IMPPAT Phytochemical information: 
Lycoricidine

Lycoricidine
Summary

SMILES: O[C@H]1C=C2[C@H]([C@@H]([C@@H]1O)O)NC(=O)c1c2cc2OCOc2c1
InChI: InChI=1S/C14H13NO6/c16-8-1-6-5-2-9-10(21-4-20-9)3-7(5)14(19)15-11(6)13(18)12(8)17/h1-3,8,11-13,16-18H,4H2,(H,15,19)/t8-,11+,12+,13-/m0/s1
InChIKey: YYDLFVZOIDOGSO-KKBFJBPOSA-N
DeepSMILES: O[C@H]C=C[C@H][C@@H][C@@H]6O))O))NC=O)cc6ccOCOc5c9
Scaffold Graph/Node/Bond level: O=C1NC2CCCC=C2c2cc3c(cc21)OCO3
Scaffold Graph/Node level: OC1NC2CCCCC2C2CC3OCOC3CC12
Scaffold Graph level: CC1CC2CCCCC2C2CC3CCCC3CC12
Functional groups: CO; cC(=CC)C; cC(=O)NC; c1cOCO1
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:
7-deoxynarciclasine
External chemical identifiers:
CID:CID_73065; ChEMBL:CHEMBL487798; ChEBI:CHEBI:6600; SureChEMBL:SCHEMBL13271851
Chemical structure download


Lycoricidine
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 291.26
Log P RDKit -0.99
Topological polar surface area (Å2) RDKit 108.25
Number of hydrogen bond acceptors RDKit 6
Number of hydrogen bond donors RDKit 4
Number of carbon atoms RDKit 14
Number of heavy atoms RDKit 21
Number of heteroatoms RDKit 7
Number of nitrogen atoms RDKit 1
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 4
Stereochemical complexity RDKit 0.29
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 9
Number of sp3 hybridized carbon atoms RDKit 5
Shape complexity RDKit 0.36
Number of rotatable bonds RDKit 0
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


Lycoricidine
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 1
Ghose rule RDKit Failed
Veber rule RDKit Good
Egan rule RDKit Good
GSK 4/400 rule RDKit Good
Pfizer 3/75 rule RDKit Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.49


Lycoricidine
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 -9.04
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 No
P-glycoprotein substrate SwissADME No