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(=O)C
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:
Protopine, fumarine, corydinine, protopine, biflorine, Fumarine
External chemical identifiers:
CID:CID_4970; ChEMBL:CHEMBL453019; ChEBI: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 353.37
Log P RDKit 2.56
Topological polar surface area (Å2) RDKit 57.23
Number of hydrogen bond acceptors RDKit 6
Number of hydrogen bond donors RDKit 0
Number of carbon atoms RDKit 20
Number of heavy atoms RDKit 26
Number of heteroatoms RDKit 6
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 13
Number of sp3 hybridized carbon atoms RDKit 7
Shape complexity RDKit 0.35
Number of rotatable bonds RDKit 0
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 3
Number of aliphatic rings RDKit 3
Number of aromatic carbocycles RDKit 2
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 2
Total number of rings RDKit 5
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 5
Protopine
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 0
Lipinski’s rule of 5 filter RDKit Passed
Number of Ghose filter violations RDKit 0
Ghose filter RDKit Passed
Veber filter RDKit Good
Pfizer 3/75 filter RDKit Bad
GSK 4/400 filter RDKit Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.725541
Protopine
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 -6.47
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 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
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.