IMPPAT Phytochemical information: 
Lagerine

Lagerine
Summary

SMILES: COc1ccc2c(c1O)Oc1ccc(cc1)CCC(=O)O[C@@H]1C[C@@H]2N2CCCC[C@@H]2C1
InChI: InChI=1S/C25H29NO5/c1-29-22-11-10-20-21-15-19(14-17-4-2-3-13-26(17)21)30-23(27)12-7-16-5-8-18(9-6-16)31-25(20)24(22)28/h5-6,8-11,17,19,21,28H,2-4,7,12-15H2,1H3/t17-,19+,21+/m1/s1
InChIKey: OBHAUUFTXJOWIW-LMNJBCLMSA-N
DeepSMILES: COcccccc6O))Occcccc6))CCC=O)O[C@@H]C[C@@H]%14NCCCC[C@@H]6C%10
Scaffold Graph/Node/Bond level: O=C1CCc2ccc(cc2)Oc2ccccc2C2CC(CC3CCCCN32)O1
Scaffold Graph/Node level: OC1CCC2CCC(CC2)OC2CCCCC2C2CC(CC3CCCCN32)O1
Scaffold Graph level: CC1CCC2CCC(CC2)CC2CCCCC2C2CC(C1)CC1CCCCC12
Functional groups: cOC; cO; cOc; CC(=O)OC; CN(C)C
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Phenylpropanoids and polyketides
ClassyFire Class: Macrolides and analogues
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Lysine alkaloids
NP Classifier Class: Quinolizidine alkaloids
Synonymous chemical names:
Lagerine, lagerine
External chemical identifiers:
CID:CID_101473393; ZINC:ZINC000238769949
Chemical structure download


Lagerine
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 423.51
Log P RDKit 4.74
Topological polar surface area (Å2) RDKit 68.23
Number of hydrogen bond acceptors RDKit 6
Number of hydrogen bond donors RDKit 1
Number of carbon atoms RDKit 25
Number of heavy atoms RDKit 31
Number of heteroatoms RDKit 6
Number of nitrogen atoms RDKit 1
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 3
Stereochemical complexity RDKit 0.12
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 13
Number of sp3 hybridized carbon atoms RDKit 12
Shape complexity RDKit 0.48
Number of rotatable bonds RDKit 1
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 4
Number of aliphatic rings RDKit 4
Number of aromatic carbocycles RDKit 2
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 2
Total number of rings RDKit 6
Number of saturated carbocycles RDKit 0
Number of saturated heterocycles RDKit 2
Number of saturated rings RDKit 2
Number of Smallest Set of Smallest Rings (SSSR) RDKit 6


Lagerine
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 0
Lipinski’s rule of 5 filter RDKit Passed
Number of Ghose filter violations RDKit 0
Ghose filter RDKit Passed
Veber filter RDKit Good
Pfizer 3/75 filter RDKit Bad
GSK 4/400 filter RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.668457


Lagerine
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Moderately 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 -5.86
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 0
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME Yes
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME Yes
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME Yes