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

• ChemBase ID: 167477
• Molecular Formular: C35H54O11
• Molecular Mass: 650.79666
• Monoisotopic Mass: 650.36661255
• SMILES: C1C[C@@H](C[C@@H]2[C@]1([C@@H]1[C@@H](CC2)[C@@]2([C@]([C@@H](C1)O)([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)O)O
• Canonical SMILES: O=C1OCC(=C1)[C@H]1CC[C@]2([C@]1(C)[C@H](O)C[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)O
• InChI: InChI=1S/C35H54O11/c1-17-31(40)25(36)14-30(43-17)46-32-18(2)44-29(15-26(32)37)45-21-7-9-33(3)20(12-21)5-6-23-24(33)13-27(38)34(4)22(8-10-35(23,34)41)19-11-28(39)42-16-19/h11,17-18,20-27,29-32,36-38,40-41H,5-10,12-16H2,1-4H3/t17?,18?,20-,21+,22-,23-,24+,25-,26-,27-,29+,30+,31-,32-,33+,34+,35+/m1/s1
• InChIKey: NTSBMKIZRSBFTA-ZAUSNHKQSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-[(1S,2S,5S,7R,10R,11S,14R,15S,16R)-5-{[(2R,4R,5S)-5-{[(2S,4R,5S)-4,5-dihydroxy-6-methyloxan-2-yl]oxy}-4-hydroxy-6-methyloxan-2-yl]oxy}-11,16-dihydroxy-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,15S,16R)-5-{[(2R,4R,5S)-5-{[(2S,4R,5S)-4,5-dihydroxy-6-methyloxan-2-yl]oxy}-4-hydroxy-6-methyloxan-2-yl]oxy}-11,16-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadecan-14-yl]-5H-furan-2-one
• Synonyms: (3β,5β,12β)-3-[[2,6-Dideoxy-4-O-(2,6-dideoxy-β-D-ribo-hexopyranosyl)-β-D-ribo-hexopyranosyl]oxy]-12,14-dihydroxycard-20(22)-enolide; Digoxigenin Didigitoxoside; Bisdigoxigenin; Digoxigenin Bisdigitoxide; Digoxigenin Bisdigitoxoside

Database IDs

• CAS Number: 5297-05-2
• PubChem SID: 162261610
• PubChem CID: 71316106

CALCULATED PROPERTIES

• Acid pKa: 7.151116
• H Acceptors: 10
• H Donor: 5
• LogD (pH = 5.5): 2.1803885
• LogD (pH = 7.4): 1.747789
• Log P: 2.1899683
• Molar Refractivity: 163.8739 cm^3
• Polarizability: 66.61416 Å^3
• Polar Surface Area: 164.37 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: White to Off-White Solid
• Melting Point: 260-262°C

Safety Information

• Storage Condition: -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - D446500

A metabolite of Digoxin (Dx) (D446575).

REFERENCES

• Fujii, Y., et al.: Clin. Chem., 37, 476 (1991)
• Salphati, L., et al.: Xenobiotica, 29, 171 (1991)
• Song, S., et al.: Drug Metab. Dispos., 27, 689 (1991)