IMPPAT Phytochemical information: 
Cytisine
Cytisine
Summary

SMILES: O=c1cccc2n1C[C@@H]1CNC[C@H]2C1
InChI: InChI=1S/C11H14N2O/c14-11-3-1-2-10-9-4-8(5-12-6-9)7-13(10)11/h1-3,8-9,12H,4-7H2/t8-,9+/m0/s1
InChIKey: ANJTVLIZGCUXLD-DTWKUNHWSA-N
DeepSMILES: O=cccccn6C[C@@H]CNC[C@H]8C6
Scaffold Graph/Node/Bond level: O=c1cccc2n1CC1CNCC2C1
Scaffold Graph/Node level: OC1CCCC2C3CNCC(C3)CN12
Scaffold Graph level: CC1CCCC2C3CCCC(C3)CC12
Functional groups: c=O; CNC; cn(c)C
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Alkaloids and derivatives
ClassyFire Class: Lupin alkaloids
ClassyFire Subclass: Cytisine and derivatives
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Lysine alkaloids|Nicotinic acid alkaloids
NP Classifier Class: Pyridine alkaloids|Quinolizidine alkaloids
Synonymous chemical names:
Cytisine, Cystisine, cystisine, sophorine, cytisine
External chemical identifiers:
CID:CID_10235; ChEMBL:CHEMBL497939; ChEBI:CHEBI:4055; ZINC:ZINC000001599730; FDASRS:53S5U404NU; SureChEMBL:SCHEMBL161398; MolPort-000-880-972
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Cytisine
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 190.25
Log P RDKit 0.56
Topological polar surface area (Å2) RDKit 34.03
Number of hydrogen bond acceptors RDKit 3
Number of hydrogen bond donors RDKit 1
Number of carbon atoms RDKit 11
Number of heavy atoms RDKit 14
Number of heteroatoms RDKit 3
Number of nitrogen atoms RDKit 2
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 2
Stereochemical complexity RDKit 0.18
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 5
Number of sp3 hybridized carbon atoms RDKit 6
Shape complexity RDKit 0.55
Number of rotatable bonds RDKit 0
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 2
Number of aliphatic rings RDKit 2
Number of aromatic carbocycles RDKit 0
Number of aromatic heterocycles RDKit 1
Number of aromatic rings RDKit 1
Total number of rings RDKit 3
Number of saturated carbocycles RDKit 0
Number of saturated heterocycles RDKit 1
Number of saturated rings RDKit 1
Number of Smallest Set of Smallest Rings (SSSR) RDKit 3
Cytisine
Drug-likeness
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 0.648136
Cytisine
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 -7.33
Number of PAINS structural alerts SwissADME 0.0
Number of Brenk structural alerts SwissADME 0.0
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
Cytisine
Phytochemical - Human target proteins supported by experimental evidence associations
Human target proteins supported by experimental evidence
IMPPAT target identifierGene identifierHGNC symbolEntrez Gene identifierSource
TAR_EXP_000853ENSG00000276155MAPT4137NPASS
TAR_EXP_000833ENSG00000160789LMNA4000NPASS
TAR_EXP_000004ENSG00000094631HDAC610013ChEMBL
TAR_EXP_000280ENSG00000160868CYP3A41576NPASS
TAR_EXP_000153ENSG00000135902CHRND1144ChEMBL, NPASS
TAR_EXP_000819ENSG00000235268KDM4E390245NPASS
TAR_EXP_000144ENSG00000101204CHRNA41137ChEMBL, NPASS
TAR_EXP_000616ENSG00000111700SLCO1B328234ChEMBL, NPASS
TAR_EXP_000567ENSG00000177628GBA12629NPASS
TAR_EXP_000156ENSG00000196811CHRNG1146ChEMBL
TAR_EXP_000263ENSG00000140505CYP1A21544NPASS
TAR_EXP_000149ENSG00000160716CHRNB21141ChEMBL
TAR_EXP_000152ENSG00000117971CHRNB41143ChEMBL
TAR_EXP_001663ENSG00000162607USP17398NPASS
TAR_EXP_000146ENSG00000175344CHRNA71139BindingDB, ChEMBL, NPASS
TAR_EXP_000880ENSG00000118058KMT2A4297NPASS
TAR_EXP_000142ENSG00000080644CHRNA31136BindingDB, ChEMBL, NPASS
TAR_EXP_000141ENSG00000120903CHRNA21135ChEMBL, NPASS
TAR_EXP_000139ENSG00000138435CHRNA11134BindingDB, ChEMBL
TAR_EXP_000148ENSG00000283946CHRNB11140ChEMBL
TAR_EXP_000061ENSG00000134538SLCO1B110599ChEMBL, NPASS