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Details

Stereochemistry ABSOLUTE
Molecular Formula C18H19NO3
Molecular Weight 297.3484
Optical Activity UNSPECIFIED
Defined Stereocenters 4 / 4
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CODEINONE

SMILES

[H][C@@]12OC3=C(OC)C=CC4=C3[C@@]15CCN(C)[C@]([H])(C4)[C@]5([H])C=CC2=O

InChI

InChIKey=XYYVYLMBEZUESM-CMKMFDCUSA-N
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

HIDE SMILES / InChI

Molecular Formula C18H19NO3
Molecular Weight 297.3484
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 4 / 4
E/Z Centers 0
Optical Activity UNSPECIFIED

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: Q9SQ70
Gene ID: NA
Gene Symbol: COR1.1
Target Organism: Papaver somniferum (Opium poppy)
Target ID: P35372|||G8XRH8|||Q5TDA1|||Q9UN57
Gene ID: 4988.0
Gene Symbol: OPRM1
Target Organism: Homo sapiens (Human)
294.0 nM [EC50]
PubMed

PubMed

TitleDatePubMed
Effects of glutathione and phenobarbital on the toxicity of codeinone.
1986 May 15
Electrospray tandem mass spectrometric investigations of morphinans.
2003 Nov
A tale of three cell types: alkaloid biosynthesis is localized to sieve elements in opium poppy.
2003 Nov
The toxicity of opiates and their metabolites in HepG2 cells.
2003 Oct 25
Developmental and inducible accumulation of gene transcripts involved in alkaloid biosynthesis in opium poppy.
2003 Sep
6-oxo-morphinane oximes: pharmacology, chemistry and analytical application.
2004 Oct
Structural elucidation of chalcone reductase and implications for deoxychalcone biosynthesis.
2005 Aug 26
14-Hydroxylation of opiates: catalytic direct autoxidation of codeinone to 14-hydroxycodeinone.
2005 May 25
Effect of anticancer agents on codeinone-induced apoptosis in human cancer cell lines.
2005 Nov-Dec
The role of phloem sieve elements and laticifers in the biosynthesis and accumulation of alkaloids in opium poppy.
2006 Aug
Comparative transcript and alkaloid profiling in Papaver species identifies a short chain dehydrogenase/reductase involved in morphine biosynthesis.
2006 Oct
Structural determinants of opioid activity in derivatives of 14-aminomorphinones: effects of changes to the chain linking of the C14-amino group to the aryl ring.
2006 Oct 5
Induction of non-apoptotic cell death by morphinone in human promyelocytic leukemia HL-60 cells.
2006 Sep-Oct
Increasing morphinan alkaloid production by over-expressing codeinone reductase in transgenic Papaver somniferum.
2007 Jan
Linear-dichroic infrared spectral (IR-LD) analysis of codeine and its derivatives.
2007 May
Live cell monitoring of mu-opioid receptor-mediated G-protein activation reveals strong biological activity of close morphine biosynthetic precursors.
2007 Sep 14
Expression of Brugmansia candida Hyoscyamine 6beta-Hydroxylase gene in Saccharomyces cerevisiae and its potential use as biocatalyst.
2008 May 27
14beta-Arylpropiolylamino-17-cyclopropylmethyl-7,8-dihydronormorphinones and related opioids. Further examples of pseudoirreversible mu opioid receptor antagonists.
2009 Nov 12
Integration of deep transcriptome and proteome analyses reveals the components of alkaloid metabolism in opium poppy cell cultures.
2010 Nov 18
Patents
Substance Class Chemical
Created
by admin
on Sat Dec 16 08:19:47 GMT 2023
Edited
by admin
on Sat Dec 16 08:19:47 GMT 2023
Record UNII
22B5AW0ANN
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CODEINONE
Common Name English
6-OXOCODEINE
Common Name English
6-CODEINONE
Common Name English
(-)-CODEINONE
Common Name English
CODEINE MONOHYDRATE IMPURITY I [EP IMPURITY]
Common Name English
OXYCODONE RELATED COMPOUND C CII
USP-RS  
Common Name English
MORPHINAN-6-ONE, 7,8-DIDEHYDRO-4,5-EPOXY-3-METHOXY-17-METHYL-, (5.ALPHA.)-
Systematic Name English
OXYCODONE RELATED COMPOUND C [USP-RS]
Common Name English
CODEINE HYDROCHLORIDE DIHYDRATE IMPURITY I [EP IMPURITY]
Common Name English
MORPHINAN-6-ONE, 7,8-DIDEHYDRO-4,5.ALPHA.-EPOXY-3-METHOXY-17-METHYL-
Systematic Name English
OXYCODONE RELATED COMPOUND C
USP  
Common Name English
CODEINE PHOSPHATE HEMIHYDRATE IMPURITY I [EP IMPURITY]
Common Name English
HYDROCODONE HYDROGEN TARTRATE 2.5-HYDRATE IMPURITY E [EP IMPURITY]
Common Name English
OXYCODONE RELATED COMPOUND C [USP IMPURITY]
Common Name English
Code System Code Type Description
RS_ITEM_NUM
1485238
Created by admin on Sat Dec 16 08:19:47 GMT 2023 , Edited by admin on Sat Dec 16 08:19:47 GMT 2023
PRIMARY
WIKIPEDIA
CODEINONE
Created by admin on Sat Dec 16 08:19:47 GMT 2023 , Edited by admin on Sat Dec 16 08:19:47 GMT 2023
PRIMARY
CAS
467-13-0
Created by admin on Sat Dec 16 08:19:47 GMT 2023 , Edited by admin on Sat Dec 16 08:19:47 GMT 2023
PRIMARY
EPA CompTox
DTXSID70196909
Created by admin on Sat Dec 16 08:19:47 GMT 2023 , Edited by admin on Sat Dec 16 08:19:47 GMT 2023
PRIMARY
ECHA (EC/EINECS)
207-386-1
Created by admin on Sat Dec 16 08:19:47 GMT 2023 , Edited by admin on Sat Dec 16 08:19:47 GMT 2023
PRIMARY
CHEBI
58473
Created by admin on Sat Dec 16 08:19:47 GMT 2023 , Edited by admin on Sat Dec 16 08:19:47 GMT 2023
PRIMARY
FDA UNII
22B5AW0ANN
Created by admin on Sat Dec 16 08:19:47 GMT 2023 , Edited by admin on Sat Dec 16 08:19:47 GMT 2023
PRIMARY
PUBCHEM
5459910
Created by admin on Sat Dec 16 08:19:47 GMT 2023 , Edited by admin on Sat Dec 16 08:19:47 GMT 2023
PRIMARY
CHEBI
18399
Created by admin on Sat Dec 16 08:19:47 GMT 2023 , Edited by admin on Sat Dec 16 08:19:47 GMT 2023
PRIMARY
Related Record Type Details
SALT/SOLVATE -> PARENT
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PARENT -> METABOLITE
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PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
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PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP