CHEBI:16714 - codeine

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ChEBI Name codeine
ChEBI ID CHEBI:16714
Definition A morphinane alkaloid found in the opium poppy, Papaver somniferum var. album; has analgesic, anti-tussive and anti-diarrhoeal properties.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:3803, CHEBI:14006, CHEBI:23348
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Formula C18H21NO3
Net Charge 0
Average Mass 299.36420
Monoisotopic Mass 299.152
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
InChIKey OROGSEYTTFOCAN-DNJOTXNNSA-N
SMILES [H][C@]12C=C[C@H](O)[C@@H]3Oc4c(OC)ccc5C[C@H]1N(C)CC[C@@]23c45
Roles Classification
Chemical Role(s): environmental contaminant
Any minor or unwanted substance introduced into the environment that can have undesired effects.
Biological Role(s): opioid receptor agonist
An agent that selectively binds to and activates an opioid receptor.
opioid analgesic
A narcotic or opioid substance, synthetic or semisynthetic agent producing profound analgesia, drowsiness, and changes in mood.
xenobiotic
A xenobiotic (Greek, xenos "foreign"; bios "life") is a compound that is foreign to a living organism. Principal xenobiotics include: drugs, carcinogens and various compounds that have been introduced into the environment by artificial means.
metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
(via alkaloid )
Application(s): antitussive
An agent that suppresses cough. Antitussives have a central or a peripheral action on the cough reflex, or a combination of both. Compare with expectorants, which are considered to increase the volume of secretions in the respiratory tract, so facilitating their removal by ciliary action and coughing, and mucolytics, which decrease the viscosity of mucus, facilitating its removal by ciliary action and expectoration.
opioid receptor agonist
An agent that selectively binds to and activates an opioid receptor.
prodrug
A compound that, on administration, must undergo chemical conversion by metabolic processes before becoming the pharmacologically active drug for which it is a prodrug.
opioid analgesic
A narcotic or opioid substance, synthetic or semisynthetic agent producing profound analgesia, drowsiness, and changes in mood.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing codeine (CHEBI:16714) has functional parent morphine (CHEBI:17303)
codeine (CHEBI:16714) has role antitussive (CHEBI:51177)
codeine (CHEBI:16714) has role environmental contaminant (CHEBI:78298)
codeine (CHEBI:16714) has role opioid analgesic (CHEBI:35482)
codeine (CHEBI:16714) has role opioid receptor agonist (CHEBI:60606)
codeine (CHEBI:16714) has role prodrug (CHEBI:50266)
codeine (CHEBI:16714) has role xenobiotic (CHEBI:35703)
codeine (CHEBI:16714) is a morphinane alkaloid (CHEBI:25418)
codeine (CHEBI:16714) is a organic heteropentacyclic compound (CHEBI:38164)
codeine (CHEBI:16714) is conjugate base of codeine(1+) (CHEBI:57871)
Incoming dihydrocodeine phosphate (CHEBI:31489) has functional parent codeine (CHEBI:16714)
norcodeine (CHEBI:80579) has functional parent codeine (CHEBI:16714)
codeine(1+) (CHEBI:57871) is conjugate acid of codeine (CHEBI:16714)
IUPAC Name
3-methoxy-17-methyl-7,8-didehydro-4,5α-epoxymorphinan-6α-ol
INNs Sources
codeína ChEBI
codeine ChEBI
codéine ChEBI
Synonyms Sources
(−)-Codeine HMDB
(1S,13R,14S,17R)-10-methoxy-4-methyl-12-oxa-4-azapentacyclo[9.6.1.01,13.05,17.07,18]octadeca-7(18),8,10,15-tetraen-14-ol HMDB
(5alpha,6alpha)-7,8-Didehydro-4,5-epoxy-3-methoxy-17-methylmorphinan-6-ol KEGG COMPOUND
7,8-didehydro-4,5α-epoxy-3-methoxy-17-methylmorphinan-6α-ol NIST Chemistry WebBook
Codein ChEBI
Codeine KEGG COMPOUND
codeine anhydrous DrugBank
l-codeine ChemIDplus
methylmorphine ChemIDplus
morphine 3-methyl ether ChemIDplus
morphine monomethyl ether ChemIDplus
morphine-3-methyl ether ChemIDplus
O3-methylmorphine ChemIDplus
Brand Names Sources
Codicept DrugBank
Coducept DrugBank
Database Links Databases
725 DrugCentral
C00001837 KNApSAcK
C06174 KEGG COMPOUND
Codeine Wikipedia
DB00318 DrugBank
View more database links
Registry Numbers Types Sources
232454 Gmelin Registry Number Gmelin
5303198 Beilstein Registry Number Beilstein
5768734 Beilstein Registry Number Beilstein
76-57-3 CAS Registry Number ChemIDplus
76-57-3 CAS Registry Number NIST Chemistry WebBook
94996 Beilstein Registry Number Beilstein
94996 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
2215478 PubMed citation Europe PMC
23507688 PubMed citation Europe PMC
24069665 PubMed citation Europe PMC
24176887 PubMed citation Europe PMC
24324229 PubMed citation Europe PMC
24396053 PubMed citation Europe PMC
24458010 PubMed citation Europe PMC
24491926 PubMed citation Europe PMC
24517264 PubMed citation Europe PMC
9776433 PubMed citation Europe PMC
Last Modified
22 February 2017