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Chemistry

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Also known as: Artemotil [inn], Artemotil (inn), Beta arteether, Beta-dihydroartemisinin ethyl ether, Ethoxy(trimethyl)[?], Xgl7gfb9yi

Molecular Formula

C₁₇H₂₈O₅

Molecular Weight

312.4 g/mol

InChI Key

NLYNIRQVMRLPIQ-BVCZABNKSA-N

1 2D Structure

Arteether

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

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

2.1.2 InChI

InChI=1S/C17H28O5/c1-5-18-14-11(3)13-7-6-10(2)12-8-9-16(4)20-15(19-14)17(12,13)22-21-16/h10-15H,5-9H2,1-4H3/t10-,11-,12+,13+,14+,15-,16?,17-/m1/s1

2.1.3 InChI Key

NLYNIRQVMRLPIQ-BVCZABNKSA-N

2.1.4 Canonical SMILES

CCOC1C(C2CCC(C3C24C(O1)OC(CC3)(OO4)C)C)C

2.1.5 Isomeric SMILES

CCO[C@@H]1[C@@H]([C@@H]2CC[C@H]([C@H]3[C@]24[C@H](O1)OC(CC3)(OO4)C)C)C

2.2 Synonyms

2.2.1 MeSH Synonyms

1. Arteether

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

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

4. Artemotil

5. Artether

6. Beta-artether

7. Sm-227

2.2.2 Depositor-Supplied Synonyms

1. Artemotil [inn]

2. Artemotil (inn)

3. Beta Arteether

4. Beta-dihydroartemisinin Ethyl Ether

5. Ethoxy(trimethyl)[?]

6. Xgl7gfb9yi

7. Unii-xgl7gfb9yi

8. Sm 227

9. 109716-83-8

10. Nsc 665971

11. Ethyl-ether-quinghaosu

12. Dsstox_cid_31610

13. Dsstox_rid_97494

14. Dsstox_gsid_57821

15. Schembl1648554

16. Chembl3560584

17. Dtxsid6057821

18. Tox21_113883

19. Ncgc00253770-01

20. 3,12-epoxy-12h-pyrano(4,3-j)-1,2-benzodioxepin, 10-ethoxydecahydro-3,6,9-trimethyl-, (3s-(3alpha,5alpha,6alpha,8aalpha,9beta,10beta,12beta,12aalpha))-

21. 3,12-epoxy-12h-pyrano(4,3-j)-1,2-benzodioxepin, Decahydro-10-ethoxy-3,6,9-trimethyl-, (3r-(3alpha,5abeta,6beta,8abeta,9alpha,10alpha,12beta,12ar*))-

22. Cas-75887-54-6

23. Wr-255131

24. D07361

25. A915244

26. (3r,12ar)-3,6alpha,9beta-trimethyl-10beta-ethoxy-3beta,12alpha-epoxy-3,4,5,5aalpha,6,7,8,8aalpha,9,10-decahydropyrano[4,3-j]-1,2-benzodioxepin

27. 3,12-epoxy-12h-pyrano[4,3-j]-1,2-benzodioxepin, 10-ethoxydecahydro-3,6,9-trimethyl-, (3r,5as,6r,8as,9r,10s,12r,12ar)-

2.3 Create Date

2005-08-01

3 Chemical and Physical Properties

Molecular Formula	C₁₇H₂₈O₅
Molecular Weight	312.4 g/mol
XLogP3	3.4
Hydrogen Bond Donor Count	0
Hydrogen Bond Acceptor Count	5
Rotatable Bond Count	2
Exact Mass	312.19367399 g/mol
Monoisotopic Mass	312.19367399 g/mol
Topological Polar Surface Area	46.2 Å²
Heavy Atom Count	22
Formal Charge	0
Complexity	443
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.)

Schistosomicides

Agents that act systemically to kill adult schistosomes. (See all compounds classified as Schistosomicides.)

Amebicides

Agents which are destructive to amebae, especially the parasitic species causing AMEBIASIS in man and animal. (See all compounds classified as Amebicides.)

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