IMPPAT Phytochemical information: 
8-Azabicyclo[3.2.1]oct-3-yl 4-hydroxy-3-methoxybenzoate
8-Azabicyclo[3.2.1]oct-3-yl 4-hydroxy-3-methoxybenzoate
Summary

SMILES: COc1cc(ccc1O)C(=O)OC1CC2CCC(C1)N2
InChI: InChI=1S/C15H19NO4/c1-19-14-6-9(2-5-13(14)17)15(18)20-12-7-10-3-4-11(8-12)16-10/h2,5-6,10-12,16-17H,3-4,7-8H2,1H3
InChIKey: GWWGRYGNRKFSSX-UHFFFAOYSA-N
DeepSMILES: COcccccc6O))))C=O)OCCCCCCC7)N5
Scaffold Graph/Node/Bond level: O=C(OC1CC2CCC(C1)N2)c1ccccc1
Scaffold Graph/Node level: OC(OC1CC2CCC(C1)N2)C1CCCCC1
Scaffold Graph level: CC(CC1CC2CCC(C2)C1)C1CCCCC1
Functional groups: cOC; cO; cC(=O)OC; CNC
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Benzenoids
ClassyFire Class: Benzene and substituted derivatives
ClassyFire Subclass: Benzoic acids and derivatives
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Ornithine alkaloids
NP Classifier Class: Tropane alkaloids
Synonymous chemical names:
convolidine
External chemical identifiers:
CID:CID_573663
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
8-Azabicyclo[3.2.1]oct-3-yl 4-hydroxy-3-methoxybenzoate
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 277.32
Log P RDKit 1.84
Topological polar surface area (Å2) RDKit 67.79
Number of hydrogen bond acceptors RDKit 5
Number of hydrogen bond donors RDKit 2
Number of carbon atoms RDKit 15
Number of heavy atoms RDKit 20
Number of heteroatoms RDKit 5
Number of nitrogen atoms RDKit 1
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 2
Stereochemical complexity RDKit 0.13
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 7
Number of sp3 hybridized carbon atoms RDKit 8
Shape complexity RDKit 0.53
Number of rotatable bonds RDKit 4
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 2
Number of aliphatic rings RDKit 2
Number of aromatic carbocycles RDKit 1
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 1
Total number of rings RDKit 3
Number of saturated carbocycles RDKit 0
Number of saturated heterocycles RDKit 2
Number of saturated rings RDKit 2
Number of Smallest Set of Smallest Rings (SSSR) RDKit 3
8-Azabicyclo[3.2.1]oct-3-yl 4-hydroxy-3-methoxybenzoate
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 0.83
8-Azabicyclo[3.2.1]oct-3-yl 4-hydroxy-3-methoxybenzoate
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME Yes
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -6.22
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