4-[(1S,2S,5S,7R,10R,11S,14R,15S,16R)-5-{[(2R,4R,5S)-4,5-dihydroxy-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: 167478
• Molecular Formular: C29H44O8
• Molecular Mass: 520.65486
• Monoisotopic Mass: 520.30361837
• 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)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)O
• InChI: InChI=1S/C29H44O8/c1-15-26(33)22(30)13-25(36-15)37-18-6-8-27(2)17(11-18)4-5-20-21(27)12-23(31)28(3)19(7-9-29(20,28)34)16-10-24(32)35-14-16/h10,15,17-23,25-26,30-31,33-34H,4-9,11-14H2,1-3H3/t15?,17-,18+,19-,20-,21+,22-,23-,25+,26-,27+,28+,29+/m1/s1
• InChIKey: JFSXBMIFXZFKHD-GPIQKIIUSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-[(1S,2S,5S,7R,10R,11S,14R,15S,16R)-5-{[(2R,4R,5S)-4,5-dihydroxy-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)-4,5-dihydroxy-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-β-D-ribo-hexopyranosyl)oxy]-12,14-dihydroxycard-20(22)-enolide; Digoxigenin 3-Monodigitoxide; Digoxigenin Monodigitoxide; Digoxigenin Monodigitoxoside

Database IDs

• CAS Number: 5352-63-6
• PubChem SID: 162261611
• PubChem CID: 71316107

CALCULATED PROPERTIES

• Acid pKa: 7.151116
• H Acceptors: 7
• H Donor: 4
• LogD (pH = 5.5): 2.003676
• LogD (pH = 7.4): 1.5710768
• Log P: 2.0132558
• Molar Refractivity: 134.515 cm^3
• Polarizability: 54.226227 Å^3
• Polar Surface Area: 125.68 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: White Solid
• Melting Point: 228-230°C

Safety Information

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

DETAILS

Toronto Research Chemicals - D446505

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)