IMPPAT Phytochemical information: 
Cinchonaminone

Cinchonaminone
Summary

SMILES: OCCc1c([nH]c2c1cccc2)C(=O)C[C@@H]1CCNC[C@@H]1C=C
InChI: InChI=1S/C19H24N2O2/c1-2-13-12-20-9-7-14(13)11-18(23)19-16(8-10-22)15-5-3-4-6-17(15)21-19/h2-6,13-14,20-22H,1,7-12H2/t13-,14-/m0/s1
InChIKey: DPFKPQCJYMDGGR-KBPBESRZSA-N
DeepSMILES: OCCcc[nH]cc5cccc6)))))))C=O)C[C@@H]CCNC[C@@H]6C=C
Scaffold Graph/Node/Bond level: O=C(CC1CCNCC1)c1cc2ccccc2[nH]1
Scaffold Graph/Node level: OC(CC1CCNCC1)C1CC2CCCCC2N1
Scaffold Graph level: CC(CC1CCCCC1)C1CC2CCCCC2C1
Functional groups: CO; c[nH]c; cC(C)=O; CNC; C=CC
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organoheterocyclic compounds
ClassyFire Class: Indoles and derivatives
ClassyFire Subclass: Indoles
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Tryptophan alkaloids
NP Classifier Class: Corynanthe type
Synonymous chemical names:
cinchonaminone
External chemical identifiers:
CID:CID_10358166; ZINC:ZINC000013397009
Chemical structure download


Cinchonaminone
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 312.41
Log P RDKit 2.69
Topological polar surface area (Å2) RDKit 65.12
Number of hydrogen bond acceptors RDKit 3
Number of hydrogen bond donors RDKit 3
Number of carbon atoms RDKit 19
Number of heavy atoms RDKit 23
Number of heteroatoms RDKit 4
Number of nitrogen atoms RDKit 2
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 2
Stereochemical complexity RDKit 0.11
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 11
Number of sp3 hybridized carbon atoms RDKit 8
Shape complexity RDKit 0.42
Number of rotatable bonds RDKit 6
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 1
Number of saturated rings RDKit 1
Number of Smallest Set of Smallest Rings (SSSR) RDKit 3


Cinchonaminone
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 0.57


Cinchonaminone
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 -6.48
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