IMPPAT Phytochemical information: 
Lyoniol-A
Lyoniol-A
Summary

SMILES: CC(=O)O[C@@H]1[C@@H](O)[C@@]2(O)[C@H]([C@]([C@H]3[C@@]41C[C@H]([C@](C4)(C)O)CC3)(C)O)[C@H]1[C@@H](C2(C)C)O1
InChI: InChI=1S/C22H34O7/c1-10(23)28-17-15(24)22(27)14(13-16(29-13)18(22,2)3)20(5,26)12-7-6-11-8-21(12,17)9-19(11,4)25/h11-17,24-27H,6-9H2,1-5H3/t11-,12+,13+,14+,15-,16+,17-,19-,20-,21-,22+/m1/s1
InChIKey: IONWCZKSTMAXMV-CRRNJOFASA-N
DeepSMILES: CC=O)O[C@@H][C@@H]O)[C@@]O)[C@H][C@][C@H][C@]7C[C@H][C@]C5)C)O))CC6))))))C)O))[C@H][C@@H]C5C)C))O3
Scaffold Graph/Node/Bond level: C1CC2CC3C(CCC24CCC1C4)CC1OC13
Scaffold Graph/Node level: C1CC2CC3C(CCC24CCC1C4)CC1OC13
Scaffold Graph level: C1CC2CC3C(CCC24CCC1C4)CC1CC13
Functional groups: CC(=O)OC; CO; C[C@H]1O[C@H]1C
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Lipids and lipid-like molecules
ClassyFire Class: Prenol lipids
ClassyFire Subclass: Diterpenoids
NP Classifier Biosynthetic pathway: Terpenoids
NP Classifier Superclass: Diterpenoids
NP Classifier Class: Grayanotoxane diterpenoids
Synonymous chemical names:
lyoniol a, Lyoniatoxin, Lyoniol A, lyoniatoxin
External chemical identifiers:
CID:CID_161699; ZINC:ZINC000095753670
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Lyoniol-A
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 410.51
Log P RDKit 0.76
Topological polar surface area (Å2) RDKit 119.75
Number of hydrogen bond acceptors RDKit 7
Number of hydrogen bond donors RDKit 4
Number of carbon atoms RDKit 22
Number of heavy atoms RDKit 29
Number of heteroatoms RDKit 7
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 11
Stereochemical complexity RDKit 0.5
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 1
Number of sp3 hybridized carbon atoms RDKit 21
Shape complexity RDKit 0.95
Number of rotatable bonds RDKit 2
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 0
Number of aromatic rings RDKit 0
Total number of rings RDKit 5
Number of saturated carbocycles RDKit 4
Number of saturated heterocycles RDKit 1
Number of saturated rings RDKit 5
Number of Smallest Set of Smallest Rings (SSSR) RDKit 5
Lyoniol-A
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 0
Lipinski’s rule of 5 RDKit Passed
Number of Ghose rule violations RDKit 0
Ghose rule RDKit Passed
Veber rule RDKit Good
Egan rule RDKit Good
GSK 4/400 rule RDKit Bad
Pfizer 3/75 rule RDKit Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.37
Lyoniol-A
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -8.62
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 1
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