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Melatonin (FDB004234)

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
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
Not AvailableNot Available
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)splash10-03k9-1900000000-45ee4fdc7acdb33dad3b2014-09-20View Spectrum
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 - Quattro_QQQ 10V, Positive (Annotated)splash10-00di-0920000000-f90ec9b77e1a245e35a82012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-05fr-0900000000-49e4482c65e82ac64b662012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-003r-0900000000-8a4ae0fd610cca992d742012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-0159-0090000000-939a1caf5760c0ba189c2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-0006-0930000000-9e6fcea2c634ac9d85a02012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-0006-0900000000-ddd29e731a7de56c18082012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-0006-0900000000-34b4fb52810a15ea5bd62012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-001i-0090000000-5ca2df63ec2baefdae8c2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-001i-0190000000-5bae6e63e9b40e60e0a42012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-00di-0900000000-529bf6d5c2091993f8652012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-00di-0900000000-158a60fe696120b23b412012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-0a5c-0900000000-5e86b2de659ce47762c02012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-001i-0900000000-881c0d57239d56c46f2d2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positivesplash10-00di-0910000000-f256f78adbcbeb2464de2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positivesplash10-0a4i-0900000000-bd15d952a2fc6c5cbb232012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - DI-ESI-qTof , Positivesplash10-05fr-0900000000-7acf9405f4beeb34566c2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - DI-ESI-qTof , Positivesplash10-00di-0900000000-13245183cd8c8cd511c32017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-05ai-2900000000-07b3d32f002dba733c102017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0159-0090000000-939a1caf5760c0ba189c2017-09-14View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0019-0950000000-3561167f9cf6abf874652017-07-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00dr-0900000000-7c590c12649f6abfac962017-07-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-006x-1900000000-6fc07c212072dc15cda12017-07-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-1390000000-afe87f80bc60da102bf62017-07-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0019-3940000000-44812f1a2c7f6216bd232017-07-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-9300000000-995e110e7943eff538ad2017-07-26View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, 90 MHz, CDCl3, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 22.53 MHz, CDCl3, experimental)Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Spectrum
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).