)O[C@H]1[C@@H](O)C[C@@H](O[C@H]1C)O[C@H]1CC[C@]2([C@@H](C1)CC[C@@H]1[C@@H]2C[C@@H](O)[C@]2([C@]1(O)CC[C@@H]2C1=CC(=O)OC1)C)C
• InChI: InChI=1S/C42H66O14/c1-20-37(49-6)29(43)16-35(51-20)55-39-22(3)53-36(18-31(39)45)56-38-21(2)52-34(17-30(38)44)54-25-9-11-40(4)24(14-25)7-8-27-28(40)15-32(46)41(5)26(10-12-42(27,41)48)23-13-33(47)50-19-23/h13,20-22,24-32,34-39,43-46,48H,7-12,14-19H2,1-6H3/t20-,21-,22-,24-,25+,26-,27-,28+,29+,30+,31+,32-,34+,35+,36+,37-,38-,39-,40+,41+,42+/m1/s1
• InChIKey: IYJMSDVSVHDVGT-PEQKVOOWSA-N

NAMES AND DATABASE IDS

Names

• 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-5-methoxy-6-methyloxan-2-yl]oxy}-6-methyloxan-2-yl]oxy}-6-methyloxan-2-yl]oxy}-2,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadecan-14-yl]-2,5-dihydrofuran-2-one
• IUPAC Traditional name: metildigoxin
• Synonyms: (3β,5β,12β)-3-[(O-2,6-Dideoxy-4-O-methyl-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; 4'''-Methyldigoxin; 4'''-O-Methyldigoxin; Lanirapid; Lanitop; Medigoxin; Methyldigoxin; Metildigoxin; β-Methyl Digoxin

Database IDs

• CAS Number: 30685-43-9
• PubChem SID: 164229467
• PubChem CID: 443946

CALCULATED PROPERTIES

• Acid pKa: 7.1511164
• H Acceptors: 13
• H Donor: 5
• LogD (pH = 5.5): 3.0002272
• LogD (pH = 7.4): 2.5676284
• Log P: 3.009807
• Molar Refractivity: 197.984 cm^3
• Polarizability: 80.9063 Å^3
• Polar Surface Area: 192.06 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO
• Apperance: White Solid
• Melting Point: 200-202°C (dec.)

Safety Information

• Storage Condition: Hygroscopic, Refrigerator, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - M301850

Cardiotonic. Obtained by the O-methylation of Digoxin.

REFERENCES

• Hunter, J., et al.: J. Biol. Chem., 268, 14991 (1993)
• Greiner, B., et al.: J. Clin. Invest., 104, 147 (1993)
• Jun, A., et al.: J. Pharm.Pharm. Sci., 4, 263 (1993)
• Sugiyama, D., et al.: Drug Metab. Dispos., 30, 220 (1993)