IMPPAT Phytochemical information: 
Protopine
Protopine
Summary

SMILES: CN1CCc2cc3OCOc3cc2C(=O)Cc2c(C1)c1OCOc1cc2
InChI: InChI=1S/C20H19NO5/c1-21-5-4-13-7-18-19(25-10-24-18)8-14(13)16(22)6-12-2-3-17-20(15(12)9-21)26-11-23-17/h2-3,7-8H,4-6,9-11H2,1H3
InChIKey: GPTFURBXHJWNHR-UHFFFAOYSA-N
DeepSMILES: CNCCcccOCOc5cc9C=O)CccC%17)cOCOc5cc9
Scaffold Graph/Node/Bond level: O=C1Cc2ccc3c(c2CNCCc2cc4c(cc21)OCO4)OCO3
Scaffold Graph/Node level: OC1CC2CCC3OCOC3C2CNCCC2CC3OCOC3CC12
Scaffold Graph level: CC1CC2CCC3CCCC3C2CCCCC2CC3CCCC3CC12
Functional groups: CN(C)C; c1cOCO1; cC(C)=O
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Alkaloids and derivatives
ClassyFire Class: Protopine alkaloids
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Tyrosine alkaloids
NP Classifier Class: Isoquinoline alkaloids|Protopine alkaloids
Synonymous chemical names:
biflorine, corydinine, fumarine, protopine
External chemical identifiers:
CID:4970; ChEMBL:CHEMBL453019; ChEBI:16415; ZINC:ZINC000020111233; FDASRS:UIW569HT35; SureChEMBL:SCHEMBL178013; MolPort-000-882-087
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Protopine
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 0
Log P RDKit 0
Topological polar surface area (Å2) RDKit
Number of hydrogen bond acceptors RDKit
Number of hydrogen bond donors RDKit
Number of carbon atoms RDKit
Number of heavy atoms RDKit
Number of heteroatoms RDKit
Number of nitrogen atoms RDKit
Number of sulfur atoms RDKit
Number of chiral carbon atoms RDKit
Stereochemical complexity RDKit 0
Number of sp hybridized carbon atoms RDKit
Number of sp2 hybridized carbon atoms RDKit
Number of sp3 hybridized carbon atoms RDKit
Shape complexity RDKit
Number of rotatable bonds RDKit
Number of aliphatic carbocycles RDKit
Number of aliphatic heterocycles RDKit
Number of aliphatic rings RDKit
Number of aromatic carbocycles RDKit
Number of aromatic heterocycles RDKit
Number of aromatic rings RDKit
Total number of rings RDKit
Number of saturated carbocycles RDKit
Number of saturated heterocycles RDKit
Number of saturated rings RDKit
Number of Smallest Set of Smallest Rings (SSSR) RDKit
Protopine
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 0.73
Protopine
ADMET 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 -6.47
Number of PAINS structural alerts SwissADME 0.0
Number of Brenk structural alerts SwissADME 0.0
CYP1A2 inhibitor SwissADME Yes
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME Yes
CYP2D6 inhibitor SwissADME Yes
CYP3A4 inhibitor SwissADME Yes
P-glycoprotein substrate SwissADME Yes
Protopine
Predicted human target proteins
Protein identifierHGNC symbolCombined score from STITCH database
ENSP00000300035KIAA0101800
ENSP00000308541F2786
ENSP00000380247HRH1800
The human target proteins were predicted using STITCH, a database of Chemical-Protein interaction networks.