IMPPAT Phytochemical information: 
UNII-Z32OFX7V17 component BDLSDHWCOJPHIE-PEKXWBJKSA-N
UNII-Z32OFX7V17 component BDLSDHWCOJPHIE-PEKXWBJKSA-N
Summary

SMILES: COc1ccc2c3c1O[C@@H]1[C@@]43CC[N@+]([C@H](C2)[C@@H]4C=C[C@@H]1O)([O-])C
InChI: InChI=1S/C18H21NO4/c1-19(21)8-7-18-11-4-5-13(20)17(18)23-16-14(22-2)6-3-10(15(16)18)9-12(11)19/h3-6,11-13,17,20H,7-9H2,1-2H3/t11-,12+,13-,17-,18-,19+/m0/s1
InChIKey: BDLSDHWCOJPHIE-PEKXWBJKSA-N
DeepSMILES: COcccccc6O[C@@H][C@]5CC[N@+][C@H]C%11)[C@@H]6C=C[C@@H]%10O))))))[O-])C
Scaffold Graph/Node/Bond level: C1=CC2C3Cc4cccc5c4C2(CC[NH2+]3)C(C1)O5
Scaffold Graph/Node level: C1CC2CC3NCCC45C(CCCC34)OC(C1)C25
Scaffold Graph level: C1CC2CC3CCCC45C(CCCC34)CC(C1)C25
Functional groups: cOC; C[N@@+]([O-])(C)C; CC=CC; CO
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Alkaloids and derivatives
ClassyFire Class: Morphinans
Synonymous chemical names:
codeine-n-oxide, codeine-N-oxide, codeine n-oxide
External chemical identifiers:
CID:CID_71314936; ZINC:ZINC000261506586
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
UNII-Z32OFX7V17 component BDLSDHWCOJPHIE-PEKXWBJKSA-N
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 315.37
Log P RDKit 1.51
Topological polar surface area (Å2) RDKit 61.75
Number of hydrogen bond acceptors RDKit 4
Number of hydrogen bond donors RDKit 1
Number of carbon atoms RDKit 18
Number of heavy atoms RDKit 23
Number of heteroatoms RDKit 5
Number of nitrogen atoms RDKit 1
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 5
Stereochemical complexity RDKit 0.28
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 8
Number of sp3 hybridized carbon atoms RDKit 10
Shape complexity RDKit 0.56
Number of rotatable bonds RDKit 1
Number of aliphatic carbocycles RDKit 2
Number of aliphatic heterocycles RDKit 2
Number of aliphatic rings RDKit 4
Number of aromatic carbocycles RDKit 1
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 1
Total number of rings RDKit 5
Number of saturated carbocycles RDKit 0
Number of saturated heterocycles RDKit 1
Number of saturated rings RDKit 1
Number of Smallest Set of Smallest Rings (SSSR) RDKit 5
UNII-Z32OFX7V17 component BDLSDHWCOJPHIE-PEKXWBJKSA-N
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 0.48
UNII-Z32OFX7V17 component BDLSDHWCOJPHIE-PEKXWBJKSA-N
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -7.74
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 2
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME Yes