Dihydroartemisinin

ID: ALA25164

Chembl Id: CHEMBL25164

Cas Number: 131175-87-6

PubChem CID: 6918483

Max Phase: Preclinical

Molecular Formula: C15H24O5

Molecular Weight: 284.35

Molecule Type: Small molecule

Names and Identifiers

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

Alternative Forms

1. Parent:

   

   ALA25164

   Artenimol

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

Calculated 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

1. Phainuphong P, Rukachaisirikul V, Saithong S, Phongpaichit S, Bowornwiriyapan K, Muanprasat C, Srimaroeng C, Duangjai A, Sakayaroj J..  (2016)  Lovastatin Analogues from the Soil-Derived Fungus Aspergillus sclerotiorum PSU-RSPG178.,  79  (6): [PMID:27228159] [10.1021/acs.jnatprod.5b00961]

2. Senadeera SPD, Lucantoni L, Duffy S, Avery VM, Carroll AR..  (2018)  Antiplasmodial β-Triketone-Flavanone Hybrids from the Flowers of the Australian Tree Corymbia torelliana.,  81  (7): [PMID:29969262] [10.1021/acs.jnatprod.8b00154]

3. Fröhlich T, Kiss A, Wölfling J, Mernyák E, Kulmány ÁE, Minorics R, Zupkó I, Leidenberger M, Friedrich O, Kappes B, Hahn F, Marschall M, Schneider G, Tsogoeva SB..  (2018)  Synthesis of Artemisinin-Estrogen Hybrids Highly Active against HCMV, P. falciparum, and Cervical and Breast Cancer.,  9  (11): [PMID:30429957] [10.1021/acsmedchemlett.8b00381]

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]

6. Isaka M, Chinthanom P, Thummarukcharoen T, Boonpratuang T, Choowong W..  (2019)  Highly Modified Lanostane Triterpenes from Fruiting Bodies of the Basidiomycete Tomophagus sp.,  82  (5): [PMID:30983350] [10.1021/acs.jnatprod.8b00869]

7. Knestrick MA, Wilson NG, Roth A, Adams JH, Baker BJ..  (2019)  Friomaramide, a Highly Modified Linear Hexapeptide from an Antarctic Sponge, Inhibits Plasmodium falciparum Liver-Stage Development.,  82  (8): [PMID:31403291] [10.1021/acs.jnatprod.9b00362]

8. Yu JY, Li XQ, Wei MX..  (2019)  Synthesis and biological activities of artemisinin-piperazine-dithiocarbamate derivatives.,  169  [PMID:30852384] [10.1016/j.ejmech.2019.02.071]

9. Ortalli M, Varani S, Rosso C, Quintavalla A, Lombardo M, Trombini C..  (2019)  Evaluation of synthetic substituted 1,2-dioxanes as novel agents against human leishmaniasis.,  170  [PMID:30878827] [10.1016/j.ejmech.2019.02.070]

10. Kornsakulkarn J, Palasarn S, Choowong W, Thongpanchang T, Boonyuen N, Choeyklin R, Boonpratuang T, Isaka M, Thongpanchang C..  (2020)  Antimalarial 9-Methoxystrobilurins, Oudemansins, and Related Polyketides from Cultures of Basidiomycete Favolaschia Species.,  83  (4): [PMID:32193929] [10.1021/acs.jnatprod.9b00647]

11. Aucamp J,Zuma NH,N'Da DD.  (2020)  In vitro efficacy of synthesized artemisinin derivatives against Leishmania promastigotes.,  30  (22): [PMID:32987134] [10.1016/j.bmcl.2020.127581]

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]

15. Dassonville-Klimpt A, Schneider J, Damiani C, Tisnerat C, Cohen A, Azas N, Marchivie M, Guillon J, Mullié C, Agnamey P, Totet A, Dormoi J, Taudon N, Pradines B, Sonnet P..  (2022)  Design, synthesis, and characterization of novel aminoalcohol quinolines with strong in vitro antimalarial activity.,  228  [PMID:34782182] [10.1016/j.ejmech.2021.113981]

16. Gao F, Sun Z, Kong F, Xiao J..  (2020)  Artemisinin-derived hybrids and their anticancer activity.,  188  [PMID:31945642] [10.1016/j.ejmech.2020.112044]

17. Patel OPS, Beteck RM, Legoabe LJ..  (2021)  Exploration of artemisinin derivatives and synthetic peroxides in antimalarial drug discovery research.,  213  [PMID:33508479] [10.1016/j.ejmech.2021.113193]

18. Wu YJ, Meanwell NA..  (2021)  Geminal Diheteroatomic Motifs: Some Applications of Acetals, Ketals, and Their Sulfur and Nitrogen Homologues in Medicinal Chemistry and Drug Design.,  64  (14.0): [PMID:34213340] [10.1021/acs.jmedchem.1c00790]

19. Zhang C, Lum KY, Taki AC, Gasser RB, Byrne JJ, Montaner LJ, Tietjen I, Avery VM, Davis RA..  (2023)  Using a Bioactive Eremophila-Derived Serrulatane Scaffold to Generate a Unique Carbamate Library for Anti-infective Evaluations.,  86  (3): [PMID:36799121] [10.1021/acs.jnatprod.2c01041]

Source

Source(3):

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