(2S,3R,4S,5S,6R)-2-{[(2S,3R,4S,5S,6R)-2-{[(2S,3R,4S,6R)-2-{[(2R,3R,4R,5R,6R)-4,5-dihydroxy-2-(hydroxymethyl)-6-[(1'R,2R,2'S,3'S,4'R,5R,7'S,8'R,9'S,12'S,13'S,15'R,16'R,18'S)-5,7',9',13'-tetramethyl-5'-oxaspiro[oxane-2,6'-pentacyclo[10.8.0.02,9.04,8.013,18]icosane]-3',15'-dioloxy]oxan-3-yl]oxy}-5-hydroxy-6-(hydroxymethyl)-4-{[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxy}oxan-3-yl]oxy}-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

• ChemBase ID: 127025
• Molecular Formular: C56H92O29
• Molecular Mass: 1229.31228
• Monoisotopic Mass: 1228.57242692
• SMILES: O[C@@H]1[C@@H](O)[C@H](O)[C@H](O[C@H]1O[C@@H]1[C@@H](O)[C@@H](O[C@H](CO)[C@@H]1O)O[C@@H]1[C@@H](O[C@@H]2OC[C@@H](O)[C@H](O)[C@H]2O)C(O)[C@H](O[C@H]1O[C@@H]1[C@H](O)[C@@H](O)[C@@H](O[C@@H]1CO)O[C@H]1[C@H](O)C[C@@]2(C)[C@@H](CC[C@@H]3[C@@H]2CC[C@@]2([C@@H]4[C@@H](O[C@@]5(OC[C@@H](CC5)C)[C@H]4C)[C@@H](O)[C@@H]32)C)C1)CO)CO
• Canonical SMILES: OC[C@H]1O[C@@H](O[C@@H]2C[C@@H]3CC[C@@H]4[C@@H]([C@]3(C[C@H]2O)C)CC[C@]2([C@H]4[C@H](O)[C@H]3[C@@H]2[C@@H]([C@]2(O3)CC[C@H](CO2)C)C)C)[C@@H]([C@H]([C@H]1O[C@@H]1O[C@H](CO)C([C@@H]([C@H]1O[C@@H]1O[C@H](CO)[C@@H]([C@@H]([C@H]1O)O[C@@H]1O[C@H](CO)[C@H]([C@@H]([C@H]1O)O)O)O)O[C@@H]1OC[C@H]([C@@H]([C@H]1O)O)O)O)O)O
• InChI: InChI=1S/C56H92O29/c1-19-7-10-56(75-17-19)20(2)31-45(85-56)37(67)32-22-6-5-21-11-26(24(61)12-55(21,4)23(22)8-9-54(31,32)3)76-50-42(72)39(69)44(30(16-60)80-50)81-53-48(47(36(66)29(15-59)79-53)83-49-40(70)33(63)25(62)18-74-49)84-52-43(73)46(35(65)28(14-58)78-52)82-51-41(71)38(68)34(64)27(13-57)77-51/h19-53,57-73H,5-18H2,1-4H3/t19-,20+,21+,22-,23+,24-,25-,26-,27-,28-,29-,30-,31+,32-,33+,34-,35+,36?,37+,38+,39-,40-,41-,42-,43-,44+,45-,46+,47+,48-,49+,50-,51+,52+,53+,54-,55+,56-/m1/s1
• InChIKey: UVYVLBIGDKGWPX-YCCXZQINSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3R,4S,5S,6R)-2-{[(2S,3R,4S,5S,6R)-2-{[(2S,3R,4S,6R)-2-{[(2R,3R,4R,5R,6R)-4,5-dihydroxy-2-(hydroxymethyl)-6-[(1'R,2R,2'S,3'S,4'R,5R,7'S,8'R,9'S,12'S,13'S,15'R,16'R,18'S)-5,7',9',13'-tetramethyl-5'-oxaspiro[oxane-2,6'-pentacyclo[10.8.0.0^2,^9.0^4,^8.0^1^3,^1^8]icosane]-3',15'-dioloxy]oxan-3-yl]oxy}-5-hydroxy-6-(hydroxymethyl)-4-{[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxy}oxan-3-yl]oxy}-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol
• IUPAC Traditional name: digitonin
• Synonyms: digitin; Digitonin

Database IDs

• CAS Number: 11024-24-1
• EC Number: 234-255-6
• PubChem SID: 162221348
• PubChem CID: 25444
• CHEMBL: 404811
• Chemspider ID: 23753
• KEGG ID: C00765
• Wikipedia Title: Digitonin

CALCULATED PROPERTIES

• Acid pKa: 11.676212
• H Acceptors: 29
• H Donor: 17
• LogD (pH = 5.5): -4.962812
• LogD (pH = 7.4): -4.962835
• Log P: -4.962812
• Molar Refractivity: 278.1659 cm^3
• Polarizability: 115.55539 Å^3
• Polar Surface Area: 454.67 Å^2
• Rotatable Bonds: 14
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Optical Rotation: -47 to -49° (10 g/100 ml 75% acetic acid at 25 °C)