IMPPAT Phytochemical information: 
Pithecolobine

Pithecolobine
Summary

SMILES: CCCCCCCCCC1NCCCNCCCCNCCCNC(=O)C1
InChI: InChI=1S/C22H46N4O/c1-2-3-4-5-6-7-8-13-21-20-22(27)26-19-12-17-24-15-10-9-14-23-16-11-18-25-21/h21,23-25H,2-20H2,1H3,(H,26,27)
InChIKey: QEGMJRQKNQFEEZ-UHFFFAOYSA-N
DeepSMILES: CCCCCCCCCCNCCCNCCCCNCCCNC=O)C%17
Scaffold Graph/Node/Bond level: O=C1CCNCCCNCCCCNCCCN1
Scaffold Graph/Node level: OC1CCNCCCNCCCCNCCCN1
Scaffold Graph level: CC1CCCCCCCCCCCCCCCC1
Functional groups: CNC; CNC(=O)C
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Phenylpropanoids and polyketides
ClassyFire Class: Macrolactams
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Ornithine alkaloids
NP Classifier Class: Polyamines
Synonymous chemical names:
pithecolobine
External chemical identifiers:
CID:CID_442870; ChEBI:CHEBI:8253; SureChEMBL:SCHEMBL6315456
Chemical structure download


Pithecolobine
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 382.64
Log P RDKit 3.34
Topological polar surface area (Å2) RDKit 65.19
Number of hydrogen bond acceptors RDKit 4
Number of hydrogen bond donors RDKit 4
Number of carbon atoms RDKit 22
Number of heavy atoms RDKit 27
Number of heteroatoms RDKit 5
Number of nitrogen atoms RDKit 4
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 1
Stereochemical complexity RDKit 0.05
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 1
Number of sp3 hybridized carbon atoms RDKit 21
Shape complexity RDKit 0.95
Number of rotatable bonds RDKit 7
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 0
Number of aromatic rings RDKit 0
Total number of rings RDKit 1
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 1


Pithecolobine
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 1
Ghose filter RDKit Failed
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 0.486234


Pithecolobine
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Moderately soluble
Solubility class [Silicos-IT] SwissADME Poorly soluble
Blood Brain Barrier permeation SwissADME Yes
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -5.83
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 Yes
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME No