IMPPAT Phytochemical information: 
Narceinone
Narceinone
Summary

SMILES: COc1c(OC)ccc(c1C(=O)O)C(=O)C(=O)c1c(CCN(C)C)cc2c(c1OC)OCO2
InChI: InChI=1S/C23H25NO9/c1-24(2)9-8-12-10-15-21(33-11-32-15)22(31-5)16(12)19(26)18(25)13-6-7-14(29-3)20(30-4)17(13)23(27)28/h6-7,10H,8-9,11H2,1-5H3,(H,27,28)
InChIKey: HXFMRYFLZVSZMP-UHFFFAOYSA-N
DeepSMILES: COccOC))cccc6C=O)O)))C=O)C=O)ccCCNC)C))))cccc6OC)))OCO5
Scaffold Graph/Node/Bond level: O=C(C(=O)c1ccc2c(c1)OCO2)c1ccccc1
Scaffold Graph/Node level: OC(C1CCCCC1)C(O)C1CCC2OCOC2C1
Scaffold Graph level: CC(C1CCCCC1)C(C)C1CCC2CCCC2C1
Functional groups: c1cOCO1; cOC; cC(=O)O; cC(=O)C(c)=O; CN(C)C
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Phenylpropanoids and polyketides
ClassyFire Class: Stilbenes
Synonymous chemical names:
Narceinone, narceinone(14-oxonarceine), narceinone
External chemical identifiers:
CID:CID_14355673; ZINC:ZINC000014612406
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Narceinone
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 459.45
Log P RDKit 2.31
Topological polar surface area (Å2) RDKit 120.83
Number of hydrogen bond acceptors RDKit 9
Number of hydrogen bond donors RDKit 1
Number of carbon atoms RDKit 23
Number of heavy atoms RDKit 33
Number of heteroatoms RDKit 10
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 15
Number of sp3 hybridized carbon atoms RDKit 8
Shape complexity RDKit 0.35
Number of rotatable bonds RDKit 10
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 1
Number of aliphatic rings RDKit 1
Number of aromatic carbocycles RDKit 2
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 2
Total number of rings RDKit 3
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 3
Narceinone
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 Good
GSK 4/400 filter RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.418422
Narceinone
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 No
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -8.97
Number of PAINS structural alerts SwissADME 1
Number of Brenk structural alerts SwissADME 1
CYP1A2 inhibitor SwissADME Yes
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME Yes
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME Yes
P-glycoprotein substrate SwissADME Yes