IMPPAT Phytochemical information: 
Narceine

Narceine
Summary

SMILES: COc1c(CC(=O)c2ccc(c(c2C(=O)O)OC)OC)c(CCN(C)C)cc2c1OCO2
InChI: InChI=1S/C23H27NO8/c1-24(2)9-8-13-10-18-22(32-12-31-18)20(29-4)15(13)11-16(25)14-6-7-17(28-3)21(30-5)19(14)23(26)27/h6-7,10H,8-9,11-12H2,1-5H3,(H,26,27)
InChIKey: DEXMFYZAHXMZNM-UHFFFAOYSA-N
DeepSMILES: COccCC=O)cccccc6C=O)O)))OC)))OC))))))))cCCNC)C))))ccc6OCO5
Scaffold Graph/Node/Bond level: O=C(Cc1ccc2c(c1)OCO2)c1ccccc1
Scaffold Graph/Node level: OC(CC1CCC2OCOC2C1)C1CCCCC1
Scaffold Graph level: CC(CC1CCC2CCCC2C1)C1CCCCC1
Functional groups: cOC; cC(C)=O; cC(=O)O; CN(C)C; c1cOCO1
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Phenylpropanoids and polyketides
ClassyFire Class: Stilbenes
Synonymous chemical names:
narceine, Narceine
External chemical identifiers:
CID:CID_8564; ChEMBL:CHEMBL486305; ChEBI:CHEBI:7480; ZINC:ZINC000001531508; FDASRS:CTT09X2F1M; SureChEMBL:SCHEMBL24919
Chemical structure download


Narceine
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 445.47
Log P RDKit 2.67
Topological polar surface area (Å2) RDKit 103.76
Number of hydrogen bond acceptors RDKit 8
Number of hydrogen bond donors RDKit 1
Number of carbon atoms RDKit 23
Number of heavy atoms RDKit 32
Number of heteroatoms RDKit 9
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 14
Number of sp3 hybridized carbon atoms RDKit 9
Shape complexity RDKit 0.39
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


Narceine
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 Bad
Pfizer 3/75 rule RDKit Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.55


Narceine
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 -8.68
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 No
CYP3A4 inhibitor SwissADME Yes
P-glycoprotein substrate SwissADME Yes