IMPPAT Phytochemical information: 
N-Formylcytisine

N-Formylcytisine
Summary

SMILES: O=CN1CC2CC(C1)c1n(C2)c(=O)ccc1
InChI: InChI=1S/C12H14N2O2/c15-8-13-5-9-4-10(7-13)11-2-1-3-12(16)14(11)6-9/h1-3,8-10H,4-7H2
InChIKey: PCYQRXYBKKZUSR-UHFFFAOYSA-N
DeepSMILES: O=CNCCCCC6)cnC6)c=O)ccc6
Scaffold Graph/Node/Bond level: O=c1cccc2n1CC1CNCC2C1
Scaffold Graph/Node level: OC1CCCC2C3CNCC(C3)CN12
Scaffold Graph level: CC1CCCC2C3CCCC(C3)CC12
Functional groups: CN(C=O)C; cn(c)C; c=O
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 N-formyl, Cytisine, N-formyl, n-formylcytisine
External chemical identifiers:
CID:CID_589870; ChEMBL:CHEMBL1433686; MolPort-009-752-666
Chemical structure download


N-Formylcytisine
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 218.26
Log P RDKit 0.42
Topological polar surface area (Å2) RDKit 42.31
Number of hydrogen bond acceptors RDKit 3
Number of hydrogen bond donors RDKit 0
Number of carbon atoms RDKit 12
Number of heavy atoms RDKit 16
Number of heteroatoms RDKit 4
Number of nitrogen atoms RDKit 2
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 2
Stereochemical complexity RDKit 0.17
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 6
Number of sp3 hybridized carbon atoms RDKit 6
Shape complexity RDKit 0.5
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


N-Formylcytisine
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 Good
Pfizer 3/75 rule RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.64


N-Formylcytisine
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 -7.55
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