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]
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
CHEMBL257627
CAS Number
467-13-0
TTD ID
D00PYB
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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]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
Cytochrome c (CYCS) OTBFALJD CYC_HUMAN Protein Interaction/Cellular Processes [2]
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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) 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.