Record Information
Version1.0
Creation date2010-04-08 22:06:09 UTC
Update date2019-11-26 02:59:53 UTC
Primary IDFDB004234
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameMelatonin
DescriptionMelatonin, also known chemically as N-acetyl-5-methoxytryptamine, is a naturally occurring compound found in animals, plants and microbes. In animals, circulating levels of the hormone melatonin vary in a daily cycle, thereby allowing the entrainment of the circadian rhythms of several biological functions.
CAS Number73-31-4
Structure
Thumb
Synonyms
SynonymSource
{N-[2-(5-methoxy-1H-indol-3-yl)ethyl]-} acetamideHMDB
{N-[2-(5-methoxyindol-3-yl)ethyl]-} acetamideHMDB
5-Methoxy-N-acetyltryptaminebiospider
Acetamide, N-(2-(5-methoxy-1H-indol-3-yl)ethyl)- (9CI)biospider
Acetamide, N-[2-(5-methoxyindol-3-yl)ethyl]- (6CI,8CI)biospider
Circadinbiospider
Melapurebiospider
Melatolbiospider
Melatonin (synth.) standard-gradeHMDB
Melatonin (synth.) ultra-pureHMDB
Melatoninebiospider
Melovinebiospider
MT6HMDB
N-(2-(5-Methoxy-1H-indol-3-yl)ethyl)acetamidebiospider
N-(2-(5-Methoxyindol-3-yl)ethyl)-acetamidebiospider
N-(2-(5-Methoxyindol-3-yl)ethyl)acetamideHMDB
N-[2-(5-Methoxy-1H-indol-3-yl)-ethyl]-acetamidebiospider
N-[2-(5-Methoxy-1H-indol-3-yl)ethyl)acetamideHMDB
N-[2-(5-Methoxy-1H-indol-3-yl)ethyl]-acetamideHMDB
N-[2-(5-Methoxy-1H-indol-3-yl)ethyl]acetamideHMDB
N-[2-(5-Methoxyindol-3-yl)ethyl]-acetamidebiospider
N-[2-(5-Methoxyindol-3-yl)ethyl]acetamideChEBI
N-Acetyl-5-methoxy-tryptaminebiospider
N-Acetyl-5-methoxy-tryptamine melatonineHMDB
N-Acetyl-5-methoxytryptamineChEBI
RegulinHMDB
Predicted PropertiesNot Available
Chemical FormulaC13H16N2O2
IUPAC name
InChI IdentifierInChI=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)
InChI KeyDRLFMBDRBRZALE-UHFFFAOYSA-N
Isomeric SMILESCOC1=CC=C2NC=C(CCNC(C)=O)C2=C1
Average Molecular Weight232.2783
Monoisotopic Molecular Weight232.121177766
Classification
ClassificationNot classified
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Biological role:

Industrial application:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting Point117 oC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
Charge0
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MSNot Available
MS/MSNot Available
NMRNot Available
ChemSpider ID872
ChEMBL IDCHEMBL45
KEGG Compound IDC01598
Pubchem Compound ID896
Pubchem Substance IDNot Available
ChEBI ID16796
Phenol-Explorer IDNot Available
DrugBank IDDB01065
HMDB IDHMDB01389
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDMELATONIN
BIGG ID37965
KNApSAcK IDNot Available
HET IDML1
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDMelatonin
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
anaphrodisiacDUKE
anti aggregantDUKE
anti convulsant52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti depressant52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti gonadotrophicDUKE
anti insomniac52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
antioxidant22586 A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides. In European countries, E-numbers for permitted antioxidant food additives are from E 300 to E 324.DUKE
anti radicularDUKE
anti thyreotropicDUKE
aphrodisiacDUKE
contraceptive52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
cyclooxygenase-2 inhibitor50629 A cyclooxygenase inhibitor that interferes with the action of cyclooxygenase 2.DUKE
cyclooxygenase inhibitor35544 A compound or agent that combines with cyclooxygenases (EC 1.14.99.1) and thereby prevents its substrate-enzyme combination with arachidonic acid and the formation of icosanoids, prostaglandins, and thromboxanes.DUKE
depressantDUKE
GABA nergic51374 A substance, such as agonists, antagonists, degradation or uptake inhibitors, depleters, precursors, and modulators of receptor function, used for its pharmacological actions on GABAergic systems.DUKE
gonadotrophicDUKE
hypnoticDUKE
hypocholesterolemicDUKE
hypothermicDUKE
immunostimulant50847 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.DUKE
progesteronigenicDUKE
serotoninergic48278 DUKE
thyrotropicDUKE
hormone24621 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.CHEBI
Enzymes
NameGene NameUniProt ID
Estrogen receptorESR1P03372
Nuclear receptor ROR-betaRORBQ92753
Pathways
NameSMPDB LinkKEGG Link
Tryptophan MetabolismSMP00063 map00380
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).