IMPPAT Phytochemical information: 
Pilocarpine

Pilocarpine
Summary

SMILES: CC[C@@H]1C(=O)OC[C@@H]1Cc1cncn1C
InChI: InChI=1S/C11H16N2O2/c1-3-10-8(6-15-11(10)14)4-9-5-12-7-13(9)2/h5,7-8,10H,3-4,6H2,1-2H3/t8-,10-/m0/s1
InChIKey: QCHFTSOMWOSFHM-WPRPVWTQSA-N
DeepSMILES: CC[C@@H]C=O)OC[C@@H]5Cccncn5C
Scaffold Graph/Node/Bond level: O=C1CC(Cc2cnc[nH]2)CO1
Scaffold Graph/Node level: OC1CC(CC2CNCN2)CO1
Scaffold Graph level: CC1CCC(CC2CCCC2)C1
Functional groups: COC(=O)C; cnc; cn(C)c
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Alkaloids and derivatives
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Histidine alkaloids
NP Classifier Class: Imidazole alkaloids
Synonymous chemical names:
pilocarpine
External chemical identifiers:
CID:CID_5910; ChEMBL:CHEMBL550; ChEBI:CHEBI:8207; ZINC:ZINC000000075008; FDASRS:01MI4Q9DI3; SureChEMBL:SCHEMBL15146; MolPort-002-512-506
Chemical structure download


Pilocarpine
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 208.26
Log P RDKit 1.16
Topological polar surface area (Å2) RDKit 44.12
Number of hydrogen bond acceptors RDKit 4
Number of hydrogen bond donors RDKit 0
Number of carbon atoms RDKit 11
Number of heavy atoms RDKit 15
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 0.18
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 4
Number of sp3 hybridized carbon atoms RDKit 7
Shape complexity RDKit 0.64
Number of rotatable bonds RDKit 3
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 1
Number of aliphatic rings RDKit 1
Number of aromatic carbocycles RDKit 0
Number of aromatic heterocycles RDKit 1
Number of aromatic rings RDKit 1
Total number of rings RDKit 2
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 2


Pilocarpine
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 0.700091


Pilocarpine
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 Yes
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -7.49
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