Showing Compound Card for Azadirachtin (CDB006186)

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Record Information
Version1.0
Created at2020-07-28 20:14:31 UTC
Updated at2020-11-18 16:40:13 UTC
CannabisDB IDCDB006186
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameAzadirachtin
Descriptionazadirachtin A, also known as bioneem or neemix, 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. Thus, azadirachtin a is considered to be an isoprenoid lipid molecule. azadirachtin A is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
AzadirachtinChEBI
AzadyrachtinMeSH
BioneemMeSH
NeemixMeSH
Chemical FormulaC35H44O16
Average Molecular Weight720.721
Monoisotopic Molecular Weight720.262935337
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
CAS Registry NumberNot Available
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 Identifier
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
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
Ontology
Not Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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
EI-MS/GC-MSNot Available
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 10V, positivesplash10-0006-0000000900-a767b591cd606c69591d2020-08-04View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 20V, positivesplash10-0006-0000000900-311d49a0dc3e51b09eeb2020-08-04View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 40V, positivesplash10-004i-0000037900-54c864419fd23134c5032020-08-04View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0239-2000009400-3c1fb4772e868f83f7832019-02-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0m1i-7200039300-2e5cfc7ec9a4454e0a6a2019-02-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ue9-9000036100-11b3151eebeada9832142019-02-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00kr-1100009300-35d3934aba6c690fbef52019-02-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0pb9-4000009300-d1fe939ccbeb51f636482019-02-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00mn-3000943100-185556fffc88132f60342019-02-23View Spectrum
NMRNot Available
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDC00003698
Chemspider IDNot Available
KEGG Compound IDC08748
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkAzadirachtin
METLIN IDNot Available
PubChem Compound5281303
PDB IDNot Available
ChEBI ID2942
References
General References
  1. Taylor A, Birkett JW: Pesticides in cannabis: A review of analytical and toxicological considerations. Drug Test Anal. 2020 Feb;12(2):180-190. doi: 10.1002/dta.2747. Epub 2020 Jan 19. [PubMed:31834671 ]