IMPPAT Phytochemical information: 
Morphine N-oxide

Morphine N-oxide
Summary

SMILES: O[C@H]1C=C[C@@H]2[C@@]34[C@H]1Oc1c4c(C[C@H]2[N+](CC3)([O-])C)ccc1O
InChI: InChI=1S/C17H19NO4/c1-18(21)7-6-17-10-3-5-13(20)16(17)22-15-12(19)4-2-9(14(15)17)8-11(10)18/h2-5,10-11,13,16,19-20H,6-8H2,1H3/t10-,11+,13-,16-,17-,18?/m0/s1
InChIKey: AMAPEXTUMXQULJ-APQDOHRLSA-N
DeepSMILES: O[C@H]C=C[C@@H][C@][C@H]6Occ5cC[C@H]9[N+]CC%11))[O-])C))))ccc6O
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: CO; CC=CC; cOC; C[N+](C)([O-])C; cO
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Alkaloids and derivatives
ClassyFire Class: Morphinans
Synonymous chemical names:
morphine-n-oxide, morphine n-oxide
External chemical identifiers:
CID:CID_5362459; ChEBI:CHEBI:7002; ZINC:ZINC000004102209; FDASRS:9E77NL2Y9I; SureChEMBL:SCHEMBL619646
Chemical structure download


Morphine N-oxide
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 301.34
Log P RDKit 1.21
Topological polar surface area (Å2) RDKit 72.75
Number of hydrogen bond acceptors RDKit 4
Number of hydrogen bond donors RDKit 2
Number of carbon atoms RDKit 17
Number of heavy atoms RDKit 22
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 0.29
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 8
Number of sp3 hybridized carbon atoms RDKit 9
Shape complexity RDKit 0.53
Number of rotatable bonds RDKit 0
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


Morphine 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 0.43


Morphine N-oxide
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Very soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -8.27
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