IMPPAT Phytochemical information: 
Guvacoline

Guvacoline
Summary

SMILES: COC(=O)C1=CCCNC1
InChI: InChI=1S/C7H11NO2/c1-10-7(9)6-3-2-4-8-5-6/h3,8H,2,4-5H2,1H3
InChIKey: DYPLDWLIOGXSSE-UHFFFAOYSA-N
DeepSMILES: COC=O)C=CCCNC6
Scaffold Graph/Node/Bond level: C1=CCNCC1
Scaffold Graph/Node level: C1CCNCC1
Scaffold Graph level: C1CCCCC1
Functional groups: CC=C(C(=O)OC)C; CNC
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Alkaloids and derivatives
NP Classifier Biosynthetic pathway: Alkaloids
Synonymous chemical names:
guvacoline, norarecoline
External chemical identifiers:
CID:CID_160492; ChEMBL:CHEMBL268808; ChEBI:CHEBI:80754; ZINC:ZINC000003638105; FDASRS:YT3OF85P98; SureChEMBL:SCHEMBL3019132; MolPort-022-366-584
Chemical structure download


Guvacoline
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 141.17
Log P RDKit 0.08
Topological polar surface area (Å2) RDKit 38.33
Number of hydrogen bond acceptors RDKit 3
Number of hydrogen bond donors RDKit 1
Number of carbon atoms RDKit 7
Number of heavy atoms RDKit 10
Number of heteroatoms RDKit 3
Number of nitrogen atoms RDKit 1
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 0
Stereochemical complexity RDKit 0
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 3
Number of sp3 hybridized carbon atoms RDKit 4
Shape complexity RDKit 0.57
Number of rotatable bonds RDKit 2
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 0
Number of saturated rings RDKit 0
Number of Smallest Set of Smallest Rings (SSSR) RDKit 1


Guvacoline
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 2
Ghose rule RDKit Failed
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 0.53


Guvacoline
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 -7.12
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