IMPPAT Phytochemical information: 
Secodine

Secodine
Summary

SMILES: COC(=O)C(=C)c1[nH]c2c(c1CCN1CCC=C(C1)CC)cccc2
InChI: InChI=1S/C21H26N2O2/c1-4-16-8-7-12-23(14-16)13-11-18-17-9-5-6-10-19(17)22-20(18)15(2)21(24)25-3/h5-6,8-10,22H,2,4,7,11-14H2,1,3H3
InChIKey: WWMXJSGSUURDQK-UHFFFAOYSA-N
DeepSMILES: COC=O)C=C)c[nH]ccc5CCNCCC=CC6)CC))))))))))cccc6
Scaffold Graph/Node/Bond level: C1=CCN(CCc2c[nH]c3ccccc23)CC1
Scaffold Graph/Node level: C1CCN(CCC2CNC3CCCCC23)CC1
Scaffold Graph level: C1CCC(CCC2CCC3CCCCC32)CC1
Functional groups: cC(=C)C(=O)OC; c[nH]c; CN(C)C; CC=C(C)C
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organoheterocyclic compounds
ClassyFire Class: Indoles and derivatives
ClassyFire Subclass: Tryptamines and derivatives
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Tryptophan alkaloids
NP Classifier Class: Simple indole alkaloids
Synonymous chemical names:
secodine
External chemical identifiers:
CID:CID_101967023; ZINC:ZINC000014693887
Chemical structure download


Secodine
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 338.45
Log P RDKit 3.94
Topological polar surface area (Å2) RDKit 45.33
Number of hydrogen bond acceptors RDKit 3
Number of hydrogen bond donors RDKit 1
Number of carbon atoms RDKit 21
Number of heavy atoms RDKit 25
Number of heteroatoms RDKit 4
Number of nitrogen atoms RDKit 2
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 0
Stereochemical complexity RDKit 0
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 13
Number of sp3 hybridized carbon atoms RDKit 8
Shape complexity RDKit 0.38
Number of rotatable bonds RDKit 7
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 1
Number of aliphatic rings RDKit 1
Number of aromatic carbocycles RDKit 1
Number of aromatic heterocycles RDKit 1
Number of aromatic rings RDKit 2
Total number of rings RDKit 3
Number of saturated carbocycles RDKit 0
Number of saturated heterocycles RDKit 0
Number of saturated rings RDKit 0
Number of Smallest Set of Smallest Rings (SSSR) RDKit 3


Secodine
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 Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.492881


Secodine
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 -5.64
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 2
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME Yes
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME Yes
CYP3A4 inhibitor SwissADME Yes
P-glycoprotein substrate SwissADME No