Azadirachtin

Basic Info

Common NameAzadirachtin(F05892)
2D Structure
FRCD IDF05892
CAS Number
PubChem CID5281303
FormulaC35H44O16
IUPAC Name

None

InChI Key

FTNJWQUOZFUQQJ-NDAWSKJSSA-N

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

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

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

Synonyms
        
            O4U1SAF85H
        
            azadirachtin
        
            Azadirachtin A
        
            bioneem
        
            NeemAzal
        
            Azadirachtin-A
        
            UNII-O4U1SAF85H
        
            CHEBI:2942
        
            HSDB 7372
        
            EPA Pesticide Chemical Code 121701
Classifies
                

                  
                    Pesticide
Update DateNov 13, 2018 17:07

Chemical Taxonomy

KingdomOrganic compounds
SuperclassLipids and lipid-like molecules
ClassPrenol lipids
SubclassTriterpenoids
Intermediate Tree NodesNot available
Direct ParentLimonoids
Alternative Parents
Molecular FrameworkAliphatic heteropolycyclic compounds
SubstituentsLimonoid skeleton - Tetracarboxylic acid or derivatives - Furopyran - Fatty acid ester - Oxepane - Oxane - Fatty acyl - Pyran - Cyclic alcohol - Dihydrofuran - Furan - Alpha,beta-unsaturated carboxylic ester - Tertiary alcohol - Enoate ester - Tetrahydrofuran - Methyl ester - Hemiacetal - Carboxylic acid ester - Secondary alcohol - Dialkyl ether - Acetal - Carboxylic acid derivative - Ether - Oxirane - Organoheterocyclic compound - Oxacycle - Organooxygen compound - Alcohol - Carbonyl group - Organic oxygen compound - Organic oxide - Hydrocarbon derivative - Aliphatic heteropolycyclic compound
DescriptionThis compound belongs to the class of organic compounds known as limonoids. These are highly oxygenated, modified terpenoids with a prototypical structure either containing or derived from a precursor with a 4,4,8-trimethyl-17-furanylsteroid skeleton. All naturally occurring citrus limonoids contain a furan ring attached to the D-ring, at C-17, as well as oxygen containing functional groups at C-3, C-4, C-7, C-16 and C-17.

Properties

Property NameProperty Value
Molecular Weight720.721
Hydrogen Bond Donor Count3
Hydrogen Bond Acceptor Count16
Rotatable Bond Count10
Complexity1660
Monoisotopic Mass720.263
Exact Mass720.263
XLogP-0.6
Formal Charge0
Heavy Atom Count51
Defined Atom Stereocenter Count16
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count1
Undefined Bond Stereocenter Count0
Isotope Atom Count0
Covalently-Bonded Unit Count1

ADMET

Model Result Probability
Absorption
Blood-Brain BarrierBBB-0.7733
Human Intestinal AbsorptionHIA+0.8895
Caco-2 PermeabilityCaco2-0.7106
P-glycoprotein SubstrateSubstrate0.8346
P-glycoprotein InhibitorInhibitor0.6724
Non-inhibitor0.5340
Renal Organic Cation TransporterNon-inhibitor0.7729
Distribution
Subcellular localizationMitochondria0.7795
Metabolism
CYP450 2C9 SubstrateNon-substrate0.8572
CYP450 2D6 SubstrateNon-substrate0.8722
CYP450 3A4 SubstrateSubstrate0.7144
CYP450 1A2 InhibitorNon-inhibitor0.8868
CYP450 2C9 InhibitorNon-inhibitor0.8452
CYP450 2D6 InhibitorNon-inhibitor0.9435
CYP450 2C19 InhibitorNon-inhibitor0.8327
CYP450 3A4 InhibitorNon-inhibitor0.7696
CYP Inhibitory PromiscuityLow CYP Inhibitory Promiscuity0.8863
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.9919
Non-inhibitor0.5690
AMES ToxicityNon AMES toxic0.7563
CarcinogensNon-carcinogens0.9455
Fish ToxicityHigh FHMT0.9835
Tetrahymena Pyriformis ToxicityHigh TPT0.9757
Honey Bee ToxicityHigh HBT0.8287
BiodegradationNot ready biodegradable1.0000
Acute Oral ToxicityI0.6952
Carcinogenicity (Three-class)Non-required0.5886
Model Value Unit
Absorption
Aqueous solubility-3.8348LogS
Caco-2 Permeability0.5422LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity4.3477LD50, mol/kg
Fish Toxicity0.5753pLC50, mg/L
Tetrahymena Pyriformis Toxicity0.6863pIGC50, ug/L

