(3R,4R,6S)-6-{[(3S,4R,6S)-6-{[(3S,4R,6R)-6-{[(1S,2S,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}-2-methyl-3-{[(2S,4R,5S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-4-yl acetate

• ChemBase ID: 172192
• Molecular Formular: C49H76O20
• Molecular Mass: 985.11574
• Monoisotopic Mass: 984.49299483
• SMILES: C1([C@H]([C@@H](C([C@@H](O1)O[C@@H]1C(O[C@H](C[C@H]1OC(=O)C)O[C@@H]1C(O[C@H](C[C@H]1O)O[C@@H]1C(O[C@H](C[C@H]1O)OC1C[C@@H]2[C@](CC1)([C@@H]1[C@@H](CC2)[C@@]2([C@]([C@@H](C1)O)([C@H](CC2)C1=CC(=O)OC1)C)O)C)C)C)C)O)O)O)CO
• Canonical SMILES: OCC1O[C@@H](O[C@@H]2C(C)O[C@H](C[C@H]2OC(=O)C)O[C@H]2[C@H](O)C[C@@H](OC2C)O[C@H]2[C@H](O)C[C@@H](OC2C)OC2CC[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)C([C@H]([C@@H]1O)O)O
• InChI: InChI=1S/C49H76O20/c1-21-43(67-38-17-32(53)44(22(2)62-38)68-39-18-33(64-24(4)51)45(23(3)63-39)69-46-42(58)41(57)40(56)34(19-50)66-46)31(52)16-37(61-21)65-27-9-11-47(5)26(14-27)7-8-29-30(47)15-35(54)48(6)28(10-12-49(29,48)59)25-13-36(55)60-20-25/h13,21-23,26-35,37-46,50,52-54,56-59H,7-12,14-20H2,1-6H3/t21?,22?,23?,26-,27?,28-,29-,30+,31-,32-,33-,34?,35-,37+,38+,39+,40-,41-,42?,43-,44-,45-,46+,47+,48+,49+/m1/s1
• InChIKey: JAYAGJDXJIDEKI-FVBOYCDESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3R,4R,6S)-6-{[(3S,4R,6S)-6-{[(3S,4R,6R)-6-{[(1S,2S,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}-2-methyl-3-{[(2S,4R,5S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-4-yl acetate
• IUPAC Traditional name: (3R,4R,6S)-6-{[(3S,4R,6S)-6-{[(3S,4R,6R)-6-{[(1S,2S,7R,10R,11S,14R,15S,16R)-11,16-dihydroxy-2,15-dimethyl-14-(5-oxo-2H-furan-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}-2-methyl-3-{[(2S,4R,5S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-4-yl acetate
• Synonyms: (3β,5β,12β)-3-[(O-β-D-Glucopyranosyl-(14)-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; Allocor; Cedilanid; Ceglunat; Isolanid; Isolanide; Lanatigen C; Lanimerck; NSC 119991; NSC 7533; Lanatoside C

Database IDs

• CAS Number: 17575-22-3
• PubChem SID: 164228102
• PubChem CID: 71749735

CALCULATED PROPERTIES

• Acid pKa: 7.1511126
• H Acceptors: 18
• H Donor: 8
• LogD (pH = 5.5): 1.0273905
• LogD (pH = 7.4): 0.59478515
• Log P: 1.0369705
• Molar Refractivity: 234.7976 cm^3
• Polarizability: 96.60534 Å^3
• Polar Surface Area: 288.28 Å^2
• Rotatable Bonds: 12
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Ethanol; Methanol; Pyridine
• Apperance: White Solid
• Melting Point: 246-248°C

Safety Information

• Storage Condition: Hygroscopic, -20°C Freezer, Under inert atmosphere

DETAILS

Toronto Research Chemicals - L173800

Glycosides isolated from various species of Digitalis. Cardiotonic.

REFERENCES

• Novotny, J., et al.: J. Biol. Chem., 258, 14433 (1983)
• Farr, C., et al.: J. Med. Chem., 45, 3257 (1983)
• Van Dongen, M., et al.: Drug Discov. Today, 7, 471 (1983)