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2D Structure
Also known as: Azadirachtin a, 11141-17-6, Neemazal, Nimbicidine, Nimurin, Ornazin
Molecular Formula
C35H44O16
Molecular Weight
720.7  g/mol
InChI Key
FTNJWQUOZFUQQJ-NDAWSKJSSA-N
FDA UNII
O4U1SAF85H

azadirachtin is a natural product found in Azadirachta and Azadirachta indica with data available.
1 2D Structure

2D Structure

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
dimethyl (1S,4S,5R,6S,7S,8R,11S,12R,14S,15R)-12-acetyloxy-4,7-dihydroxy-6-[(1S,2S,6S,8S,9R,11S)-2-hydroxy-11-methyl-5,7,10-trioxatetracyclo[6.3.1.02,6.09,11]dodec-3-en-9-yl]-6-methyl-14-[(E)-2-methylbut-2-enoyl]oxy-3,9-dioxatetracyclo[6.6.1.01,5.011,15]pentadecane-4,11-dicarboxylate
2.1.2 InChI
InChI=1S/C35H44O16/c1-8-15(2)24(38)49-18-12-19(48-16(3)36)32(26(39)43-6)13-46-21-22(32)31(18)14-47-34(42,27(40)44-7)25(31)29(4,23(21)37)35-20-11-17(30(35,5)51-35)33(41)9-10-45-28(33)50-20/h8-10,17-23,25,28,37,41-42H,11-14H2,1-7H3/b15-8+/t17-,18+,19-,20+,21-,22-,23-,25+,28+,29-,30+,31+,32+,33+,34+,35+/m1/s1
2.1.3 InChI Key
FTNJWQUOZFUQQJ-NDAWSKJSSA-N
2.1.4 Canonical SMILES
CC=C(C)C(=O)OC1CC(C2(COC3C2C14COC(C4C(C3O)(C)C56C7CC(C5(O6)C)C8(C=COC8O7)O)(C(=O)OC)O)C(=O)OC)OC(=O)C
2.1.5 Isomeric SMILES
C/C=C(\C)/C(=O)O[C@H]1C[C@H]([C@]2(CO[C@@H]3[C@@H]2[C@]14CO[C@@]([C@H]4[C@]([C@@H]3O)(C)[C@@]56[C@@H]7C[C@H]([C@@]5(O6)C)[C@]8(C=CO[C@H]8O7)O)(C(=O)OC)O)C(=O)OC)OC(=O)C
2.2 Other Identifiers
2.2.1 UNII
O4U1SAF85H
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Azadirachtin A

2. Azadyrachtin

3. Bioneem

4. Neemix

2.3.2 Depositor-Supplied Synonyms

1. Azadirachtin A

2. 11141-17-6

3. Neemazal

4. Nimbicidine

5. Nimurin

6. Ornazin

7. Azatin

8. Suneem

9. Bioneem

10. O4u1saf85h

11. Chebi:2942

12. Azadirachtin-a

13. Superneem

14. Ecozin

15. Gronim

16. Align

17. Oikos

18. Hsdb 7372

19. Safer Bioneem

20. Dimethyl Acetoxy-dihydroxy-[hydroxy(methyl)[?]yl]-methyl-[(e)-2-methylbut-2-enoyl]oxy-[?]dicarboxylate

21. Azadiractin

22. Biosal

23. Nsc 368675

24. Azadirachtin [mi]

25. Unii-o4u1saf85h

26. Schembl27784

27. Ccris 9142

28. Chembl509309

29. Dtxsid0037497

30. Zinc8221317

31. Mfcd00210582

32. Lmpr0106100001

33. Ncgc00163746-01

34. Hy-126741

35. Cs-0107060

36. C08748

37. Q793471

38. 176087-49-3

39. 1h,7h-naphtho(1,8-bc:4,4a-c')difuran-5,10a(8h)-dicarboxylic Acid, 10-(acetyloxy)octahydro-3,5-dihydroxy-4-methyl-8-(((2e)-2-methyl-1-oxo-2-butenyl)oxy)-4-((1ar,2s,3as,6as,7s,7as)-3a,6a,7,7a-tetrahydro-6a-hydroxy-7a-methyl-2,7-methanofuro(2,3-b)oxireno(e)oxepin-1a(2h)-yl)-, Dimethyl Ester, (2ar,3s,4s,4ar,5s,7as,8s,10r,10as,10br)-

