4-[(1S,2S,5S,7R,10R,11S,14R,15S,16R)-5-[(5-{[5-({5-[(4,5-dihydroxy-6-methyloxan-2-yl)oxy]-4-hydroxy-6-methyloxan-2-yl}oxy)-4-hydroxy-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: 167479
• Molecular Formular: C47H74O17
• Molecular Mass: 911.08026
• Monoisotopic Mass: 910.49260091
• 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)OC1OC(C(C(C1)O)OC1OC(C(C(C1)O)OC1OC(C(C(C1)O)OC1OC(C(C(C1)O)O)C)C)C)C
• 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)OC1CC(O)C(C(O1)C)OC1CC(O)C(C(O1)C)OC1CC(O)C(C(O1)C)OC1CC(O)C(C(O1)C)O)O
• InChI: InChI=1S/C47H74O17/c1-21-41(54)31(48)16-38(57-21)62-43-23(3)59-40(18-33(43)50)64-44-24(4)60-39(19-34(44)51)63-42-22(2)58-37(17-32(42)49)61-27-9-11-45(5)26(14-27)7-8-29-30(45)15-35(52)46(6)28(10-12-47(29,46)55)25-13-36(53)56-20-25/h13,21-24,26-35,37-44,48-52,54-55H,7-12,14-20H2,1-6H3/t21?,22?,23?,24?,26-,27+,28-,29-,30+,31?,32?,33?,34?,35-,37?,38?,39?,40?,41?,42?,43?,44?,45+,46+,47+/m1/s1
• InChIKey: RDWJFVWFSYHOTB-GMBKPALGSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-[(1S,2S,5S,7R,10R,11S,14R,15S,16R)-5-[(5-{[5-({5-[(4,5-dihydroxy-6-methyloxan-2-yl)oxy]-4-hydroxy-6-methyloxan-2-yl}oxy)-4-hydroxy-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-[(5-{[5-({5-[(4,5-dihydroxy-6-methyloxan-2-yl)oxy]-4-hydroxy-6-methyloxan-2-yl}oxy)-4-hydroxy-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-[(O-2,6-Dideoxy-β-D-ribo-hexopyranosyl-(1-4)-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)oxy]-12,14-dihydroxycard-20(22)-enolide; Digoxoside; Digoxigenin Tetradigitoxide; Digoxigenin TetradigitoxosideDISCONTINUED

Database IDs

• CAS Number: 31539-05-6
• PubChem SID: 162261612
• PubChem CID: 71316108

CALCULATED PROPERTIES

• Acid pKa: 7.151116
• H Acceptors: 16
• H Donor: 7
• LogD (pH = 5.5): 2.5338132
• LogD (pH = 7.4): 2.1012135
• Log P: 2.5433931
• Molar Refractivity: 222.5917 cm^3
• Polarizability: 91.404755 Å^3
• Polar Surface Area: 241.75 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - D446510

Digoxin (Dx) (D446575) impurity.

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)