IMPPAT Phytochemical information: 
Vepaol
Vepaol
Summary

SMILES: CO[C@H]1O[C@@H]2[C@@](C1)(O)[C@@H]1C[C@H](O2)[C@@]2([C@@]1(C)O2)[C@]1(C)[C@H](O)[C@@H]2OC[C@]3([C@H]2[C@@]2([C@H]1[C@](O)(OC2)C(=O)OC)[C@@H](OC(=O)/C(=C/C)/C)C[C@H]3OC(=O)C)C(=O)OC
InChI: InChI=1S/C36H48O17/c1-9-15(2)25(39)50-18-11-19(49-16(3)37)33(27(40)45-7)13-47-22-23(33)32(18)14-48-35(43,28(41)46-8)26(32)30(4,24(22)38)36-20-10-17(31(36,5)53-36)34(42)12-21(44-6)52-29(34)51-20/h9,17-24,26,29,38,42-43H,10-14H2,1-8H3/b15-9+/t17-,18+,19-,20+,21+,22-,23-,24-,26+,29-,30-,31+,32+,33+,34+,35+,36+/m1/s1
InChIKey: HAIAPLNAMFKNPR-CMRNRKAMSA-N
DeepSMILES: CO[C@H]O[C@@H][C@@]C5)O)[C@@H]C[C@H]O6)[C@@][C@@]5C)O3))[C@]C)[C@H]O)[C@@H]OC[C@][C@H]5[C@@][C@H]9[C@]O)OC5))C=O)OC)))))[C@@H]OC=O)/C=C/C))/C))))C[C@H]6OC=O)C))))))))C=O)OC
Scaffold Graph/Node/Bond level: C1CC2COC3CC(C45OC4C4CC5OC5OCCC54)C4COCC4(C1)C23
Scaffold Graph/Node level: C1CC2COC3CC(C45OC4C4CC5OC5OCCC54)C4COCC4(C1)C23
Scaffold Graph level: C1CC2CC3CC(C2C1)C1CC31C1CC2CCC3CCCC4(CCCC14)C32
Functional groups: CO[C@@H]1CC[C@H](OC)O1; CO; C[C@@]1(C)O[C@]1(C)C; COC; COC(=O)[C@](O)(C)OC; C/C=C(\C)C(=O)OC; CC(=O)OC; COC(C)=O
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:
vepaol, 22,23-dihydro-23-beta-methoxy-azadirachtin (vepaol)
External chemical identifiers:
CID:CID_21725519; ChEBI:CHEBI:67301; ZINC:ZINC000096085752
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Vepaol
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 752.76
Log P RDKit -0.35
Topological polar surface area (Å2) RDKit 224.57
Number of hydrogen bond acceptors RDKit 17
Number of hydrogen bond donors RDKit 3
Number of carbon atoms RDKit 36
Number of heavy atoms RDKit 53
Number of heteroatoms RDKit 17
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 17
Stereochemical complexity RDKit 0.47
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 6
Number of sp3 hybridized carbon atoms RDKit 30
Shape complexity RDKit 0.83
Number of rotatable bonds RDKit 11
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 5
Number of saturated rings RDKit 8
Number of Smallest Set of Smallest Rings (SSSR) RDKit 8
Vepaol
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 0.130746
Vepaol
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 -10.18
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