AFCDB: Melatonin (FDB004234)

Record Information

Version

1.0

Creation date

2010-04-08 22:06:09 UTC

Update date

2019-11-26 02:59:53 UTC

Primary ID

FDB004234

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Melatonin

Description

Melatonin, 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 Number

73-31-4

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
Not Available	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.14 g/L	ALOGPS
logP	1.42	ALOGPS
logP	1.15	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	15.8	ChemAxon
pKa (Strongest Basic)	-1.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	54.12 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	66.28 m³·mol⁻¹	ChemAxon
Polarizability	25.65 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C13H16N2O2

IUPAC name

N-[2-(5-methoxy-1H-indol-3-yl)ethyl]acetamide

InChI Identifier

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)

InChI Key

DRLFMBDRBRZALE-UHFFFAOYSA-N

Isomeric SMILES

COC1=CC=C2NC=C(CCNC(C)=O)C2=C1

Average Molecular Weight

232.2783

Monoisotopic Molecular Weight

232.121177766

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.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Indoles

Direct Parent

3-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 Framework

Aromatic heteropolycyclic compounds

External Descriptors

acetamides (CHEBI:16796 )
tryptamines (CHEBI:16796 )
Indole alkaloids (C01598 )
Melatonin (C01598 )
a small molecule (N-ACETYL-5-METHOXY-TRYPTAMINE )

Ontology

Physiological effect

Health effect:

Health condition:

Psychiatric disorders:

Autism spectrum disorder

Observation:

Drowsiness

Disposition

Route of exposure:

Enteral:

Ingestion

Naturally occurring process:

Biological process:

Biochemical process:

Sleep

System process:

Reproduction

Hormone

Industrial application:

Pharmaceutical industry:

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Solid
Physical Description	Not Available
Mass Composition	Not Available
Melting Point	117 oC
Boiling Point	Not Available
Experimental Water Solubility	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Isoelectric point	Not Available
Charge	0
Optical Rotation	Not Available
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
EI-MS	Mass Spectrum (Electron Ionization)	splash10-03k9-1900000000-45ee4fdc7acdb33dad3b	2014-09-20	View Spectrum
GC-MS	Melatonin, non-derivatized, GC-MS Spectrum	splash10-001i-0490000000-aa93967315af900a76ce	Spectrum
GC-MS	Melatonin, non-derivatized, GC-MS Spectrum	splash10-03k9-0900000000-a15ee6def3f8d75b1231	Spectrum
GC-MS	Melatonin, non-derivatized, GC-MS Spectrum	splash10-001j-0490000000-94ef1be9ab930060778a	Spectrum
GC-MS	Melatonin, 2 TMS, GC-MS Spectrum	splash10-001i-1490000000-03e24298c7bd1ed4066a	Spectrum
GC-MS	Melatonin, non-derivatized, GC-MS Spectrum	splash10-001i-1490000000-03e24298c7bd1ed4066a	Spectrum
GC-MS	Melatonin, non-derivatized, GC-MS Spectrum	splash10-001j-0590000000-63d5e32dd5f7877a4402	Spectrum
GC-MS	Melatonin, non-derivatized, GC-MS Spectrum	splash10-001i-0590000000-52b3a733f8b49582d3fb	Spectrum
GC-MS	Melatonin, non-derivatized, GC-MS Spectrum	splash10-0229-1900000000-d81c6f617bc486066136	Spectrum
Predicted GC-MS	Melatonin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0076-4920000000-a8d9d614e9f8769a1359	Spectrum
Predicted GC-MS	Melatonin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Melatonin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-00di-0920000000-f90ec9b77e1a245e35a8	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-05fr-0900000000-49e4482c65e82ac64b66	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-003r-0900000000-8a4ae0fd610cca992d74	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-0159-0090000000-939a1caf5760c0ba189c	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-0006-0930000000-9e6fcea2c634ac9d85a0	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative	splash10-0006-0900000000-ddd29e731a7de56c1808	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative	splash10-0006-0900000000-34b4fb52810a15ea5bd6	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-001i-0090000000-5ca2df63ec2baefdae8c	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive	splash10-001i-0190000000-5bae6e63e9b40e60e0a4	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive	splash10-00di-0900000000-529bf6d5c2091993f865	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive	splash10-00di-0900000000-158a60fe696120b23b41	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive	splash10-0a5c-0900000000-5e86b2de659ce47762c0	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive	splash10-001i-0900000000-881c0d57239d56c46f2d	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positive	splash10-00di-0910000000-f256f78adbcbeb2464de	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positive	splash10-0a4i-0900000000-bd15d952a2fc6c5cbb23	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - DI-ESI-qTof , Positive	splash10-05fr-0900000000-7acf9405f4beeb34566c	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - DI-ESI-qTof , Positive	splash10-00di-0900000000-13245183cd8c8cd511c3	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-qTof , Positive	splash10-05ai-2900000000-07b3d32f002dba733c10	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0159-0090000000-939a1caf5760c0ba189c	2017-09-14	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0019-0950000000-3561167f9cf6abf87465	2017-07-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00dr-0900000000-7c590c12649f6abfac96	2017-07-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-006x-1900000000-6fc07c212072dc15cda1	2017-07-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-1390000000-afe87f80bc60da102bf6	2017-07-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0019-3940000000-44812f1a2c7f6216bd23	2017-07-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-052f-9300000000-995e110e7943eff538ad	2017-07-26	View Spectrum

NMR

Type	Description	View
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 90 MHz, CDCl₃, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 22.53 MHz, CDCl₃, experimental)	Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Spectrum

External Links

ChemSpider ID

ChEMBL ID

KEGG Compound ID

Pubchem Compound ID

Pubchem Substance ID

Not Available

ChEBI ID

16796

Phenol-Explorer ID

Not Available

DrugBank ID

DB01065

HMDB ID

HMDB01389

CRC / DFC (Dictionary of Food Compounds) ID

Not Available

EAFUS ID

Not Available

Dr. Duke ID

MELATONIN

BIGG ID

37965

KNApSAcK ID

Not Available

HET ID

ML1

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

Not Available

SuperScent ID

Not Available

Wikipedia ID

Melatonin

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

Food	Content Range	Average	Reference
Food			Reference

Biological Effects and Interactions

Health Effects / Bioactivities

Descriptor	ID	Definition	Reference
anaphrodisiac			DUKE
anti aggregant			DUKE
anti convulsant	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti depressant	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti gonadotrophic			DUKE
anti insomniac	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
antioxidant	22586	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 radicular			DUKE
anti thyreotropic			DUKE
aphrodisiac			DUKE
contraceptive	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
cyclooxygenase-2 inhibitor	50629	A cyclooxygenase inhibitor that interferes with the action of cyclooxygenase 2.	DUKE
cyclooxygenase inhibitor	35544	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
depressant			DUKE
GABA nergic	51374	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
gonadotrophic			DUKE
hypnotic			DUKE
hypocholesterolemic			DUKE
hypothermic			DUKE
immunostimulant	50847	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
progesteronigenic			DUKE
serotoninergic	48278		DUKE
thyrotropic			DUKE
hormone	24621	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

Name	Gene Name	UniProt ID
Estrogen receptor	ESR1	P03372
Nuclear receptor ROR-beta	RORB	Q92753

Pathways

Name	SMPDB Link	KEGG Link
Tryptophan Metabolism	SMP00063	map00380

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Not Available

Files

MSDS

show

References

Synthesis Reference

Not Available

General Reference

Not Available

Content Reference

— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).

Melatonin (FDB004234)

Structure for FDB004234 (Melatonin)