IMPPAT Phytochemical information: 
Azadirinin
Azadirinin
Summary

SMILES: CC(=O)O[C@@H]1C2C(C)(C)[C@H](OC(=O)C)C[C@@H]([C@]2(C)[C@@H]2[C@]([C@@H]1O)(C)C1=CC(=O)O[C@H]([C@@]1(CC2)C)c1ccoc1)OC(=O)/C=C/c1ccccc1
InChI: InChI=1S/C39H46O10/c1-22(40)46-28-20-29(48-30(42)14-13-24-11-9-8-10-12-24)39(7)26-15-17-37(5)27(19-31(43)49-35(37)25-16-18-45-21-25)38(26,6)34(44)32(47-23(2)41)33(39)36(28,3)4/h8-14,16,18-19,21,26,28-29,32-35,44H,15,17,20H2,1-7H3/b14-13+/t26-,28+,29-,32+,33?,34+,35-,37+,38+,39-/m0/s1
InChIKey: GIFPHLCYIOHODV-QYXPMSDWSA-N
DeepSMILES: CC=O)O[C@@H]CCC)C)[C@H]OC=O)C)))C[C@@H][C@]6C)[C@@H][C@][C@@H]%10O))C)C=CC=O)O[C@H][C@@]6CC%10))C))cccoc5)))))))))))))OC=O)/C=C/cccccc6
Scaffold Graph/Node/Bond level: O=C(C=Cc1ccccc1)OC1CCCC2CCC3C4=CC(=O)OC(c5ccoc5)C4CCC3C21
Scaffold Graph/Node level: OC(CCC1CCCCC1)OC1CCCC2CCC3C4CC(O)OC(C5CCOC5)C4CCC3C21
Scaffold Graph level: CC(CCC1CCCCC1)CC1CCCC2CCC3C4CC(C)CC(C5CCCC5)C4CCC3C21
Functional groups: CC(=O)OC; coc; c/C=C/C(=O)OC; CO; CC1=CC(=O)OCC1
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organoheterocyclic compounds
ClassyFire Class: Naphthopyrans
NP Classifier Biosynthetic pathway: Terpenoids
NP Classifier Superclass: Triterpenoids
NP Classifier Class: Limonoids
Synonymous chemical names:
azadirinin
External chemical identifiers:
CID:CID_102275331
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Azadirinin
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 674.79
Log P RDKit 6.14
Topological polar surface area (Å2) RDKit 138.57
Number of hydrogen bond acceptors RDKit 10
Number of hydrogen bond donors RDKit 1
Number of carbon atoms RDKit 39
Number of heavy atoms RDKit 49
Number of heteroatoms RDKit 10
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 10
Stereochemical complexity RDKit 0.26
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 18
Number of sp3 hybridized carbon atoms RDKit 21
Shape complexity RDKit 0.54
Number of rotatable bonds RDKit 9
Number of aliphatic carbocycles RDKit 3
Number of aliphatic heterocycles RDKit 1
Number of aliphatic rings RDKit 4
Number of aromatic carbocycles RDKit 1
Number of aromatic heterocycles RDKit 1
Number of aromatic rings RDKit 2
Total number of rings RDKit 6
Number of saturated carbocycles RDKit 3
Number of saturated heterocycles RDKit 0
Number of saturated rings RDKit 3
Number of Smallest Set of Smallest Rings (SSSR) RDKit 6
Azadirinin
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 4
Ghose rule RDKit Failed
Veber rule RDKit Good
Egan rule RDKit Bad
GSK 4/400 rule RDKit Bad
Pfizer 3/75 rule RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.22
Azadirinin
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Poorly soluble
Solubility class [Silicos-IT] SwissADME Poorly soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME Low
Log Kp (Skin permeation, cm/s) SwissADME -6.13
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