IMPPAT Phytochemical information: 
Rhetsinine
Rhetsinine
Summary

SMILES: CNc1ccccc1C(=O)N1CCc2c(C1=O)[nH]c1c2cccc1
InChI: InChI=1S/C19H17N3O2/c1-20-15-8-4-3-7-14(15)18(23)22-11-10-13-12-6-2-5-9-16(12)21-17(13)19(22)24/h2-9,20-21H,10-11H2,1H3
InChIKey: RAEOYMOPVHBBKE-UHFFFAOYSA-N
DeepSMILES: CNcccccc6C=O)NCCccC6=O))[nH]cc5cccc6
Scaffold Graph/Node/Bond level: O=C(c1ccccc1)N1CCc2c([nH]c3ccccc23)C1=O
Scaffold Graph/Node level: OC(C1CCCCC1)N1CCC2C3CCCCC3NC2C1O
Scaffold Graph level: CC(C1CCCCC1)C1CCC2C3CCCCC3CC2C1C
Functional groups: cNC; cC(=O)N(C)C(=O)c; c[nH]c
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organoheterocyclic compounds
ClassyFire Class: Indoles and derivatives
ClassyFire Subclass: Pyridoindoles
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Tryptophan alkaloids
NP Classifier Class: Carboline alkaloids
Synonymous chemical names:
Rhetsinine, rhetsinine, rhetsinine (hydroxyevodiamine)
External chemical identifiers:
CID:CID_99652; ChEMBL:CHEMBL508030; SureChEMBL:SCHEMBL14478778
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Rhetsinine
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 319.36
Log P RDKit 3.05
Topological polar surface area (Å2) RDKit 65.2
Number of hydrogen bond acceptors RDKit 3
Number of hydrogen bond donors RDKit 2
Number of carbon atoms RDKit 19
Number of heavy atoms RDKit 24
Number of heteroatoms RDKit 5
Number of nitrogen atoms RDKit 3
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 16
Number of sp3 hybridized carbon atoms RDKit 3
Shape complexity RDKit 0.16
Number of rotatable bonds RDKit 1
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 1
Number of aliphatic rings RDKit 1
Number of aromatic carbocycles RDKit 2
Number of aromatic heterocycles RDKit 1
Number of aromatic rings RDKit 3
Total number of rings RDKit 4
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 4
Rhetsinine
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 0.71
Rhetsinine
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Moderately soluble
Solubility class [Silicos-IT] SwissADME Poorly soluble
Blood Brain Barrier permeation SwissADME Yes
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -5.51
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 1
CYP1A2 inhibitor SwissADME Yes
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME Yes
CYP2D6 inhibitor SwissADME Yes
CYP3A4 inhibitor SwissADME Yes
P-glycoprotein substrate SwissADME No