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
Supplier Information ChemicalBook:CB2142160, ChemicalBook:CB8443186, eMolecules:1984979, ZINC000001529638
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para-Nitrophenylphosphate (pNPP) is a non-proteinaceous chromogenic substrate for alkaline and acid phosphatases used in ELISA and conventional spectrophotometric assays. Phosphatases catalyze the hydrolysis of pNPP liberating inorganic phosphate and the conjugate base of para-nitrophenol (pNP). The resulting phenolate is yellow, with a maximal absorption at 405 nm. This property can be used to determine the activity of various phosphatases including alkaline phosphatase (AP) and protein tyrosine phosphatase (PTP). PNPP is classified as a chromogenic substrate because of its ability to transform from a colorless compound to a colored compound through a biological mechanism, dephosphorylation. PNPP is used because of its low cost and the rate of the reactions can be measured over a wide range of substrate concentrations because the concentration of the substrate is not a limiting factor in the reaction. The limitations of PNPP is that it is a small molecule and perhaps does not entirely represent the conditions and structures that are encountered physiologically. A PNPP assay involves mixing the sample with a PNPP-containing mixture and permitting the reaction to run its course for a predetermined period of time. After that point, the process is halted through the addition of a stop solution, often made of a potent alkali like sodium hydroxide. The substance is sensitive to light, and thus should be stored protected from light. This is also important after adding the substrate to the mixture and before reading. −20 °C is the optimal storage temperature. To get precise and credible findings, the assay parameters must be carefully regulated because the reaction is sensitive to factors such as pH, temperature, and the varying degree of inhibitors or stimulants.
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Formula C18H21NO3
Net Charge 0
Average Mass 299.36420
Monoisotopic Mass 299.15214
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.
drug allergen
Any drug which causes the onset of an allergic reaction.
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.
drug allergen
Any drug which causes the onset of an allergic reaction.
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 drug allergen (CHEBI:88188)
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
Manual Xrefs 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 Reaxys Registry Number Reaxys
Citations
Last Modified
04 March 2019