Showing Compound 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
5-Methoxy-N-acetyltryptamine	ChEBI
Melatonine	ChEBI
N-[2-(5-Methoxyindol-3-yl)ethyl]acetamide	ChEBI
N-Acetyl-5-methoxytryptamine	ChEBI
Melatonina	Kegg
Circadin	HMDB
Melatol	HMDB
Melatonin (synth.) standard-grade	HMDB
Melatonin (synth.) ultra-pure	HMDB
Melovine	HMDB
MT6	HMDB
N-(2-(5-Methoxy-1H-indol-3-yl)ethyl)acetamide	HMDB
N-(2-(5-Methoxyindol-3-yl)ethyl)-acetamide	HMDB
N-(2-(5-Methoxyindol-3-yl)ethyl)acetamide	HMDB
N-Acetyl-5-methoxy-tryptamine	HMDB
N-Acetyl-5-methoxy-tryptamine melatonine	HMDB
N-[2-(5-Methoxy-1H-indol-3-yl)ethyl)acetamide	HMDB
N-[2-(5-Methoxy-1H-indol-3-yl)ethyl]-acetamide	HMDB
N-[2-(5-Methoxy-1H-indol-3-yl)ethyl]acetamide	HMDB
N-[2-(5-Methoxyindol-3-yl)ethyl]-acetamide	HMDB
Regulin	HMDB
{N-[2-(5-methoxy-1H-indol-3-yl)ethyl]-} acetamide	HMDB
{N-[2-(5-methoxyindol-3-yl)ethyl]-} acetamide	HMDB
3-(2-Acetamidoethyl)-5-methoxyindole	HMDB
Melatonin	HMDB
Acetamide, N-(2-(5-methoxy-1H-indol-3-yl)ethyl)- (9CI)	biospider
Acetamide, N-[2-(5-methoxyindol-3-yl)ethyl]- (6CI,8CI)	biospider
Melapure	biospider
N-[2-(5-Methoxy-1H-indol-3-yl)-ethyl]-acetamide	biospider

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		An agent that reduces or suppresses sexual desire, used therapeutically to manage hypersexuality, sex addiction, or paraphilias, and in treating conditions like priapism or excessive sexual arousal.	DUKE
Anti-aggregant		An agent that prevents platelet aggregation, reducing blood clot formation. Its biological role is to inhibit platelet activation, and its therapeutic applications include preventing thrombosis and stroke. Key medical uses include treating cardiovascular diseases, such as myocardial infarction and atrial fibrillation, and managing conditions that increase the risk of blood clots.	DUKE
Anti convulsant	52217	An agent that reduces or prevents seizures, commonly used in managing epilepsy, neuropathic pain, and mood disorders, by stabilizing abnormal electrical activity in the brain.	DUKE
Anti depressant	52217	An agent that regulates mood, reducing symptoms of depression and anxiety by altering neurotransmitter levels in the brain, commonly used in managing depression, anxiety disorders, and other mood disorders.	DUKE
Anti gonadotrophic		An agent that inhibits gonadotropin production or activity, regulating reproductive hormone secretion. It has therapeutic applications in managing conditions like precocious puberty, hormone-sensitive cancers, and infertility, with key medical uses including contraception and treatment of endometriosis.	DUKE
Anti-insomniac	52217	An agent that promotes sleep, reducing insomnia symptoms. It regulates the body's sleep-wake cycle, commonly used in managing sleep disorders, such as chronic insomnia, and improving overall sleep quality.	DUKE
Anti-oxidant	22586	An agent that neutralizes free radicals, reducing oxidative stress and cell damage. Its biological role involves protecting cells from harm, and it has therapeutic applications in managing chronic diseases, such as cancer, diabetes, and neurodegenerative disorders, with key medical uses including anti-aging, anti-inflammatory, and cardio protective effects.	DUKE
Anti radicular		An agent that relieves inflammation or irritation of the nerve root of a tooth, reducing pain and discomfort. Its biological role is to target and alleviate radicular pain, with therapeutic applications in endodontics and key medical uses in root canal treatments and tooth sensitivity management.	DUKE
Anti-thyreotropic		An antibody that inhibits thyrotropin, regulating thyroid hormone production. It has therapeutic applications in managing thyroid disorders, such as hyperthyroidism, and key medical uses include treating conditions like Graves' disease.	DUKE
Aphrodisiac		A substance that stimulates sexual desire, playing a biological role in enhancing libido. It has therapeutic applications in treating sexual dysfunction and key medical uses in managing conditions such as erectile dysfunction and low sex drive.	DUKE
Contraceptive	52217	An agent that prevents pregnancy by inhibiting ovulation, fertilization, or implantation, used to control birth rates, manage menstrual disorders, and reduce the risk of sexually transmitted infections, commonly applied in various forms such as pills, injections, and barrier methods.	DUKE
