Details of the Drug

General Information of Drug (ID: DM08WPL)

Drug Name

CODEINONE

Synonyms

Codeinone; 6-Codeinone; 467-13-0; UNII-22B5AW0ANN; (5alpha)-7,8-Didehydro-4,5-epoxy-3-methoxy-17-methylmorphinan-6-one; EINECS 207-386-1; BRN 0094188; 22B5AW0ANN; CHEBI:18399; 3-methoxy-17-methyl-7,8-didehydro-4,5alpha-epoxymorphinan-6-one; Morphinan-6-one, 7,8-didehydro-4,5-alpha-epoxy-3-methoxy-17-methyl-; 6-Oxocodeine; (-)-Codeinone; SCHEMBL100655; CHEMBL257627; DTXSID70196909; XYYVYLMBEZUESM-CMKMFDCUSA-N; ZINC4097036; API0000487; LS-92114; C06171; 7,8-Didehydro-4,5; A-epoxy-3-methoxy-17-methyl-morphinan-6-one

Indication

Disease Entry	ICD 11	Status	REF
Discovery agent	N.A.	Investigative	[1]
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Drug Type

Small molecular drug

Structure

3D MOL

2D MOL

#Ro5 Violations (Lipinski): 0

Molecular Weight (mw)

297.3

Logarithm of the Partition Coefficient (xlogp)

2.2

Rotatable Bond Count (rotbonds)

1

Hydrogen Bond Donor Count (hbonddonor)

0

Hydrogen Bond Acceptor Count (hbondacc)

4

Chemical Identifiers

Formula: C18H19NO3
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
Canonical SMILES: 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
InChIKey: XYYVYLMBEZUESM-CMKMFDCUSA-N

Cross-matching ID

PubChem CID: 5459910
ChEBI ID: CHEBI:18399
CAS Number: 467-13-0
TTD ID: D00PYB

Molecular Interaction Atlas of This Drug

Drug Therapeutic Target (DTT)

DTT Name	DTT ID	UniProt ID	MOA	REF
Opioid receptor mu (MOP)	TTKWM86	OPRM_HUMAN	Inhibitor	[1]

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Drug Off-Target (DOT)

DOT Name	DOT ID	UniProt ID	Interaction	REF
Apoptosis regulator BAX (BAX)	OTAW0V4V	BAX_HUMAN	Gene/Protein Processing	[2]
Apoptosis regulator Bcl-2 (BCL2)	OT9DVHC0	BCL2_HUMAN	Gene/Protein Processing	[2]
Caspase-3 (CASP3)	OTIJRBE7	CASP3_HUMAN	Gene/Protein Processing	[2]
Caspase-9 (CASP9)	OTD4RFFG	CASP9_HUMAN	Gene/Protein Processing	[2]
Cytochrome c (CYCS)	OTBFALJD	CYC_HUMAN	Protein Interaction/Cellular Processes	[2]

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Molecular Interaction Atlas (MIA)

MIA Detail

Jump to Detail Molecular Interaction Atlas of This Drug

Molecular Expression Atlas of This Drug

The Studied Disease

Discovery agent

ICD Disease Classification

N.A.

Molecule Name	Molecule Type	Gene Name	p-value	Fold-Change	Z-score
Opioid receptor mu (MOP)	DTT	OPRM1	5.94E-01	-0.02	-0.17

Molecular Expression Atlas (MEA)

MEA Detail

Jump to Detail Molecular Expression Atlas of This Drug

References

1	Live cell monitoring of mu-opioid receptor-mediated G-protein activation reveals strong biological activity of close morphine biosynthetic precursors. J Biol Chem. 2007 Sep 14;282(37):27126-32.
2	Analysis of apoptosis signaling pathway in human cancer cells by codeinone, a synthetic derivative of codeine. Anticancer Res. 2003 May-Jun;23(3B):2569-76.