4-[(1S,2S,5S,7R,10R,11S,14R,15R)-11-hydroxy-2,15-dimethyl-5-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]tetracyclo[8.7.0.02,7.011,15]heptadecan-14-yl]-2,5-dihydrofuran-2-one

• ChemBase ID: 168835
• 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@](CC1)([C@H](CC2)C1=CC(=O)OC1)C)O)C)OC1C(C(C(C(O1)C)O)O)O
• Canonical SMILES: O=C1OCC(=C1)[C@H]1CC[C@]2([C@]1(C)CC[C@H]1[C@H]2CC[C@H]2[C@]1(C)CC[C@@H](C2)OC1OC(C)C(C(C1O)O)O)O
• InChI: InChI=1S/C29H44O8/c1-15-23(31)24(32)25(33)26(36-15)37-18-6-9-27(2)17(13-18)4-5-21-20(27)7-10-28(3)19(8-11-29(21,28)34)16-12-22(30)35-14-16/h12,15,17-21,23-26,31-34H,4-11,13-14H2,1-3H3/t15?,17-,18+,19-,20+,21-,23?,24?,25?,26?,27+,28-,29+/m1/s1
• InChIKey: WQMLFJWIKARBFW-PBZBCQJQSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-[(1S,2S,5S,7R,10R,11S,14R,15R)-11-hydroxy-2,15-dimethyl-5-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]tetracyclo[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,15R)-11-hydroxy-2,15-dimethyl-5-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]tetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadecan-14-yl]-5H-furan-2-one
• Synonyms: (3β,5β)-3-[(6-Deoxy-α-L-mannopyranosyl)oxy]-14-hydroxycard-20(22)-enolide; Digitoxigenin 3-Rhamnoside; Digitoxigenin Rhamnoside; Digitoxigenin α-L-Rhamnoside; Digitoxigenin-3β-O-α-L-rhamnopyranoside; Evomonoside

Database IDs

• CAS Number: 508-93-0
• PubChem SID: 162262967
• PubChem CID: 71316702

CALCULATED PROPERTIES

• Acid pKa: 7.1826324
• H Acceptors: 7
• H Donor: 4
• LogD (pH = 5.5): 2.334511
• LogD (pH = 7.4): 1.9210728
• Log P: 2.3434289
• Molar Refractivity: 134.5102 cm^3
• Polarizability: 54.226227 Å^3
• Polar Surface Area: 125.68 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - E947500

Evomonoside, a Digitoxigenin analogue was isolated from seeds of L. apetalum, and showed antitumor activity.

REFERENCES

• Brown, L., et al.: Biochem. Pharmacol., 32, 2767 (1983)
• Rathore, H., et al.: J. Med. Chem., 29, 1945 (1983)
• Katz, A., et al.: J. Biol. Chem., 285, 19582 (1983)