Codeinone

Details

• Internal ID: 4e4be1f9-2750-4939-9fad-f3f71b8d406c
• Taxonomy: Alkaloids and derivatives > Morphinans
• IUPAC Name: (4R,4aR,7aR,12bS)-9-methoxy-3-methyl-1,2,4,4a,7a,13-hexahydro-4,12-methanobenzofuro[3,2-e]isoquinolin-7-one
• SMILES (Canonical): CN1CCC23C4C1CC5=C2C(=C(C=C5)OC)OC3C(=O)C=C4
• SMILES (Isomeric): CN1CC[C@]23[C@@H]4[C@H]1CC5=C2C(=C(C=C5)OC)O[C@H]3C(=O)C=C4
• 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
• InChI Key: XYYVYLMBEZUESM-CMKMFDCUSA-N
• Popularity: 210 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₈H₁₉NO₃
• Molecular Weight: 297.30 g/mol
• Exact Mass: 297.13649347 g/mol
• Topological Polar Surface Area (TPSA): 38.80 Ų
• XlogP: 2.20

Synonyms

• 6-Codeinone
• 467-13-0
• UNII-22B5AW0ANN
• EINECS 207-386-1
• 22B5AW0ANN
• (5alpha)-7,8-Didehydro-4,5-epoxy-3-methoxy-17-methylmorphinan-6-one
• BRN 0094188
• CHEBI:18399
• 4-27-00-03599 (Beilstein Handbook Reference)
• Morphinan-6-one, 7,8-didehydro-4,5-alpha-epoxy-3-methoxy-17-methyl-
• Morphinan-6-one, 7,8-didehydro-4,5-epoxy-3-methoxy-17-methyl-, (5-alpha)-
• (4R,4aR,7aR,12bS)-9-methoxy-3-methyl-1,2,4,4a,7a,13-hexahydro-4,12-methanobenzofuro[3,2-e]isoquinolin-7-one
• 3-methoxy-17-methyl-7,8-didehydro-4,5alpha-epoxymorphinan-6-one
• 6-Oxocodeine
• (-)-Codeinone
• (4R,4aR,7aR,12bS)-9-methoxy-3-methyl-1,2,4,4a,7a,13-hexahydro-4,12-methanobenzofuro[3,2-e]isoquinoline-7-one
• SCHEMBL100655
• CHEMBL257627
• DTXSID70196909
• XYYVYLMBEZUESM-CMKMFDCUSA-N
• LS-92114
• C06171
• CODEINE MONOHYDRATE IMPURITY I [EP IMPURITY]
• Q4918787
• CODEINE HYDROCHLORIDE DIHYDRATE IMPURITY I [EP IMPURITY]
• CODEINE PHOSPHATE HEMIHYDRATE IMPURITY I [EP IMPURITY]
• HYDROCODONE HYDROGEN TARTRATE 2.5-HYDRATE IMPURITY E [EP IMPURITY]
• MORPHINAN-6-ONE, 7,8-DIDEHYDRO-4,5-EPOXY-3-METHOXY-17-METHYL-, (5.ALPHA.)-
• MORPHINAN-6-ONE, 7,8-DIDEHYDRO-4,5.ALPHA.-EPOXY-3-METHOXY-17-METHYL-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
No predicted properties yet!

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL233	P35372	Mu opioid receptor	294 nM; 294 nM	EC50; EC50	via Super-PRED; PMID: 17616524

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	99.01%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	95.65%	95.56%
CHEMBL5608	Q16288	NT-3 growth factor receptor	92.35%	95.89%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	91.68%	94.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.49%	86.33%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	89.64%	94.45%
CHEMBL253	P34972	Cannabinoid CB2 receptor	88.74%	97.25%
CHEMBL4247	Q9UM73	ALK tyrosine kinase receptor	84.54%	96.86%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	83.61%	97.14%
CHEMBL4829	O00763	Acetyl-CoA carboxylase 2	83.48%	98.00%
CHEMBL4895	P30530	Tyrosine-protein kinase receptor UFO	83.38%	90.95%
CHEMBL217	P14416	Dopamine D2 receptor	82.50%	95.62%
CHEMBL4208	P20618	Proteasome component C5	82.22%	90.00%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	82.02%	93.40%
CHEMBL2335	P42785	Lysosomal Pro-X carboxypeptidase	80.59%	100.00%

Plants that contains it

• Aloe microstigma
• Chrozophora plicata
• Papaver somniferum

Cross-Links

• PubChem: 5459910
• NPASS: NPC214629
• ChEMBL: CHEMBL257627
• LOTUS: LTS0095594
• wikiData: Q4918787