Azadirachtin (CED0005871)

Record Information
Version1.0
Creation Date2016-06-03 11:30:01 UTC
Update Date2026-04-15 16:46:26 UTC
Accession NumberCHEM043970
Identification
Common NameAzadirachtin
ClassSmall Molecule
Description
Azadirachtin is a compound with the chemical formula C35H44O16. Azadirachtin belongs to the triterpenoids, a subclass of prenol lipids within the organic compounds. With an average molecular weight of 720.72 g/mol, Azadirachtin is a heavy molecule. In industrial applications, it is used as an insecticide (PMC13471739). The compound has been recorded in three sources, including drinking water and water supply, floors within building and construction, and auxiliary devices in electrical and electronic equipment. The recorded route of exposure for this substance is oral.
Contaminant TypeNot Available
Chemical Structure
Synonyms
ValueSource
AzadirachtinChEBI
AzadyrachtinMeSH
BioneemMeSH
NeemixMeSH
Chemical FormulaC35H44O16
Average Molecular Mass720.721 g/mol
Monoisotopic Mass720.263 g/mol
CAS Registry Number11141-17-6
IUPAC Name4,11-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[6.3.1.0^{2,6}.0^{9,11}]dodec-3-en-9-yl]-6-methyl-14-{[(2E)-2-methylbut-2-enoyl]oxy}-3,9-dioxatetracyclo[6.6.1.0^{1,5}.0^{11,15}]pentadecane-4,11-dicarboxylate
Traditional Name4,11-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[6.3.1.0^{2,6}.0^{9,11}]dodec-3-en-9-yl]-6-methyl-14-{[(2E)-2-methylbut-2-enoyl]oxy}-3,9-dioxatetracyclo[6.6.1.0^{1,5}.0^{11,15}]pentadecane-4,11-dicarboxylate
SMILES[H]\C(C)=C(\C)C(=O)O[C@@]1([H])C[C@@]([H])(OC(C)=O)[C@]2(CO[C@]3([H])[C@]2([H])[C@]11CO[C@](O)(C(=O)OC)[C@@]1([H])[C@@](C)([C@]3([H])O)[C@]12O[C@@]1(C)[C@@]1([H])C[C@]2([H])O[C@]2([H])OC=C[C@]12O)C(=O)OC
InChI IdentifierInChI=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
InChI KeyFTNJWQUOZFUQQJ-NDAWSKJSSA-N
Chemical Taxonomy
Description 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.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassTriterpenoids
Direct ParentLimonoids
Alternative Parents
Substituents
  • Limonoid 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
Molecular FrameworkAliphatic heteropolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Organoleptic EffectsNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.98 g/LALOGPS
logP1.53ALOGPS
logP-0.13ChemAxon
logS-2.9ALOGPS
pKa (Strongest Acidic)9.43ChemAxon
pKa (Strongest Basic)-3.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count12ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area215.34 ŲChemAxon
Rotatable Bond Count10ChemAxon
Refractivity166.24 m³·mol⁻¹ChemAxon
Polarizability70.35 ųChemAxon
Number of Rings8ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
LC-MS/MSLC-MS/MS Spectrumsplash10-0006-0000000900-a767b591cd606c69591dNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0006-0000000900-311d49a0dc3e51b09eebNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-004i-0000037900-54c864419fd23134c503Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0239-2000009400-3c1fb4772e868f83f783Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0m1i-7200039300-2e5cfc7ec9a4454e0a6aNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0ue9-9000036100-11b3151eebeada983214Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00kr-1100009300-35d3934aba6c690fbef5Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0pb9-4000009300-d1fe939ccbeb51f63648Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00mn-3000943100-185556fffc88132f6034Not AvailableView Spectrum
Toxicity Profile
Mechanism of ToxicityNot Available
Carcinogenicity (IARC Classification)Not Available
Minimum Risk LevelNot Available
SymptomsNot Available
TreatmentNot Available
Toxicity ValuesNot Available
Health Effects
Health EffectRelationshipDirectionReference
Exposure Sources
Source IDSourceSectorReference
115Drinking waterDrinking water & water supplyNot Available
497FloorsBuilding & ConstructionNot Available
507Auxiliary DevicesElectrical & Electronic EquipmentNot Available
597ChemosterilantsAgriculture & land managementNot Available
598Fertiliser DistributorsAgriculture & land managementNot Available
607Rodenticides(1)Agriculture & land managementNot Available
608RodenticidesAgriculture & land managementNot Available
634BucklesTextiles, leather & furnishingsNot Available
Pathways
0 pathways

