IMPPAT Phytochemical information: 
(S)-Stylopine
(S)-Stylopine
Summary

SMILES: C1Oc2c(O1)cc1c(c2)CCN2[C@H]1Cc1ccc3c(c1C2)OCO3
InChI: InChI=1S/C19H17NO4/c1-2-16-19(24-10-21-16)14-8-20-4-3-12-6-17-18(23-9-22-17)7-13(12)15(20)5-11(1)14/h1-2,6-7,15H,3-5,8-10H2/t15-/m0/s1
InChIKey: UXYJCYXWJGAKQY-HNNXBMFYSA-N
DeepSMILES: COccO5)cccc6)CCN[C@H]6Ccccccc6C%10))OCO5
Scaffold Graph/Node/Bond level: c1cc2c(c3c1CC1c4cc5c(cc4CCN1C3)OCO5)OCO2
Scaffold Graph/Node level: C1OC2CC3CCN4CC5C(CCC6OCOC65)CC4C3CC2O1
Scaffold Graph level: C1CC2CC3CCC4CC5C(CCC6CCCC65)CC4C3CC2C1
Functional groups: c1cOCO1; CN(C)C
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Alkaloids and derivatives
ClassyFire Class: Protoberberine alkaloids and derivatives
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Tyrosine alkaloids
NP Classifier Class: Isoquinoline alkaloids|Protoberberine alkaloids
Synonymous chemical names:
(-)-stylopine, Stylopine, Tetrahydrocoptisine, stylopine, l-tetrahydrocoptisine, tetrahydrocoptisine, (-) stylopine
External chemical identifiers:
CID:CID_440583; ChEMBL:CHEMBL1922602; ChEBI:CHEBI:18285; ZINC:ZINC000020470300; SureChEMBL:SCHEMBL18891073; MolPort-016-638-302
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
(S)-Stylopine
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 323.35
Log P RDKit 2.8
Topological polar surface area (Å2) RDKit 40.16
Number of hydrogen bond acceptors RDKit 5
Number of hydrogen bond donors RDKit 0
Number of carbon atoms RDKit 19
Number of heavy atoms RDKit 24
Number of heteroatoms RDKit 5
Number of nitrogen atoms RDKit 1
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 12
Number of sp3 hybridized carbon atoms RDKit 7
Shape complexity RDKit 0.37
Number of rotatable bonds RDKit 0
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 4
Number of aliphatic rings RDKit 4
Number of aromatic carbocycles RDKit 2
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 2
Total number of rings RDKit 6
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 6
(S)-Stylopine
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 0.75
(S)-Stylopine
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Moderately soluble
Solubility class [Silicos-IT] SwissADME Moderately soluble
Blood Brain Barrier permeation SwissADME Yes
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -6.16
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 0
CYP1A2 inhibitor SwissADME Yes
CYP2C19 inhibitor SwissADME Yes
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME Yes
CYP3A4 inhibitor SwissADME Yes
P-glycoprotein substrate SwissADME No