Cyclooxygenase-2 inhibitor	50629	An agent that blocks the activity of cyclooxygenase-2 (COX-2), reducing inflammation and pain. Therapeutically, it is used to manage conditions such as arthritis, menstrual cramps, and other inflammatory disorders, providing relief from symptoms with reduced gastrointestinal side effects compared to non-selective NSAIDs.	DUKE
Cyclooxygenase inhibitor	35544	An agent that blocks the activity of cyclooxygenase enzymes, reducing inflammation and pain. Therapeutically, it is used to treat conditions such as arthritis, headaches, and menstrual cramps, by decreasing prostaglandin production, a key mediator of inflammation.	DUKE
Depressant		An agent that lowers neurotransmission levels, reducing arousal or stimulation in the brain, used therapeutically to treat anxiety, insomnia, and seizures, and medically to induce sedation and relieve symptoms of certain conditions.	DUKE
GABA nergic	51374	A neurotransmitter regulator that enhances GABA (gamma-aminobutyric acid) activity, promoting relaxation and reducing anxiety. Therapeutically, it's used as an anxiolytic, anticonvulsant, and muscle relaxant, commonly applied in managing anxiety disorders, epilepsy, and insomnia.	DUKE
Gonadotrophic		A hormone-stimulating agent that regulates reproductive functions, promoting gonadal growth and development. Therapeutically, it is used to treat infertility, hypogonadism, and menstrual disorders, stimulating the production of sex hormones such as estrogen and testosterone.	DUKE
Hypnotic		An agent that induces sleep, used to treat insomnia and facilitate surgical anesthesia, playing a key role in regulating sleep patterns and providing therapeutic relief for sleep disorders.	DUKE
Hypocholesterolemic		An agent that lowers cholesterol levels in the blood, playing a crucial role in preventing cardiovascular disease. Therapeutically, it is used to manage hyperlipidemia and reduce the risk of heart disease, with key medical applications including the treatment of high cholesterol, atherosclerosis, and coronary artery disease.	DUKE
Hypothermic		A condition of abnormally low body temperature, playing a biological role in reducing metabolic rate and oxygen demand. Therapeutically, it has applications in neuroprotection, cardiac surgery, and trauma care. Key medical uses include treating heatstroke, cardiac arrest, and brain injuries, as well as preserving organs for transplantation.	DUKE
Immunostimulant	50847	An agent that stimulates the immune system, enhancing its response to infections and diseases. Therapeutically, it boosts the body's natural defenses, commonly used to treat immunodeficiency disorders, prevent infections, and support cancer treatment, as well as manage chronic conditions like hepatitis and HIV.	DUKE
Progesteronigenic		An agent that stimulates progesterone production, regulating menstrual cycles, pregnancy, and embryogenesis. Therapeutically, it's used to treat menstrual disorders, infertility, and pregnancy-related issues, such as preventing miscarriage and supporting embryonic development.	DUKE
Serotoninergic	48278	An agent that modulates serotonin activity, regulating mood, appetite, and sleep. It has therapeutic applications in treating depression, anxiety, and mood disorders, with key medical uses including antidepressants, anxiolytics, and anti-migraine medications.	DUKE
Thyrotropic		An agent stimulating or regulating the thyroid gland's secretory activity, playing a crucial role in hormone production. Therapeutically, it is used to manage thyroid disorders, such as hypothyroidism, and certain types of cancer, including thyroid cancer. Key medical uses include diagnosing and treating thyroid conditions, and regulating metabolism.	DUKE
Hormone	24621	A chemical messenger produced by glands, regulating various bodily functions such as growth, metabolism, and reproductive processes. Therapeutically, hormones are used to treat hormonal imbalances, menopausal symptoms, and certain cancers, as well as to regulate fertility and manage endocrine disorders, including diabetes and thyroid conditions.	CHEBI