FComEx: N-Acetylserotonin (PC000633)

Record Information

Version

1.0

Creation date

2015-10-09 22:31:40 UTC

Update date

2017-01-19 02:36:30 UTC

FoodComEx ID

PC000633

FoodDB Record

FDB022505

Chemical Information

Name

N-Acetylserotonin

Description

N-Acetylserotonin is an intermediate in the metabolic pathway of melatonin and indoleamine in the pineal gland of mammalians. Serotonin-N-acetyltransferase (SNAT), which regulates the rate of melatonin biosynthesis in the pineal gland, catalyzes the acetylation of 5HT to N-acetylserotonin (NAS). A methyl group from S-adenosylmethionine is transferred to NAS by hydroxyindole-O-methyltransferase (HIOMT), and finally NAS is converted to 5-methoxy-N-acetyltryptamine, or melatonin. In most mammalian species the content of NAS (and melatonin) in the pineal gland shows clear circadian changes with the highest level occurring during the dark period. This elevation of the contents of NAS (and melatonin) in the dark period is due to the increase of SNAT activity and the elevation of SNAT gene expression. Experimental studies show that N-acetylserotonin possess free radical scavenging activity. Acute administration of irreversible and reversible selective MAO-A inhibitors and high doses (or chronic administration of low doses) of relatively selective MAO-B inhibitors (but not of highly selective MAO-B inhibitors) suppressed MAO-A activity and stimulated N-acetylation of pineal serotonin into N-acetylserotonin, the immediate precursor of melatonin. N-acetylserotonin increase after MAO-A inhibitors might mediate their antidepressive and antihypertensive effects. N-Acetylserotonin is the product of the O-demethylation of melatonin mediated by cytochrome P-450 isoforms: Cytochrome p450, subfamily IIc, polypeptide 19 (CYP2C19, a clinically important enzyme that metabolizes a wide variety of drugs), with a minor contribution from Cytochrome p450, subfamily I, polypeptide (2CYP1A2, involved in O-deethylation of phenacetin). (PMID 15616152, 11103901, 10721079, 10591054) [HMDB]. N-Acetylserotonin is found in many foods, some of which are oregon yampah, barley, ostrich fern, and lovage.

CAS Number

1210-83-9

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
5-Hydroxy-N-acetyltryptamine	hmdb
5-Hydroxymelatonin	hmdb
ASE	hmdb
Desmethylmelatonin	HMDB
N-(2-(5-Hydroxy-1H-indol-3-yl)ethyl)acetamide	ChEBI
N-Acetyl-5-hydroxytryptamine	hmdb
N-Acetylserotonin	hmdb
O-Demethylmelatonin	HMDB

Chemical Formula

C12H14N2O2

IUPAC name

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

InChI Identifier

InChI=1S/C12H14N2O2/c1-8(15)13-5-4-9-7-14-12-3-2-10(16)6-11(9)12/h2-3,6-7,14,16H,4-5H2,1H3,(H,13,15)

InChI Key

MVAWJSIDNICKHF-UHFFFAOYSA-N

Isomeric SMILES

CC(=O)NCCC1=CNC2=C1C=C(O)C=C2

Average Molecular Weight

218.2518

Monoisotopic Molecular Weight

218.105527702

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hydroxyindoles. These are organic compounds containing an indole moiety that carries a hydroxyl group.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Hydroxyindoles

Direct Parent

Hydroxyindoles

Alternative Parents