40. 1h,7h-naphtho[1,8-bc:4,4a-c']difuran-5,10a(8h)-dicarboxylic Acid, 10-(acetyloxy)octahydro-3,5-dihydroxy-4-methyl-8-[[(2e)-2-methyl-1-oxo-2-buten-1-yl]oxy]-4-[(1ar,2s,3as,6as,7s,7as)-3a,6a,7,7a-tetrahydro-6a-hydroxy-7a-methyl-2,7-methanofuro[2,3-b]oxireno[e]oxepin-1a(2h)-yl]-, 5,10a-dimethyl Ester, (2ar,3s,4s,4ar,5s,7as,8s,10r,10as,10br)-

41. Dimethyl (1s,4s,5r,6s,7s,8r,11s,12r,14s,15r)-12-acetyloxy-4,7-dihydroxy-6-[(1s,2s,6s,8s,9r,11s)-2-hydroxy-11-methyl-5,7,10-trioxatetracyclo[6.3.1.02,6.09,11]dodec-3-en-9-yl]-6-methyl-14-[(e)-2-methylbut-2-enoyl]oxy-3,9-dioxatetracyclo[6.6.1.01,5.011,15]pentadecane-4,11-dicarboxylate

42. Dimethyl (1s,4s,5r,6s,7s,8r,11s,12r,14s,15r)-12-acetyloxy-4,7-dihydroxy-6-[(1s,2s,6s,9r,11s)-2-hydroxy-11-methyl-5,7,10-trioxatetracyclo[6.3.1.02,6.09,11]dodec-3-en-9-yl]-6-methyl-14-[(e)-2-methylbut-2-enoyl]oxy-3,9-dioxatetracyclo[6.6.1.01,5.011,15]pentadecane-4,11-dicarboxylate

43. Dimethyl (2ar,3s,4s,4ar,5s,7as,8s,10r,10as,10br)-10-acetoxy-3,5-dihydroxy-4-[(1ar,2s,3as,6as,7s,7as)-6a-hydroxy-7a-methyl-3a,6a,7,7a-tetrahydro-2,7-methanofuro[2,3-b]oxireno[e]oxepin-1a(2h)-yl]-4-methyl-8-{[(2e)-2-methylbut-2-enoyl]oxy}octahydro-1h-naphtho[1,8a-c:4,5-b'c']difuran-5,10a(8h)-dicarboxylate

2.4 Create Date
2005-06-24
3 Chemical and Physical Properties
Molecular Weight 720.7 g/mol
Molecular Formula C35H44O16
XLogP3-0.6
Hydrogen Bond Donor Count3
Hydrogen Bond Acceptor Count16
Rotatable Bond Count10
Exact Mass720.26293531 g/mol
Monoisotopic Mass720.26293531 g/mol
Topological Polar Surface Area215 Ų
Heavy Atom Count51
Formal Charge0
Complexity1660
Isotope Atom Count0
Defined Atom Stereocenter Count16
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count1
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Pharmacology and Biochemistry
4.1 MeSH Pharmacological Classification

Insecticides

Pesticides designed to control insects that are harmful to man. The insects may be directly harmful, as those acting as disease vectors, or indirectly harmful, as destroyers of crops, food products, or textile fabrics. (See all compounds classified as Insecticides.)


4.2 Metabolism/Metabolites

Injection of a tritiated azadirachtin derivative, (22,23-(3)H)dihydroazadirachtin into locusts indicated fast clearing of radiolabeled material from the blood. Ninety percent of the applied radioactivity was excreted during the first 7 hr with the feces, whereas the remaining (22,23-(3)H)dihydroazadirachtin accumulated in the Malpighian tubules where it could be detected even 24 days after treatment. After the first 24 hr, feces contained at least three polar, unidentified metabolites but no (22,23-(3)H)dihydroazadirachtin.

Krieger, R. (ed.). Handbook of Pesticide Toxicology. Volume 1, 2nd ed. 2001. Academic Press, San Diego, California., p. 132