codeine   Click here for help

GtoPdb Ligand ID: 1673

Synonyms: Codicept® | methylmorphine
Approved drug
codeine is an approved drug (FDA (no history prior to 2009))
Comment: Codeine is an opioid analgesic related to, but less potent than morphine.
Marketed formulations may contain codeine sulfate (PubChem CID 6098421).
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 2
Hydrogen bond donors 1
Rotatable bonds 1
Topological polar surface area 41.93
Molecular weight 299.15
XLogP 0.81
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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Canonical SMILES COc1ccc2c3c1OC1C43CCN(C(C2)C4C=CC1O)C
Isomeric SMILES COc1ccc2c3c1O[C@@H]1[C@@]43CCN([C@H](C2)[C@@H]4C=C[C@@H]1O)C
InChI InChI=1S/C18H21NO3/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/h3-6,11-13,17,20H,7-9H2,1-2H3/t11-,12+,13-,17-,18-/m0/s1
InChI Key OROGSEYTTFOCAN-DNJOTXNNSA-N
Classification Click here for help
Compound class Natural product or derivative
Approved drug? Yes (FDA (no history prior to 2009))
WHO Essential Medicine WHO Essential Medicines List (EML) (22nd List, 2021). Access PDF version.
Click to view more information about the WHO Model Lists of Essential Medicines.
IUPAC Name Click here for help
(1S,5R,13R,14S,17R)-10-methoxy-4-methyl-12-oxa-4-azapentacyclo[9.6.1.0^{1,13}.0^{5,17}.0^{7,18}]octadeca-7,9,11(18),15-tetraen-14-ol
Synonyms Click here for help
Codicept® | methylmorphine
Database Links Click here for help
BindingDB Ligand 50019351
CAS Registry No. 76-57-3
ChEBI CHEBI:16714
ChEMBL Ligand CHEMBL485
DrugBank Ligand DB00318
DrugCentral Ligand 725
GtoPdb PubChem SID 135650117
PubChem CID 5284371
Search Google for chemical match using the InChIKey OROGSEYTTFOCAN-DNJOTXNNSA-N
Search Google for chemicals with the same backbone OROGSEYTTFOCAN
UniChem Compound Search for chemical match using the InChIKey OROGSEYTTFOCAN-DNJOTXNNSA-N
UniChem Connectivity Search for chemical match using the InChIKey OROGSEYTTFOCAN-DNJOTXNNSA-N
Wikipedia Codeine