IMPPAT Phytochemical information: 
Narcissidine
Narcissidine
Summary

SMILES: CO[C@H]1[C@H](O)C2=CCN3[C@H]2[C@@H]([C@@H]1O)c1cc(OC)c(cc1C3)OC
InChI: InChI=1S/C18H23NO5/c1-22-12-6-9-8-19-5-4-10-15(19)14(11(9)7-13(12)23-2)17(21)18(24-3)16(10)20/h4,6-7,14-18,20-21H,5,8H2,1-3H3/t14-,15+,16+,17-,18-/m0/s1
InChIKey: OHZXJDOKMFHAFO-PNKHAZJDSA-N
DeepSMILES: CO[C@H][C@H]O)C=CCN[C@H]5[C@@H][C@@H]9O))cccOC))ccc6C%10)))OC
Scaffold Graph/Node/Bond level: C1=C2CCCC3c4ccccc4CN(C1)C23
Scaffold Graph/Node level: C1CCC2C(C1)CN1CCC3CCCC2C31
Scaffold Graph level: C1CCC2C(C1)CC1CCC3CCCC2C31
Functional groups: COC; CO; CC=C(C)C; CN(C)C; cOC
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organoheterocyclic compounds
ClassyFire Class: Quinolines and derivatives
ClassyFire Subclass: Benzoquinolines
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Tyrosine alkaloids
NP Classifier Class: Amarylidaceae alkaloids
Synonymous chemical names:
narcissidine, Narcissidine
External chemical identifiers:
CID:CID_443686; ChEMBL:CHEMBL4552547; ChEBI:CHEBI:31896; ZINC:ZINC000030727846
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Narcissidine
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 333.38
Log P RDKit 0.66
Topological polar surface area (Å2) RDKit 71.39
Number of hydrogen bond acceptors RDKit 6
Number of hydrogen bond donors RDKit 2
Number of carbon atoms RDKit 18
Number of heavy atoms RDKit 24
Number of heteroatoms RDKit 6
Number of nitrogen atoms RDKit 1
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 5
Stereochemical complexity RDKit 0.28
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 8
Number of sp3 hybridized carbon atoms RDKit 10
Shape complexity RDKit 0.56
Number of rotatable bonds RDKit 3
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 1
Number of saturated heterocycles RDKit 0
Number of saturated rings RDKit 1
Number of Smallest Set of Smallest Rings (SSSR) RDKit 4
Narcissidine
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 0.792207
Narcissidine
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Very soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -8.64
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 1
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME No