CHEBI:16796 - melatonin

ChEBI IDCHEBI:16796
ChEBI Namemelatonin
Stars
DefinitionA 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.
Secondary ChEBI IDsCHEBI:6730, CHEBI:14577, CHEBI:25180
Last Modified26 October 2021
DownloadsMolfile
FormulaC13H16N2O2
Net Charge0
Average Mass232.283
Monoisotopic Mass232.12118
SMILESCOc1ccc2ncc(CCNC(C)=O)c2c1
InChIInChI=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)
InChIKeyDRLFMBDRBRZALE-UHFFFAOYSA-N
Wikipedia
Species of MetaboliteComponentSourceComments
Homo sapiens (ncbitaxon:9606) - DOI (10.1038/nbt.2488)
Mus musculus (ncbitaxon:10090) - PubMed (19425150) Source: BioModels - MODEL1507180067
Roles Classification
Chemical Role:
radical scavenger  A role played by a substance that can react readily with, and thereby eliminate, radicals.
Biological Roles:
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.
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.
mouse metabolite  Any mammalian metabolite produced during a metabolic reaction in a mouse (Mus musculus).
human metabolite  Any mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens).
Applications:
geroprotector  Any compound that supports healthy aging, slows the biological aging process, or extends lifespan.
anticonvulsant  A drug used to prevent seizures or reduce their severity.
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.
central nervous system depressant  A loosely defined group of drugs that tend to reduce the activity of the central nervous system.
ChEBI Ontology
Outgoing Relation(s)
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 geroprotector (CHEBI:176497)
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 Relation(s)
2-hydroxymelatonin (CHEBI:145792) has functional parent melatonin (CHEBI:16796)
6-hydroxymelatonin (CHEBI:2198) has functional parent melatonin (CHEBI:16796)
IUPAC Name 
N-[2-(5-methoxy-1H-indol-3-yl)ethyl]acetamide
Synonyms  Source
5-methoxy-N-acetyltryptamineChemIDplus
N-[2-(5-methoxyindol-3-yl)ethyl]acetamideNIST Chemistry WebBook
MelatoninKEGG COMPOUND
mélatonineChEBI
N-Acetyl-5-methoxytryptamineKEGG COMPOUND
UniProt Name  Source
melatoninUniProt
Manual XrefsDatabases
1672DrugCentral
C01598KEGG COMPOUND
D08170KEGG DRUG
DB01065DrugBank
HMDB0001389HMDB
LSM-4779LINCS
MelatoninWikipedia
ML1PDBeChem
N-ACETYL-5-METHOXY-TRYPTAMINEMetaCyc
Registry NumbersSources
Reaxys:205542Reaxys
CAS:73-31-4ChemIDplus
CAS:73-31-4KEGG COMPOUND
CAS:73-31-4NIST Chemistry WebBook
Citations