IMPPAT Phytochemical information: 
Canaline

Canaline
Summary

SMILES: N[C@H](C(=O)O)CCON
InChI: InChI=1S/C4H10N2O3/c5-3(4(7)8)1-2-9-6/h3H,1-2,5-6H2,(H,7,8)/t3-/m0/s1
InChIKey: FQPGMQABJNQLLF-VKHMYHEASA-N
DeepSMILES: N[C@H]C=O)O))CCON
Functional groups: CN; CC(=O)O; CON
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organic acids and derivatives
ClassyFire Class: Carboxylic acids and derivatives
ClassyFire Subclass: Amino acids, peptides, and analogues
NP Classifier Biosynthetic pathway: Amino acids and Peptides
NP Classifier Superclass: Small peptides
NP Classifier Class: Aminoacids
Synonymous chemical names:
l-canaline, canaline
External chemical identifiers:
CID:CID_441443; ChEMBL:CHEMBL1231652; ChEBI:CHEBI:41401; ZINC:ZINC000001531042; FDASRS:T7H2XP1ZNS; SureChEMBL:SCHEMBL440859; MolPort-019-904-731
Chemical structure download


Canaline
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 134.14
Log P RDKit -1.32
Topological polar surface area (Å2) RDKit 98.57
Number of hydrogen bond acceptors RDKit 4
Number of hydrogen bond donors RDKit 3
Number of carbon atoms RDKit 4
Number of heavy atoms RDKit 9
Number of heteroatoms RDKit 5
Number of nitrogen atoms RDKit 2
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 1
Stereochemical complexity RDKit 0.25
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 1
Number of sp3 hybridized carbon atoms RDKit 3
Shape complexity RDKit 0.75
Number of rotatable bonds RDKit 4
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 0
Number of aliphatic rings RDKit 0
Number of aromatic carbocycles RDKit 0
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 0
Total number of rings RDKit 0
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 0


Canaline
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 4
Ghose filter RDKit Failed
Veber filter RDKit Good
Pfizer 3/75 filter RDKit Good
GSK 4/400 filter RDKit Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.413975


Canaline
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Highly soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -10.38
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


Canaline
Human target proteins
Protein identifierHGNC symbolCombined score from STITCH database
ENSP00000039007OTC914
ENSP00000357838OAT968
The human target proteins were predicted using STITCH, a database of Chemical-Protein interaction networks.