IMPPAT Phytochemical information: 
Azadirachtanin
Azadirachtanin
Summary

SMILES: CC(=O)O[C@@H]1OC[C@@]23C([C@]1(C)[C@H](OC(=O)C)C[C@@H]2O)C[C@H]([C@@]1([C@@H]3C(=O)[C@H](OC(=O)C)[C@@]2(C1=CC[C@H]2c1ccoc1)C)C)O
InChI: InChI=1S/C32H40O11/c1-15(33)41-24-12-23(37)32-14-40-28(43-17(3)35)31(24,6)21(32)11-22(36)30(5)20-8-7-19(18-9-10-39-13-18)29(20,4)27(42-16(2)34)25(38)26(30)32/h8-10,13,19,21-24,26-28,36-37H,7,11-12,14H2,1-6H3/t19-,21?,22+,23-,24+,26-,27-,28-,29-,30+,31+,32+/m0/s1
InChIKey: YQSXXKRVYCLMRM-WUOCKYMVSA-N
DeepSMILES: CC=O)O[C@@H]OC[C@@]C[C@]6C)[C@H]OC=O)C)))C[C@@H]6O)))))C[C@H][C@@][C@@H]6C=O)[C@H]OC=O)C)))[C@@]C6=CC[C@H]5cccoc5)))))))))C)))))C))O
Scaffold Graph/Node/Bond level: O=C1CC2C(=CCC2c2ccoc2)C2CCC3C4CCCC3(COC4)C12
Scaffold Graph/Node level: OC1CC2C(C3CCOC3)CCC2C2CCC3C4CCCC3(COC4)C12
Scaffold Graph level: CC1CC2C(C3CCCC3)CCC2C2CCC3C4CCCC3(CCC4)C12
Functional groups: CC=C(C)C; CO[C@@H](OC(C)=O)C; coc; CO; CC(=O)OC; CC(=O)C
Chemical classification

NP Classifier Biosynthetic pathway: Terpenoids
NP Classifier Superclass: Triterpenoids
NP Classifier Class: Limonoids
Synonymous chemical names:
azadirachtanin
External chemical identifiers:
CID:CID_177468348
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Azadirachtanin
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 600.66
Log P RDKit 2.83
Topological polar surface area (Å2) RDKit 158.8
Number of hydrogen bond acceptors RDKit 11
Number of hydrogen bond donors RDKit 2
Number of carbon atoms RDKit 32
Number of heavy atoms RDKit 43
Number of heteroatoms RDKit 11
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 12
Stereochemical complexity RDKit 0.38
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 10
Number of sp3 hybridized carbon atoms RDKit 22
Shape complexity RDKit 0.69
Number of rotatable bonds RDKit 7
Number of aliphatic carbocycles RDKit 4
Number of aliphatic heterocycles RDKit 1
Number of aliphatic rings RDKit 5
Number of aromatic carbocycles RDKit 0
Number of aromatic heterocycles RDKit 1
Number of aromatic rings RDKit 1
Total number of rings RDKit 6
Number of saturated carbocycles RDKit 3
Number of saturated heterocycles RDKit 1
Number of saturated rings RDKit 4
Number of Smallest Set of Smallest Rings (SSSR) RDKit 6
Azadirachtanin
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 2
Lipinski’s rule of 5 RDKit Failed
Number of Ghose rule violations RDKit 3
Ghose rule RDKit Failed
Veber rule RDKit Bad
Egan rule RDKit Bad
GSK 4/400 rule RDKit Bad
Pfizer 3/75 rule RDKit Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.3
Azadirachtanin
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.17
Solubility class [ESOL] SwissADME Moderately soluble
Solubility class [Silicos-IT] SwissADME Moderately soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME Low
Log Kp (Skin permeation, cm/s) SwissADME -8.63
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 2
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME Yes