IMPPAT Phytochemical information: 
Papracinine

Papracinine
Summary

SMILES: COc1cc2CC[N+]([C@]3(c2cc1O)Cc1c(C3)c2OCOc2cc1)([O-])C
InChI: InChI=1S/C20H21NO5/c1-21(23)6-5-12-7-18(24-2)16(22)8-15(12)20(21)9-13-3-4-17-19(14(13)10-20)26-11-25-17/h3-4,7-8,22H,5-6,9-11H2,1-2H3/t20-,21?/m1/s1
InChIKey: JNIPFMUGTLRRJS-VQCQRNETSA-N
DeepSMILES: COcccCC[N+][C@]c6cc%10O))))CccC5)cOCOc5cc9)))))))))))[O-])C
Scaffold Graph/Node/Bond level: c1ccc2c(c1)CC[NH2+]C21Cc2ccc3c(c2C1)OCO3
Scaffold Graph/Node level: C1CCC2C(C1)CCNC21CC2CCC3OCOC3C2C1
Scaffold Graph level: C1CCC2C(C1)CCCC21CC2CCC3CCCC3C2C1
Functional groups: cOC; C[N+](C)([O-])C; cO; c1cOCO1
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organoheterocyclic compounds
ClassyFire Class: Tetrahydroisoquinolines
Synonymous chemical names:
papracinine, Papracinine
External chemical identifiers:
CID:CID_101630423; ZINC:ZINC000015219648
Chemical structure download


Papracinine
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 355.39
Log P RDKit 2.62
Topological polar surface area (Å2) RDKit 70.98
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 26
Number of heteroatoms RDKit 6
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 8
Shape complexity RDKit 0.4
Number of rotatable bonds RDKit 1
Number of aliphatic carbocycles RDKit 1
Number of aliphatic heterocycles RDKit 2
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


Papracinine
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 0.628944


Papracinine
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Soluble
Solubility class [Silicos-IT] SwissADME Moderately soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -6.63
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 1
CYP1A2 inhibitor SwissADME Yes
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME Yes
CYP3A4 inhibitor SwissADME Yes
P-glycoprotein substrate SwissADME Yes