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 as circadin or melatol, belongs to the class of organic compounds known as 3-alkylindoles. 3-alkylindoles are compounds containing an indole moiety that carries an alkyl chain at the 3-position. Melatonin is an extremely weak basic (essentially neutral) compound (based on its pKa). Melatonin exists in all living organisms, ranging from bacteria to humans. Melatonin is found, on average, in the highest concentration within corns and milk (cow). Melatonin has also been detected, but not quantified in, several different foods, such as cornmints, sacred lotus, pomes, burdocks, and giant butterburs. This could make melatonin a potential biomarker for the consumption of these foods. Melatonin is a potentially toxic compound.
CAS Number73-31-4
Structure
Thumb
Synonyms
SynonymSource
5-Methoxy-N-acetyltryptamineChEBI
MelatonineChEBI
N-[2-(5-Methoxyindol-3-yl)ethyl]acetamideChEBI
N-Acetyl-5-methoxytryptamineChEBI
MelatoninaKegg
CircadinHMDB
MelatolHMDB
Melatonin (synth.) standard-gradeHMDB
Melatonin (synth.) ultra-pureHMDB
MelovineHMDB
MT6HMDB
N-(2-(5-Methoxy-1H-indol-3-yl)ethyl)acetamideHMDB
N-(2-(5-Methoxyindol-3-yl)ethyl)-acetamideHMDB
N-(2-(5-Methoxyindol-3-yl)ethyl)acetamideHMDB
N-Acetyl-5-methoxy-tryptamineHMDB
N-Acetyl-5-methoxy-tryptamine melatonineHMDB
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]-acetamideHMDB
RegulinHMDB
{N-[2-(5-methoxy-1H-indol-3-yl)ethyl]-} acetamideHMDB
{N-[2-(5-methoxyindol-3-yl)ethyl]-} acetamideHMDB
3-(2-Acetamidoethyl)-5-methoxyindoleHMDB
MelatoninHMDB
Acetamide, N-(2-(5-methoxy-1H-indol-3-yl)ethyl)- (9CI)biospider
Acetamide, N-[2-(5-methoxyindol-3-yl)ethyl]- (6CI,8CI)biospider
Melapurebiospider
N-[2-(5-Methoxy-1H-indol-3-yl)-ethyl]-acetamidebiospider
Predicted Properties
PropertyValueSource
Water Solubility0.14 g/LALOGPS
logP1.42ALOGPS
logP1.15ChemAxon
logS-3.2ALOGPS
pKa (Strongest Acidic)15.8ChemAxon
pKa (Strongest Basic)-1.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area54.12 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity66.28 m³·mol⁻¹ChemAxon
Polarizability25.65 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC13H16N2O2
IUPAC nameN-[2-(5-methoxy-1H-indol-3-yl)ethyl]acetamide
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
Description Belongs to the class of organic compounds known as 3-alkylindoles. 3-Alkylindoles are compounds containing an indole moiety that carries an alkyl chain at the 3-position.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassIndoles and derivatives
Sub ClassIndoles
Direct Parent3-alkylindoles
Alternative Parents
Substituents
  • 3-alkylindole
  • Anisole
  • Alkyl aryl ether
  • Substituted pyrrole
  • Benzenoid
  • Pyrrole
  • Heteroaromatic compound
  • Propargyl-type 1,3-dipolar organic compound
  • Ether
  • Carboximidic acid derivative
  • Carboximidic acid
  • Organic 1,3-dipolar compound
  • Azacycle
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Organic nitrogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
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-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-03k9-1900000000-45ee4fdc7acdb33dad3bSpectrum
GC-MSMelatonin, non-derivatized, GC-MS Spectrumsplash10-001i-0490000000-aa93967315af900a76ceSpectrum
GC-MSMelatonin, non-derivatized, GC-MS Spectrumsplash10-03k9-0900000000-a15ee6def3f8d75b1231Spectrum
GC-MSMelatonin, non-derivatized, GC-MS Spectrumsplash10-001j-0490000000-94ef1be9ab930060778aSpectrum
GC-MSMelatonin, 2 TMS, GC-MS Spectrumsplash10-001i-1490000000-03e24298c7bd1ed4066aSpectrum
GC-MSMelatonin, non-derivatized, GC-MS Spectrumsplash10-001i-1490000000-03e24298c7bd1ed4066aSpectrum
GC-MSMelatonin, non-derivatized, GC-MS Spectrumsplash10-001j-0590000000-63d5e32dd5f7877a4402Spectrum
GC-MSMelatonin, non-derivatized, GC-MS Spectrumsplash10-001i-0590000000-52b3a733f8b49582d3fbSpectrum
GC-MSMelatonin, non-derivatized, GC-MS Spectrumsplash10-0229-1900000000-d81c6f617bc486066136Spectrum
Predicted GC-MSMelatonin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0076-4920000000-a8d9d614e9f8769a1359Spectrum
Predicted GC-MSMelatonin, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSMelatonin, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-0159-0090000000-939a1caf5760c0ba189cSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-0006-0930000000-9e6fcea2c634ac9d85a0Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-0006-0900000000-ddd29e731a7de56c1808Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-0006-0900000000-34b4fb52810a15ea5bd6Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-001i-0090000000-5ca2df63ec2baefdae8cSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0159-0090000000-939a1caf5760c0ba189cSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0006-0930000000-9e6fcea2c634ac9d85a0Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0006-0900000000-ddd29e731a7de56c1808Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0006-0900000000-34b4fb52810a15ea5bd6Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-001i-0090000000-5ca2df63ec2baefdae8cSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-00lr-0090000000-3c42f6997539afb44682Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-014m-0960000000-7991e64dacb3c7f5cf32Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0006-0900000000-882be43bc196e928a3cfSpectrum
MS/MSLC-MS/MS Spectrum - , negativesplash10-014i-0190000000-ddda9232f0e8e1b402f7Spectrum
MS/MSLC-MS/MS Spectrum - 60V, Negativesplash10-0006-0900000000-24977ebbbf8d80633142Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-02u0-0960000000-a53f0bcd21c20cd44cfaSpectrum
MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-00kf-0950000000-58b73ecf5d765d8f6c01Spectrum
MS/MSLC-MS/MS Spectrum - 15V, Negativesplash10-0159-0090000000-de8a238bc05d176027cfSpectrum
MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-00kf-0910000000-9996bcba8fb3d61347d4Spectrum
MS/MSLC-MS/MS Spectrum - 75V, Negativesplash10-0006-0900000000-a290024caadd7d64fe8fSpectrum
MS/MSLC-MS/MS Spectrum - 90V, Negativesplash10-0006-0900000000-8be298c9d42d7769f129Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-0006-0900000000-a041de616cbb390bca58Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-0006-0900000000-d7ba873af42444fb4b0aSpectrum
MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-00kf-1940000000-9556b19d359c6c0f9d66Spectrum
MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-014i-0190000000-6462edd7b08702e1f49eSpectrum
NMR
TypeDescriptionView
1D NMR1H NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
2D NMR[1H,13C] 2D NMR SpectrumSpectrum
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).