IMPPAT Phytochemical information: 
Deacetylazadirachtinol
Deacetylazadirachtinol
Summary

SMILES: COC(=O)[C@H]1OC[C@]23[C@@H]1[C@@](C)([C@H](O)[C@H]1[C@H]3[C@@]([C@@H](C[C@@H]2O)OC(=O)/C(=C/C)/C)(CO1)C(=O)OC)[C@@]12O[C@@]2(C)[C@H]2C[C@@H]1O[C@H]1[C@]2(O)C=CO1
InChI: InChI=1S/C33H42O14/c1-7-14(2)24(36)45-17-11-16(34)30-12-44-20(25(37)40-5)21(30)28(3,23(35)19-22(30)31(17,13-43-19)26(38)41-6)33-18-10-15(29(33,4)47-33)32(39)8-9-42-27(32)46-18/h7-9,15-23,27,34-35,39H,10-13H2,1-6H3/b14-7+/t15-,16+,17-,18+,19-,20+,21+,22-,23-,27+,28+,29+,30-,31+,32+,33+/m1/s1
InChIKey: USRBWQQLHKQWAV-ZGKQVQOISA-N
DeepSMILES: COC=O)[C@H]OC[C@@][C@@H]5[C@@]C)[C@H]O)[C@H][C@H]6[C@@][C@@H]C[C@@H]%10O)))OC=O)/C=C/C))/C)))))CO5))C=O)OC)))))))[C@]O[C@@]3C)[C@H]C[C@@H]6O[C@H][C@]6O)C=CO5
Scaffold Graph/Node/Bond level: C1=CC2C(O1)OC1CC2C2OC12C1CC2OCC3CCCC4(COCC14)C32
Scaffold Graph/Node level: C1CC2COC3CC(C45OC4C4CC5OC5OCCC54)C4COCC4(C1)C23
Scaffold Graph level: C1CC2CC3CC(C2C1)C1CC31C1CC2CCC3CCCC4(CCCC14)C32
Functional groups: COC(C)=O; COC; CO; C/C=C(\C)C(=O)OC; C[C@@]1(C)O[C@]1(C)C; CO[C@H]1CC=CO1
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: Limonoids
Synonymous chemical names:
deacetyl-azadirachtinol, deacetyl-azadirachtinol(=3-tigoylazadirachtol)
External chemical identifiers:
CID:CID_21725521; ChEMBL:CHEMBL451665; ZINC:ZINC000049841184; FDASRS:X5T1RMZ28I; MolPort-047-605-848
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Deacetylazadirachtinol
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 662.69
Log P RDKit -0.09
Topological polar surface area (Å2) RDKit 189.04
Number of hydrogen bond acceptors RDKit 14
Number of hydrogen bond donors RDKit 3
Number of carbon atoms RDKit 33
Number of heavy atoms RDKit 47
Number of heteroatoms RDKit 14
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 16
Stereochemical complexity RDKit 0.48
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 8
Number of aliphatic carbocycles RDKit 3
Number of aliphatic heterocycles RDKit 5
Number of aliphatic rings RDKit 8
Number of aromatic carbocycles RDKit 0
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 0
Total number of rings RDKit 8
Number of saturated carbocycles RDKit 3
Number of saturated heterocycles RDKit 4
Number of saturated rings RDKit 7
Number of Smallest Set of Smallest Rings (SSSR) RDKit 8
Deacetylazadirachtinol
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 2
Lipinski’s rule of 5 filter RDKit Failed
Number of Ghose filter violations RDKit 3
Ghose filter RDKit Failed
Veber filter RDKit Bad
Pfizer 3/75 filter RDKit Good
GSK 4/400 filter RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.153266
Deacetylazadirachtinol
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.17
Solubility class [ESOL] SwissADME Moderately soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME Low
Log Kp (Skin permeation, cm/s) SwissADME -9.43
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 3
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