IMPPAT Phytochemical information: 
3-(4-Hydroxy-3-methoxy-phenyl)-acrylic acid octahydro-quinolizin-1-ylmethyl ester
3-(4-Hydroxy-3-methoxy-phenyl)-acrylic acid octahydro-quinolizin-1-ylmethyl ester
Summary

SMILES: COc1cc(/C=C/C(=O)OC[C@H]2CCCN3[C@@H]2CCCC3)ccc1O
InChI: InChI=1S/C20H27NO4/c1-24-19-13-15(7-9-18(19)22)8-10-20(23)25-14-16-5-4-12-21-11-3-2-6-17(16)21/h7-10,13,16-17,22H,2-6,11-12,14H2,1H3/b10-8+/t16-,17-/m1/s1
InChIKey: PWEDVDRRTZZEER-WVDJOFFCSA-N
DeepSMILES: COccc/C=C/C=O)OC[C@H]CCCN[C@@H]6CCCC6)))))))))))))))ccc6O
Scaffold Graph/Node/Bond level: O=C(C=Cc1ccccc1)OCC1CCCN2CCCCC12
Scaffold Graph/Node level: OC(CCC1CCCCC1)OCC1CCCN2CCCCC12
Scaffold Graph level: CC(CCC1CCCCC1)CCC1CCCC2CCCCC21
Functional groups: cOC; c/C=C/C(=O)OC; CN(C)C; cO
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Phenylpropanoids and polyketides
ClassyFire Class: Cinnamic acids and derivatives
ClassyFire Subclass: Hydroxycinnamic acids and derivatives
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Lysine alkaloids
NP Classifier Class: Quinolizidine alkaloids
Synonymous chemical names:
(+)-trans-4'-hydroxy-3'-methoxy-cinnamoyl epilupinine
External chemical identifiers:
CID:CID_643006; ZINC:ZINC000032302903
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
3-(4-Hydroxy-3-methoxy-phenyl)-acrylic acid octahydro-quinolizin-1-ylmethyl ester
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 345.44
Log P RDKit 3.22
Topological polar surface area (Å2) RDKit 59
Number of hydrogen bond acceptors RDKit 5
Number of hydrogen bond donors RDKit 1
Number of carbon atoms RDKit 20
Number of heavy atoms RDKit 25
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 0.1
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 9
Number of sp3 hybridized carbon atoms RDKit 11
Shape complexity RDKit 0.55
Number of rotatable bonds RDKit 6
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
3-(4-Hydroxy-3-methoxy-phenyl)-acrylic acid octahydro-quinolizin-1-ylmethyl ester
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 0.66
3-(4-Hydroxy-3-methoxy-phenyl)-acrylic acid octahydro-quinolizin-1-ylmethyl ester
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 -5.92
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 Yes
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME No