IMPPAT Phytochemical information: 
Cathafoline

Cathafoline
Summary

SMILES: COC(=O)[C@@H]1[C@H]2C[C@H]3[C@H]4[C@@]1(CCN3C/C/2=C/C)c1ccccc1N4
InChI: InChI=1S/C20H24N2O2/c1-3-12-11-22-9-8-20-14-6-4-5-7-15(14)21-18(20)16(22)10-13(12)17(20)19(23)24-2/h3-7,13,16-18,21H,8-11H2,1-2H3/b12-3-/t13?,16-,17-,18-,20?/m0/s1
InChIKey: UBWVEGSADBOAEC-TZZZHGQUSA-N
DeepSMILES: COC=O)[C@@H][C@H]C[C@H][C@H][C@@]6CCN6C/C/%10=C/C)))))))cccccc6N9
Scaffold Graph/Node/Bond level: C=C1CN2CCC34CC1CC2C3Nc1ccccc14
Scaffold Graph/Node level: CC1CN2CCC34CC1CC2C3NC1CCCCC14
Scaffold Graph level: CC1CC2CCC34CC1CC2C3CC1CCCCC14
Functional groups: COC(C)=O; CN(C)C; C/C=C(/C)C; cNC
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: Corynanthe type|Strychnos type
Synonymous chemical names:
cathafoline
External chemical identifiers:
CID:CID_101548614; ZINC:ZINC000238740564
Chemical structure download


Cathafoline
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 324.42
Log P RDKit 2.56
Topological polar surface area (Å2) RDKit 41.57
Number of hydrogen bond acceptors RDKit 4
Number of hydrogen bond donors RDKit 1
Number of carbon atoms RDKit 20
Number of heavy atoms RDKit 24
Number of heteroatoms RDKit 4
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 2
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 1
Number of saturated heterocycles RDKit 2
Number of saturated rings RDKit 3
Number of Smallest Set of Smallest Rings (SSSR) RDKit 5


Cathafoline
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 0.636701


Cathafoline
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME 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 -6.60
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 1
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