Azadirachtin (CHEM043970)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-06-03 11:30:01 UTC
Update Date2016-11-09 01:23:01 UTC
Accession NumberCHEM043970
Identification
Common NameAzadirachtin
ClassSmall Molecule
DescriptionA member of the family of azadirachtins that is isolated from the neem tree (Azadirachta indica).
Contaminant Sources
  • STOFF IDENT Compounds
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
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
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot 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
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 10V, positivesplash10-0006-0000000900-a767b591cd606c69591dSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 20V, positivesplash10-0006-0000000900-311d49a0dc3e51b09eebSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 40V, positivesplash10-004i-0000037900-54c864419fd23134c503Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0239-2000009400-3c1fb4772e868f83f783Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0m1i-7200039300-2e5cfc7ec9a4454e0a6aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ue9-9000036100-11b3151eebeada983214Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00kr-1100009300-35d3934aba6c690fbef5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0pb9-4000009300-d1fe939ccbeb51f63648Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00mn-3000943100-185556fffc88132f6034Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
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