IMPPAT Phytochemical information: 
Hydroxycodeinone

Hydroxycodeinone
Summary

SMILES: COc1ccc2c3c1O[C@@H]1[C@@]43CCN([C@H](C2)[C@]4(O)C=CC1=O)C
InChI: InChI=1S/C18H19NO4/c1-19-8-7-17-14-10-3-4-12(22-2)15(14)23-16(17)11(20)5-6-18(17,21)13(19)9-10/h3-6,13,16,21H,7-9H2,1-2H3/t13-,16+,17+,18-/m1/s1
InChIKey: YYCRAERBSFHMPL-XFKAJCMBSA-N
DeepSMILES: COcccccc6O[C@@H][C@]5CCN[C@H]C%11)[C@]6O)C=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; CO; 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:
14-hydroxycodeinone
External chemical identifiers:
CID:CID_9926820; ZINC:ZINC000014447051; FDASRS:91138F771G; SureChEMBL:SCHEMBL38000
Chemical structure download


Hydroxycodeinone
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 313.35
Log P RDKit 0.82
Topological polar surface area (Å2) RDKit 59
Number of hydrogen bond acceptors RDKit 5
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 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


Hydroxycodeinone
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 0.83


Hydroxycodeinone
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 -7.42
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