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Dihydroartemisinin

Synopsis, Chemistry

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Also known as: Artenimol, Dihydroqinghaosu, Cotecxin, Cotexin, Dynamax, Salaxin

Molecular Formula

C₁₅H₂₄O₅

Molecular Weight

284.35 g/mol

InChI Key

BJDCWCLMFKKGEE-KXTPALSWSA-N

1 2D Structure

Dihydroartemisinin

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(4S,5R,8S,9R,10S,12R,13R)-1,5,9-trimethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.04,13.08,13]hexadecan-10-ol

2.1.2 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

2.1.3 InChI Key

BJDCWCLMFKKGEE-KXTPALSWSA-N

2.1.4 Canonical SMILES

CC1CCC2C(C(OC3C24C1CCC(O3)(OO4)C)O)C

2.1.5 Isomeric SMILES

C[C@@H]1CC[C@H]2[C@H]([C@H](O[C@H]3[C@@]24[C@H]1CCC(O3)(OO4)C)O)C

2.2 Synonyms

2.2.1 MeSH Synonyms

1. (3r,5as,6r,8as,9r,10s,12r,12ar)-decahydro-3,6,9-trimethyl-3,12-epoxy-12h-pyrano(4,3-j)-1,2-benzodioxepin-10-ol

2. 3alpha-hydroxydeoxydihydroartemisinin

3. 8alpha-hydroxydeoxyartemisinin

4. 9alpha-hydroxydeoxyartemisinin

5. Alaxin

6. Artemisinin, Dihydro-

7. Artenimol

8. Cotecxin

9. Cotexin

10. Dihydroartemisinine

11. Dihydroqinghaosu

12. Dihydroquinghaosu

13. Dihydroquinghaosu, (3r-(3alpha,5abeta,6beta,8abeta,9alpha,10alpha,12alpha,12ar*))-isomer

14. Dihydroquinghaosu, (3r-(3alpha,5abeta,6beta,8abeta,9alpha,10beta,12alpha,12ar*))-isomer

15. Quinghaosu, Dihydro-

16. Salaxin

17. Santecxin

2.2.2 Depositor-Supplied Synonyms

1. Artenimol

2. Dihydroqinghaosu

3. Cotecxin

4. Cotexin

5. Dynamax

6. Salaxin

7. Santecxin

8. Alaxin

9. 71939-50-9

10. Chembl307261

11. Dihydroartemisinine

12. Artenimol [inn]

13. 81496-81-3

14. Beta-dihydroartemisinin

15. Artenimol (inn)

16. Artemisinin, Dihydro

17. Dhqhs 2

18. Dihydroquinghoasu

19. Unii-6a9o50735x

20. 6a9o50735x

21. 81496-82-4

22. Dihydroartemisinin + Proveblue

23. Schembl2132158

24. Jav-110

25. Act02652

26. Bdbm50578409

27. Vm3352

28. Akos015962875

29. Akos026749923

30. Ac-2067

31. D3793

32. D07362

33. [3r-(3.alpha.,5a.beta.,6.beta.,8a.beta.,9.alpha.,10.alpha.,12.beta.,12ar*)]-decahydro-10-hydroxy-3,6,9-trimethyl-3,12-epoxy-12h-pyrano[4.3-j]-1,2-benzodioxepin

34. 3,12-epoxy-12h-pyrano(4,3-j)-1,2-benzodioxepin-10-ol, Decahydro-3,6,9-trimethyl-, (3r-(3alpha,5abeta,6beta,8abeta,9alpha,10alpha,12beta,12ar*))-

2.3 Create Date

2005-08-01

3 Chemical and Physical Properties

Molecular Formula	C₁₅H₂₄O₅
Molecular Weight	284.35 g/mol
XLogP3	2.5
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	5
Rotatable Bond Count	0
Exact Mass	284.16237386 g/mol
Monoisotopic Mass	284.16237386 g/mol
Topological Polar Surface Area	57.2 Å²
Heavy Atom Count	20
Formal Charge	0
Complexity	415
Isotope Atom Count	0
Defined Atom Stereocenter Count	7
Undefined Atom Stereocenter Count	1
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Pharmacology and Biochemistry

4.1 MeSH Pharmacological Classification

Antimalarials

Agents used in the treatment of malaria. They are usually classified on the basis of their action against plasmodia at different stages in their life cycle in the human. (From AMA, Drug Evaluations Annual, 1992, p1585) (See all compounds classified as Antimalarials.)

4.2 ATC Code

P - Antiparasitic products, insecticides and repellents

P01 - Antiprotozoals

P01B - Antimalarials

P01BE - Artemisinin and derivatives, plain

P01BE05 - Artenimol