Tibolone

ID: ALA2103774

Chembl Id: CHEMBL2103774

Cas Number: 5630-53-5

PubChem CID: 444008

Product Number: T274740

Max Phase: Approved

Molecular Formula: C21H28O2

Molecular Weight: 312.45

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Tibolone | NSC-759898 | ORG OD 14 | ORG-OD 14 | tibolone|5630-53-5|Liviella|Livial|Org OD 14|Tibolona|Tibolonum|Xyvion|Boltin|17-Hydroxy-7alpha-methyl-19-nor-17alpha-pregn-5(10)-en-20-yn-3-one|ORG-OD 14|(7R,8R,9S,13S,14S,17R)-17-ethynyl-17-hydroxy-7,13-dimethyl-1,2,4,6,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-3-one|DTXSID5023667|CHEBI:32223|FF9X0205V2|NSC-759898|(1S,9R,10R,11S,14R,15S)-14-ethynyl-14-hydroxy-9,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-2(7)-en-5-one|DTShow More⌵

Trade Names(1): Livial

Canonical SMILES:  C#C[C@]1(O)CC[C@H]2[C@@H]3[C@H](C)CC4=C(CCC(=O)C4)[C@H]3CC[C@@]21C

Standard InChI:  InChI=1S/C21H28O2/c1-4-21(23)10-8-18-19-13(2)11-14-12-15(22)5-6-16(14)17(19)7-9-20(18,21)3/h1,13,17-19,23H,5-12H2,2-3H3/t13-,17-,18+,19-,20+,21+/m1/s1

Standard InChI Key:  WZDGZWOAQTVYBX-XOINTXKNSA-N

Alternative Forms

1. Parent:

   

   ALA2103774

   Tibolone (Liviella) (Livial)

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

Calculated Properties

Molecular Weight: 312.45

Molecular Weight (Monoisotopic): 312.2089

AlogP: 3.88

#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: 3.10

CX LogD: 3.10

Aromatic Rings: 0

Heavy Atoms: 23

QED Weighted: 0.54

Np Likeness Score: 1.90

References

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

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

3. PubChem BioAssay data set, 

4. Unpublished dataset, 

5. PubChem BioAssay data set, 

6. 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]

7. Loi CM, Smith DA, Dalvie D..  (2013)  Which metabolites circulate?,  41  (5): [PMID:23454828] [10.1124/dmd.112.050278]

8. WHO Anatomical Therapeutic Chemical Classification, 

9. British National Formulary (72nd edition), 

10. Unpublished dataset, 

11. 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]

12. Katie Heiser, Peter F. McLean, Chadwick T. Davis, Ben Fogelson, Hannah B. Gordon, Pamela Jacobson, Brett Hurst, Ben Miller, Ronald W. Alfa, Berton A. Earnshaw, Mason L. Victors, Yolanda T. Chong, Imran S. Haque, Adeline S. Low, Christopher C. Gibson.  (2020)  Identification of potential treatments for COVID-19 through artificial intelligence-enabled phenomic analysis of human cells infected with SARS-CoV-2,  [10.1101/2020.04.21.054387]

13. 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]

14. 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(10):

• Scientific Literature
• PubChem BioAssays
• Clinical Candidates
• USP Dictionary of USAN and International Drug Names
• DrugMatrix
• Gene Expression Atlas Compounds
• CO-ADD antimicrobial screening data
• WHO Anatomical Therapeutic Chemical Classification
• British National Formulary
• SARS-CoV-2 Screening Data 2020-21