IMPPAT Phytochemical information: 
Codeinone

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Summary

SMILES: COc1ccc2c3c1O[C@@H]1[C@@]43CCN([C@H](C2)[C@@H]4C=CC1=O)C
InChI: InChI=1S/C18H19NO3/c1-19-8-7-18-11-4-5-13(20)17(18)22-16-14(21-2)6-3-10(15(16)18)9-12(11)19/h3-6,11-12,17H,7-9H2,1-2H3/t11-,12+,17-,18-/m0/s1
InChIKey: XYYVYLMBEZUESM-CMKMFDCUSA-N
DeepSMILES: COcccccc6O[C@@H][C@]5CCN[C@H]C%11)[C@@H]6C=CC%10=O))))))C
Scaffold Graph/Node/Bond level: O=C1C=CC2C3Cc4cccc5c4C2(CCN3)C1O5
Scaffold Graph/Node level: OC1CCC2C3CC4CCCC5OC1C2(CCN3)C45
Scaffold Graph level: CC1CCC2C3CCCC24C1CC1CCCC(C3)C14
Functional groups: cOC; CN(C)C; CC=CC(=O)C
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Alkaloids and derivatives
ClassyFire Class: Morphinans
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Tyrosine alkaloids
NP Classifier Class: Isoquinoline alkaloids|Morphinan alkaloids
Synonymous chemical names:
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External chemical identifiers:
CID:CID_5459910; ChEMBL:CHEMBL257627; ChEBI:CHEBI:18399; ZINC:ZINC000004097036; FDASRS:22B5AW0ANN; SureChEMBL:SCHEMBL100655
Chemical structure download


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Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 297.35
Log P RDKit 1.71
Topological polar surface area (Å2) RDKit 38.77
Number of hydrogen bond acceptors RDKit 4
Number of hydrogen bond donors RDKit 0
Number of carbon atoms RDKit 18
Number of heavy atoms RDKit 22
Number of heteroatoms RDKit 4
Number of nitrogen atoms RDKit 1
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 4
Stereochemical complexity RDKit 0.22
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 9
Number of sp3 hybridized carbon atoms RDKit 9
Shape complexity RDKit 0.5
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


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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 0.790869


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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 Yes
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -6.55
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 0
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME Yes
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME No


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Human target proteins
Protein identifierHGNC symbolCombined score from STITCH database
ENSP00000330237CASP9700
ENSP00000311032CASP3700
The human target proteins were predicted using STITCH, a database of Chemical-Protein interaction networks.