IMPPAT Phytochemical information: 
Egenine
Egenine
Summary

SMILES: CN1CCc2c([C@H]1[C@@H]1O[C@@H](c3c1ccc1c3OCO1)O)cc1c(c2)OCO1
InChI: InChI=1S/C20H19NO6/c1-21-5-4-10-6-14-15(25-8-24-14)7-12(10)17(21)18-11-2-3-13-19(26-9-23-13)16(11)20(22)27-18/h2-3,6-7,17-18,20,22H,4-5,8-9H2,1H3/t17-,18+,20-/m0/s1
InChIKey: YMHFBUOKLSWOQF-NSHGMRRFSA-N
DeepSMILES: CNCCcc[C@H]6[C@@H]O[C@@H]cc5cccc6OCO5)))))))))O)))))cccc6)OCO5
Scaffold Graph/Node/Bond level: c1c2c(cc3c1OCO3)C(C1OCc3c1ccc1c3OCO1)NCC2
Scaffold Graph/Node level: C1CC2CC3OCOC3CC2C(C2OCC3C2CCC2OCOC23)N1
Scaffold Graph level: C1CC2CC3CCCC(C4CCC5C6CCCC6CCC54)C3CC2C1
Functional groups: CN(C)C; c[C@@H](O)OC; c1cOCO1
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organoheterocyclic compounds
ClassyFire Class: Tetrahydroisoquinolines
NP Classifier Biosynthetic pathway: Alkaloids|Polyketides
NP Classifier Superclass: Tyrosine alkaloids|Cyclic polyketides
NP Classifier Class: Isoquinoline alkaloids|Phthalide derivatives|Tetrahydroisoquinoline alkaloids
Synonymous chemical names:
Egenine,(+)-, egenine, Egenine
External chemical identifiers:
CID:CID_189685; ZINC:ZINC000005966937; SureChEMBL:SCHEMBL12904807
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Egenine
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 369.37
Log P RDKit 2.44
Topological polar surface area (Å2) RDKit 69.62
Number of hydrogen bond acceptors RDKit 7
Number of hydrogen bond donors RDKit 1
Number of carbon atoms RDKit 20
Number of heavy atoms RDKit 27
Number of heteroatoms RDKit 7
Number of nitrogen atoms RDKit 1
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 3
Stereochemical complexity RDKit 0.15
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 12
Number of sp3 hybridized carbon atoms RDKit 8
Shape complexity RDKit 0.4
Number of rotatable bonds RDKit 1
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 4
Number of aliphatic rings RDKit 4
Number of aromatic carbocycles RDKit 2
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 2
Total number of rings RDKit 6
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 6
Egenine
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 0.83
Egenine
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -7.24
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 Yes
CYP3A4 inhibitor SwissADME Yes
P-glycoprotein substrate SwissADME No