IMPPAT Phytochemical information: 
Eburnamenine

Eburnamenine
Summary

SMILES: CC[C@@]12CCCN3[C@H]2c2n(C=C1)c1c(c2CC3)cccc1
InChI: InChI=1S/C19H22N2/c1-2-19-9-5-11-20-12-8-15-14-6-3-4-7-16(14)21(13-10-19)17(15)18(19)20/h3-4,6-7,10,13,18H,2,5,8-9,11-12H2,1H3/t18-,19+/m0/s1
InChIKey: VKTOXAGUZWAECL-RBUKOAKNSA-N
DeepSMILES: CC[C@]CCCN[C@H]6cnC=C%10))ccc5CC9)))cccc6
Scaffold Graph/Node/Bond level: C1=Cn2c3c(c4ccccc42)CCN2CCCC1C32
Scaffold Graph/Node level: C1CCC2C(C1)C1CCN3CCCC4CCN2C1C43
Scaffold Graph level: C1CC2CCC3C4CCCCC4C4CCC(C1)C2C34
Functional groups: cn(c)C=CC; CN(C)C
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Alkaloids and derivatives
ClassyFire Class: Eburnan-type alkaloids
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Tryptophan alkaloids
NP Classifier Class: Aspidosperma type
Synonymous chemical names:
eburnamenine
External chemical identifiers:
CID:CID_6857502; ChEMBL:CHEMBL3912953; ChEBI:CHEBI:35644; ZINC:ZINC000038190839
Chemical structure download


Eburnamenine
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 278.4
Log P RDKit 4.22
Topological polar surface area (Å2) RDKit 8.17
Number of hydrogen bond acceptors RDKit 2
Number of hydrogen bond donors RDKit 0
Number of carbon atoms RDKit 19
Number of heavy atoms RDKit 21
Number of heteroatoms RDKit 2
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 10
Number of sp3 hybridized carbon atoms RDKit 9
Shape complexity RDKit 0.47
Number of rotatable bonds RDKit 1
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 3
Number of aliphatic rings RDKit 3
Number of aromatic carbocycles RDKit 1
Number of aromatic heterocycles RDKit 1
Number of aromatic rings RDKit 2
Total number of rings RDKit 5
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 5


Eburnamenine
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 Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.758153


Eburnamenine
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Moderately 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 -5.38
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 Yes
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME Yes