ID: ALA404811

Max Phase: Preclinical

Molecular Formula: C56H92O29

Molecular Weight: 1229.32

Molecule Type: Small molecule

Representations

Synonyms (1): Digitonin
Synonyms from Alternative Forms(1):

Canonical SMILES:  C[C@@H]1CC[C@@]2(OC1)O[C@H]1[C@@H](O)[C@H]3[C@@H]4CC[C@H]5C[C@@H](O[C@@H]6O[C@H](CO)[C@H](O[C@@H]7O[C@H](CO)C(O)[C@H](O[C@@H]8OC[C@@H](O)[C@H](O)[C@H]8O)[C@H]7O[C@@H]7O[C@H](CO)[C@H](O)[C@H](O[C@@H]8O[C@H](CO)[C@@H](O)[C@H](O)[C@H]8O)[C@H]7O)[C@H](O)[C@H]6O)[C@H](O)C[C@]5(C)[C@H]4CC[C@]3(C)[C@H]1[C@@H]2C

Standard 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

Standard InChI Key:  UVYVLBIGDKGWPX-YCCXZQINSA-N

Molecule Features

Natural Product: Yes

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Properties

Molecular Weight: 1229.32

Molecular Weight (Monoisotopic): 1228.5724

AlogP:

#Rotatable Bonds:

Polar Surface Area:

Molecular Species:

HBA:

HBD:

#RO5 Violations:

HBA (Lipinski):

HBD (Lipinski):

#RO5 Violations (Lipinski):

CX Acidic pKa:

CX Basic pKa:

CX LogP:

CX LogD:

Aromatic Rings:

Heavy Atoms:

QED Weighted:

Np Likeness Score:

References

1. Biessen EA, Broxterman H, van Boom JH, van Berkel TJ..  (1995)  The cholesterol derivative of a triantennary galactoside with high affinity for hepatic asialoglycoprotein receptor: a potent cholesterol lowering agent.,  38  (11): [PMID:7783116] [10.1021/jm00011a003]

2. Danieli B, Luisetti M, Steurer S, Michelitsch A, Likussar W, Riva S, Reiner J, Schubert-Zsilavecz M..  (1999)  Application of lipase-catalyzed regioselective esterification in the preparation of digitonin derivatives.,  62  (5): [PMID:10346941] [10.1021/np9803068]

3. Yoshimatsu K, Satake M, Shimomura K, Sawada JI, Terao T..  (1990)  Determination of cardenolides in hairy root cultures of Digitalis lanata by enzyme-linked immunosorbent assay.,  53  (6): [PMID:2089119] [10.1021/np50072a015]

4. Felth J, Rickardson L, Rosén J, Wickström M, Fryknäs M, Lindskog M, Bohlin L, Gullbo J..  (2009)  Cytotoxic effects of cardiac glycosides in colon cancer cells, alone and in combination with standard chemotherapeutic drugs.,  72  (11): [PMID:19894733] [10.1021/np900210m]

5. Scott S. Auerbach, DrugMatrix¨ and ToxFX¨ Coordinator National Toxicology Program. DrugMatrix in vitro pharmacology data, 

6. PubChem BioAssay data set, 

7. Böttger S, Hofmann K, Melzig MF..  (2012)  Saponins can perturb biologic membranes and reduce the surface tension of aqueous solutions: a correlation?,  20  (9): [PMID:22503361] [10.1016/j.bmc.2012.03.032]

8. De Geyter E, Smagghe G, Rahbé Y, Geelen D..  (2012)  Triterpene saponins of Quillaja saponaria show strong aphicidal and deterrent activity against the pea aphid Acyrthosiphon pisum.,  68  (2): [PMID:21717567] [10.1002/ps.2235]

9. Gilabert-Oriol R, Mergel K, Thakur M, von Mallinckrodt B, Melzig MF, Fuchs H, Weng A..  (2013)  Real-time analysis of membrane permeabilizing effects of oleanane saponins.,  21  (8): [PMID:23454223] [10.1016/j.bmc.2013.01.061]

10. De Bruyn T, van Westen GJ, Ijzerman AP, Stieger B, de Witte P, Augustijns PF, Annaert PP..  (2013)  Structure-based identification of OATP1B1/3 inhibitors.,  83  (6): [PMID:23571415] [10.1124/mol.112.084152]

11. Fobofou SA, Franke K, Sanna G, Porzel A, Bullita E, La Colla P, Wessjohann LA..  (2015)  Isolation and anticancer, anthelminthic, and antiviral (HIV) activity of acylphloroglucinols, and regioselective synthesis of empetrifranzinans from Hypericum roeperianum.,  23  (19): [PMID:26358281] [10.1016/j.bmc.2015.08.028]

12. DrugMatrix,  [10.6019/CHEMBL3885881]

13. EUbOPEN.  (2023)  EUbOPEN Chemogenomics Library - Multiplex,  [10.6019/CHEMBL5303300]

14. EUbOPEN.  (2023)  EUbOPEN Chemogenomics Library - IncuCyte,  [10.6019/CHEMBL5303304]

15. EUbOPEN.  (2023)  Tm Shift (DSF) assay results for EUbOPEN Chemogenomics Library,  [10.6019/CHEMBL5308504]

Source

Source(4):

• Scientific Literature
• PubChem BioAssays
• DrugMatrix
• EUbOPEN Chemogenomic Library