MRLs

FoodProduct CodeCountryMRLsApplication DateNotes
Grapefruits (Natsudaidais, Shaddocks/pomelos, Sweeties/oroblancos, Tangelolos, Tangelos (except minneolas)/Ugli®, Other hybrids of Citrus paradisi, not elsewhere mentioned,)0110010European Union0.501/09/2008
Lemons (Buddha's hands/Buddha's fingers, Citrons,)0110030European Union0.501/09/2008
Limes (Indian sweet limes/Palestine sweet limes, Kaffir limes, Sweet limes/mosambis, Tahiti limes, Limequats,)0110040European Union0.01*01/09/2008
Others (2)0110990European Union0.01*01/09/2008
Almonds (Apricot kernels, Bitter almonds, Canarium nuts/galip nuts, Pili nuts, Okari nuts,)0120010European Union101/09/2008
Brazil nuts0120020European Union0.01*01/09/2008
Cashew nuts0120030European Union0.01*01/09/2008
Chestnuts0120040European Union101/09/2008
Coconuts (Areca nuts/betel nuts,)0120050European Union0.01*01/09/2008
Hazelnuts/cobnuts (Acorns, Filberts,)0120060European Union101/09/2008
Macadamias0120070European Union0.01*01/09/2008
Pecans (Hickory nuts,)0120080European Union0.01*01/09/2008
Pine nut kernels (Pine nut kernels from other species than Pinus pinea, Pine nut kernels from other species than Pinus pinea, Pine nut kernels from other species than Pinus pinea, Pine nut kernels ...0120090European Union0.01*01/09/2008
Pistachios0120100European Union0.01*01/09/2008
Walnuts0120110European Union101/09/2008
Others (2)0120990European Union0.01*01/09/2008
Pome fruits0130000European Union101/09/2008
Apples (Crab apples/wild apples, Tejocotes,)0130010European Union101/09/2008
Pears (Nashi pears/Oriental pears, Wild pears, Ya pears/Chinese white pears,)0130020European Union101/09/2008
Quinces (Chinese quinces, Japanese quinces,)0130030European Union101/09/2008

References

TitleJournalDatePubmed ID
The reduced-risk insecticide azadirachtin poses a toxicological hazard to stingless bee Partamona helleri (Friese, 1900) queens.Chemosphere2018 Jun29533804
Pesticides and passive dispersal: acaricide- and starvation-induced take-off ofthe predatory mite Neoseiulus baraki.Pest Manag Sci2018 Jun29316207
Mosquito larvicidal activity of Cassia tora seed extract and its keyanthraquinones aurantio-obtusin and obtusin.Parasit Vectors2017 Nov 1029126433
Azadirachtin induced larval avoidance and antifeeding by disruption of foodintake and digestive enzymes in Drosophila melanogaster (Diptera: Drosophilidae).Pestic Biochem Physiol2017 Nov29183582
Identification of Meliatoxins in Melia azedarach Extracts Using Mass Spectrometry for Quality Control.Planta Med2017 Feb27599262
A new azadirachta from the crude extracts of neem (Azadirachta Indica A. Juss)seeds.Nat Prod Res2017 Aug28278641
Preimaginal exposure to azadirachtin affects food selection and digestive enzymesin adults of Drosophila melanogaster (Diptera: Drosophilidae).Pestic Biochem Physiol2017 Aug28755695
Acute and Chronic Toxicities of an Annonin-Based Commercial Bioinsecticide and a Joint Mixture with a Limonoid-Based Formulation to the Fall Armyworm.Neotrop Entomol2017 Apr27730568
Transmission blocking effects of neem (Azadirachta indica) seed kernel limonoids on Plasmodium berghei early sporogonic development.Fitoterapia2016 Oct27642038
Evaluation of antimicrobial effect of azadirachtin plant extract (Soluneem (™))on commonly found root canal pathogenic microorganisms (viz. Enterococcusfaecalis) in primary teeth: A microbiological study.J Indian Soc Pedod Prev Dent2016 Jul-Sep27461802
In vitro and ex vivo activity of an Azadirachta indica A.Juss. seed kernelextract on early sporogonic development of Plasmodium in comparison withazadirachtin A, its most abundant constituent.Phytomedicine2016 Dec 1527912876
Ultrasound-assisted extraction of azadirachtin from dried entire fruits ofAzadirachta indica A. Juss. (Meliaceae) and its determination by a validatedHPLC-PDA method.Talanta201626717816
Preparation and Characterization of Azadirachtin Alginate-Biosorbent BasedFormulations: Water Release Kinetics and Photodegradation Study.J Agric Food Chem2015 Sep 3026345112
Effect of Neem (Azadirachta indica) on the Survival of Escherichia coli O157:H7 in Dairy Manure.Int J Environ Res Public Health2015 Jul 1026184255
Lethal and sublethal effects of azadirachtin on the bumblebee Bombus terrestris(Hymenoptera: Apidae).Ecotoxicology2015 Jan25300506
Morphological effects of neem (Azadirachta indica A. Juss) seed oil with knownazadirachtin concentrations on the oocytes of semi-engorged Rhipicephalussanguineus ticks (Acari: Ixodidae).Parasitol Res2015 Feb25346198
Laboratory and field efficacy of entomopathogenic fungi for the management of thesweetpotato weevil, Cylas formicarius (Coleoptera: Brentidae).J Invertebr Pathol2014 Oct25111763
In vitro phytotherapy of vector snails by binary combinations of larvicidal active components in effective control of fascioliasis.Rev Inst Med Trop Sao Paulo2013 Sep-Oct24037283
Development of a methodology and evaluation of pesticides against Aceria litchii and its predator Phytoseius intermedius (Acari: Eriophyidae, Phytoseiidae).J Econ Entomol2013 Oct24224263
Do biopesticides affect the demographic traits of a parasitoid wasp and its biocontrol services through sublethal effects?PLoS One201324098793