IMPPAT Phytochemical information: 
Echinopsine

Echinopsine
Summary

SMILES: Cn1ccc(=O)c2c1cccc2
InChI: InChI=1S/C10H9NO/c1-11-7-6-10(12)8-4-2-3-5-9(8)11/h2-7H,1H3
InChIKey: CSJAXRKDCCWCSJ-UHFFFAOYSA-N
DeepSMILES: Cnccc=O)cc6cccc6
Scaffold Graph/Node/Bond level: O=c1cc[nH]c2ccccc12
Scaffold Graph/Node level: OC1CCNC2CCCCC12
Scaffold Graph level: CC1CCCC2CCCCC12
Functional groups: cn(C)c; c=O
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organoheterocyclic compounds
ClassyFire Class: Quinolines and derivatives
ClassyFire Subclass: Quinolones and derivatives
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Tryptophan alkaloids|Anthranilic acid alkaloids
NP Classifier Class: Quinoline alkaloids
Synonymous chemical names:
Echinopsine, echinopsine
External chemical identifiers:
CID:CID_6748; ChEBI:CHEBI:4749; ZINC:ZINC000000265414; FDASRS:17MMY7OK1U; SureChEMBL:SCHEMBL1809581; MolPort-000-882-179
Chemical structure download


Echinopsine
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 159.19
Log P RDKit 1.54
Topological polar surface area (Å2) RDKit 22
Number of hydrogen bond acceptors RDKit 2
Number of hydrogen bond donors RDKit 0
Number of carbon atoms RDKit 10
Number of heavy atoms RDKit 12
Number of heteroatoms RDKit 2
Number of nitrogen atoms RDKit 1
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 9
Number of sp3 hybridized carbon atoms RDKit 1
Shape complexity RDKit 0.1
Number of rotatable bonds RDKit 0
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 0
Number of aliphatic rings RDKit 0
Number of aromatic carbocycles RDKit 1
Number of aromatic heterocycles RDKit 1
Number of aromatic rings RDKit 2
Total number of rings RDKit 2
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 2


Echinopsine
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 1
Ghose rule RDKit Failed
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


Echinopsine
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Very soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME Yes
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -6.96
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 0
CYP1A2 inhibitor SwissADME Yes
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME No