Secondary metabolite: Sinensine



Sinensine
Summary
Molecular formula: C15H15NO3
SMILES: Oc1cc(O)cc(c1)c1ncc(c2c1[C@@H](O)CC2)C
InChI: InChI=1S/C15H15NO3/c1-8-7-16-15(14-12(8)2-3-13(14)19)9-4-10(17)6-11(18)5-9/h4-7,13,17-19H,2-3H2,1H3/t13-/m0/s1
InChIKey: DSRKIBHIKLYUOK-ZDUSSCGKSA-N
Chemical classification
Kingdom: Organic compounds
Super class: Organoheterocyclic compounds
Class: Pyridines and derivatives
Sub class: Phenylpyridines
Synonymous chemical names:
sinensine
Chemical structure download



Sinensine
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 257.29
Log P RDKit 2.45
Topological polar surface area (Å2) RDKit 73.58
Number of hydrogen bond acceptors RDKit 4
Number of hydrogen bond donors RDKit 3
Number of carbon atoms RDKit 15
Number of heavy atoms RDKit 19
Number of heteroatoms RDKit 4
Number of nitrogen atoms RDKit 1
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 1
Stereochemical complexity RDKit 0.07
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 11
Number of sp3 hybridized carbon atoms RDKit 4
Fraction of sp3 hybridized carbon atoms (Fsp3) RDKit 0.27
Shape complexity RDKit 0.27
Number of rotatable bonds SwissADME 1
Number of aliphatic carbocycles RDKit 1
Number of aliphatic heterocycles RDKit 0
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



Sinensine
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’s 3/75 filter RDKit Bad
GSK 4/400 filter RDKit Good
Number of Leadlikeness violations SwissADME 0
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.73



Sinensine
ADMET 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 -6.66
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 No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME Yes




Designed by R.P. Vivek-Ananth, M Karthikeyan and Ajaya Kumar Sahoo