ID: ALA25164

Max Phase: Preclinical

Molecular Formula: C15H24O5

Molecular Weight: 284.35

Molecule Type: Small molecule

Representations

Canonical SMILES:  C[C@@H]1CC[C@H]2[C@@H](C)C(O)O[C@@H]3O[C@@]4(C)CC[C@@H]1[C@]32OO4

Standard InChI:  InChI=1S/C15H24O5/c1-8-4-5-11-9(2)12(16)17-13-15(11)10(8)6-7-14(3,18-13)19-20-15/h8-13,16H,4-7H2,1-3H3/t8-,9-,10+,11+,12?,13-,14-,15-/m1/s1

Standard InChI Key:  BJDCWCLMFKKGEE-HVDUHBCDSA-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: 284.35

Molecular Weight (Monoisotopic): 284.1624

AlogP: 2.19

#Rotatable Bonds: 0

Polar Surface Area: 57.15

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: 0

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 12.11

CX Basic pKa:

CX LogP: 2.84

CX LogD: 2.84

Aromatic Rings: 0

Heavy Atoms: 20

QED Weighted: 0.69

Np Likeness Score: 3.88

References

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4. 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]

5. Hu Y, Li N, Zhang J, Wang Y, Chen L, Sun J..  (2019)  Artemisinin-indole and artemisinin-imidazole hybrids: Synthesis, cytotoxic evaluation and reversal effects on multidrug resistance in MCF-7/ADR cells.,  29  (9): [PMID:30837097] [10.1016/j.bmcl.2019.02.021]

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12. Yu Y,Yu J,Zou X,Xu W,Zhang J,Bian H,Dong X,Shen Z.  (2020)  Studies on the stereoselective synthesis and immunosuppressive activity of dihydroartemisinin-O-glycoside derivatives.,  30  (16): [PMID:32631539] [10.1016/j.bmcl.2020.127338]

13. Xu C,Xiao L,Zhang X,Zhuang T,Mu L,Yang X.  (2021)  Synthesis and biological activities of novel mitochondria-targeted artemisinin ester derivatives.,  39  [PMID:33691167] [10.1016/j.bmcl.2021.127912]

14. 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]

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Source

Source(3):

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