IMPPAT Phytochemical information: 
Azedarachin A
Azedarachin A
Summary

SMILES: CCC(C(=O)O[C@@H]1OC[C@@]23[C@H]([C@@]1(C)[C@H](OC(=O)C)C[C@@H]2O)C[C@H]([C@@]1([C@@H]3C(=O)[C@H](O)[C@@]2([C@]31O[C@@H]3C[C@H]2c1ccoc1)C)C)O)C
InChI: InChI=1S/C33H44O11/c1-7-15(2)27(39)43-28-29(4)19-11-20(35)31(6)25(32(19,14-41-28)21(36)12-22(29)42-16(3)34)24(37)26(38)30(5)18(17-8-9-40-13-17)10-23-33(30,31)44-23/h8-9,13,15,18-23,25-26,28,35-36,38H,7,10-12,14H2,1-6H3/t15?,18-,19-,20+,21-,22+,23+,25-,26-,28-,29-,30+,31+,32+,33+/m0/s1
InChIKey: GFWAUGVHDIJBDI-SMRKTTIESA-N
DeepSMILES: CCCC=O)O[C@@H]OC[C@@][C@H][C@@]6C)[C@H]OC=O)C)))C[C@@H]6O)))))C[C@H][C@@][C@@H]6C=O)[C@H]O)[C@@][C@@]6O[C@@H]3C[C@H]6cccoc5))))))))))C)))))C))O))))))))))C
Scaffold Graph/Node/Bond level: O=C1CC2C(c3ccoc3)CC3OC32C2CCC3C4CCCC3(COC4)C12
Scaffold Graph/Node level: OC1CC2C(C3CCOC3)CC3OC32C2CCC3C4CCCC3(COC4)C12
Scaffold Graph level: CC1CC2C(C3CCCC3)CC3CC32C2CCC3C4CCCC3(CCC4)C12
Functional groups: C[C@H]1O[C@@]1(C)C; CO[C@@H](OC(C)=O)C; coc; CO; CC(=O)OC; CC(=O)C
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Lipids and lipid-like molecules
ClassyFire Class: Prenol lipids
ClassyFire Subclass: Triterpenoids
NP Classifier Biosynthetic pathway: Terpenoids
NP Classifier Superclass: Triterpenoids
NP Classifier Class: Lanostane, Tirucallane and Euphane triterpenoids|Limonoids
Synonymous chemical names:
azedarachin a
External chemical identifiers:
CID:CID_101930511
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Azedarachin A
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 616.7
Log P RDKit 2.49
Topological polar surface area (Å2) RDKit 165.26
Number of hydrogen bond acceptors RDKit 11
Number of hydrogen bond donors RDKit 3
Number of carbon atoms RDKit 33
Number of heavy atoms RDKit 44
Number of heteroatoms RDKit 11
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 15
Stereochemical complexity RDKit 0.45
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 7
Number of sp3 hybridized carbon atoms RDKit 26
Shape complexity RDKit 0.79
Number of rotatable bonds RDKit 7
Number of aliphatic carbocycles RDKit 4
Number of aliphatic heterocycles RDKit 2
Number of aliphatic rings RDKit 6
Number of aromatic carbocycles RDKit 0
Number of aromatic heterocycles RDKit 1
Number of aromatic rings RDKit 1
Total number of rings RDKit 7
Number of saturated carbocycles RDKit 4
Number of saturated heterocycles RDKit 2
Number of saturated rings RDKit 6
Number of Smallest Set of Smallest Rings (SSSR) RDKit 7
Azedarachin A
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 0.33
Azedarachin A
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 -8.59
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