IMPPAT Phytochemical information: 
Preocoteine N-oxide

Preocoteine N-oxide
Summary

SMILES: COc1cc2-c3c(O)c(OC)c(c4c3[C@H](Cc2cc1OC)[N+]([O-])(C)CC4)OC
InChI: InChI=1S/C21H25NO6/c1-22(24)7-6-12-17-14(22)8-11-9-15(25-2)16(26-3)10-13(11)18(17)19(23)21(28-5)20(12)27-4/h9-10,14,23H,6-8H2,1-5H3/t14-,22?/m0/s1
InChIKey: OSXSNRJLKQQRJZ-XLEXHMCLSA-N
DeepSMILES: COccc-ccO)cOC))ccc6[C@H]Cc%10cc%14OC))))))[N+][O-])C)CC6))))))OC
Scaffold Graph/Node/Bond level: c1ccc2c(c1)CC1[NH2+]CCc3cccc-2c31
Scaffold Graph/Node level: C1CCC2C(C1)CC1NCCC3CCCC2C31
Scaffold Graph level: C1CCC2C(C1)CC1CCCC3CCCC2C31
Functional groups: cOC; cO; C[N+]([O-])(C)C
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Alkaloids and derivatives
ClassyFire Class: Aporphines
Synonymous chemical names:
preocoteine n-oxide
External chemical identifiers:
CID:CID_15286471; ZINC:ZINC000014639532
Chemical structure download


Preocoteine N-oxide
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 387.43
Log P RDKit 3.19
Topological polar surface area (Å2) RDKit 80.21
Number of hydrogen bond acceptors RDKit 6
Number of hydrogen bond donors RDKit 1
Number of carbon atoms RDKit 21
Number of heavy atoms RDKit 28
Number of heteroatoms RDKit 7
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 9
Shape complexity RDKit 0.43
Number of rotatable bonds RDKit 4
Number of aliphatic carbocycles RDKit 1
Number of aliphatic heterocycles RDKit 1
Number of aliphatic rings RDKit 2
Number of aromatic carbocycles RDKit 2
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 2
Total number of rings RDKit 4
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 4


Preocoteine N-oxide
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 0.64


Preocoteine N-oxide
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 -6.86
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