IMPPAT Phytochemical information: 
Lagunamine

Lagunamine
Summary

SMILES: COC(=O)C1=C2Nc3c([C@]42[C@H]2[C@H]([C@@H]1CCN2CC4)[C@@H](O)C)cccc3
InChI: InChI=1S/C20H24N2O3/c1-11(23)15-12-7-9-22-10-8-20(18(15)22)13-5-3-4-6-14(13)21-17(20)16(12)19(24)25-2/h3-6,11-12,15,18,21,23H,7-10H2,1-2H3/t11-,12-,15-,18+,20+/m0/s1
InChIKey: ZRLPIWDSOJCSDR-ADQWLHOYSA-N
DeepSMILES: COC=O)C=CNcc[C@@]5[C@H][C@H][C@@H]9CCN6CC9))))))[C@@H]O)C)))))cccc6
Scaffold Graph/Node/Bond level: C1=C2Nc3ccccc3C23CCN2CCC1CC23
Scaffold Graph/Node level: C1CCC2C(C1)NC1CC3CCN4CCC12C4C3
Scaffold Graph level: C1CCC2C(C1)CC1CC3CCC4CCC12C4C3
Functional groups: cNC(=C(C(=O)OC)C)C; CN(C)C; CO
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Alkaloids and derivatives
ClassyFire Class: Strychnos alkaloids
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Tryptophan alkaloids
NP Classifier Class: Aspidosperma type|Corynanthe type|Strychnos type
Synonymous chemical names:
Lagunamine, lagunamine
External chemical identifiers:
CID:CID_14706138; ZINC:ZINC000238780466
Chemical structure download


Lagunamine
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 340.42
Log P RDKit 1.88
Topological polar surface area (Å2) RDKit 61.8
Number of hydrogen bond acceptors RDKit 5
Number of hydrogen bond donors RDKit 2
Number of carbon atoms RDKit 20
Number of heavy atoms RDKit 25
Number of heteroatoms RDKit 5
Number of nitrogen atoms RDKit 2
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 5
Stereochemical complexity RDKit 0.25
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 9
Number of sp3 hybridized carbon atoms RDKit 11
Shape complexity RDKit 0.55
Number of rotatable bonds RDKit 3
Number of aliphatic carbocycles RDKit 1
Number of aliphatic heterocycles RDKit 3
Number of aliphatic rings RDKit 4
Number of aromatic carbocycles RDKit 1
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 1
Total number of rings RDKit 5
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 5


Lagunamine
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 0.81


Lagunamine
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 Yes
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -7.01
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 0
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME Yes
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME Yes