ID: ALA520530

Max Phase: Preclinical

Molecular Formula: C15H22O4

Molecular Weight: 266.34

Molecule Type: Small molecule

Representations

Synonyms (1): Anhydrodihydroartemisinin
Synonyms from Alternative Forms(1):

Canonical SMILES:  CC1=CO[C@@H]2O[C@]3(C)CC[C@H]4[C@H](C)CC[C@@H]1[C@@]24OO3

Standard InChI:  InChI=1S/C15H22O4/c1-9-4-5-11-10(2)8-16-13-15(11)12(9)6-7-14(3,17-13)18-19-15/h8-9,11-13H,4-7H2,1-3H3/t9-,11+,12+,13-,14+,15+/m1/s1

Standard InChI Key:  UKXCIQFCSITOCY-IONOKRPISA-N

Molecule Features

Natural Product: No

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: 266.34

Molecular Weight (Monoisotopic): 266.1518

AlogP: 3.14

#Rotatable Bonds: 0

Polar Surface Area: 36.92

Molecular Species: NEUTRAL

HBA: 4

HBD: 0

#RO5 Violations: 0

HBA (Lipinski): 4

HBD (Lipinski): 0

#RO5 Violations (Lipinski): 0

CX Acidic pKa:

CX Basic pKa:

CX LogP: 3.21

CX LogD: 3.21

Aromatic Rings: 0

Heavy Atoms: 19

QED Weighted: 0.63

Np Likeness Score: 4.00

References

1. Lin AJ, Lee M, Klayman DL..  (1989)  Antimalarial activity of new water-soluble dihydroartemisinin derivatives. 2. Stereospecificity of the ether side chain.,  32  (6): [PMID:2657065] [10.1021/jm00126a017]

2. Grellepois F, Chorki F, Ourévitch M, Charneau S, Grellier P, McIntosh KA, Charman WN, Pradines B, Crousse B, Bonnet-Delpon D, Bégué JP..  (2004)  Orally active antimalarials: hydrolytically stable derivatives of 10-trifluoromethyl anhydrodihydroartemisinin.,  47  (6): [PMID:14998331] [10.1021/jm030947m]

3. Galal AM, Ross SA, Jacob M, ElSohly MA..  (2005)  Antifungal activity of artemisinin derivatives.,  68  (8): [PMID:16124777] [10.1021/np050074u]

4. Woerdenbag HJ, Moskal TA, Pras N, Malingré TM, el-Feraly FS, Kampinga HH, Konings AW..  (1993)  Cytotoxicity of artemisinin-related endoperoxides to Ehrlich ascites tumor cells.,  56  (6): [PMID:8350087] [10.1021/np50096a007]

5. Dembitsky VM..  (2008)  Bioactive peroxides as potential therapeutic agents.,  43  (2): [PMID:17618015] [10.1016/j.ejmech.2007.04.019]

6. Slade D, Galal AM, Gul W, Radwan MM, Ahmed SA, Khan SI, Tekwani BL, Jacob MR, Ross SA, Elsohly MA..  (2009)  Antiprotozoal, anticancer and antimicrobial activities of dihydroartemisinin acetal dimers and monomers.,  17  (23): [PMID:19879765] [10.1016/j.bmc.2009.10.019]

7. Blazquez AG, Fernandez-Dolon M, Sanchez-Vicente L, Maestre AD, Gomez-San Miguel AB, Alvarez M, Serrano MA, Jansen H, Efferth T, Marin JJ, Romero MR..  (2013)  Novel artemisinin derivatives with potential usefulness against liver/colon cancer and viral hepatitis.,  21  (14): [PMID:23685181] [10.1016/j.bmc.2013.04.059]

Source

Source(1):

• Scientific Literature