ID: ALA757

Max Phase: Phase

Molecular Formula: C18H26O2

Molecular Weight: 274.40

Molecule Type: Small molecule

Representations

Synonyms (4): Deca-Durabolin | Durabolin | Nandrolone | NSC-3351
Synonyms from Alternative Forms(4):

Canonical SMILES:  C[C@]12CC[C@H]3[C@@H](CCC4=CC(=O)CC[C@@H]43)[C@@H]1CC[C@@H]2O

Standard InChI:  InChI=1S/C18H26O2/c1-18-9-8-14-13-5-3-12(19)10-11(13)2-4-15(14)16(18)6-7-17(18)20/h10,13-17,20H,2-9H2,1H3/t13-,14+,15+,16-,17-,18-/m0/s1

Standard InChI Key:  NPAGDVCDWIYMMC-IZPLOLCNSA-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: 274.40

Molecular Weight (Monoisotopic): 274.1933

AlogP: 3.49

#Rotatable Bonds: 0

Polar Surface Area: 37.30

Molecular Species: NEUTRAL

HBA: 2

HBD: 1

#RO5 Violations: 0

HBA (Lipinski): 2

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 0

CX Acidic pKa:

CX Basic pKa:

CX LogP: 3.07

CX LogD: 3.07

Aromatic Rings: 0

Heavy Atoms: 20

QED Weighted: 0.73

Np Likeness Score: 2.56

References

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10. Kotani T, Higashiura K..  (2004)  Comparative molecular active site analysis (CoMASA). 1. An approach to rapid evaluation of 3D QSAR.,  47  (11): [PMID:15139751] [10.1021/jm030364c]

11. Crippen GM..  (1997)  Validation of EGSITE2, a mixed integer program for deducing objective site models for experimental binding data.,  40  (20): [PMID:9379435] [10.1021/jm970211n]

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14. So SS, Karplus M..  (1997)  Three-dimensional quantitative structure-activity relationships from molecular similarity matrices and genetic neural networks. 1. Method and validations.,  40  (26): [PMID:9435904] [10.1021/jm970487v]

15. Good AC, So SS, Richards WG..  (1993)  Structure-activity relationships from molecular similarity matrices.,  36  (4): [PMID:8474098] [10.1021/jm00056a002]

16. Robinson DD, Winn PJ, Lyne PD, Richards WG..  (1999)  Self-organizing molecular field analysis: a tool for structure-activity studies.,  42  (4): [PMID:10052964] [10.1021/jm9810607]

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19. Cherkasov A, Ban F, Santos-Filho O, Thorsteinson N, Fallahi M, Hammond GL..  (2008)  An updated steroid benchmark set and its application in the discovery of novel nanomolar ligands of sex hormone-binding globulin.,  51  (7): [PMID:18330978] [10.1021/jm7011485]

20. Ahlin G, Karlsson J, Pedersen JM, Gustavsson L, Larsson R, Matsson P, Norinder U, Bergström CA, Artursson P..  (2008)  Structural requirements for drug inhibition of the liver specific human organic cation transport protein 1.,  51  (19): [PMID:18788725] [10.1021/jm8003152]

21. Pedersen JM, Matsson P, Bergström CA, Norinder U, Hoogstraate J, Artursson P..  (2008)  Prediction and identification of drug interactions with the human ATP-binding cassette transporter multidrug-resistance associated protein 2 (MRP2; ABCC2).,  51  (11): [PMID:18457386] [10.1021/jm7015683]

22. PubChem BioAssay data set, 

23. Kruhlak NL, Choi SS, Contrera JF, Weaver JL, Willard JM, Hastings KL, Sancilio LF..  (2008)  Development of a phospholipidosis database and predictive quantitative structure-activity relationship (QSAR) models.,  18  (2): [PMID:20020916] [10.1080/15376510701857262]

24. PubChem BioAssay data set, 

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

26. Liu Z, Shi Q, Ding D, Kelly R, Fang H, Tong W..  (2011)  Translating clinical findings into knowledge in drug safety evaluation--drug induced liver injury prediction system (DILIps).,  7  (12): [PMID:22194678] [10.1371/journal.pcbi.1002310]

27. PubChem BioAssay data set, 

28. PubChem BioAssay data set, 

29. Biour M, Ben Salem C, Chazouillères O, Grangé JD, Serfaty L, Poupon R..  (2004)  [Drug-induced liver injury; fourteenth updated edition of the bibliographic database of liver injuries and related drugs].,  28  (8-9): [PMID:15646539] [10.1016/s0399-8320(04)95062-2]

30. PubChem BioAssay data set, 

31. PubChem BioAssay data set, 

32. Lee DL, Kollman PA, Marsh FJ, Wolff ME..  (1977)  Quantitative relationships between steroid structure and binding to putative progesterone receptors.,  20  (9): [PMID:926114] [10.1021/jm00219a006]

33. Unpublished dataset, 

34. Franck Touret, Magali Gilles, Karine Barral, Antoine Nougairède, Etienne Decroly, Xavier de Lamballerie, Bruno Coutard.  (2020)  In vitro screening of a FDA approved chemical library reveals potential inhibitors of SARS-CoV-2 replication,  [10.1101/2020.04.03.023846]

35. 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]

36. 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]

37. 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]

38. Johannes Zuegg, Alysha Elliott, Maite Amado, Emma Cowie, Ali Hinton, Geraldine Kaeslin, Angela Kavanagh, Anne Kunert, Gabriell Lowe, Soumya Ramu, Janet Reid, Robin Trauer, Mathilde Desselle, Ruth Neale, Karl Hansford, Mark Blascovich, Matthew Cooper. CO-ADD screening of NIH (USA) - Clinical Collection,  [10.6019/CHEMBL4513141]

39. Unpublished dataset, 

40. Ellen Van Damme.  (2021)  Screening of ~5500 FDA-approved drugs and clinical candidates for anti-SARS-CoV-2 activity,  [10.6019/CHEMBL4651402]

41. 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(9):

• Scientific Literature
• PubChem BioAssays
• Clinical Candidates
• DrugMatrix
• CO-ADD antimicrobial screening data
• SARS-CoV-2 Screening Data 2020-21
• Active Ingredient of a Prodrug
• IMI-CARE SARS-CoV-2 Data
• Fraunhofer HDAC6