CHEBI:16796 - melatonin

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ChEBI Name melatonin
ChEBI ID CHEBI:16796
Definition A member of the class of acetamides that is acetamide in which one of the hydrogens attached to the nitrogen atom is replaced by a 2-(5-methoxy-1H-indol-3-yl)ethyl group. It is a hormone secreted by the pineal gland in humans.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:6730, CHEBI:25180, CHEBI:14577
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Formula C13H16N2O2
Net Charge 0
Average Mass 232.27830
Monoisotopic Mass 232.121
InChI InChI=1S/C13H16N2O2/c1-9(16)14-6-5-10-8-15-13-4-3-11(17-2)7-12(10)13/h3-4,7-8,15H,5-6H2,1-2H3,(H,14,16)
InChIKey DRLFMBDRBRZALE-UHFFFAOYSA-N
SMILES COc1ccc2[nH]cc(CCNC(C)=O)c2c1
Metabolite of Species Details
Mus musculus (NCBI:10090) Source: BioModels - MODEL1507180067 See: PubMed
Homo sapiens (NCBI:9606) See: DOI
Roles Classification
Chemical Role(s): radical scavenger
A role played by a substance that can react readily with, and thereby eliminate, radicals.
Biological Role(s): hormone
Originally referring to an endogenous compound that is formed in specialized organ or group of cells and carried to another organ or group of cells, in the same organism, upon which it has a specific regulatory function, the term is now commonly used to include non-endogenous, semi-synthetic and fully synthetic analogues of such compounds.
immunological adjuvant
A substance that augments, stimulates, activates, potentiates, or modulates the immune response at either the cellular or humoral level. A classical agent (Freund's adjuvant, BCG, Corynebacterium parvum, et al.) contains bacterial antigens. It could also be endogenous (e.g., histamine, interferon, transfer factor, tuftsin, interleukin-1). Its mode of action is either non-specific, resulting in increased immune responsiveness to a wide variety of antigens, or antigen-specific, i.e., affecting a restricted type of immune response to a narrow group of antigens. The therapeutic efficacy is related to its antigen-specific immunoadjuvanticity.
human metabolite
Any mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens).
mouse metabolite
Any mammalian metabolite produced during a metabolic reaction in a mouse (Mus musculus).
Application(s): anticonvulsant
A drug used to prevent seizures or reduce their severity.
central nervous system depressant
A loosely defined group of drugs that tend to reduce the activity of the central nervous system.
immunological adjuvant
A substance that augments, stimulates, activates, potentiates, or modulates the immune response at either the cellular or humoral level. A classical agent (Freund's adjuvant, BCG, Corynebacterium parvum, et al.) contains bacterial antigens. It could also be endogenous (e.g., histamine, interferon, transfer factor, tuftsin, interleukin-1). Its mode of action is either non-specific, resulting in increased immune responsiveness to a wide variety of antigens, or antigen-specific, i.e., affecting a restricted type of immune response to a narrow group of antigens. The therapeutic efficacy is related to its antigen-specific immunoadjuvanticity.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing melatonin (CHEBI:16796) has functional parent tryptamine (CHEBI:16765)
melatonin (CHEBI:16796) has role anticonvulsant (CHEBI:35623)
melatonin (CHEBI:16796) has role central nervous system depressant (CHEBI:35488)
melatonin (CHEBI:16796) has role hormone (CHEBI:24621)
melatonin (CHEBI:16796) has role human metabolite (CHEBI:77746)
melatonin (CHEBI:16796) has role immunological adjuvant (CHEBI:50847)
melatonin (CHEBI:16796) has role mouse metabolite (CHEBI:75771)
melatonin (CHEBI:16796) has role radical scavenger (CHEBI:48578)
melatonin (CHEBI:16796) is a acetamides (CHEBI:22160)
melatonin (CHEBI:16796) is a tryptamines (CHEBI:27162)
Incoming 6-hydroxymelatonin (CHEBI:2198) has functional parent melatonin (CHEBI:16796)
IUPAC Name
N-[2-(5-methoxy-1H-indol-3-yl)ethyl]acetamide
Synonyms Sources
5-methoxy-N-acetyltryptamine ChemIDplus
Melatonin KEGG COMPOUND
melatonin UniProt
mélatonine ChEBI
N-[2-(5-methoxyindol-3-yl)ethyl]acetamide NIST Chemistry WebBook
N-Acetyl-5-methoxytryptamine KEGG COMPOUND
Database Links Databases
C01598 KEGG COMPOUND
D08170 KEGG DRUG
DB01065 DrugBank
HMDB01389 HMDB
LSM-4779 LINCS
Melatonin Wikipedia
ML1 PDBeChem
N-ACETYL-5-METHOXY-TRYPTAMINE MetaCyc
View more database links
Registry Numbers Types Sources
205542 Beilstein Registry Number Beilstein
205542 Reaxys Registry Number Reaxys
73-31-4 CAS Registry Number ChemIDplus
73-31-4 CAS Registry Number NIST Chemistry WebBook
Citations Waiting for Citations Types Sources
16678784 PubMed citation CiteXplore
18212404 PubMed citation CiteXplore
18485664 PubMed citation CiteXplore
Last Modified
25 February 2016