IMPPAT Phytochemical information: 
Izmirine

Izmirine
Summary

SMILES: COC1=CC(=O)CC2C1/C(=C\NCc1c(/C=C\2)ccc2c1OC(O2)C)/O
InChI: InChI=1S/C20H21NO5/c1-11-25-17-6-5-12-3-4-13-7-14(22)8-18(24-2)19(13)16(23)10-21-9-15(12)20(17)26-11/h3-6,8,10-11,13,19,21,23H,7,9H2,1-2H3/b4-3-,16-10+
InChIKey: SPOGIZLQHQHSKI-IEZDCIAISA-N
DeepSMILES: COC=CC=O)CCC6/C=C\NCcc/C=C\%10))cccc6OCO5)C))))))))))))/O
Scaffold Graph/Node/Bond level: O=C1C=CC2C=CNCc3c(ccc4c3OCO4)C=CC2C1
Scaffold Graph/Node level: OC1CCC2CCNCC3C(CCC2C1)CCC1OCOC13
Scaffold Graph level: CC1CCC2CCCCC3C(CCC2C1)CCC1CCCC13
Functional groups: COC(=CC(=O)C)C; CN/C=C(/O)C; c/C=C\C; CC1OccO1
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organoheterocyclic compounds
ClassyFire Class: Benzodioxoles
NP Classifier Biosynthetic pathway: Alkaloids
Synonymous chemical names:
Izmirine, izmirine
External chemical identifiers:
CID:CID_6442966
Chemical structure download


Izmirine
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 355.39
Log P RDKit 3.06
Topological polar surface area (Å2) RDKit 77.02
Number of hydrogen bond acceptors RDKit 6
Number of hydrogen bond donors RDKit 2
Number of carbon atoms RDKit 20
Number of heavy atoms RDKit 26
Number of heteroatoms RDKit 6
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 13
Number of sp3 hybridized carbon atoms RDKit 7
Shape complexity RDKit 0.35
Number of rotatable bonds RDKit 1
Number of aliphatic carbocycles RDKit 1
Number of aliphatic heterocycles RDKit 2
Number of aliphatic rings RDKit 3
Number of aromatic carbocycles RDKit 1
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 1
Total number of rings RDKit 4
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 4


Izmirine
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 0.806268


Izmirine
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Moderately soluble
Solubility class [Silicos-IT] SwissADME Poorly soluble
Blood Brain Barrier permeation SwissADME Yes
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -6.62
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 1
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME Yes
CYP2C9 inhibitor SwissADME Yes
CYP2D6 inhibitor SwissADME Yes
CYP3A4 inhibitor SwissADME Yes
P-glycoprotein substrate SwissADME Yes