4-[(1S,2S,5S,7R,10R,11S,14R,15R)-5-{[(2R,4R,5S)-5-{[(2S,4R,5S)-5-{[(2S,4R,5S)-4,5-dihydroxy-6-methyloxan-2-yl]oxy}-4-hydroxy-6-methyloxan-2-yl]oxy}-4-hydroxy-6-methyloxan-2-yl]oxy}-11-hydroxy-2,15-dimethyltetracyclo[8.7.0.02,7.011,15]heptadecan-14-yl]-2,5-dihydrofuran-2-one

• ChemBase ID: 167444
• Molecular Formular: C41H64O13
• Molecular Mass: 764.93906
• Monoisotopic Mass: 764.43469211
• SMILES: C1C[C@@H](C[C@@H]2[C@]1([C@@H]1[C@@H](CC2)[C@@]2([C@](CC1)([C@H](CC2)C1=CC(=O)OC1)C)O)C)O[C@H]1C[C@H]([C@@H](C(O1)C)O[C@H]1C[C@H]([C@@H](C(O1)C)O[C@H]1C[C@H]([C@@H](C(O1)C)O)O)O)O
• Canonical SMILES: O=C1OCC(=C1)[C@H]1CC[C@]2([C@]1(C)CC[C@H]1[C@H]2CC[C@H]2[C@]1(C)CC[C@@H](C2)O[C@H]1C[C@@H](O)[C@@H](C(O1)C)O[C@H]1C[C@@H](O)[C@@H](C(O1)C)O[C@H]1C[C@@H](O)[C@@H](C(O1)C)O)O
• InChI: InChI=1S/C41H64O13/c1-20-36(46)29(42)16-34(49-20)53-38-22(3)51-35(18-31(38)44)54-37-21(2)50-33(17-30(37)43)52-25-8-11-39(4)24(15-25)6-7-28-27(39)9-12-40(5)26(10-13-41(28,40)47)23-14-32(45)48-19-23/h14,20-22,24-31,33-38,42-44,46-47H,6-13,15-19H2,1-5H3/t20?,21?,22?,24-,25+,26-,27+,28-,29-,30-,31-,33+,34+,35+,36-,37-,38-,39+,40-,41+/m1/s1
• InChIKey: WDJUZGPOPHTGOT-NJHFADPQSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-[(1S,2S,5S,7R,10R,11S,14R,15R)-5-{[(2R,4R,5S)-5-{[(2S,4R,5S)-5-{[(2S,4R,5S)-4,5-dihydroxy-6-methyloxan-2-yl]oxy}-4-hydroxy-6-methyloxan-2-yl]oxy}-4-hydroxy-6-methyloxan-2-yl]oxy}-11-hydroxy-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: 4-[(1S,2S,5S,7R,10R,11S,14R,15R)-5-{[(2R,4R,5S)-5-{[(2S,4R,5S)-5-{[(2S,4R,5S)-4,5-dihydroxy-6-methyloxan-2-yl]oxy}-4-hydroxy-6-methyloxan-2-yl]oxy}-4-hydroxy-6-methyloxan-2-yl]oxy}-11-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadecan-14-yl]-5H-furan-2-one
• Synonyms: (3β,5β)-3-[(O-2,6-Dideoxy-β-D-ribo-hexopyranosyl-(1-4)-O-2,6-dideoxy-β-D-ribo-hexopyranosyl-(1-4)-2,6-dideoxy-β-D-ribo-hexopyranosyl)oxyl]-14-hydroxycard-20(22)-enolide; Digitalin; Crystalline; Carditoxin; Digicor; Digimed; Myodigin; Digitoxin

Database IDs

• CAS Number: 71-63-6
• PubChem SID: 162261577
• PubChem CID: 46783411

CALCULATED PROPERTIES

• Acid pKa: 7.182636
• H Acceptors: 12
• H Donor: 5
• LogD (pH = 5.5): 3.5885735
• LogD (pH = 7.4): 3.175141
• Log P: 3.5974917
• Molar Refractivity: 191.7173 cm^3
• Polarizability: 78.34437 Å^3
• Polar Surface Area: 182.83 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Acetone; Alcohol; Chloroform; Ethyl Acetate
• Apperance: White Solid
• Melting Point: 224-228°C

Safety Information

• Storage Condition: Hygroscopic, Refrigerator, Under inert atmosphere

DETAILS

Toronto Research Chemicals - D445950

Cardiotonic.

REFERENCES

• Foerster, et al.: Arch. Int. Pharmacodyn. Ther., 159, 1 (1966)
• Jakovljevic, I.M., Anal. Profiles Drug Subs., 3, 149 (1974)