ID: ALA1200647

Max Phase: Approved

First Approval: 1982

Molecular Formula: C59H84N2O18

Molecular Weight: 1109.32

Molecule Type: Small molecule

Representations

Synonyms Trade Names(1): Vanobid

Canonical SMILES:  CC1/C=C/C=C/C=C/C=C/C=C/C=C/C=C/C(OC2O[C@H](C)[C@@H](O)[C@H](N)[C@@H]2O)CC(O)C(C(=O)O)C(O)CC(=O)CC(O)CC(O)CC(O)CC(=O)CCCC(=O)CC(=O)OC1C(C)CC(C)C(O)CC(=O)c1ccc(N)cc1

Standard InChI:  InChI=1S/C59H84N2O18/c1-35-18-15-13-11-9-7-5-6-8-10-12-14-16-21-47(78-59-56(74)54(61)55(73)38(4)77-59)33-51(71)53(58(75)76)50(70)31-46(67)30-45(66)29-44(65)28-43(64)27-41(62)19-17-20-42(63)32-52(72)79-57(35)37(3)26-36(2)48(68)34-49(69)39-22-24-40(60)25-23-39/h5-16,18,21-25,35-38,43-45,47-48,50-51,53-57,59,64-66,68,70-71,73-74H,17,19-20,26-34,60-61H2,1-4H3,(H,75,76)/b6-5+,9-7+,10-8+,13-11+,14-12+,18-15+,21-16+/t35?,36?,37?,38-,43?,44?,45?,47?,48?,50?,51?,53?,54+,55-,56+,57?,59?/m1/s1

Standard InChI Key:  OPGSFDUODIJJGF-JBUZINEHSA-N

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: Yes

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Properties

Molecular Weight: 1109.32

Molecular Weight (Monoisotopic): 1108.5719

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. Garcia-Domenech R, de Gregorio Alapont C, de Julian-Ortiz J, Galvez J, Popa L.  (1997)  Molecular connectivity to find -blockers with low toxicity,  7  (5): [10.1016/S0960-894X(97)00046-2]

2. Unpublished dataset, 

3. USP Dictionary of USAN and International Names (2010 edition) and USAN registrations 2007-date, 

4. Gershon H, Shanks L..  (1977)  Antifungal properties of 2-bromo-3-fluorosuccinic acid esters and related compounds.,  20  (4): [PMID:321785] [10.1021/jm00214a038]

5. Gershon H, Shanks L, Gawiak DE..  (1976)  Antifungal activity of 4-substituted crotonic acid esters.,  19  (8): [PMID:787525] [10.1021/jm00230a019]

6. WHO Anatomical Therapeutic Chemical Classification, 

7. 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]

8. Stevens M, Abdeen S, Salim N, Ray AM, Washburn A, Chitre S, Sivinski J, Park Y, Hoang QQ, Chapman E, Johnson SM..  (2019)  HSP60/10 chaperonin systems are inhibited by a variety of approved drugs, natural products, and known bioactive molecules.,  29  (9): [PMID:30852084] [10.1016/j.bmcl.2019.02.028]

9. 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]

10. 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]

11. 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]

Source

Source(6):

• Scientific Literature
• FDA Approved Drug Products with Therapeutic Equivalence Evaluations (Orange Book)
• USP Dictionary of USAN and International Drug Names
• WHO Anatomical Therapeutic Chemical Classification
• SARS-CoV-2 Screening Data 2020-21
• Fraunhofer HDAC6