4-[(1S,2S,5S,7R,10R,11S,14R,15S,16R)-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}-11,16-dihydroxy-2,15-dimethyltetracyclo[8.7.0.02,7.011,15]heptadecan-14-yl]-2,5-dihydro(2H3)furan-2-one

• ChemBase ID: 167491
• Molecular Formular: C41H64O14
• Molecular Mass: 780.93846
• Monoisotopic Mass: 780.42960673
• 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)O)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)O)O
• InChI: InChI=1S/C41H64O14/c1-19-36(47)28(42)15-34(50-19)54-38-21(3)52-35(17-30(38)44)55-37-20(2)51-33(16-29(37)43)53-24-8-10-39(4)23(13-24)6-7-26-27(39)14-31(45)40(5)25(9-11-41(26,40)48)22-12-32(46)49-18-22/h12,19-21,23-31,33-38,42-45,47-48H,6-11,13-18H2,1-5H3/t19?,20?,21?,23-,24+,25-,26-,27+,28?,29?,30?,31-,33?,34?,35?,36?,37?,38?,39+,40+,41+/m1/s1
• InChIKey: LTMHDMANZUZIPE-GDNXHHNLSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-[(1S,2S,5S,7R,10R,11S,14R,15S,16R)-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}-11,16-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadecan-14-yl]-2,5-dihydro(^2H₃)furan-2-one
• IUPAC Traditional name: 4-[(1S,2S,5S,7R,10R,11S,14R,15S,16R)-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}-11,16-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadecan-14-yl](^2H₃)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)-2,6-dideoxy-β-D-ribo-hexopyranosyl)oxyl]-12,14-dihydroxycard-20(22)-enolide-d3; Digacin-d3; Dilanacin-d3; Lanicor-d3; Digoxin-d3

Database IDs

• CAS Number: 127299-95-0
• PubChem SID: 162261624
• PubChem CID: 71316114

CALCULATED PROPERTIES

• Acid pKa: 7.151116
• H Acceptors: 13
• H Donor: 6
• LogD (pH = 5.5): 2.3571007
• LogD (pH = 7.4): 1.9245013
• Log P: 2.3666806
• Molar Refractivity: 193.2328 cm^3
• Polarizability: 79.00782 Å^3
• Polar Surface Area: 203.06 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Chloroform; DMSO; Methanol
• Apperance: White to Off-White Solid
• Melting Point: >230°C (dec.)

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - D446577

Labelled Diogoxin (D446575). Cardiotonic. A representative lot is 95.4% d3, 3.4% d2, 1.2% d1 no dectable d0.

REFERENCES

• Aronson, J.K., et al.: Clin. Pharmacokinet, 5,137 (1980)
• Foss, P.R.B., Anal. Profiles Drug Subs., 9, 207 (1980)