IMPPAT Phytochemical information: 
Leonotinin

Leonotinin
Summary

SMILES: O=C1O[C@H]2[C@H]3[C@]1(C)CCC[C@]3(C)[C@@]([C@@]1(C2)CO1)(O)CCc1cocc1
InChI: InChI=1S/C20H26O5/c1-17-6-3-7-18(2)15(17)14(25-16(17)21)10-19(12-24-19)20(18,22)8-4-13-5-9-23-11-13/h5,9,11,14-15,22H,3-4,6-8,10,12H2,1-2H3/t14-,15+,17+,18+,19-,20+/m1/s1
InChIKey: TYPXWADRUZBXSO-FHZWTMRJSA-N
DeepSMILES: O=CO[C@H][C@H][C@]5C)CCC[C@]6C)[C@@][C@@]C%10)CO3)))O)CCccocc5
Scaffold Graph/Node/Bond level: O=C1OC2CC3(CO3)C(CCc3ccoc3)C3CCCC1C23
Scaffold Graph/Node level: OC1OC2CC3(CO3)C(CCC3CCOC3)C3CCCC1C23
Scaffold Graph level: CC1CC2CC3(CC3)C(CCC3CCCC3)C3CCCC1C23
Functional groups: COC(=O)C; C[C@]1(C)CO1; CO; coc
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organoheterocyclic compounds
ClassyFire Class: Lactones
ClassyFire Subclass: Gamma butyrolactones
NP Classifier Biosynthetic pathway: Terpenoids
NP Classifier Superclass: Diterpenoids
NP Classifier Class: Labdane diterpenoids
Synonymous chemical names:
Leonotinin, leonotinin
External chemical identifiers:
CID:CID_636934; ChEMBL:CHEMBL2036989; ZINC:ZINC000032296446
Chemical structure download


Leonotinin
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 346.42
Log P RDKit 2.85
Topological polar surface area (Å2) RDKit 72.2
Number of hydrogen bond acceptors RDKit 5
Number of hydrogen bond donors RDKit 1
Number of carbon atoms RDKit 20
Number of heavy atoms RDKit 25
Number of heteroatoms RDKit 5
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 6
Stereochemical complexity RDKit 0.3
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 5
Number of sp3 hybridized carbon atoms RDKit 15
Shape complexity RDKit 0.75
Number of rotatable bonds RDKit 3
Number of aliphatic carbocycles RDKit 2
Number of aliphatic heterocycles RDKit 2
Number of aliphatic rings RDKit 4
Number of aromatic carbocycles RDKit 0
Number of aromatic heterocycles RDKit 1
Number of aromatic rings RDKit 1
Total number of rings RDKit 5
Number of saturated carbocycles RDKit 2
Number of saturated heterocycles RDKit 2
Number of saturated rings RDKit 4
Number of Smallest Set of Smallest Rings (SSSR) RDKit 5


Leonotinin
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 Good
Pfizer 3/75 rule RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.67


Leonotinin
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Soluble
Solubility class [Silicos-IT] SwissADME Moderately soluble
Blood Brain Barrier permeation SwissADME Yes
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -6.68
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 Yes
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME No