ID: ALA4285883

Max Phase: Phase

Molecular Formula: C32H48O9

Molecular Weight: 576.73

Molecule Type: Small molecule

Representations

Synonyms (3): Anvirzel | Oleandrin | NSC-692219
Synonyms from Alternative Forms(3):

Canonical SMILES:  CO[C@H]1C[C@H](O[C@H]2CC[C@@]3(C)[C@H](CC[C@@H]4[C@@H]3CC[C@]3(C)[C@@H](C5=CC(=O)OC5)[C@@H](OC(C)=O)C[C@]43O)C2)O[C@@H](C)[C@@H]1O

Standard InChI:  InChI=1S/C32H48O9/c1-17-29(35)24(37-5)14-27(39-17)41-21-8-10-30(3)20(13-21)6-7-23-22(30)9-11-31(4)28(19-12-26(34)38-16-19)25(40-18(2)33)15-32(23,31)36/h12,17,20-25,27-29,35-36H,6-11,13-16H2,1-5H3/t17-,20+,21-,22-,23+,24-,25-,27-,28-,29-,30-,31+,32-/m0/s1

Standard InChI Key:  JLPDBLFIVFSOCC-XYXFTTADSA-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: Yes

Availability: No

Prodrug: No

Properties

Molecular Weight: 576.73

Molecular Weight (Monoisotopic): 576.3298

AlogP: 3.68

#Rotatable Bonds: 5

Polar Surface Area: 120.75

Molecular Species: NEUTRAL

HBA: 9

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 9

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 6.82

CX Basic pKa:

CX LogP: 2.95

CX LogD: 2.27

Aromatic Rings: 0

Heavy Atoms: 41

QED Weighted: 0.37

Np Likeness Score: 3.03

References

1. Arai MA, Akamine R, Hayashi N, Koyano T, Kowithayakorn T, Ishibashi M..  (2018)  The Notch Inhibitors Isolated from Nerium indicum.,  81  (5): [PMID:29693393] [10.1021/acs.jnatprod.7b01031]

2. Unpublished dataset, 

3. Bernhard Ellinger, Denisa Bojkova, Andrea Zaliani, Jindrich Cinatl, Carsten Claussen, Sandra Westhaus, Jeanette Reinshagen, Maria Kuzikov, Markus Wolf, Gerd Geisslinger, Philip Gribbon, Sandra Ciesek.  (2020)  Identification of inhibitors of SARS-CoV-2 in-vitro cellular toxicity in human (Caco-2) cells using a large scale drug repurposing collection,  [10.21203/rs.3.rs-23951/v1]

4. Michalak K, Rárová L, Kubala M, Čechová P, Strnad M, Wicha J..  (2019)  Synthesis and evaluation of cytotoxic and Na⁺/K⁺-ATP-ase inhibitory activity of selected 5α-oleandrigenin derivatives.,  180  [PMID:31325787] [10.1016/j.ejmech.2019.07.028]

5. Maria Kuzikov, Elisa Costanzi, Jeanette Reinshagen, Francesca Esposito, Laura Vangeel, Markus Wolf, Bernhard Ellinger, Carsten Claussen, Gerd Geisslinger, Angela Corona, Daniela Iaconis, Carmine Talarico, Candida Manelfi, Rolando Cannalire, Giulia Rossetti, Jonas Gossen, Simone Albani, Francesco Musiani, Katja Herzog, Yang Ye, Barbara Giabbai, Nicola Demitri, Dirk Jochmans, Steven De Jonghe, Jasper Rymenants, Vincenzo Summa, Enzo Tramontano, Andrea R. Beccari, Pieter Leyssen, Paola Storici, Johan Neyts, Philip Gribbon, and Andrea Zaliani.  (2020)  Identification of inhibitors of SARS-Cov2 M-Pro enzymatic activity using a small molecule repurposing screen,  [10.6019/CHEMBL4495564]

6. Andrea Zaliani, Laura Vangeel, Jeanette Reinshagen, Daniela Iaconis, Maria Kuzikov, Oliver Keminer, Markus Wolf, Bernhard Ellinger, Francesca Esposito, Angela Corona, Enzo Tramontano, Candida Manelfi, Katja Herzog, Dirk Jochmans, Steven De Jonghe, Winston Chiu, Thibault Francken, Joost Schepers, Caroline Collard, Kayvan Abbasi, Carsten Claussen , Vincenzo Summa, Andrea R. Beccari, Johan Neyts, Philip Gribbon and Pieter Leyssen.  (2020)  Cytopathic SARS-Cov2 screening on VERO-E6 cells in a large repurposing effort,  [10.6019/CHEMBL4495565]

7. Michalak K,Rárová L,Kubala M,Štenclová T,Strnad M,Wicha J.  (2020)  Synthesis and evaluation of Na/K-ATP-ase inhibiting and cytotoxic in vitro activities of oleandrigenin and its selected 17β-(butenolidyl)- and 17β-(3-furyl)- analogues.,  202  [PMID:32645647] [10.1016/j.ejmech.2020.112520]

8. Bernhard Ellinger, Justus Dick, Vanessa Lage-Rupprecht, Bruce Schultz, Andrea Zaliani, Marcin Namysl, Stephan Gebel, Ole Pless, Jeanette Reinshagen, Christian Ebeling, Alexander Esser, Marc Jacobs, Carsten Claussen, and Martin Hofmann-Apitius.  (2021)  HDAC6 screening dataset using tau-based substrate in an enzymatic assay yields selective inhibitors and activators,  [10.6019/CHEMBL4808148]

9. Sutherland JJ, Yonchev D, Fekete A, Urban L..  (2023)  A preclinical secondary pharmacology resource illuminates target-adverse drug reaction associations of marketed drugs.,  14  (1): [PMID:37468498] [10.1038/s41467-023-40064-9]

Source

Source(4):

• Scientific Literature
• Clinical Candidates
• SARS-CoV-2 Screening Data 2020-21
• Fraunhofer HDAC6