No pathways found

No metabolic pathways have been associated with this synthetic chemical

Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Click to view 3D structureTransient receptor potential cation channel subfamily M member 2E9PTA2Rattus norvegicusPredicted (SEA)12.4559
Click to view 3D structureAdenylate cyclase type 1P19754Bos taurusPredicted (SEA)6.85073
Click to view 3D structureGlycogen [starch] synthase, liverP54840HumansPredicted (SEA)37.1341
Click to view 3D structureGlucose-6-phosphatase catalytic subunit 1P43428Rattus norvegicusPredicted (SEA)37.1341
Growth hormone-releasing hormone receptor structureClick to view 3D structureGrowth hormone-releasing hormone receptorQ02643HumansPredicted (SEA)38.1461
Solute carrier family 2, facilitated glucose transporter member 1 structureClick to view 3D structureSolute carrier family 2, facilitated glucose transporter member 1P11166HumansPredicted (SEA)5555.32
Delta-type opioid receptor structureClick to view 3D structureDelta-type opioid receptorP41143HumansPredicted (SEA)7078.21
Kappa-type opioid receptor structureClick to view 3D structureKappa-type opioid receptorP41145HumansPredicted (SEA)7433.51
Mu-type opioid receptor structureClick to view 3D structureMu-type opioid receptorP35372HumansPredicted (SEA)7414.9
Click to view 3D structureNeurogenic locus notch homolog protein 1Q01705Mus musculusPredicted (SEA)36.2777
Solute carrier organic anion transporter family member 1B1 structureClick to view 3D structureSolute carrier organic anion transporter family member 1B1Q9Y6L6HumansPredicted (SEA)5014.27
Solute carrier organic anion transporter family member 1B3 structureClick to view 3D structureSolute carrier organic anion transporter family member 1B3Q9NPD5HumansPredicted (SEA)3257.29
Myosin light chain kinase, smooth muscle structureClick to view 3D structureMyosin light chain kinase, smooth muscleQ15746HumansPredicted (SEA)6658.37
Click to view 3D structureAdenosine receptor A1P28190Bos taurusPredicted (SEA)4214.45
Serine/threonine-protein kinase PLK1 structureClick to view 3D structureSerine/threonine-protein kinase PLK1P53350HumansPredicted (SEA)7563.6
Epidermal growth factor receptor structureClick to view 3D structureEpidermal growth factor receptorP00533HumansPredicted (SEA)7677.72
Click to view 3D structureKappa-type opioid receptorP33534Mus musculusPredicted (SEA)3388.54
Aurora kinase A structureClick to view 3D structureAurora kinase AO14965HumansPredicted (SEA)7594.19
Vascular endothelial growth factor receptor 2 structureClick to view 3D structureVascular endothelial growth factor receptor 2P35968HumansPredicted (SEA)7676.4
High affinity nerve growth factor receptor structureClick to view 3D structureHigh affinity nerve growth factor receptorP04629HumansPredicted (SEA)7594.66
Adenosine receptor A2a structureClick to view 3D structureAdenosine receptor A2aP29274HumansPredicted (SEA)7406.81
Protein kinase C theta type structureClick to view 3D structureProtein kinase C theta typeQ04759HumansPredicted (SEA)7472.05
Rho-associated protein kinase 2 structureClick to view 3D structureRho-associated protein kinase 2O75116HumansPredicted (SEA)7637.79
Adenosine receptor A1 structureClick to view 3D structureAdenosine receptor A1P30542HumansPredicted (SEA)7355.12
Click to view 3D structureA1 adenosine receptorQ4VQ11Sus scrofaPredicted (SEA)363.089
Concentrations
Not Available
External Links
DrugBank IDNot Available
HMDB IDNot Available
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDC00003698
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkAzadirachtin
Chemspider IDNot Available
ChEBI ID2942
PubChem Compound ID5281303
Kegg Compound IDC08748
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=11990361
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=24708208