Structure Database (LMSD)
Common Name
Azadirachtin A
Systematic Name
Synonyms
3D model of Azadirachtin A
Please note: Where there are chiral atoms but the stereochemistry is undefined, the 3D model takes an arbitrary conformation
Classification
Category
Main Class
Sub Class
Level 4 Class
Biological Context
Azadirachtin is a naturally-occurring insecticide originally isolated from the seeds of A. indica.1 It inhibits feeding behavior, molting, and/or ovarian development in a species-dependent manner in insects.2 Azadirachtin inhibits feeding on G. barbadense leaves and cotyledon disks by third instar H. zea larvae with protection concentrations (PC95s) of 6.2 and 6.8 μg/disk, respectively.3 It inhibits ecdysis and growth of H. zea, H. virescens, S. frugiperda, and P. gossypiella with ecdysis inhibition values (EI95s) ranging from 1 to 10 ppm and ED50 values ranging from 0.4 to 0.7 ppm. Azadirachtin inhibits the growth of freshly molted fourth instar E. varivestis larva (LC50 = 1.66 ppm).2 It is lethal to A. stephensi first, second, third, and fourth instar larva, pupa, and adults at a concentration of 0.1 ppm.4
This information has been provided by Cayman Chemical
References
1. Butterworth, J.H., and Morgan, E.D. Isolation of a substance that suppresses feeding in locusts. Chem. Commun. (Lond.) 1, 23-24 (1968).
2. Rembold, H. Azadirachtins. Their structure and mode of action. Insecticides of Plant Origin 150-163 (1989).
3. Kubo, I., and Kocke, J.A. Azadirachtin, insect ecdysis inhibitor. Agr. Biol. Chem. 46(7), 1951-1953 (1982).
4. Nathan, S.S., Kalaivani, K., and Murugan, K. Effects of neem limonoids on the malaria vector Anopheles stephensi Liston (Diptera: Culicidae). Acta. Trop. 96(1), 47-55 (2005).
References
String Representations
InChiKey (Click to copy)
FTNJWQUOZFUQQJ-NDAWSKJSSA-N
InChi (Click to copy)
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
SMILES (Click to copy)
[C@@]12(O[C@@]1(C)[C@H]1C[C@@H]2O[C@@]2([H])[C@]1(O)C=CO2)[C@]1(C)[C@H](O)[C@@]2([H])[C@@]3([H])[C@@](CO2)(C(=O)OC)[C@@H](C[C@H](OC(=O)/C(/C)=C/C)[C@]23CO[C@](O)(C(=O)OC)[C@@]12[H])OC(=O)C
Other Databases
Calculated Physicochemical Properties
Heavy Atoms
51
Rings
8
Aromatic Rings
0
Rotatable Bonds
10
Van der Waals Molecular Volume
639.98
Topological Polar Surface Area
223.62
Hydrogen Bond Donors
3
Hydrogen Bond Acceptors
16
logP
3.23
Molar Refractivity
170.38
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Created at
-
Updated at
11th Mar 2025